Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H36O2 |
| Molecular Weight | 308.4986 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC
InChI
InChIKey=FMMOOAYVCKXGMF-MURFETPASA-N
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-
| Molecular Formula | C20H36O2 |
| Molecular Weight | 308.4986 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24508058Curator's Comment: description was created based on several sources, including http://www.google.ru/patents/US3198704
https://www.ncbi.nlm.nih.gov/pubmed/5984527
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24508058
Curator's Comment: description was created based on several sources, including http://www.google.ru/patents/US3198704
https://www.ncbi.nlm.nih.gov/pubmed/5984527
Ethyl linoleate (ELA) is an essential fatty acid used in many cosmetics for its anti-inflammatory properties. It 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.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5928125
Curator's Comment: Ethyl linoleate (Mandenole), an ethyl ester of linoleic acid in a 10 per cent aqueous emulsion, was developed by Mr. K. N. Roy, of Messrs. Martin and Harris Private Ltd
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0032306 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24508058 |
3.7 µM [IC50] | ||
Target ID: GO:0002537 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24508058 |
3.4 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Preventing | Unknown Approved UseUnknown |
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| Palliative | Unknown Approved UseUnknown |
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| Palliative | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Chinese yam extracts containing β-sitosterol and ethyl linoleate protect against atherosclerosis in apolipoprotein E-deficient mice and inhibit muscular expression of VCAM-1 in vitro. | 2014-04 |
|
| Ethyl linoleate from garlic attenuates lipopolysaccharide-induced pro-inflammatory cytokine production by inducing heme oxygenase-1 in RAW264.7 cells. | 2014-04 |
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| Salicylic acid peel incorporating triethyl citrate and ethyl linoleate in the treatment of moderate acne: a new therapeutic approach. | 2013-08 |
|
| Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms. | 2010-08 |
|
| Double-blind, randomized, placebo-controlled study of a lotion containing triethyl citrate and ethyl linoleate in the treatment of acne vulgaris. | 2007-09 |
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| The effect of a single oral dose of ethyl linoleate on urinary prostaglandin E2 excretion in essential fatty acid-deficient rats. | 1985-01 |
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| Studies in burns: XIV, Heling in burn wounds treated with Ethyl Linoleate alone or in combination with selected topical antibacterial agents. | 1975-11 |
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| Effects of ethyl linoleate on chronic liver diseases with special reference to lipid metabolism. | 1966-12 |
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| Ethyl linoleate as an antiatherogenic agent. An experimental study in rabbits. | 1966-10 |
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| Effects of ethyl-linoleate on the atheromatous changes caused by high cholesterol diet in the rabbit. | 1966-03 |
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| ETHYL LINOLEATE IN EXPERIMENTAL ATHEROGENESIS. | 1965-02 |
|
| Xanthomatous biliary cirrhosis treated with ethyl linoleate. | 1959-04-25 |
|
| A case of xanthomatous biliary cirrhosis treated with ethyl linoleate. | 1959-02-07 |
Patents
Sample Use Guides
1.8 g/day for 28 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24508058
The effect of Ethyl linoleate (ELA) on p38, ERK1/2, JNK, and Akt activation was examined in LPS-stimulated RAW 264.7 cells. The activation of MAPKs was recorded after 15 min of treatment with LPS (1 μg/mL). When the cells were pretreated with ELA at the indicated concentrations for 1 h, followed by stimulation with 1 μg/mL LPS for 15 min, they showed an ELA dose-dependent decrease in phosphorylation of ERK1/2, JNK, p38, and Akt as compared to cells treated with LPS alone. These data suggest that ELA significantly suppressed the LPS-induced activation of ERK1/2, JNK, p38, and Akt in RAW 264.7 cells
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 17:33:57 GMT 2025
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Mon Mar 31 17:33:57 GMT 2025
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| Record UNII |
MJ2YTT4J8M
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| Record Status |
Validated (UNII)
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| Record Version |
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1879 (Number of products:1)
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