OLEIC ACID
OLEIC ACID
Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils.
Oleic acid is an odorless, colorless oil, although commercial samples may be yellowish.
In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9.
Oleic acid has the formula CH3(CH2)7CH=CH(CH2)7COOH.
The name derives from the Latin word oleum, which means oil.
Oleic acid is the most common fatty acid in nature.
The salts and esters of oleic acid are called oleates.
EC / List no.: 204-007-1
CAS no.: 112-80-1
Oleic acid is an octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.
It has a role as an EC 3.1.1.1 (carboxylesterase) inhibitor, an Escherichia coli metabolite, a plant metabolite, a Daphnia galeata metabolite, a solvent, an antioxidant and a mouse metabolite.
It is a conjugate acid of an oleate. It derives from a hydride of a cis-octadec-9-ene.
Oleic acid is a monounsaturated fatty acid and it has good resistance to rancidity, for example, due to the high content of fatty acid and low content of polyunsaturated fatty acids (only containing 2–4% polyunsaturated fatty acids) in sunflower seed oil with rich oleic acid, the sunflower seed oil has excellent oxidation stability
Oleic Acid (also called cis-9-octadecenoic acid) is an example of a fatty acid found in animal and vegetable oils.
It is a mono-unsaturated fatty acid, due to the presence of a single double bond.
The physical properties of fatty acids like oleic acid are determined by the number, geometry, and position of the double bonds in the chain, along with the degree of unsaturation (i.e. number of double bonds).
In naturally occurring fatty acids, such as those found in vegetable oils, the double bonds are all in the cis configuration (shown in red in the figure), making the molecules bent or curved.
This also makes the molecules much less flexible than those of fully saturated fatty acids (e.g. stearic acid).
Their bent shape also hinders crystallisation, and explains why these acids are oils at room temperature.
(Saturated acids have straight chains and can pack easily into a crystal lattice, and so are solid at room temperature, e.g. butter).
Oleic acid is an unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature.
It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. Oleic acid occurs naturally in various animal and vegetable fats and oils. It is a component of the normal human diet as a part of animal fats and vegetable oils. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil. Oleic acid has being shown to have a potential anticancer activity.
Oleic acid is used as an emulsifying agent for facial creams and lotions, as an accelerator in the rubber industry, as an emollient, as a solubilizing agent in aerosol products and as a soldering flux in stained glass work for joining lead came.
Oleic acid is used in the preparation of oleates and lotions.
Oleic acid acts as intermediate for drilling and fracking fluids in the oil and gas industry.
Oleic acid finds application as an excipient in pharmaceuticals.
Applications
Chemical manufacturing: Esters, amides, amines, soaps, food additives
CASE: Alkyd resins, plasticizers
Personal care: Skin care, hair care, color cosmetics
Oilfield: Emulsifiers and corrosion inhibitors for drilling muds
Lubricants & metalworking: Group IV base oils, corrosion inhibitors, defoamers
HIC: Specialty industrial & household cleaners
Paper Chemicals: Defoamers
Asphalt: Emulsifier, anti-strip
Concrete: Air entrainment, mold release, curing agent
Oleic acid (18:1) is considered to be highly stable to oxidation and also can enhance the activity of antioxidants and antipolymerization agents.
In combination with antioxidants like tocopherols, it can be blended with other oils to prevent oxidation.
These blends of oleic acid and tocopherols have been reported to have better protective effects than α-tocopherol alone (Lampi and Kamal-Eldin, 1998).
It has also been reported that isocaloric replacement of about 5% of energy from saturated fatty acids by oleic acid reduced coronary heart disease risk by 20–40%, mainly via low-density lipoprotein (LDL) cholesterol reduction (Kris-Etherton, 1999).
It is generally recognized that higher intakes of oleic acid and a limited intake of saturated fats are beneficial and may help protect against cardiovascular disease.
Oleic acid is obtained by hydrolysis of olive oil. It is insoluble in water and very soluble in alcohol. This acid is used in the elaboration of topic formulations as excipient, e.g., of emulsions, due to its capacity to react with alkalis forming soaps with emulgent properties.
Oleic acid can act as a percutaneous absorption enhancer of several drugs, as it induces the disruption of the lipid structure of the stratum corneum, allowing drug permeation.
This organic acid is able to increase the bioavailability of the corticoids betamethasone 17-benzoate and betamethasone 17-valerate, ketorolac, metronidazole, hydrocortisone, progesterone and estradiol, to cite just a few (Bennet et al., 1985; Brian and Adrian, 1988; Yu et al., 1988).
Oleic acid is also used in the preparation of the benzyl benzoate lotion for the treatment of scabies.
Oleic and linoleic acid can induce the in vitro suppression of the skin pigmentation.
Oleic acid is a solid with a low melting point; two crystalline forms (α-form, melting point 13.4 °C [56 °F], and β-form, melting point 16.3 °C [61 °F]) are known.
It is a long-chain carboxylic acid; its molecule contains one double bond between C9 and C10 with the cis configuration.
The structure of oleic acid may be deduced from the following reactions.
Treatment with selenium or oxides of nitrogen partially transforms it into the trans isomer elaidic acid.
The arrangement of its 18 carbon atoms and the position of the double bond are demonstrated by its catalytic hydrogenation to stearic acid, CH3(CH2)16CO2H, and its oxidative cleavage to nonanoic (pelargonic) acid, CH3(CH2)7CO2H, and azelaic acid, HO2C(CH2)7CO2H.
When oleic acid is heated with alkali, migration of the double bond occurs, giving the α,β-unsaturated acid CH3(CH2)14CH=CHCO2H, and this, on further heating with alkali, gives palmitic acid, CH3(CH2)14CO2H.
Oleic acid shows the standard reactions of a carboxylic acid and a disubstituted ethylene, including the formation of a dibromide with bromine and a glycol with dilute aqueous potassium permanganate.
Oleic acid is an unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature.
It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent.
Oleic acid is a monounsaturated fatty acid that occurs naturally in the fats and oils of both animals and vegetables.
It is naturally odorless and colorless, although commercial products made with it may be yellowish.
Scientifically, it is a monounsaturated omega-9 fatty acid, and its name means “derived from oil or olive.”
What are the atoms that make up oleic acid?
It has the formula CH3(CH2)7CH=CH(CH2)7COOH, and it’s part of the carboxylic acid group. Oleic acid is called an omega-9 fat because it has a carbon-carbon double bond in the ninth bond from the methyl end of the fatty acid.
Oleic acid is needed by the body’s cells for proper membrane fluidity — making sure the cell membrane has a thick enough layer.
This is important for fighting pathogens, transporting minerals and responding to hormones.
Oleic acid also serves as a major source of energy for our cells, and it’s used for the production and biosynthesis of many essential metabolites.
Oleic Acid vs. Linoleic Acid
The big difference between oleic acid and linoleic acid is that our bodies produce oleic acid, so the need to supplement isn’t as important.
In fact, oleic acid is the most abundant fatty acid in nature, and it’s present in most of our cells.
There is no specific recommendation for oleic acid and omega-9 fatty acid intake because these fats are considered non-essential, but research shows that increasing your consumption of omega-9s, perhaps in place of omega-6 fatty acids, can have beneficial effects.
Oleic acid as its sodium salt is a major component of soap as an emulsifying agent. Oleic acid is also used as emollient.
Small amounts of oleic acid are used as an excipient in pharmaceuticals, oleic acid is used as an emulsifying or solubilizing agent in aerosol products.
Oleic acid is a monounsaturated omega-9 fatty acid found in many healthy high-fat foods, including vegetable and animal sources. Some examples include olive oil, avocado oil, and macadamia nuts.
Omega-9 fatty acids are a family of unsaturated fats that have a carbon-carbon double bond at the omega−9 position.
Oleic acid is a common fatty acid that can be found in lots of plant oils. Its name, “oleic”, means derived from olive oil, a plant oil rich in oleic acid, but avocado, macadamia and marula oils, just to name a few, are also oleic rich.
Its chemical structure is monounsaturated, meaning it has one double bond (cis-9) that makes it less kinky than polyunsaturated fatty acids with multiple double bonds
Occurrence
Fatty acids (or their salts) often do not occur as such in biological systems.
Instead fatty acids such as oleic acid occur as their esters, commonly triglycerides, which are the greasy materials in many natural oils.
Oleic acid is the most common monounsaturated fatty acid in nature.
It is found in fats (triglycerides), the phospholipids that make membranes, cholesterol esters, and wax esters.
Triglycerides of oleic acid comprise the majority of olive oil. Free oleic acid renders olive oil inedible.
It also makes up 59–75 % of pecan oil, 61 % of canola oil, 36–67 % of peanut oil, 60% of macadamia oil, 20–80 % of sunflower oil, 15–20% of grape seed oil, sea buckthorn oil, 40% of sesame oil,[2] and 14% of poppyseed oil.
High oleic variants of plant sources such as sunflower (~80 %) and canola oil (70 %) also have been developed.
It also comprises 22.18 % of the fats from the fruit of the durian species, Durio graveolens.
Karuka contains 52.39 % oleic acid.
It is abundantly present in many animal fats, constituting 37 to 56% of chicken and turkey fat, and 44 to 47 % of lard.
Oleic acid is the most abundant fatty acid in human adipose tissue, and second in abundance in human tissues overall, following palmitic acid.
Production and chemical behaviour
The biosynthesis of oleic acid involves the action of the enzyme stearoyl-CoA 9-desaturase acting on stearoyl-CoA.
In effect, stearic acid is dehydrogenated to give the monounsaturated derivative, oleic acid.[5]
Oleic acid undergoes the reactions of carboxylic acids and alkenes.
It is soluble in aqueous base to give soaps called oleates.
Iodine adds across the double bond. Hydrogenation of the double bond yields the saturated derivative stearic acid.
Oxidation at the double bond occurs slowly in air, and is known as rancidification in foodstuffs and as drying in coatings.
Reduction of the carboxylic acid group yields oleyl alcohol. Ozonolysis of oleic acid is an important route to azelaic acid.
The coproduct is nonanoic acid:
H17C8CH=CHC7H14CO2H + 4″O” → HO2CC7H14CO2H + H17C8CO2H
Esters of azelaic acid find applications in lubrications and plasticizer.
Related compounds
The trans isomer of oleic acid is called elaidic acid or trans-9-octadecenoic acid.
These isomers have distinct physical properties and biochemical properties.
Elaidic acid, the most abundant trans fatty acid in diet, appears to have an adverse effect on health.
A reaction that converts oleic acid to elaidic acid is called elaidinization.
Another naturally occurring isomer of oleic acid is petroselinic acid.
In chemical analysis, fatty acids are separated by gas chromatography of their methyl ester derivatives. Alternatively, separation of unsaturated isomers is possible by argentation thin-layer chromatography.[17]
In ethenolysis, methyl oleate, the methyl ester of the acid, converts to 1-decene and methyl 9-decenoate:
CH3(CH2)7CH=CH(CH2)7CO2Me + CH2=CH2 → CH3(CH2)7CH=CH2 + MeO2C(CH2)7CH=CH2
Characteristics
100% naturally derived
Vegetable origin is palm, pine, canola, or sunflower
Animal origin is bleached fancy tallow
Long chain fatty acid
Low and high titer materials
Low and high iodine value materials
Resistant to oxidation and rancidity
Chemical intermediate for multiple end uses
Uses
Oleic acid is used as a component in many foods, in the form of its triglycerides. Oleic acid is a component of the normal human diet, being a part of animal fats and vegetable oils.
Oleic acid as its sodium salt is a major component of soap as an emulsifying agent. Oleic acid is also used as an emollient.
Small amounts of oleic acid are used as an excipient in pharmaceuticals, and it is used as an emulsifying or solubilizing agent in aerosol products.
Niche uses
Oleic acid is used to induce lung damage in certain types of animals for the purpose of testing new drugs and other means to treat lung diseases.
Specifically in sheep, intravenous administration of oleic acid causes acute lung injury with corresponding pulmonary edema.
Oleic acid is used as a soldering flux in stained glass work for joining lead came.
Oleic acid is widely used in the solution phase synthesis of nanoparticles, functioning as a kinetic knob to control the size and morphology of nanoparticles.
Health effects
Oleic acid is a common monounsaturated fat in human diet.
Monounsaturated fat consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol, however, its ability to raise HDL is still debated.
Presence of a ratio balancing the two types is considered essential for good health and that relationship remains subject to scientific debate as research continues.
Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit.
Adverse effects have been documented in some research of oleic acid, however, since both oleic and monounsaturated fatty acid levels in the membranes of red blood cells have been associated with increased risk of breast cancer,although other research indicates that the consumption of the oleate in olive oil has been associated with a decreased risk of breast cancer.[27]
FDA has approved a health claim on reduced risk of coronary heart disease for high oleic (> 70% oleic acid) oils.
Some oil plants have cultivars bred to increase the amount of oleic acid in the oils.
In addition to providing a health claim, the heat stability and shelf life may also be improved, but only if the increase in monounsaturated oleic acid levels correspond to a substantial reduction in polyunsaturated fatty acid (especially α-Linolenic acid) content.
When the saturated fat or trans fat in a fried food is replaced with a stable high oleic oil, consumers may be able to avoid certain health risks associated with consuming saturated fat and trans fat.[30][31]
Preferred IUPAC name: (9Z)-Octadec-9-enoic acid
Other names: Oleic acid
(9Z)-Octadecenoic acid
(Z)-Octadec-9-enoic acid
cis-9-Octadecenoic acid
cis-Δ9-Octadecenoic acid
18:1 cis-9
Identifiers
CAS Number: 112-80-1
SMILES
Properties
Chemical formula: C18H34O2
Molar mass: 282.468 g·mol−1
Appearance: Pale yellow or brownish yellow oily liquid with lard-like odor
Density: 0.895 g/mL
Melting point: 13 to 14 °C (55 to 57 °F; 286 to 287 K)
Boiling point: 360 °C (680 °F; 633 K)[1]
Solubility in water: Insoluble
Solubility in Ethanol: Soluble
Magnetic susceptibility (χ): -208.5·10−6 cm3/mol
Oleic acid is a mono-unsaturated omega-9 fatty acid found in various animal and vegetable sources.
Triglyceride esters of oleic acid comprise the majority of olive oil. Oleic acid is used as an excipient in pharmaceuticals and as an emulsifying or solubilizing agent in aerosol products.
It may hinder the progression of adrenoleukodystrophy, a fatal disease that affects the brain and adrenal glands, and it may help boost memory [74r].
Oleic acid may also be responsible for the hypo
Oleic acid, the most widely distributed of all the fatty acids, apparently occurring to some extent in all oils and fats.
In oils such as olive, palm, peanut, and sunflower, it is the principal acid obtained by saponification. Oleic acid, CH3(CH2)7CH=CH(CH2)7CO2H, like other fatty acids, does not occur in the free state but is normally found as an ester of glycerol—i.e., as a glyceride or as an ester of a long-chain alcohol.
Oleic acid is a natural, monounsaturated omega-9 fatty acid that’s found in many plants, including grape seed, olives, and sea buckthorn. It’s the primary fatty acid in olive oil, and believed to play a role in this oil’s cholesterol-lowering benefits when consumed orally.
Interestingly, research has shown that topical application of oleic acid on its own or as olive oil can disrupt skin’s barrier; however, this effect was not observed when oleic acid was blended with other fatty acids and skin-beneficial ingredients. On the upside, this kind of barrier disruption can enhance penetration of other ingredients naturally present in plant oils or in the product, so it’s not necessarily all bad (and, as we mentioned, not bad at all unless you’re applying pure oleic acid or straight olive oil to skin).
In another interesting twist, combining oleic acid with other lipids (fats) boosts its skin-calming ability, thus making oleic acid useful for reducing signs of dryness and sensitivity.
