ETHYL LINOLEATE
ETHYL LINOLEATE
CAS Number: 544-35-4
EC Number: 208-868-4
Molecular Weight: 308.5
Density: 0.876 g/mL at 25 °C (lit.)
Ethyl linoleate is reported to accelerate the healing of wounds & clinically proven to be an effective anti-acne agent.
Ethyl linoleate is also reported to correct follicular keratinization, reduce sebum production, lighten skin pigmentation, and provide anti-inflammatory benefits.
Ethyl linoleate is an unsaturated fatty acid used in many cosmetics for its various attributes, such as antibacterial and anti-inflammatory properties and clinically proven to be an effective anti-acne agent.
Ethyl linoleate may be used as a reference material in assays that quantify fatty acid ethyl esters (FAEEs) for detection of alcohol abuse.
Linoleic acid ethyl ester (Ethyl linoleate) may be used and studied as an acetylcholinesterase (AChE) inhibitor.
Ethyl linoleate solated from Oxalis triangularis inhibits forskolin-induced melanogenesis and tyrosinase activity in mouse B16 melanoma cells .
This anti-melanogenic effect is mediated by inhibiting cAMP production.
Ethyl linoleate is a long-chain fatty acid ethyl ester resulting from the formal condensation of the carboxy group of linoleic acid with the hydroxy group of ethanol. It has a role as a plant metabolite and an anti-inflammatory agent. It derives from a linoleic acid.
Ethyl linoleate is an ester of ethyl alcohol and linoleic acid.
A type of oil soluble vitamin F that is used as an emollient.
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Ethyl linoleate (ELA) is a commercially valuable compound with many positive health effects.
Here, we optimized two ELA processing steps, urea complexation (UC) and molecular distillation (MD), using single-factor and response surface analyses.
Ethyl linoleate is an unsaturated fatty acid used in many cosmetics for its various attributes, such as antibacterial and anti-inflammatory properties and clinically proven to be an effective anti-acne agent.
Ethyl linoleate is used for skin care, vitamin component. Softens, regenerates, nourishes the skin. Strengthens and promotes hair gloss. Perfume component.
Ethyl linoleate gets converted to linoleic acid in-vivo & provides all the skin benefits of linoleic acid with improved skin permeability & ease of handling.
Lower alcohol ester of linoleic acid with improved stability, skin absorption, and texture
Labelled Ethyl linoleate (E924300).
A fatty acid alkyl ester used in the vitamin industry.
Ethyl linoleate (vitamin F) is an emollient and an essential fatty acid.
Definition of Ethyl linoleate
A long-chain fatty acid ethyl ester resulting from the formal condensation of the carboxy group of linoleic acid with the hydroxy group of ethanol.
Ethyl linoleate is a long-chain fatty acid ethyl ester resulting from the formal condensation of the carboxy group of linoleic acid with the hydroxy group of ethanol.
Biological Role of Ethyl linoleate:
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Ethyl linoleate for skin care & cosmetic
For many years we’ve known how important polyunsaturated fatty acids are for the human body and that our skin is not able to synthesise them as it does not have the necessary desaturases.
Numerous studies performed on test subjects and also on humans have demonstrated the essential nature of arachidonic acid, linoleic acid and alpha-linolenic acid, and a deficiency of these causes numerous pathological changes in the skin, skin glands, skin structures, capillary structure and even at a neurological level.
Safflower oil has a high content of linoleic acid and therefore an ethyl ester was produced so the high percentage of polyunsaturated acid could be teamed with rapid absorption into the skin.
Ethyl linoleate is used in preparations for dry, rough, flaky skin.
Ethyl linoleates characteristics mean it can also be used in the pharmaceutical industry and in the production of nutritional supplements.
Chemical Structure Description of Ethyl linoleate
A chemical structure of a molecule includes the arrangement of atoms and the chemical bonds that hold the atoms together.
The Ethyl linoleate molecule contains a total of 57 bond(s) There are 21 non-H bond(s), 3 multiple bond(s), 16 rotatable bond(s), 3 double bond(s) and 1 ester(s) (aliphatic).
Ethyl linoleate (also known as RT001, di-deuterated linoleic acid ethyl ester, 11,11-d2-Ethyl linoleate, or ethyl 11,11-d2-linoleate) is an experimental, orally-bioavailable synthetic deuterated polyunsaturated fatty acid (PUFA), a part of reinforced lipids.
Ethyl linoleate is an isotopologue of linoleic acid, an essential omega-6 PUFA.
