ETHYL OLEATE
ETHYL OLEATE
Molecular Formula: C20H38O2
CAS Number: 111-62-6
Molecular Weight: 310.51
Ethyl oleate is the ester formed by the condensation of the fatty acid oleic acid and ethanol.
Ethyl oleate is a colorless to light yellow liquid.
Ethyl oleate is produced by the body during ethanol intoxication.
Ethyl Oleate, NF is used as a solubilizing agent in pharmaceutical preparations.
Ethyl Oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol.
Ethyl oleate is the liquid lipid component in nanostructured lipid carriers (NLCs).
NLC is a promising vehicle for oral trans-Ferulic acid (TFA) administration.
Use and occurrence of Ethyl oleate:
Additive:
Ethyl oleate is used by compounding pharmacies as a vehicle for intramuscular drug delivery, in some cases to prepare the daily doses of progesterone in support of pregnancy.
Studies that document the safe use of ethyl oleate in pregnancy for both the mother and the fetus have never been performed.
Ethyl oleate is regulated as a food additive in the U.S. by the Food and Drug Administration.
Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.
Ethyl oleate also finds use as a lubricant and a plasticizer.
Louis Bouveault used ethyl oleate to demonstrate Bouveault–Blanc reduction, producing oleyl alcohol and ethanol, a method which was subsequently refined and published in Organic Syntheses.
Occurrence of Ethyl oleate:
Ethyl oleate has been identified as a primer pheromone in honeybees.
Precursor to other chemicals:
By the process of ethenolysis, the methyl ester of oleic 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
Medical aspects:
Ethyl oleate is produced by the body during ethanol intoxication.
Ethyl oleate is one of the fatty acid ethyl esters (FAEE) produced after ingestion of ethanol.
Some research literature implicates FAEEs such as ethyl oleate as the toxic mediators of ethanol in the body (pancreas, liver, heart, and brain).
Ethyl oleate may be the toxic mediator of alcohol in fetal alcohol syndrome.
The oral ingestion of ethyl oleate has been carefully studied and due to rapid degradation in the digestive tract it appears safe for oral ingestion.
Ethyl oleate was used to prepare the oily phase of self-microemulsifying drug delivery system (SMEDDS) for tacrolimus (Tac).
Ethyl oleate can be used as a starting material to synthesize stearic acid hydrazide intermediate, which can undergo intermolecular cyclization reaction with various aliphatic acids and aromatic acids to yield 1,3,4-oxadiazole derivatives.
Ethyl oleate is also reduced to oleyl alcohol via Bouveault−Blanc reduction reaction.
Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.
Ethyl oleate also finds use as a lubricant and a plasticizer.
Ethyl oleate has been identified as a primer pheromone in honeybees.
Ethyl oleate is one of the fatty acid ethyl esters (FAEE) that is formed in the body after ingestion of ethanol.
There is a growing body of research literature that implicates FAEEs such as ethyl oleate as the toxic mediators of ethanol in the body (pancreas, liver, heart, and brain).
Among the speculations is that ethyl oleate may be the toxic mediator of alcohol in Fetal Alcohol Syndrome.
The oral ingestion of ethyl oleate has been carefully studied and due to rapid degradation in the digestive tract it appears safe for oral ingestion.
Ethyl oleate is not currently approved by the FDA for any injectable use.
However, Ethyl oleate is used by compounding pharmacies as a vehicle for intramuscular drug delivery, in some cases to prepare the daily doses of progesterone in support of pregnancy.
Studies which document the safe use of ethyl oleate in pregnancy for both the mother and the fetus have never been performed.
DESCRIPTION of Ethyl oleate:
Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol.
Ethyl oleate is a colorless to light yellow liquid.
Ethyl oleate is produced by the body during ethanol intoxication.
APPLICATION of Ethyl oleate:
E 1625 (OTTO) Ethyl oleate, 99% Cas 111-62-6 – used to prepare the oily phase of self-microemulsifying drug delivery system (SMEDDS) for tacrolimus (Tac).
Overview:
Ethyl oleate is a colourless liquid that is normally formed by condensing ethanol and oleic acid.
Notably, the compound is normally produced by the body during intoxication of ethanol.
Ethyl oleates other names are 9-Octadecenoic acid (Z)-, Ethyl cis-9-octadecenoate, (Z)-9-Octadecenoic acid ethyl ester, and Oleic acid, ethyl ester.
The compound contributed to approximately 17% of the total fatty acids esterified to phosphatidylcholine in porcine platelets.
Ethyl oleate is neutral and is a more lipid-soluble form of oleic acid.
The compound is one of the fatty acid ethyl esters that is generated after the breakdown of ethanol in the body.
Moreover, ethyl oleate usually acts as a toxic mediator of ethanol in the heart, liver, pancreas, and brain.
Uses of Ethyl oleate:
Pharmaceutical Industry
Ethyl oleate is utilized as an ingredient for the preparations of pharmaceutical drugs that involves lipophilic substances such as steroids.
Due to Ethyl oleates quick degradation of the digestive system, ethyl oleate is employed as a way for intramuscular drug delivery by compounding pharmacies.
In some cases, Ethyl oleate is used in the preparation of day-to-day doses of progesterone in the sustenance of pregnancy.
Transport Industry of Ethyl oleate:
Ethyl oleate is used in the transport industry as a lubricant and as a plasticiser.
Ethyl oleate is also used as a planting agent and for treating surfaces.
Ethyl oleate and Food Industry:
Ethyl oleate is used as a food additive and is regulated by the Food and Drug Administration.
Ethyl oleate is also used as a flavouring agent in food.
Description of Ethyl oleate:
Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol.
Ethyl oleate is a colorless to light yellow liquid. Ethyl oleate is produced by the body during ethanol intoxication.
Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.
Ethyl oleate also finds use as a lubricant and a plasticizer.
Ethyl oleate is regulated as a food additive by the Food and Drug Administration under “Food Additives Permitted for Direct Addition to Food for Human Consumption”.
Ethyl oleate has been identified as a primer pheromone in honeybees.
Ethyl oleate is one of the fatty acid ethyl esters (FAEE) that is formed in the body after ingestion of ethanol.
There is a growing body of research literature that implicates FAEEs such as ethyl oleate as the toxic mediators of ethanol in the body (pancreas, liver, heart, and brain).
Among the speculations is that ethyl oleate may be the toxic mediator of alcohol in fetal alcohol syndrome.
The oral ingestion of ethyl oleate has been carefully studied and due to rapid degradation in the digestive tract it appears safe for oral ingestion.
Ethyl oleate is not currently approved by the U.S. Food and Drug Administration for any injectable use.
However, Ethyl oleate is used by compounding pharmacies as a vehicle for intramuscular drug delivery, in some cases to prepare the daily doses of progesterone in support of pregnancy.
Studies which document the safe use of ethyl oleate in pregnancy for both the mother and the fetus have never been performed.
Chemical Properties of Ethyl oleate:
Ethyl oleate has a faint, floral note.
clear pale yellow oily liquid
Ethyl oleate occurs as a pale yellow to almost colorless, mobile, oily liquid with a taste resembling that of olive oil and a slight, but not rancid odor.
Ethyl oleate is described in the USP32–NF27 as consisting of esters of ethyl alcohol and high molecular weight fatty acids, principally oleic acid.
A suitable antioxidant may be included.
Uses of Ethyl oleate:
Ethyl oleate is a flavoring and fragrance agent.
Ethyl oleate was obtained by the hydrolysis of various animal and vegetable fats and oils.
Usually used to prepare the oily phase of self-microemulsifying drug delivery system (SMEDDS) for tacrolimus (Tac).
Production Methods of Ethyl oleate:
Ethyl oleate is prepared by the reaction of ethanol with oleoyl chloride in the presence of a suitable hydrogen chloride acceptor.
Definition of Ethyl oleate:
ChEBI: A long-chain fatty acid ethyl ester resulting from the formal condensation of the carboxy group of oleic acid with the hydroxy group of ethanol.
Preparation of Ethyl oleate:
By direct esterification of oleic acid with ethyl alcohol in the presence of HCl at the boil; in the presence of Twitchell’s reagent or chlorosulfonic acid.
Q: What is Ethyl oleate ?
Ethyl oleate falls under the category of Fine Chemicals and belongs to the Oleic Acid family having Molecular Weight 310.51 and Molecular Formula Molecular Formula : C20H38O2 .
Q: What is the CAS Number of Ethyl oleate ?
Ethyl oleate CAS Number is 111-62-6
Q: What are the applications of Ethyl oleate ?
Ethyl oleate was obtained by the hydrolysis of various animal and vegetable fats and oils.
Pharmaceutical Applications
Ethyl oleate is primarily used as a vehicle in certain parenteral preparations intended for intramuscular administration.
Ethyl oleate has also been used as a solvent for drugs formulated as biodegradable capsules for subdermal implantation) and in the preparation of microemulsions containing cyclosporinand norcantharidin.
Microemulsion formulations containing ethyl oleate have also been proposed for topical and ocular delivery, and for liver targeting following parenteral administration.
Ethyl oleate has been used in topical gel formulations, and in self-microemulsifying drug delivery systems for oral administration.
Ethyl oleate is a suitable solvent for steroids and other lipophilic drugs.
Ethyl oleates properties are similar to those of almond oil and peanut oil.
However, Ethyl oleate has the advantage that it is less viscous than fixed oils and is more rapidly absorbed by body tissues.
Ethyl oleate has also been evaluated as a vehicle for subcutaneous injection.
Assay: 98%
Appearance (Form): Liquid
Appearance (Colour): Clear pale yellow
Melting point: -32 °C(lit.)
Boiling point: 216-218 °C
Refractive index: n20/D 1.451(lit.)
Ethyl oleate CAS 111-62-6 is a fatty acid ester formed by the condensation of oleic acid and ethanol.
Ethyl oleate is a colorless to light yellow liquid. Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.
Ethyl oleate also finds use as a lubricant and a plasticizer.
Ethyl oleate is regulated as a food additive by the Food and Drug Administration.
Ethyl oleate has been identified as a primer pheromone in honeybees.
Purity / Analysis Method: >95.0%(GC)
Molecular Formula / Molecular Weight: C20H38O2 = 310.52
Physical State (20 deg.C): Liquid
Store Under Inert Gas: Store under inert gas
Condition to Avoid: Light Sensitive,Air Sensitive
CAS RN: 111-62-6
Reaxys Registry Number: 1727317
PubChem Substance ID: 87574147
Ethyl Oleate is a fatty acid formed by the condensation of oleic acid and ethanol.
Ethyl oleate is a colorless to light yellow or straw color liquid.
Ethyl Oleate used in many applications such as cosmetic, health, food, perfume, industrial, medical & beauty preparations.
Ethyl Oleate can function as solvent, glossing agent and emollient.
Ethyl oleate is used as a solvent for pharmaceutical preparations involving lipophilic substances.
Ethyl oleate also finds use as a lubricant and a plasticizer.
Ethyl oleate is used by compounding pharmacies as a vehicle for enhanced intramuscular compound delivery.
Description of Ethyl oleate:
Ethyl oleate, also known as ethyl oleic acid, belongs to the class of organic compounds known as fatty acid esters.
These are carboxylic ester derivatives of a fatty acid.
Based on a literature review a small amount of articles have been published on Ethyl oleate.
Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.
Ethyl oleate also finds use as a lubricant and a plasticizer.
CAS Number: 111-62-6
Molecular Weight: 310.51
Formula: C20H38O2
Density: 0.87 g/mL at 25 °C
CAS No.: 111-62-6
Storage: 2 years -20°C liquid
Smiles: CCCCCCCCC=CCCCCCCCC(=O)OCC
Ethyl Oleate is a colorless to light yellow liquid, fatty acid ester that occurs from the condensation of ethanol and oleic acid.
Ethyl oleate is most commonly used as a solvent for drug preparations of pharmaceutical nature that involve lipophilic substances.
Ethyl oleate is also used as a plasticizer and lubricant.
Ungraded products supplied by TCI America are generally suitable for common industrial uses or for research purposes but typically are not suitable for human consumption or therapeutic use.
