LINOLEIC ACID

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H32O2
Molecular Weight	280.4462
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\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	280.4462
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	2
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6422980 | https://www.ncbi.nlm.nih.gov/pubmed/12540417DOI: 10.1007/BF02640278 Retrived from http://link.springer.com/article/10.1007/BF02640278

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

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
cell proliferation 27 Target ID: GO:0008283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23341188	Activator 1343

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2502
Parenteral Nutrition 48 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020248s020lbl.pdf	Curative	Approved 8043	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
Multiple sclerosis 95 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6387534	Primary	Phase I 409	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Cerebrospinal fluid lipids in demyelinating disease. II. Linoleic acid as an index of impaired blood-CSF barrier.	1980 Jan	6153705
Physiology and pathophysiology of organic acids in cerebrospinal fluid.	1993	8412012
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	8123682
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	8040295
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	7929039
Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes.	1995 Dec 1	8536680
In Vivo Studies of the Biosynthesis of [alpha]-Eleostearic Acid in the Seed of Momordica charantia L.	1997 Apr	12223677
Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha.	1999 Jul 14	10403814
Plasma saturated and linoleic fatty acids are independently associated with blood pressure.	1999 Sep	10489397
Zinc protects against apoptosis of endothelial cells induced by linoleic acid and tumor necrosis factor alpha.	2000 Jan	10617950
Long-chain fatty acids regulate liver carnitine palmitoyltransferase I gene (L-CPT I) expression through a peroxisome-proliferator-activated receptor alpha (PPARalpha)-independent pathway.	2001 Feb 15	11171094
Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates.	2001 Jan 15	11341955
Linoleic acid, other fatty acids, and the risk of stroke.	2002 Aug	12154268
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	12101222
Divergent effects of selective peroxisome proliferator-activated receptor-gamma 2 ligands on adipocyte versus osteoblast differentiation.	2002 Jun	12021203
Polyunsaturated fatty acid status and relapse vulnerability in cocaine addicts.	2003 Aug 30	14500111
PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation.	2003 Feb	12576510
A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs.	2003 Feb 7	12565875
Linoleic acid supplementation of Barth syndrome fibroblasts restores cardiolipin levels: implications for treatment.	2003 Mar	12562862
Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40.	2003 Mar 13	12629551
The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids.	2003 Mar 28	12496284
Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization.	2003 Oct 15	12871208
Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids.	2004 Dec	15375178
Dietary alpha-linolenic acid reduces COX-2 expression and induces apoptosis of hepatoma cells.	2004 Feb	14563831
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.	2004 Oct	15491415
High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids?	2006 Aug	16895544
Cyclooxygenase-2 promoter activation by the aromatic hydrocarbon receptor in breast cancer mcf-7 cells: repressive effects of conjugated linoleic acid.	2007	18001219
Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes.	2008 Jan	18154422
Characterization of Madin-Darby bovine kidney cell line for peroxisome proliferator-activated receptors: temporal response and sensitivity to fatty acids.	2008 Jul	18565938
Comparison of hypolipidemic activity of synthetic gallic acid-linoleic acid ester with mixture of gallic acid and linoleic acid, gallic acid, and linoleic acid on high-fat diet induced obesity in C57BL/6 Cr Slc mice.	2008 Jul 30	18571153
Down-regulation of alpha-amino-beta-carboxymuconate-epsilon-semialdehyde decarboxylase by polyunsaturated fatty acids in hepatocytes is not mediated by PPARalpha.	2008 Mar	18320257
Changing ratios of omega-6 to omega-3 fatty acids can differentially modulate polychlorinated biphenyl toxicity in endothelial cells.	2008 Mar 10	18155686
A cholesterol-free, high-fat diet suppresses gene expression of cholesterol transporters in murine small intestine.	2008 May	18356535
Role of polyunsaturated fatty acids in the management of Egyptian children with autism.	2008 Sep	18582451
Sex hormone influence on hepatitis in young male A/JCr mice infected with Helicobacter hepaticus.	2008 Sep	18559427
Identification of an endogenous ligand bound to a native orphan nuclear receptor.	2009	19440305
Optimization of an enzyme-linked immunosorbent assay to screen ligand of Peroxisome proliferator-activated receptor alpha.	2009	19263263
Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms.	2010 Aug	20541177
TGF-β-SMAD3 signaling mediates hepatic bile acid and phospholipid metabolism following lithocholic acid-induced liver injury.	2012 Dec	23034213
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	22467055
Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice.	2013 Jul 5	23619606
Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor α, β, γ subtypes: an in silico approach.	2014 Jul	23843199

Patents

Sample Use Guides

In Vivo Use Guide

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 `Sat Jun 26 06:12:01 UTC 2021` Edited by `admin` on `Sat Jun 26 06:12:01 UTC 2021`
Record UNII	9KJL21T0QJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LINOLEIC ACID

Official Name

English

LINOLEIC ACID [INCI]

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

LINOLEIC ACID [WHO-DD]

Common 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