In cosmetics, oleic acid is used as a cleansing agent and texture enhancer. It’s among the more stable fatty acids, and has a unique ability to preserve the effectiveness of more delicate ingredients such as antioxidants by helping to protect them from light and air degradation.
Oleic acid (Oleate, 9-Octadecenoic Acid, Elaidoic acid) is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. Oleic acid is an abundant monounsaturated fatty acid. Oleic acid is a Na+/K+ ATPase activator.
Cosmetics and Pharmaceuticals use: Oil base for creams, lotions, lipsticks, powders, skin ointments, face cleaners, body shampoos, soaps etc,.
Use: Cosmetics and Personal Care, Cleaning and Detergents, Adhesives and Lubricants, Industrial, Inks and Coatings, Pharmaceutical and Veterinar
oleic acid
112-80-1
cis-9-Octadecenoic acid
(Z)-Octadec-9-enoic acid
cis-Oleic acid
oleate
Elaidoic acid
Glycon wo
Wecoline OO
Pamolyn 100
Glycon RO
Metaupon
Oelsauere
Vopcolene 27
Groco 5l
Groco 2
Groco 4
Groco 6
Tego-oleic 130
Emersol 211
cis-Octadec-9-enoic acid
Industrene 105
Industrene 205
Industrene 206
Pamolyn
Z-9-Octadecenoic acid
Oleinic acid
Emersol 210
Emersol 213
L’Acide oleique
Century cd fatty acid
Emersol 6321
Extraolein 90
Oleine 7503
9-Octadecenoic acid (Z)-
9-Octadecenoic acid (9Z)-
Elainic acid
Emersol 205
Emersol 233LL
Hy-phi 1055
Hy-phi 1088
Hy-phi 2066
Hy-phi 2088
Hy-phi 2102
Priolene 6906
White oleic acid
Wochem no. 320
(9Z)-octadec-9-enoic acid
Emersol 220 white oleic acid
9-octadecenoic acid
Extra Oleic 80R
Extra Oleic 90
Extra Oleic 99
Extra Olein 80
Extra Olein 90R
Lunac O-CA
Lunac O-LL
Lunac O-P
neo-Fat 92-04
Priolene 6907
Priolene 6928
Priolene 6930
Priolene 6933
9Z-Octadecenoic acid
Emersol 6313NF
cis-Oleate
Elaic acid
delta9-cis-Oleic acid
9-Octadecenoic acid, (Z)-
(9Z)-Octadecenoic acid
FEMA No. 2815
FEMA Number 2815
D 100 (fatty acid)
Emersol 221 low titer white oleic acid
K 52
Oelsaeure
HSDB 1240
Red oil
UNII-2UMI9U37CP
D 100
Oleic acid [NF]
9-octadecylenic acid
Emersol 233
18:1Delta9cis
CHEBI:16196
9,10-Octadecenoic acid
C18:1n-9
MFCD00064242
neo-Fat 90-04
.delta.9-cis-Oleic acid
9-(Z)-octadecenoic acid
(Z)-9-Octadecanoic acid
9-Octadecenoic acid, cis-
cis-.delta.9-Octadecenoate
2UMI9U37CP
CHEMBL8659
cis-.delta.9-Octadecenoic acid
cis-Delta(9)-octadecenoic acid
NSC9856
NSC-9856
Oleic acid (NF)
Oleic acid, 97%
C18:1 n-9
Octadec-9-enoic acid
NCGC00091119-02
18:1 n-9
C18:1
cis-9-octadecenoate
(9Z)- Octadecenoic acid
DSSTox_CID_5809
Oleic acid, pure
DSSTox_RID_77930
DSSTox_GSID_25809
(Z)-octadec-9-enoate
Oleic acid (natural)
Caswell No. 619
Wecoline OO (VAN)
Acide oleique [French]
Acide oleique
cis-delta9-octadecenoic acid
l’Acide oleique [French]
CAS-112-80-1
SMR000326739
CCRIS 682
NAA 35
Sulfurized oleic acid
Sulphurized oleic acid
Oleic acid, sulfurized
cis-delta(sup 9)-Octadecenoic acid
NSC 9856
EINECS 204-007-1
EPA Pesticide Chemical Code 031702
(9Z)-9-Octadecenoic acid
9-Octadecenoic acid (9Z)-, sulfurized
BRN 1726542
Distoline
Oleinate
oleaic acid
Rapinic acid
AI3-01291
oleic acid group
1gni
1hms
1vyf
2lkk
Lunac OA
Edenor ATiO5
Edenor FTiO5
Industrene 104
Z-9-Octadecenoate
EINECS 270-164-8
Oleic acid, p.a.
Emersol 213NF
Emersol 214NF
OLEICACID
Pamolyn 125
Priolene 6900
9,10-Octadecenoate
9-Octadecenoic acid (Z)-, sulfurized
Oleic acid (8CI)
oleic acid extra pure
cis-Octadec-9-enoate
Pamolyn 100 FG
Pamolyn 100 FGK
9-(Z)-octadecenoate
Emersol 7021
(Z)-9-Octadecanoate
Emersol 6313 NF
Emersol 6333 NF
PubChem24077
Oleic acid-9,10-t
(9Z)-9-Octadecenoate
9-cis-Octadecenoic acid
z-octadeca-9-enoic acid
Epitope ID:187036
Oleic acid, natural, FCC
(9Z)octadec-9-enoic acid
Emersol 220 White Oleate
Oleic acid, technical grade
SCHEMBL1138
Delta9-cis-Octadecenoic acid
WLN: QV8U9-C
4-02-00-01641 (Beilstein Handbook Reference)
68412-07-7
MLS001056779
MLS002153498
MLS002454427
9-octadecenoic acid, (9Z)-
(9Z)-9-Octadecenoic acid #
GTPL1054
Oleic acid, analytical standard
DTXSID1025809
Oleic acid, >=93% (GC)
Oleic acid, >=99% (GC)
REGID_for_CID_445639
1g74
s158
HMS2234O13
HMS3649H21
HMS3885H18
Oleic acid, technical grade, 90%
HY-N1446
ZINC6845860
Tox21_111086
Tox21_201967
Tox21_303324
BDBM50150484
HSCI1_000362
LMFA01030002
s4707
SBB058695
9-Octadecenoic acid (9Z)- (9CI)
cis-9-Octadecenoic-9,10-3H2 acid
Emersol 221 Low Titer White Oleate
AKOS017343225
cis-.delta.(sup 9)-Octadecenoic acid
CCG-267270
FA 18:1
9-Octadecenoic-9,10-t2 acid, (Z)-
Oleic Acid as an Inhibitor of Fatty Acid and Cholesterol Synthesis
● Oleic acid is the main fatty acid present in olive oil.
● Bio-active molecules in olive oil are oleic acid and some minor components, essentially phenolic compounds with a high antioxidant activity.
● Oleic acid inhibits fatty acid biosynthesis and cholesterogenesis in vivo as well as in vitro.
● In rats, an oleic acid-rich diet caused a significant reduction of the activity of the citrate carrier (CiC), a mitochondrial protein strictly connected with lipogenesis.
● In C6 glioma cells, oleic acid down-regulates the synthesis of palmitate and cholesterol through decreasing the activity, mRNA abundance and protein level of the pace-setting enzymes of the two pathways, i.e., acetyl-CoA carboxylase (ACC) and 3-hydroxy-3-methylglutaryl-CoA reductase (HMGCR), respectively.
● Oleic acid might exert its effect indirectly by down-regulating the expression of the sterol regulatory element binding protein (SREBP)-1 and -2, transcriptional factors involved in lipogenic and cholesterogenic gene expression.
● Oleic acid could regulate fatty acid and cholesterol biosynthesis through up-regulation of AMP-activated protein kinase, which phosphorylates and hence inactivates both acetyl-CoA carboxylase and 3-hydroxy-3-methyl-glutaryl CoA reductase.