The deuterated compound, while identical to natural linoleic acid except for the presence of deuterium, is resistant to lipid peroxidation which makes studies of its cell-protective properties worthwhile.
Ethyl linoleate may be used as a reference material in assays that quantify fatty acid ethyl esters (FAEEs) for detection of alcohol abuse.
Linoleic acid ethyl ester (Ethyllinoleate) may be used and studied as an acetylcholinesterase (AChE) inhibitor.
Ethyl linoleate solated from Oxalis triangularis inhibits forskolin-induced melanogenesisand tyrosinase activity in mouse B16 melanoma cells .
This anti-melanogenic effect is mediated by inhibiting cAMP production.
Ethyl linoleate or Vitamin F (Linoleic Acid) in one form gives the skin a good touch.
Ethyl linoleate also helps to balance the skin’s moisture.
Reduce excess sebum (excess sebum secretion), restore the outer layer of the skin barrier.
Suitable for dry, chapped skin, tender skin, as well as for skin that exerts an excessive level of sebum, Ethyl linoleate is also commonly used for nail care.
Ethyl linoleate has a light texture.
The product ratio of hydroperoxy epidioxides to MHPs in the aqueous oxidation of LN was lower than that of autoxidized LN in the air, showing the rapid decomposition of epidioxides in an aqueous solution.
The kinetics of the initial stages of the thermal oxidation of Ethyl linoleate (by molecular oxygen) have been investigated in the temperature range 35—75° C.
From consideration of chemical and kinetic evidence the reaction mechanism has been established: oxidation chains are initiated by thermal decomposition of Ethyl linoleate hydroperoxide (which in the early stages of oxidation is substantially the sole product).
The chain propagation reactions are identified as R— + O2 → RO2— and RO2— + RH → ROOH + R— (where RH represents Ethyl linoleate). Chain termination occurs by mutual destruction of the radical chain carriers, R— and RO2— .
Ethyl linoleate Functions:
This ingredient has several functions, most often it is:
a PERFUMING AGENT: Ethyl linoleates role is to give a fragrance to the product and / or to provide an odor or a taste, by creating a pleasant odor and / or by masking a bad odor.
an EMOLLIENT FOR THE SKIN: Ethyl linoleates role is to soften and soften the skin by acting as a lubricant.
Handling and Storage
Precautions for safe handling: Avoid contact with skin, eyes, and personal clothing.
Wash hands thoroughly after handling. Avoid breathing fumes.
Ethyl linoleate is used only with adequate ventilation.
Wear suitable protective clothing, gloves, and eye/face protection.
Keep away from sources of ignition. Minimize dust generation and accumulation.
Keep container tightly closed.
Open and handle container with care.
Do not eat, drink, or smoke while handling.
Conditions for safe storage, including any incompatibilities:
Store in a tightly-closed container when not in use.
Store in a cool, dry, well-ventilated area away from incompatible substances.
Keep away from sources of ignition.
Store long-term at 2-8°C.
Properties of Ethyl linoleate
Molecular Weight: 308.5
XLogP3-AA: 7.3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 16
Exact Mass: 308.271530387
Monoisotopic Mass: 308.271530387
Topological Polar Surface Area: 26.3 Ų
Heavy Atom Count: 22
Formal Charge: 0
Ethyl linoleate (ELA) is an essential fatty acid used in many cosmetics for its anti-inflammatory properties.
Ethyl linoleate inhibits the action of the reactive species of oxygen released by neutrophils due to an excess of bacteria, and prevents the hyperkeratinization induced by a lack of linoleic acid.
Though there are few reports stating the antiinflammatory activity of ELA, the mechanism by which ELA exhibits anti-inflammatory activity remains unclear.
An aqueous emulsion of Ethyl linoleate can be used as parenteral injection for curring ailments where a high plasma-cholesterol level of the blood is indicated.
Improvements in liver function tests during the administration of ELA were noticed in almost all cases with a few aggravated exceptions.
The administration of ELA can expect the satisfactory response to the patients both with liver cirrhosis and with chronic hepatitis.
Complexity: 292
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 2
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
biological source of Ethyl linoleate: plant oil (safflower)
assay of Ethyl linoleate: ≥99%
The oxidative stability of Ethyl linoleate (LA), ethyl linolenate (LN), and ethyl docosahexaenoate (DHA) in an aqueous solution was compared by measuring the decrease in unoxidized substrate and the formation of total hydroperoxides, conjugated dienes, and monohydroperoxides (MHPs).
