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

Details

Stereochemistry ACHIRAL
Molecular Formula C18H32O2
Molecular Weight 280.4455
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of LINOLEIC ACID

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(O)=O

InChI

InChIKey=OYHQOLUKZRVURQ-HZJYTTRNSA-N
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-

HIDE SMILES / InChI

Molecular Formula C18H32O2
Molecular Weight 280.4455
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

There is existed not much information about ammonium salt of linoleic acid, AMMONIUM LINOLEATE. But is known, that this compound is auto oxidized.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Intralipid

Approved Use

Intralipid® 10% is indicated as a source of calories and essential fatty acids for patients requiring parenteral nutrition for extended periods of time (usually for more than 5 days) and as a source of essential fatty acids for prevention of EFAD.

Launch Date

8.392896E11
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Fatty acids and derivatives as antimicrobial agents.
1972 Jul
Interaction of polyunsaturated fatty acids with animal cells and enveloped viruses.
1980 Dec
Cerebrospinal fluid lipids in demyelinating disease. II. Linoleic acid as an index of impaired blood-CSF barrier.
1980 Jan
Screening for new compounds with antiherpes activity.
1984 Oct
Physiology and pathophysiology of organic acids in cerebrospinal fluid.
1993
Evidence for a novel keratinocyte fatty acid uptake mechanism with preference for linoleic acid: comparison of oleic and linoleic acid uptake by cultured human keratinocytes, fibroblasts and a human hepatoma cell line.
1994 Feb 10
Pseudo-acylceramide with linoleic acid produces selective recovery of diminished cutaneous barrier function in essential fatty acid-deficient rats and has an inhibitory effect on epidermal hyperplasia.
1994 Jul
Equilibrium constants for the binding of fatty acids with fatty acid-binding proteins from adipocyte, intestine, heart, and liver measured with the fluorescent probe ADIFAB.
1994 Sep 30
Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes.
1995 Dec 1
T cells ignore aniline, a prohapten, but respond to its reactive metabolites generated by phagocytes: possible implications for the pathogenesis of toxic oil syndrome.
2001 Apr
Binding of prostaglandins to human PPARgamma: tool assessment and new natural ligands.
2001 Apr 6
Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates.
2001 Jan 15
Organotropic chemopreventive effects of n-3 unsaturated fatty acids in a rat multi-organ carcinogenesis model.
2001 Nov
Linoleic acid both enhances activation and blocks Kv1.5 and Kv2.1 channels by two separate mechanisms.
2001 Oct
Changes in matrix proteoglycans induced by insulin and fatty acids in hepatic cells may contribute to dyslipidemia of insulin resistance.
2001 Sep
Linoleic acid, other fatty acids, and the risk of stroke.
2002 Aug
Topical peroxisome proliferator activated receptor-alpha activators reduce inflammation in irritant and allergic contact dermatitis models.
2002 Jan
Cytosolic phospholipase A2 (cPLA2) regulation of human monocyte NADPH oxidase activity. cPLA2 affects translocation but not phosphorylation of p67(phox) and p47(phox).
2002 Jul 12
Divergent effects of selective peroxisome proliferator-activated receptor-gamma 2 ligands on adipocyte versus osteoblast differentiation.
2002 Jun
Polyunsaturated fatty acid status and relapse vulnerability in cocaine addicts.
2003 Aug 30
PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation.
2003 Feb
A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs.
2003 Feb 7
Protective action of CLA against oxidative inactivation of paraoxonase 1, an antioxidant enzyme.
2003 Jun
Linoleic acid supplementation of Barth syndrome fibroblasts restores cardiolipin levels: implications for treatment.
2003 Mar
Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40.
2003 Mar 13
The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids.
2003 Mar 28
Zinc modulates PPARgamma signaling and activation of porcine endothelial cells.
2003 Oct
Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization.
2003 Oct 15
Quercetin protects against linoleic acid-induced porcine endothelial cell dysfunction.
2004 Apr
Dietary alpha-linolenic acid reduces COX-2 expression and induces apoptosis of hepatoma cells.
2004 Feb
Binding analyses between Human PPARgamma-LBD and ligands.
2004 Jan
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004 Oct
High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids?
2006 Aug
Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha.
2006 Aug
Cyclooxygenase-2 promoter activation by the aromatic hydrocarbon receptor in breast cancer mcf-7 cells: repressive effects of conjugated linoleic acid.
2007
Role of FoxO1 in FFA-induced oxidative stress in adipocytes.
2007 Jul
Comprehensive analysis of the effects of ordinary nutrients on hepatitis C virus RNA replication in cell culture.
2007 Jun
Unsaturated fatty acids suppress the expression of the ATP-binding cassette transporter G1 (ABCG1) and ABCA1 genes via an LXR/RXR responsive element.
2007 Mar
Characterization of Madin-Darby bovine kidney cell line for peroxisome proliferator-activated receptors: temporal response and sensitivity to fatty acids.
2008 Jul
Identification of an endogenous ligand bound to a native orphan nuclear receptor.
2009
Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms.
2010 Aug
Bezafibrate mildly stimulates ketogenesis and fatty acid metabolism in hypertriglyceridemic subjects.
2010 Jul
Regulation of stearoyl-coenzyme A desaturase and fatty acid delta-6 desaturase-2 expression by linoleic acid and arachidonic acid in human sebocytes leads to enhancement of proinflammatory activity but does not affect lipogenesis.
2011 Aug
New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors.
2012 Nov
Advanced glycation end products (AGE) induce the receptor for AGE in the colonic mucosa of azoxymethane-injected Fischer 344 rats fed with a high-linoleic acid and high-glucose diet.
2012 Oct
Effects of palmitic acid on TNF-α-induced cytotoxicity in SK-Hep-1 cells.
2012 Sep
Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice.
2013 Jul 5
Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor α, β, γ subtypes: an in silico approach.
2014 Jul
Bongkrekic acid as a selective activator of the peroxisome proliferator-activated receptor γ (PPARγ) isoform.
2015 Apr
Excess Linoleic Acid Increases Collagen I/III Ratio and "Stiffens" the Heart Muscle Following High Fat Diets.
2015 Sep 18
Patents