Molecular Weight: 310.5
XLogP3-AA: 8
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 17
Exact Mass: 310.287180451
Monoisotopic Mass: 310.287180451
Topological Polar Surface Area: 26.3 Ų
Heavy Atom Count: 22
Complexity: 258
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Ethyl oleate is a fatty acid ester used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids.
In vivo studies have demonstrated that Ethyl oleate and other fatty acid esters are also rapidly hydrolyzed to ethanol and free fatty acid.
Ethyl oleate is one of the fatty acid ethyl esters (FAEE) that is formed in the body after ingestion of ethanol.
There is a growing body of research literature that implicates FAEEs such as ethyl oleate as the toxic mediators of ethanol in the body (pancreas, liver, heart, and brain).
Among the speculations is that ethyl oleate may be the toxic mediator of alcohol in fetal alcohol syndrome.
The oral ingestion of ethyl oleate has been carefully studied and due to rapid degradation in the digestive tract, it appears safe for oral ingestion.
Ethyl oleate is not currently approved by the U.S. Food and Drug Administration for any injectable use.
However, Ethyl oleate is used by compounding pharmacies as a vehicle for intramuscular drug delivery, in some cases to prepare the daily doses of progesterone in support of pregnancy.
Studies which document the safe use of ethyl oleate in pregnancy for both the mother and the fetus have never been performed.
biological source: palm oil
reg. compliance: FDA 21 CFR 117
assay: ≥85%
refractive index: n20/D 1.451 (lit.)
bp: 216-218 °C/15 mmHg
mp: −32 °C (lit.)
density: 0.87 g/mL at 25 °C (lit.)
Documentation: see Safety & Documentation for available documents
Organoleptic: waxy
application(s): flavors and fragrances
food allergen: no known allergens
SMILES string: CCCCCCCC\C=C/CCCCCCCC(=O)OCC
InChI: 1S/C20H38O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h11-12H,3-10,13-19H2,1-2H3/b12-11-
InChI key: LVGKNOAMLMIIKO-QXMHVHEDSA-N
Ethyl oleate has a high practical value in chemical, pharmaceutical and food industries.
To meet the market demand for high purity ethyl oleate, the preparation process of high purity ethyl oleate by urea inclusion of fatty acid ethyl esters from high oleic acid peanut oil was researched.
The effects of mass ratio of ethyl ester to urea, ratio of ethyl ester to 95% ethanol, reflux temperature, reflux time, crystallization temperature and crystallization time on the purity of ethyl oleate and yield of ethyl ester were studied.
The response surface methodology was employed to optimize the purity of ethyl oleate and yield of ethyl ester after inclusion.
The optimal preparation conditions were obtained as follows: mass ratio of ethyl ester to urea 1:1.2, ratio of ethyl ester to 95% ethanol 1:5, reflux temperature 50°C, reflux time 30 min, crystallization temperature 22°C, and crystallization time 1 h. Under these conditions, the purity of ethyl oleate was (90.82±0.04)% and its relative content was (90.82±0.04)%, and the yield of ethyl ester was (59.2±0.2)%.
Thus, the process had certain reference value for the industrial production of high purity (90% or more) ethyl oleate.
ETHYL OLEATE is classified as :
Emollient
Perfuming: 111-62-6
EINECS/ELINCS No: 203-889-5
COSING REF No: 76076
INN Name: ethyl oleate
Chem/IUPAC Name: Ethyl oleate
(9Z)-9-Octadécénoate d’éthyle [French] [ACD/IUPAC Name]
(Z)-9-Octadecenoic Acid Ethyl Ester
111-62-6 [RN]
203-889-5 [EINECS]
2450
9-Octadecenoic acid, ethyl ester, (9Z)- [ACD/Index Name]
9Z-octadecenoic acid, ethyl ester
Ethyl (9Z)-9-octadecenoate [ACD/IUPAC Name]
Ethyl (9Z)-octadec-9-enoate
Ethyl cis-9-octadecenoate
Ethyl oleate
Ethyl-(9Z)-9-octadecenoat [German] [ACD/IUPAC Name]
Ethylis oleas
MFCD00009579 [MDL number]
Oleic Acid ethyl ester
Oleic acid, ethyl ester
RG3715000
(9Z)-9-Octadecenoic acid ethyl ester
(Z)-octadec-9-enoic acid ethyl ester
[111-62-6]
85049-36-1 [RN]
9-Octadecenoic acid (Z)-, ethyl ester
CIS-9-OCTADECENYL ACETATE
D04090
Elhyl oleate
ethyl (9Z)octadec-9-enoate
ethyl (9Z)-octadecenoate
ethyl (Z)-octadec-9-enoate
ethyl oleate 95%
Ethyl oleate (NF)
ethyl oleate food grade
ethyl oleate(c18:1)
ethyl oleate, ??? 95.0%
ethyl oleate, 98%, mixture of homologeous fatty acid esters
ethyl oleate, tech. 70%
Ethyl oleate, USP grade
Ethyl Z-9-octadecenoate
ethyloleate
Jsp000872
oleic acid ethyl ester,98%
Oleic Acid ethyl ester|9Z-octadecenoic acid, ethyl ester
tech., 70%
Ethyl oleate
111-62-6
Ethyl cis-9-octadecenoate
ethyl (Z)-octadec-9-enoate
Oleic acid, ethyl ester
Oleic acid ethyl ester
9-Octadecenoic acid (Z)-, ethyl ester
Ethyl oleate [NF]
UNII-Z2Z439864Y
MFCD00009579
CHEBI:84940
(Z)-9-Octadecenoic acid ethyl ester
Ethyl oleate (NF)
Z2Z439864Y
ethyl octadec-9-enoate
9-Octadecenoic acid (9Z)-, ethyl ester
Ethyl Z-9-octadecenoate
ETHYLOLEATE
Ethyl oleate (natural)
Ethylis oleas
FEMA No. 2450
Ethyl 9-octadecenoate, (Z)-
Oleic acid ethyl
85049-36-1
Ethyl Oleate, NF
EINECS 203-889-5
NSC 229428
Ethyl oleate, 98%
AI3-00657
ethyl (9Z)-octadecenoate
SCHEMBL2797
DSSTox_CID_27633
DSSTox_RID_82464
DSSTox_GSID_47633
ethyl (9Z)octadec-9-enoate
ethyl (9Z)-octadec-9-enoate
CHEMBL2106289
DTXSID3047633
Ethyl (9Z)-9-octadecenoate #
Ethyl oleate, natural, >=85%
Ethyl oleate, analytical standard
HMS3650O15
HY-N7103
ZINC8214560
cis-9-Octadecenoic Acid ethyl ester
Tox21_303521
Ethyl oleate, technical grade, 70%
NSC229428
s5367
SBB060320
Oleic acid, ethyl ester (6CI,8CI)
AKOS025117011
CCG-267586
CS-W009922
NSC-229428
NCGC00257457-01
9-Octadecenoic acid, (Z)-, ethyl ester
AC-33783
CAS-111-62-6
Ethyl oleate, tested according to Ph.Eur.
O0054
O0143
Ethyl oleate, Vetec(TM) reagent grade, 98%
2539-EP2272537A2
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2539-EP2311837A1
2539-EP2314593A1
2539-EP2316470A2
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2539-EP2316831A1
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2539-EP2316834A1
2539-EP2316835A1
2539-EP2316836A1
2539-EP2374454A1
D04090
A894703
SR-01000946820
Q6578680
SR-01000946820-1
UNII-0962034MCM component LVGKNOAMLMIIKO-QXMHVHEDSA-N
UNII-2351QH8W1N component LVGKNOAMLMIIKO-QXMHVHEDSA-N
UNII-89IR26S11S component LVGKNOAMLMIIKO-QXMHVHEDSA-N
UNII-ANA2NCS6V1 component LVGKNOAMLMIIKO-QXMHVHEDSA-N
UNII-PY7890FR5M component LVGKNOAMLMIIKO-QXMHVHEDSA-N
Ethyl oleate, United States Pharmacopeia (USP) Reference Standard
9-Octadecenoic acid (Z)-, ethyl ester; Ethyl oleate, mixture of isomers;