The highest stability was shown by DHA, this being followed by LN and LA in both cases when using Fe2+-ascorbic acid and 2,2′-azobis(2,4-dimethylvaleronitrile) (AMVN) as a initiator, while the reverse order of oxidative stability was obtained when the esters were oxidized in chloroform or ethanol with AMVN.
The stability of MHPs in an aqueous solution also increased with increasing degree of unsaturation.
HPLC analyses showed little difference in the positional distribution of MHP isomers between aqueous oxidation and autoxidation in the air.
This result suggests no selective abstraction of hydrogen atoms from the bisallylic positions of polyunsaturated fatty acid in an aqueous phase.
form of Ethyl linoleate: liquid
refractive index of Ethyl linoleate: n20/D 1.455 (lit.)
bp of Ethyl linoleate: 224 °C/17 mmHg (lit.)
density of Ethyl linoleate: 0.876 g/mL at 25 °C (lit.)
functional group of Ethyl linoleate: ester
shipped in of Ethyl linoleate: ambient
storage temp of Ethyl linoleate: −20°C
Appearanc: Colorless to Light yellow clear liquid
Purity(GC): min. 97.0 %
Odor Characteristics: Fruity
Product Categories
Reference Standards, Organic
Short DescriptionEthyl linoleate 1 mL 10 mg/mL in Hexane
-Storage Condititions: Freeze (<-10° C)
-Precaution: Highly Flammable
MDL: MFCD00009535
Boiling point: 193 °C/6 mmHg
InChI: InChI=1S/C20H36O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h8-9,11-12H,3-7,10,13-19H2,1-2H3/b9-8-,12-11-
InChI key: InChIKey=FMMOOAYVCKXGMF-MURFETPASA-N
SMILES: C-C-C-C-C/C=CC/C=CC-C-C-C-C-C-C-C(=O)-O-C-C
HS code: 2916199590
Synonyms:
Ethyl linoleate
544-35-4
Linoleic acid ethyl ester
Mandenol
Ethyl linolate
ethyl (9Z,12Z)-octadeca-9,12-dienoate
Ethyl cis,cis-9,12-octadecadienoate
UNII-MJ2YTT4J8M
Linoleic acid, ethyl ester
Ethyl linoleate [JAN]
MJ2YTT4J8M
Ethyl (Z,Z)-9,12-Octadecadienoate
EthylLinoleate
CHEBI:31572
9,12-Octadecadienoic acid (9Z,12Z)-, ethyl ester
MFCD00009535
(9Z,12Z)-Ethyl octadeca-9,12-dienoate
Ethyl linoleate (JAN)
DSSTox_CID_26820
DSSTox_RID_81932
DSSTox_GSID_46820
9,12-Octadecadienoic acid ethyl ester
ethyl (9Z,12Z)octadeca-9,12-dienoate
CAS-6114-21-2
Ethyl linoleate, pure
NCGC00181039-01
Linoleic acid ethyl
EINECS 208-868-4
NSC 50447
Ethyl linoleate, 50%
Ethyl linoleate, 70%
9,Z)-, ethyl ester
EC 208-868-4
Ethyl linoleate, >=99%
9,12-Octadecadienoic acid (Z,Z)-, ethyl ester
SCHEMBL81540
Ethyl cis,12-octadecadienoate
QSPL 206
CHEMBL2106238
DTXSID1060269
ethyl (9Z,12Z)-octadecadienoate
HMS3650O09
Linoleic acid, ethyl ester (8CI)
NSC50447
ZINC4474575
Ethyl linoleate, analytical standard
Tox21_112687
NSC-50447
SBB058683
AKOS015843230
Tox21_112687_1
NCGC00181039-02
9,12,Octadececadienoic acid, ethyl ester
AC-33781
AS-63462
M416
Ethyl linoleate, technical, >=65% (GC)
DB-003652
Ethyl (9Z,12Z)-9,12-octadecadienoate #
L0055
L0135
ST51037315
cis-9,cis-12-Octadecadienoic acid ethyl ester
D01590
Fmoc-(S)-3-Amino-3-(2-naphthyl)-propionicacid
SR-01000946817
SR-01000946817-1
Q27104200
9,12-Octadecadienoic acid (Z,Z)-, ethyl ester (9CI)
UNII-0962034MCM component FMMOOAYVCKXGMF-MURFETPASA-N
UNII-89IR26S11S component FMMOOAYVCKXGMF-MURFETPASA-N
UNII-PY7890FR5M component FMMOOAYVCKXGMF-MURFETPASA-N
Ethyl linoleate, United States Pharmacopeia (USP) Reference Standard