Sample Use Guides

Linoleic acid emulsion is administered at a dose of 30 g two times daily.
Route of Administration: Oral
In Vitro Use Guide
Lymphocytes from patients with multiple sclerosis were incubated with linoleic acid at concnetration of 0.08 mg/ml and the inhibition achieved 91%.
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:35:44 UTC 2023
Edited
by admin
on Wed Jul 05 22:35:44 UTC 2023
Record UNII
9KJL21T0QJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LINOLEIC ACID
FCC   HSDB   INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
LINOLEIC ACID [INCI]
Common Name English
Linoleic acid [WHO-DD]
Common Name English
LINOLEIC ACID [MI]
Common Name English
LINOLEIC ACID [VANDF]
Common Name English
LINOLEIC ACID [HSDB]
Common Name English
LINOLEIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]
Common Name English
VITAMIN F COMPONENT LINOLEIC ACID
Common Name English
LINOLEIC ACID (CONSTITUENT OF FLAX SEED OIL) [DSC]
Common Name English
LINOLEIC ACID (CONSTITUENT OF BORAGE SEED OIL) [DSC]
Common Name English
RONACARE ASC 3
Brand Name English
LINOLIC ACID
Common Name English
NSC-281243
Code English
LINOLEIC ACID (C18:2) (CONSTITUENT OF KRILL OIL) [DSC]
Common Name English
EMERSOL 315
Brand Name English
9,12-LINOLEIC ACID
Common Name English
(Z,Z)-9,12-OCTADECADIENOIC ACID
Systematic Name English
LINOLEIC ACID [MART.]
Common Name English
FEMA NO. 3380, LINOLEIC ACID-
Code English
LINOLEATE
Systematic Name English
UNIFAC 6550
Brand Name English
C18:2 (N-6)
Common Name English
LINOLEIC ACID [FCC]
Common Name English
POLYLIN 515
Brand Name English
LINOLEIC ACID (CONSTITUENT OF SPIRULINA) [DSC]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68398
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
LOINC 35165-0
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
LOINC 2564-3
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
LOINC 90917-6
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
LOINC 75117-2
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
NCI_THESAURUS C2563
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
CFR 21 CFR 357.210
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
CFR 21 CFR 184.1065
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
LOINC 90915-0
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
LOINC 47686-1
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
DSLD 1537 (Number of products:578)
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
Code System Code Type Description
CHEBI
17351
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
WIKIPEDIA
LINOLEIC ACID
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
HSDB
5200
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
MESH
D019787
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
FDA UNII
9KJL21T0QJ
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
CAS
60-33-3
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
SMS_ID
100000077113
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
DRUG CENTRAL
3323
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
DRUG BANK
DB14104
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
MERCK INDEX
M6830
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C615
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
NSC
281243
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
PUBCHEM
5280450
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
RXCUI
6400
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
DAILYMED
9KJL21T0QJ
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-470-9
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
RXCUI
70611
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
ALTERNATIVE
EPA CompTox
DTXSID2025505
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
EVMPD
SUB14359MIG
Created by admin on Wed Jul 05 22:35:44 UTC 2023 , Edited by admin on Wed Jul 05 22:35:44 UTC 2023
PRIMARY
Related Record Type Details
LIPID -> FATTY ACID
U.S produced rice oil. Values are % of composition.
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
LIPID -> FATTY ACID
Value is % of composition. Oleic safflower variety UC-1 cited by Knowles, P, Calif. Agr. 19(12),15(1965), produced 15.00% by composition.
LIPID -> FATTY ACID
Value is fatty acid composition (%) for US corn oil w/std. deviation of 1.20% LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values are % of weight of fatty acid composition. O?Connor, RT, Herb, SF; J Am Oil Chem Soc 47, 186A, 195A, 197A(1970)(range) Brignoli, CA et al: J Am Diet Assoc 68, 224(1976)(average)
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Value is fatty acid composition (%) for international corn oil w/std. deviation of 2.4% LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
G Jurriens and ACJ Kroesen, J Am Oil Chem Soc, 42(9)(1965)(average value). Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Compound measured as 2.50% of the composition of the steam distillate of Elymus repens rhizome as per R Boesel in Planta Medica iss:4 pg:399-400, 1989.
PARENT -> CONSTITUENT ALWAYS PRESENT
LIPID -> FATTY ACID
varies depending of method of extraction
PARENT -> CONSTITUENT ALWAYS PRESENT
From Cannabis seed oil.
LIPID -> FATTY ACID
EUROPEAN SOURCE
LIPID -> FATTY ACID
USP
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
LIPID -> FATTY ACID
Value is % of total fatty acids. Maiti, S, et al; Handbook of Annual Oilseed Crops, OIBH, New Delhi, India(1988), pp.1987-90
LIPID -> FATTY ACID
Values are % of total.
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values are % of total.
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY