U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ETHYL LINOLEATE

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-

HIDE SMILES / InChI
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

Description
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

Martin & Harris
1
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

2010
465
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 3.7 µM [IC50]
Inhibitor
8297
 3.4 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Diagnostic
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Preventing
Preclinical
Unknown

Approved Use

Unknown
Palliative
Phase II
1132
Unknown

Approved Use

Unknown
Palliative
Phase II
1132
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Xanthomatous biliary cirrhosis treated with ethyl linoleate.
1959 Apr 25
Effects of ethyl-linoleate on the atheromatous changes caused by high cholesterol diet in the rabbit.
1966 Mar
The effect of a single oral dose of ethyl linoleate on urinary prostaglandin E2 excretion in essential fatty acid-deficient rats.
1985 Jan
Double-blind, randomized, placebo-controlled study of a lotion containing triethyl citrate and ethyl linoleate in the treatment of acne vulgaris.
2007 Sep
Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms.
2010 Aug
Salicylic acid peel incorporating triethyl citrate and ethyl linoleate in the treatment of moderate acne: a new therapeutic approach.
2013 Aug
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 Apr
Ethyl linoleate from garlic attenuates lipopolysaccharide-induced pro-inflammatory cytokine production by inducing heme oxygenase-1 in RAW264.7 cells.
2014 Apr
Patents

Patents

20010041188
3
JPS61257945A
1

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Each capsule contains 900 mg linoleic acid ethyl ester
1.8 g/day for 28 days
Route of Administration: Oral
In Vitro Use Guide
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
by admin
on Fri Dec 15 14:58:59 UTC 2023
Edited
by admin
on Fri Dec 15 14:58:59 UTC 2023
Record UNII
MJ2YTT4J8M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHYL LINOLEATE
INCI   JAN   MI   USP-RS   WHO-DD  
INCI  
Official Name English
Ethyl linoleate [WHO-DD]
Common Name English
LINOLEIC ACID, ETHYL ESTER
Common Name English
9,12-OCTADECADIENOIC ACID ETHYL ESTER
Systematic Name English
ETHYL LINOLEATE [USP-RS]
Common Name English
NSC-50447
Code English
9,12-OCTADECADIENOIC ACID (9Z,12Z)-, ETHYL ESTER
Common Name English
ETHYL LINOLEATE [MI]
Common Name English
ETHYL CIS,CIS-9,12-OCTADECADIENOATE
Systematic Name English
ETHYL LINOLEATE [INCI]
Common Name English
LINOLEIC ACID ETHYL ESTER
Systematic Name English
9,12-OCTADECADIENOIC ACID (Z,Z)-, ETHYL ESTER
Common Name English
ETHYL LINOLEATE [JAN]
Common Name English
MANDENOL
Common Name English
Classification Tree Code System Code
DSLD 1879 (Number of products:1)
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
Code System Code Type Description
SMS_ID
100000078992
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID1060269
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-868-4
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
PRIMARY
PUBCHEM
5282184
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
PRIMARY
FDA UNII
MJ2YTT4J8M
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
PRIMARY
RXCUI
24522
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
PRIMARY RxNorm
CHEBI
31572
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
PRIMARY
EVMPD
SUB13745MIG
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
PRIMARY
CAS
544-35-4
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
PRIMARY
NSC
50447
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
PRIMARY
ChEMBL
CHEMBL2106238
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
PRIMARY
RS_ITEM_NUM
1265843
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
PRIMARY
DAILYMED
MJ2YTT4J8M
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
PRIMARY
MERCK INDEX
m5145
Created by admin on Fri Dec 15 14:58:59 UTC 2023 , Edited by admin on Fri Dec 15 14:58:59 UTC 2023
PRIMARY Merck Index
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966