● On the basis of the results reported in the literature, healthy effects of olive oil could be related, at least in part, to oleic acid down-regulation of fatty acid and cholesterol synthesis.
Oleic acid (18:1ω9), a monounsaturated fatty acid, is the major fatty acid in human milk. Oleic acid, as well as the products resulting from its further desaturation and elongation, are called the omega-9 fatty acids. The omega-9 fatty acid 24:1ω9 is a major fatty acid in the membranes of nerves.
The omega-9 fatty acid 20:3ω9 is called the Mead acid.
Mead acid accumulates in the body in response to a deficiency in the essential fatty acids, and there is some thought that Mead acid may compensate, with the decline in linoleic acid, in serving structural purposes in membranes. Mead acid is probably not used for the synthesis of any hormone.
oleic acid has parent hydride cis-octadec-9-ene
oleic acid has role Daphnia galeata metabolite
oleic acid has role Escherichia coli metabolite
oleic acid has role antioxidant (CHEBI:22586)
oleic acid has role EC 3.1.1.1 (carboxylesterase) inhibitor
oleic acid has role mouse metabolite
oleic acid has role plant metabolite
oleic acid has role solvent
oleic acid is a octadec-9-enoic acid
oleic acid is conjugate acid of oleate
Oleic Acid
Sergio Lopez, … Francisco J.G. Muriana, in Olives and Olive Oil in Health and Disease Prevention, 2010
Evidence from epidemiological studies suggests that a higher proportion of monounsaturated fatty acids (MUFA), notably oleic acid, in the diet is linked with a reduction in the risk of coronary heart disease (CHD). To achieve this benefit, olive oil as a major source of oleic acid is to replace a similar amount of saturated fat and not increase the total number of daily calories.
The biochemical bases of the ameliorative effect of oleic acid are thought to be modification of plasma lipid and lipoprotein concentrations, inhibition of coagulation, improvement of glucose homeostasis, and attenuation of inflammation and oxidative status in fasting conditions.
More recently, a body of evidence has grown that supports the hypotheses that postprandial metabolism of dietary fats plays a causal role in the pathogenesis and progression of CHD. However, the relevance of oleic acid regarding saturated fatty acids (SFA), notably palmitic acid, in dietary fats to influence postprandial metabolic processes is only partially understood.
The proportion of oleic acid and palmitic acid in olive oil, compared to other dietary fats, could provide benefits and be considered as a nutritional determinant, at least, for regulation of coagulation and glucose homeostasis during the postprandial state.
Oleic acid (cis-9-octadecenoic acid) is an omega-nine fatty acid and has the formula C18H34O2 (CH3(CH2)7CHCH(CH2)7COOH).
It is the most widely distributed of all the natural fatty acids and present in practically all lipids.
It is the main fatty acid in olive oil pressed from the ripe fruit of the olive.
Oleic acid makes up 55–80% of olive oil, 15–20% of grape seed oil and sea buckthorn oil .
In general, edible oils such as soybean oil, palm oil and corn oil contain about 10–40% oleic acid.
Among them, olive oil contains 75% oleic acid which is more than 5 times higher than safflower oil.
Oleic acid is best obtained from a vegetable and a useful starting material especially.
It is considered one of the healthier sources of fat in the diet and commonly used as a replacement for animal fat sources that are high in saturated fat.
Oleic Acid in the Diet and What It Does: Implications for Diabetes and Its Complications
Minerva Granado-Casas, Didac Mauricio, in Bioactive Food as Dietary Interventions for Diabetes (Second Edition), 2019
1 Introduction
Oleic acid (OA) is the principal monounsaturated fatty acid (MUFA) present in olive oil and nuts, especially peanuts and walnuts.
These are two key bioactive foods of a healthy dietary pattern such as the Mediterranean Diet (MedDiet), known for its beneficial properties and as a cultural heritage of Mediterranean populations
The Oleic Acid content is approximately 15% of the total energy intake in a traditional MedDiet.6,7
Olive oil is obtained from the olive tree (Olea europaea, from the family Oleaceae), a traditional Mediterranean fruit that can be consumed as extra virgin olive oil or as a refined product.8 Differences between refined and virgin or extra virgin olive oil must be taken into account because the existing evidence supports the beneficial effects of virgin or extra virgin olive oil varieties only.
During the refining process, minor but still important compounds such as polyphenols are lost; virgin or extra virgin varieties, however, are produced with mechanical mechanisms that conserve all of the beneficial compounds.1
Olive oil has a high content of OA (56%–84% of its total fatty acids), which is a monounsaturated omega-9 fatty acid because of the single double bond in the carbon nine position.8 In contrast to omega-3 and omega-6 fatty acids, omega-9 fatty acids are not essential because humans are capable of synthesizing Oleic acid from stearic acid by the action of the enzyme △ 9-desaturase.
Additionally, Oleic Acid is the major fat component in peanuts.
For these reasons, an Oleic acid-rich diet can easily be attained with regular daily intake of olive oil and/or nuts.
There is limited evidence of the direct role of Oleic Acid in disease and health, due in part to the difficulty of separating the Oleic acid content from olive oil and nuts from the other components of a dietary pattern such as the MedDiet1; another reason is the fact that olive oil and nuts have other bioactive compounds, such as polyphenols, which have been shown to have beneficial properties in the prevention and management of diabetes.
Thus, Oleic Acid may not be the only component of these foods responsible for the potential health benefits associated with their intake.
In this chapter, the benefits of Oleic acid and MUFAs have been described because the scientific studies were designed to assess the relationship between OA as a MUFA and the prevention or progression of diabetes and its complications.
Currently, there is no evidence related to the role of Oleic acid or MUFAs in the prevention of type 1 diabetes mellitus (T1DM); this lack of data may be due to the limited interest up to now in the involvement of this nutrient in the pathogenesis of the autoimmune process that leads to the development of T1DM.
Correspondingly, few studies have examined the consumption of Oleic Acid and monounsaturated fatty acids (MUFAs) with the development of diabetic complications in T1DM (Table 1). Therefore, this chapter focuses on the evidence related to the intake of OA and MUFAs in type 2 diabetes mellitus (T2DM).
Oleic acid (cis-9 C18:1), the second predominant fatty acid in sheep milk fat, is regarded as an antiatherogenic agent.
Human diets high in oleic acid are mostly reported to decrease the level of low-density lipoprotein (LDL) cholesterol, whereas high-density lipoprotein (HDL) cholesterol levels are not affected notably. The PUFAs in sheep milk fat mainly comprise linoleic (cis-9 cis-12 C18:2) and α-linolenic (cis-9 cis-12, cis-15 C18:3) and smaller amounts of their positional and geometric isomers.
Both are the essential fatty acids and they have many diverse functions in human metabolism and they promote an antiatherogenic effect.
Sheep milk is not a rich source of linoleic and α-linolenic acids.
However, other omega-3 PUFAs are hardly found in sheep milk fat, except when animal diets are supplemented with marine oil source.
Oleic acid is a fatty acid – an organic acid with a long chain of 17 carbon atoms before ending in a carboxyl group.
One of the reasons that olive oil tends to be regarded as relatively healthy is that this is an unsaturated fatty acid – there are one or more double bonds between the carbons in the chain. In oleic acid there is just one double bond, making it monounsaturated.
Specifically, it is an omega-9 fatty acid, indicating that the double bond is positioned at the ninth carbon atom from the opposite end of the chain to the carboxyl group.
The Health Benefits of Oleic Acid
Oleic acid has many beneficial effects and is a healthy fat that deserves a place in your diet. Here are some of the benefits of oleic acid you should know.
#1: Oleic Acid Supports Cellular Health
Oleic acid has been found to have beneficial effects in cancer research.
A study conducted by the University of Edinburgh found that the monounsaturated fatty acid encourages the synthesis of a cell molecule (miR-7) that supports a reduction in cancer-causing proteins from developing.
Oleic acid could play a role in intracellular signalling pathways that are involved in cancer cell development.
A Spanish study found that this monounsaturated fatty acid helps induce cell death in cancer cells[*][*].
#2: Oleic Acid May Enhance Brain Function
Studies show that there is an inverse relationship between cognitive decline and the intake of healthy monounsaturated fats.
One study found that in older people with a Mediterranean diet, high consumption of monounsaturated fats offered protection against cognitive decline.
Scientists involved in the study concluded that these good fats may help treat Alzheimer’s disease[*].
#3: Oleic Acid May Benefit Those with Type 2 Diabetes
People with type 2 diabetes may benefit from adding oleic acid to their diet.
According to research, oleic acid has beneficial effects on type 2 diabetes and insulin sensitivity.
These beneficial effects are due to the potential anti-inflammatory properties of oleic acid and its ability to inhibit the attenuation of the insulin signaling pathway. This could potentially suggest that the intake of oleic acid can help control the amount of insulin released to increase glucose uptake from the blood[*].
#4: Diets Rich in Fatty Acids Support Weight Management
According to a pilot study, when compared to a normal lower-fat diet, a diet rich in olive oil (a source of oleic acid) led to increased weight loss in women with breast cancer.
In the study, about 80% of women who consumed a diet rich in olive oil (about three tablespoons of oil each day) experienced a weight loss of 5%. The diet also reduced triglycerides and increased high-density lipoprotein cholesterol levels[*].
Score for ketogenic and paleo diet enthusiasts everywhere!
#5: Oleic Acid May Support Heart Health
Many research studies have found that olive oil (again, a source of oleic acid) may support reductions in blood pressure and enhanced cardiovascular health in subjects.
Olive oil contains approximately 80% oleic acid, and scientists have found that the monounsaturated acid itself is responsible for the hypotensive effect of olive oil.
Consumption of olive oil and other foods rich in omega-9 fatty acids increases levels of oleic acid in membranes. The fatty acid alters the structure of the membrane and its physical properties and controls cell signaling, which leads to a decrease in blood pressure.
The research concludes that consuming olive oil decreases blood pressure because of the physical properties of oleic acid[*][*][*].
Top Oleic Acid Food Sources
The top oleic acid foods are usually found in quality fats such as oils. While the whole version of the food is typically a source of oleic acid as well, the oils provide a higher concentration of the omega-9 fatty acid, so you get the most benefit from those.
#1: Macadamia Oil
Macadamia oil is a rich source of oleic acid and other quality fats. Its fatty acid composition makes it truly unique.
Macadamia oil contains about:
60% oleic acid
19% palmitoleic acid
1-2% alpha-linolenic acid (ALA)
Many studies show that macadamia oil can support improved skin appearance[*], weight loss[*], heart health[*] and insulin sensitivity[*]. And that just scratches the surface!
#2: Olive Oil
Olive oil is also an excellent source of oleic acid[*] and is obtained from the olive fruit.
Some of the fatty acids in olive oil include:
Linolenic acid
Stearic acid
Oleic acid
Palmitoleic acid
Palmitic acids[*]
Consuming one or two tablespoons of olive oil daily is sufficient to get adequate amounts of oleic acid[*]. Luckily, olive oil is the perfect type of oil to cook with!
#3: Eggs
Eggs are a source of monounsaturated fatty acids (MUFA) that are considered one of the highest quality animal products commonly found in the American diet.
Oleic acid is the major fatty acid found in eggs (42-45%[*] and is found in the yolk of the egg.
Eggs are also an excellent source of protein, omega-3 fatty acids, vitamins D and A, and vitamin B-6.
Another reason to add eggs to your diet!
#4: Cheese
Cheese is a known source of oleic acid, as well as other beneficial fats and proteins, such as linoleic acid and others.
In fact, research suggests that “Grazing dairy cows produce milk with high levels of unsaturated fatty acids and conjugated linoleic acid, which are able to reduce cardiovascular diseases and have some anticancer properties[*].”
Choose cheese from pasture-raised, grass-fed cows that are raised ethically without any added hormones or antibiotics to score the best quality nutritional profile[*].
#5: Sunflower Oil
High oleic sunflower oil contains high amounts of oleic acid (about 80%).
This neutral-tasting oil has several uses including spray coating oils for dried fruits, crackers, and cereal.
Sunflower oil is a vegetable oil, however, and doesn’t withstand heat very well. This is not your healthiest source of oleic acid.
Other Food Sources
Poultry, and other meats are also good sources of oleic acid.
You can find this monounsaturated fatty acid in a wide range of foods, such as yeast bread, dairy desserts, salad dressing, potato chips, burgers, pizza, nuts, and grain-based desserts[*].
That’s because these foods often contain high-oleic acid foods, such as cheese (pizza, burgers), milk and eggs (desserts), and oils (chips, salad dressing).
Oleic acid is an omega-9 fatty acid that packs some impressive health benefits.
IUPAC Name
(9Z)-octadec-9-enoic acid
Synonyms
(9Z)-Octadecenoic acid
(Z)-Octadec-9-enoic acid
18:1 n-9
18:1Δ9cis
C18:1 n-9
cis-9-octadecenoic acid
cis-Δ9-octadecenoic acid
cis-oleic acid
FA 18:1 ChEBI
Octadec-9-enoic acid
Oelsäure Deutsch
Oleate
Oleic acid
OLEIC ACID
Ölsäure Deutsch
Absorption
Fatty acid uptake by different tissues may be mediated via passive diffusion to facilitated diffusion or a combination of both.
Fatty acids taken up by tissues are then stored in the form of triglycerides or oxidized 2. Oleic acid was shown to penetrate rat skin .
Following oral administration of Brucea javanica oil emulsion in rats, the time of oleic acid to reach peak plasma concentration was approximately 15.6 hours
Volume of distribution
Radio-labelled oleic acid was detected in the heart, liver, lung, spleen, kidney, muscle, intestine, adrenal, blood, and lymph, and adipose, mucosal, and dental tissues.
Oleic acid is primarily transported via the lymphatic system 2.
Protein binding
As with other fatty acids originating from adipose tissue stores, oleic acid may bind to serum albumin or remain unesterified in the blood.
Metabolism
Like most fatty acids, oleic acid may undergo oxidation via beta-oxidation and tricarboxylic acid cycle pathways of catabolism, where an additional isomerization reaction is required for the complete catabolism of oleic acid.
Via a series of elongation and desaturation steps, oleic acid may be converted into longer chain eicosatrienoic and nervonic acid.
Route of elimination
Following oral administration of trace amounts of oleic acid, less than 10% of total oleic acid was found to be eliminated via fecal excretion.
This compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
Oleic acid [NF] [Wiki]
(9Z)- Octadecenoic acid
(9Z)-9-Octadecenoic acid [ACD/IUPAC Name]
(9Z)-9-Octadecensäure [German] [ACD/IUPAC Name]
(9Z)-Octadec-9-enoic acid
(9Z)-Octadecenoic acid
(Z)-9-Octadecanoic acid
(Z)-9-Octadecenoic Acid
(Z)-Octadec-9-enoic acid
(Z)-Octadeca-9-enoic acid
112-80-1 [RN]
1726542 [Beilstein]
205-591-0 [EINECS]
9-(Z)-octadecenoic acid
9-cis-Octadecenoic acid
9-Octadecenoic acid [ACD/IUPAC Name]
9-Octadecenoic acid (9Z)-
9-Octadecenoic acid (Z)-
9-Octadecenoic acid, (9Z)- [ACD/Index Name]
9-Octadecenoic acid, (Z)-
9-Octadecenoic acid, cis-
9Z-Octadecenoic acid
Acide (9Z)-9-octadécénoïque [French] [ACD/IUPAC Name]
Acide oleique [French]
cis-9-Octadecanoic acid
cis-9-Octadecenoic acid
cis-Octadec-9-enoic acid
cis-Oleic acid
EUNATROL
MFCD00064242 [MDL number]
Oleoyl alcohol
osteum
Z-9-Octadecenoic acid
Distoline
Industrene 104
Pamolyn 125
(9Z)octadec-9-enoic acid
(9Z)-oleic acid
(Z)-9-Octadecanoate
112-79-8 [RN]
1190712-11-8 secondary RN [RN]
1190965-71-9 secondary RN [RN]
17156-84-2 secondary RN [RN]
223487-44-3 [RN]
4-02-00-01641 [Beilstein]
56833-51-3 secondary RN [RN]
8046-01-3 secondary RN [RN]
9-octadecylenic acid
cis-9-Octadecenoic Acid, 18:1
cis-9-octadecenoicacid
cis-δ(9)-octadecenoic acid
cis-δ(sup 9)-Octadecenoic acid
cis-δ(sup 9)-Octadecenoic acid
cis-δ9-octadecenoic acid
cis-δ9-Octadecenoic acid
Edenor ATiO5
Elaidic Acid [Wiki]
Emersol 205
Glycon RO
Glycon WO
Groco 2
Groco 4
Groco 5L
Groco 6
http://www.hmdb.ca/metabolites/HMDB0000207
http://www.hmdb.ca/metabolites/HMDB0000573
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16196
Industrene 105
Industrene 205
Industrene 206
l’Acide oleique [French]
Lunac OA
Lunac O-CA
Lunac O-LL
Lunac O-P
Metaupon
neo-Fat 90-04
Neo-Fat 92-04
octadec-9-enoic acid
Octadecenoic Acid, 9-Octadecenoic Acid
Oelsaeure
Oelsauere
Oleat
Oleic Acid – CAS 112-80-1 – Calbiochem
Oleic acid, 70%
Oleic acid, 85%
oleic acid, from sunflower
Oleic Acid-d17
oleic acid-药用级
oleic acid
Oleinic acid
OmniPur Oleic Acid
Pamolyn
Pamolyn 100
QV8U9-C [WLN]
Red oil
Tego-oleic 130
Vopcolene 27
Wecoline OO
Wecoline OO (VAN)
Wochem No. 320
δ9-cis-Octadecenoic acid
δ9-cis-Oleic acid
δ9-cis-Oleic acid
Stereoisomers:
9-Octadecenoic acid, (E)-
9-Octadecenoic acid
Other names: 9-Octadecenoic acid (Z)-; Δ9-cis-Oleic acid; cis-Oleic Acid; cis-9-Octadecenoic Acid; Emersol 211; Emersol 220 White Oleic Acid; Emersol 221 Low Titer White Oleic Acid; Oelsauere; Oleine 7503; Pamolyn 100; Vopcolene 27; Wecoline OO; Z-9-Octadecenoic acid; cis-Octadec-9-enoic acid; cis-Δ9-octadecenoic acid; cis-Δ9-Octadecenoate; neo-Fat 90-04; neo-Fat 92-04; Century cd fatty acid; Elaidoic acid; Emersol 210; Emersol 213; Emersol 6321; Glycon RO; Glycon WO; Groco 2; Groco 4; Groco 5l; Groco 6; Hy-phi 1055; Hy-phi 1088; Hy-phi 2066; Hy-phi 2088; Hy-phi 2102; K 52; L’Acide oleique; Metaupon; Tego-oleic 130; 9-Octadecenoic acid, cis-; Elaic acid; Industrene 105; Industrene 205; Industrene 206; Oleinic acid; Pamolyn; Wochem no. 320; (Z)-9-Octadecanoic acid; Emersol 6313 NF; Priolene 6906; 9-(Z)-octadecenoic acid; (Z)-Octadec-9-enoic acid; 9-Octadecenoic acid (9Z)-; D 100; Emersol 205; Extraolein 90
IUPAC names
(9Z)-Octadec-9-enoic acid
(9Z)-octadec-9-enoic acid
(Z)-octadec-9-enoic acid
9-Octadecanoic acid
9-Octadecenoic acid (9Z)-
9-Octadecenoic acid, (Z)-
C18H34O2
cis-9-octadecenoic acid
kyselina olejová
octadec-9-enoic acid
Octadecanoic acid
octadecanoic acid
Olajsav
OLEIC ACID
Oleic Acid
Oleic acid
oleic acid
Other names
9-Octadecenoic acid (9Z)-
Oleic acid
Oleic acid is a naturally occurring, odorless, colorless oil.
Oleic acid is found in flaxseed oil, borage (a Mediterranean herb) oil, evening primrose oil, olive oil (less in virgin olive oil), pecan oil, canola oil, peanut oil, macadamia oil, sunflower oil, grape seed oil, sea buckthorn oil and sesame oil.
You can also find it in animal fat.
Oleic acid at appropriate levels has been implicated in cancer prevention in some (but not all studies), and reduces cholesterol levels.
However, this does not mean that everyone should deliberately consume excessive olive oil.
Scientists have found that oleic acid in excess blocks the body from using linoleic acid, another important fatty acid.
This is a great example of too much of a good thing! Another major issue is that too much oleic acid can cause lipid accumulation in the liver — or fatty liver.
In fact, scientists use oleic acid to create fatty liver simulations in the lab, then test antioxidants with the cells to see which ones can reverse the disease.
Oleic Acid, a monounsaturated fatty acid originally derived from Olea europaea, has been shown to be an anti-proliferative agent. This compound has also been reported to promote neuronal differentiation in murine cell cultures. Mechanistic studies suggest that these Oleic Acid effects are mediated by PPARβ. Furthermore, Oleic Acid has demonstrated the ability to stimulate an increase in secretion of collagen I, TGF-β secretion, and extracellular signal-regulated kinase1/2. Oleic Acid is an activator of PKC and CaMKII.
Super Refined Oleic Acid is a highly purified oleic acid suitable for use in topical, oral and nasal dose applications. It acts as a solubiliser, emulsifying agent and transdermal penetration enhancer and can be used in Self Emulsifying Drug Delivery Systems (SEDDS) to improve the bioavailability of poorly water soluble drugs. The proprietary Super Refining process removes impurities without altering the chemical composition of the excipient. This reduces the potential for adverse interactions between the excipient and the API, enhancing active stability and efficacy. Super Refined Oleic Acid demonstrates improved oxidative stability and reduced irritation potential compared to standard pharmaceutical oleic acid. Please download the product overview sheet for more details.
Pharmacopoeia Compliance
FDA-IID Listed
JP
PhEur
USP/NF
Oleic acid is a monounsaturated fatty acid and a major component of membrane phospholipids that has been found in human plasma, cell membranes, and adipose tissue
(9Z)-9-Octadecenoate
(9Z)-9-Octadecenoic acid
(9Z)-Octadecenoate
(9Z)-Octadecenoic acid
(Z)-9-Octadecanoate
(Z)-9-Octadecanoic acid
(Z)-9-octadecenoic acid, ion(1-)
(Z)-Octadec-9-enoate
(Z)-Octadec-9-enoic acid
9-(Z)-octadecenoate
9-(Z)-octadecenoic acid
9-Octadecenoate
9-Octadecenoic acid
9,10-Octadecenoate
9,10-Octadecenoic acid
Century cd fatty acid
cis-9-Octadecenoate
cis-9-Octadecenoic acid
cis-Octadec-9-enoate
cis-Octadec-9-enoic acid
cis-Oleate
cis-Oleic acid
Distoline
Elaate
Elaic acid
Elaidoate
Elaidoic acid
Ethyl linoleate (JAN)
L’acide oleique
Metaupon
Oelsauere
Oleat
Oleate
Oleic acid
oleic acid anion
oleic acid extra pure
Oleinate
Oleinic acid
Red oil
Z-9-Octadecenoate
Z-9-Octadecenoic acid
18:1 N-9
18:1DElta9cis
C18:1 N-9
cis-Delta(9)-Octadecenoic acid
FA 18:1
Octadec-9-enoic acid
Oelsaeure
cis-delta(9)-Octadecenoate
cis-Δ(9)-octadecenoate
cis-Δ(9)-octadecenoic acid
Octadec-9-enoate
Emersol 210
Emersol 211
Emersol 213
Emersol 220 white oleate
Emersol 220 white oleic acid
Emersol 221 low titer white oleate
Emersol 221 low titer white oleic acid
Emersol 233LL
Emersol 6321
Emersol 6333 NF
Emersol 7021
Glycon ro
Glycon wo
Groco 2
Groco 4
Groco 5l
Groco 6
Industrene 104
Industrene 105
Industrene 205
Industrene 206
Pamolyn
Pamolyn 100
Pamolyn 100 FG
Pamolyn 100 FGK
Pamolyn 125
Priolene 6900
Tego-oleic 130
Vopcolene 27
Wecoline oo
Acid, 9-octadecenoic
Acid, oleic
9 Octadecenoic acid
Acid, cis-9-octadecenoic
cis 9 Octadecenoic acid
FA(18:1(9Z))
FA(18:1n9)
Applications/uses of Oleic Acid
Adhesives/sealants-B&C
Commerical printing inks
Paints & coatings
Polymer modification
Protective coatings
Key attributes
Excellent color stability
Exceptionally high purity
Low odor level & uniform fatty acid composition
Low saturated acids and unsaponifiables content
Water-white initial color
Oleic acid is a fatty acid. It is classified as a monounsaturated omega-9 fatty acid.
It is used in in the manufacture of soaps and detergents. It is an emulsifier and acts as an emollient.
Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It’s an odourless and colourless oil, although commercial samples may be yellowish.
Oleic acid is the most abundant of the unsaturated fatty acids in nature. It’s a monounsaturated omega-9 fatty acid found in various animal and vegetable sources. It’s been identified in various foods such as brown rice and beef. It’s a pale yellow or brownish yellow oily liquid with a lard-like odour, insoluble in water. It’s often used in the food industry to make synthetic butters and cheeses, and to flavour baked goods, sweets, ice cream and lemonade. It’s also used for cosmetics in the preparation of moisturisers and ointments.
Oleic acid, or Omega-9, is a pale yellow, oily liquid with a lard-like odor. It is also a monounsaturated fatty acid. Fatty acids are the main components of food fats, oils and fat deposits in animals and man. Besides the work they do inside the body, monounsaturated fats like oleic acid are less susceptible to spoilage than some other fats, which makes them useful in food preservation.
Sources
Oleic acid is widely distributed in nature. The highest sources of oleic acid are avocados, olive oil, table olives and canola oil. The second-best sources are beef tallow, peanut oil, lard and palm oil. Corn oil, butterfat, soybean oil and sunflower oil are fair sources of oleic acid.
Uses
If you have recently eaten any bakery product or used soap or skin cream, chances are you used oleic acid.
Foods prepared with oleic acid will remain safe to eat for longer periods, even without refrigeration.
Such foods include bakery goods such as breads, cakes and pies. Oleic acid is also used as a cleaning agent in the manufacturing of soaps and detergents and as an emollient, or softening agent, in creams, lotions, lipsticks and skin products.
Abstract
Purpose: Bacterial eye infections are routinely treated with topical antibiotics.
Antibiotics carry the risk of systemic side effects which are particularly serious in children. Increasing development of antibiotics resistance calls for testing compounds that are natural, safe and can help in combating antibiotic resistance. Oleic acid is one such compound that is found in skin lipids and tears lipids.
It is known to be effective against bacteria in skin infections.
The purpose of this study was to test efficacy of oleic acid as an antibacterial against bacteria common in ocular surface infections.
Methods: Antibacterial effects of oleic acid against ocular pathogenic bacteria (Staphylococcus aureus, Pseudomonas aeruginosa, Serratia marcescens, and Pseudomonas aeruginosa) were tested in Mueller-Hinton broth using broth dilution technique.
Bacterial cells were imaged using scanning electron microscopy to observe changes in cell morphology caused by oleic acid.
Results: Oleic acid inhibited growth of all bacterial isolates in a concentration-dependent manner.
Percentage growth inhibition with various concentrations of oleic acid varied among bacteria but all showed complete growth inhibition in the presence of 1% oleic acid.
Scanning electron microscopy showed morphological damages to bacterial cells in the presence of oleic acid.
Types of damages included cellular distortions, blebs, loss of cellular content and cell lysis.
Conclusions: Oleic acid is capable of preventing growth of various ocular pathogenic Gram negative and Gram positive bacteria.
It can provide antibacterial defence to tears and can be used to develop lipid based treatment options for eye infections helping in reducing antibiotics usage.
Oleic acid is the most common monounsaturated fatty acid in human cells.
Oleic acid is incorporated into cell membrane phospholipids, where it is important for proper membrane fluidity.
Hormone responsiveness, infectivity of pathogens, mineral transport and immune competence are affected by membrane fluidity.
Oleic acid is a major energy source for cells.
Oleic acid is catabolized to acetyl groups used for energy (ATP) production and biosynthesis of many essential metabolites.
Oleic acid is obtained by cells from endogenous biosynthesis or from serum triglycerides.
Biosynthesis of fatty acids (like oleic acid) utilizes the same enzymes responsible for elongation of other fatty acids which are precursors for eicosanoids (prostaglandins).
Thus, deficient oleic acid status may also indicate deficient eicosanoid production, signifying a need for essential fatty acids.
Deficiency Symptoms: No deficiency symptoms are clearly defined for oleic acid since a dietary intake is not absolutely essential. Monounsaturated fat intake may be beneficial for reducing high blood cholesterol levels.
A need for oleic acid may possibly reflect a need for essential fatty acids (linoleic acid) or omega-3 fatty acids (alpha linolenic acid, EPA and DHA).
Repletion Information: Dietary sources rich in oleic acid include: Canola Oil Olive Oil Avocado Oil Almond Oil Avocados High Oleic Safflower Oil Although some margarines and shortenings are high in monounsaturated fats, a considerable amount is in the form of trans-monosaturated isomers (elaidic acid).
Reductions in these foods are recommended to improve oleic acid status
Oleic acid is a monounsaturated fatty acid and natural constituent of a number of foods, particularly vegetable oils.
On the basis of proven beneficial health effects, it is also a possible ingredient in processed functional foods.
However, due to its high energy content it is not recommended to increase the consumption of any particular fat, but to substitute other lipids with oleic acid.
While there is a well-established consensus that replacing saturated fats in the diet with oleic acid or other unsaturated fats contributes to the maintenance of normal blood cholesterol levels, a series of other effects has also been studied, including the modulation of inflammatory markers, blood pressure, insulin sensitivity, gastrointestinal functions and even various cancers.
Oleic acid is used as an emulsifying agent for facial creams and lotions, as an accelerator in the rubber industry, as an emollient, as a solubilizing agent in aerosol products and as a soldering flux in stained glass work for joining lead came. It is used in the preparation of oleates and lotions. It acts as intermediate for drilling and fracking fluids in the oil and gas industry. It finds application as an excipient in pharmaceuticals.
FATTY ACIDS
Please note that we are dealing here with fatty acids forming part of the triacylglycerol molecule. We will address the free fatty acids in the next section. The fatty acid composition of olive oil varies widely depending on the cultivar, maturity of the fruit, altitude, climate, and several other factors.
A fatty acid has the general formula: CH3(CH2)nCOOH where n is typically an even number between 12 and 22.
If no double bonds are present the molecule is called a saturated fatty acid.
If a chain contains double bonds, it is called an unsaturated fatty acid.
A single double bond makes a monounsaturated fatty acid.
More than one double bond makes a polyunsaturated fatty acid.
The major fatty acids in olive oil triacylglycerols are:
Oleic Acid (C18:1), a monounsaturated omega-9 fatty acid. It makes up 55 to 83% of olive oil.
Linoleic Acid (C18:2), a polyunsaturated omega-6 fatty acid that makes up about 3.5 to 21% of olive oil.
Palmitic Acid (C16:0), a saturated fatty acid that makes up 7.5 to 20% of olive oil.
Stearic Acid (C18:0), a saturated fatty acid that makes up 0.5 to 5% of olive oil.
Linolenic Acid (C18:3)(specifically alpha-Linolenic Acid), a polyunsaturated omega-3 fatty acid that makes up 0 to 1.5% of olive oil.
Triacylglycerols are normally composed of a mixture of three fatty acids. Most prevalent in olive oil is the oleic-oleic-oleic (OOO) triacylglycerol, followed, in order of incidence, by palmitic-oleic-oleic (POO), then oleic-oleic-linoleic (OOL), then palmitic-oleic-linoleic (POL), then stearic-oleic-oleic (SOO), and so on.
Olive oil contains more oleic acid and less linoleic and linolenic acids than other vegetable oils, that is, more monounsaturated than polyunsaturated fatty acids. This renders olive oil more resistant to oxidation because generally, the greater the number of double bonds in the fatty acid, the more unstable and easily broken down by heat, light, and other factors the oil is. It is generally accepted that cooler regions (e.g. Tuscany) will yield oil with higher oleic acid than warmer climates. That is, a cool region olive oil may be more monounsaturated in content than a warm region oil.
Trans Fatty Acids
Note that olive oil has no trans fatty acids. When oil is partially hydrogenated, it can be in the “cis” or “trans” conformation; this refers to which side of the fatty acid double bond the hydrogen is on. Olive oil is not a trans fatty acid because it has not been partially hydrogenated in a factory to make it solid at room temperature like margarine has.
Long Chain Fatty Acids
Long chain fatty acids have from 12 to 20 carbon atoms.
The primary fatty acids in olive oil are all long chain fatty acids. Very long-chain fatty acids have greater than 20 carbon atoms. These tend to be more solid at room temperature, such as waxes. There are not appreciable amounts of these in olive oil.
Percentage of Linolenic Acid Allowed in Olive Oil
Regarding the polyunsaturated fatty acids (PUFAs), there is a wide range acceptable for extra virgin olive oil, however the linolenic acid has to be less than 0.9% per the International Olive Oil Council (IOOC) guidelines. Higher levels, e.g. 1.5%, do not present a nutritional problem, but the IOOC uses the linolenic acid level to establish the authenticity of the olive oil. Seed oils like canola oil have higher levels of linolenic acid.
“Essential” Fatty Acids
In scientific writing the term essential fatty acid refers to all the omega-3 or omega-6 fatty acids. This is a historical convention, not a medical definition. From a medical point of view, essential fatty acids are the ones that the human body cannot make. There are only two, which are the building blocks from which many of the other omega-3 and omega-6 fatty acids are made in a healthy body: linoleic acid and alpha-linolenic acid.
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FREE FATTY ACIDS (FFA) AND ACIDITY
The “acidity” in olive oil is the result of the degree of breakdown of the triacylglycerols, due to a chemical reaction called hydrolysis or lipolysis, in which free fatty acids are formed. (In exceptional circumstances, even oils made from fresh, healthy olives can have significant amounts of acidity, caused by anomalies during the actual biosynthesis of the oil in the olive fruit). Oil extracted carelessly and/or from poor quality fruit suffers from a very significant breakdown of the triacylglycerides into fatty acids. These “broken off” fatty acids are called Free Fatty Acids. Sometimes just one of the three fatty acids breaks off, leaving a diacylglycerol. If two fatty acids break off, we are left with a monoacylglycerol. If all three break off, were are left with glycerol.
Factors which lead to a high free fatty acidity in an oil include fruit fly infestation, delays between harvesting and extraction (especially if the fruit has been bruised or damaged during harvesting), fungal diseases in the fruit (gloesporium, macrophoma, etc.), prolonged contact between oil and vegetation water (after extraction), and careless extraction methods. Storing olives in heaps or silos to encourage enzymatic breakdown of cell structure, and thus facilitate oil release (as is the tradition in Portugal and other countries) is certainly not conducive to producing a high quality, low acidity oil.
The free fatty acidity is thus a direct measure of the quality of the oil, and reflects the care taken right from blossoming and fruit set to the eventual sale and consumption of the oil.
Measurement of free fatty acidity is a very simple procedure which can done at a testing lab.
The results are presented as grams of oleic acid per 100 grams oil, commonly known as the free fatty acidity of the oil in percent. Freshly pressed oil, made carefully, without the use of excessive heat, from sound, healthy, freshly picked olives, normally has a pretty low “acidity”, well under 0.5% FFA.
Extra virgin olive oils have less than 0.8% FFA.
Olive oil is at least 85% unsaturated fats. It’s composed mostly of monounsaturated fats that include Oleic acid: (70.0%) and Palmitoleic acid: (0.3 – 3.5%) and polyunsaturated that are Linoleic acid: 15.0% and α‑Linolenic acid: 0.5%.
Reactivity Profile
OLEIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them.
They react in this way with all bases, both organic (for example, the amines) and inorganic.
Their reactions with bases, called “neutralizations”, are accompanied by the evolution of substantial amounts of heat.
Neutralization between an acid and a base produces water plus a salt.
Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water.
Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions.
The pH of solutions of carboxylic acids is therefore less than 7.0.
Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt.
Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt.
Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry.
Even “insoluble” carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers.
Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide.
The reaction is slower for dry, solid carboxylic acids.
Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide.
Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides.
Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat.
Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents.
These reactions generate heat.
A wide variety of products is possible.
Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
CENTURY CD FATTY ACID
CIS-8-HEPTADECYLENECARBOXYLIC ACID
CIS-9-OCTADECANOIC ACID
CIS-9-OCTADECENOIC ACID
CIS-DELTA(SUP 9)-OCTADECANOIC ACID
CIS-DELTA9-OCTADECENOIC ACID
CIS-OCTADEC-9-ENOIC ACID
9-CIS-OCTADECENOIC ACID
CIS-OLEIC ACID
DELTA9-CIS-OCTADECENOIC ACID
DELTA9-CIS-OLEIC ACID
EDENOR ATIO5
EDENOR FTIO5
EMERSOL 205
EMERSOL 210
EMERSOL 211
EMERSOL 213
EMERSOL 213NF
EMERSOL 214NF
EMERSOL 220 WHITE OLEIC ACID
EMERSOL 221 LOW TITER WHITE OLEIC ACID
EMERSOL 233LL
EMERSOL 6313NF
EMERSOL 6321
EXTRA OLEIC 80R
EXTRA OLEIC 90
EXTRA OLEIC 99
EXTRA OLEIN 80
EXTRA OLEIN 90R
EXTRAOLEIN 90
GLYCON RO
GLYCON WO
GROCO 2
GROCO 4
GROCO 5L
GROCO 6
HY-PHI 1055
HY-PHI 1088
HY-PHI 2066
HY-PHI 2088
HY-PHI 2102
INDUSTRENE 105
INDUSTRENE 106
K 52
LUNAC O-CA
LUNAC O-LL
LUNAC O-P
METAUPON
NAA 34
NAA 35
NEO-FAT 90-04
NEO-FAT 92-04
9,10-OCTADECANOIC ACID
9-OCTADECENOIC ACID (Z)-
9-OCTADECENOIC ACID, (Z)-
OLEIC ACID
OLEINE 7503
PAMOLYN 100
PRIOLENE 6907
PRIOLENE 6930
RED OIL
TEGO-OLEIC 130
VOPCOLENE 27
WECOLINE OO
(Z)-9-OCTADECANOIC ACID
Z-9-OCTADECENOIC ACID
Oleic acid also called cis‐9‐Octadecenoic acid, is a monounsaturated omega-9 fatty acid (MUFA) that is the most widely distributed and abundant fatty acid in nature.
Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils.
Oleic acid is a constituent of tall oil and present in fruits.
Oleic acid is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent 1). Oleic acid is an odorless, colorless oil, although commercial samples may be yellowish. Oleic acid has the molecular formula C18H34O2.
The term “oleic” means related to, or derived from, oil or olive, the oil that is predominantly composed of oleic acid.
Oleic acid biological source: oleic acid major constituent of plant oils e. g. olive oil (about 80%), almond oil (about 80%) and many others, mainly as glyceride.
Oleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.