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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
Interaction of polyunsaturated fatty acids with animal cells and enveloped viruses.
1980 Dec
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
In Vivo Studies of the Biosynthesis of [alpha]-Eleostearic Acid in the Seed of Momordica charantia L.
1997 Apr
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
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
The ligands/activators for peroxisome proliferator-activated receptor alpha (PPARalpha) and PPARgamma increase Cu2+,Zn2+-superoxide dismutase and decrease p22phox message expressions in primary endothelial cells.
2001 Jan
A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs.
2003 Feb 7
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
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
Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids.
2004 Dec
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004 Oct
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
Formation of Nepsilon-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification.
2006 Jul
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
Down-regulation of alpha-amino-beta-carboxymuconate-epsilon-semialdehyde decarboxylase by polyunsaturated fatty acids in hepatocytes is not mediated by PPARalpha.
2008 Mar
A cholesterol-free, high-fat diet suppresses gene expression of cholesterol transporters in murine small intestine.
2008 May
Sex hormone influence on hepatitis in young male A/JCr mice infected with Helicobacter hepaticus.
2008 Sep
A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis.
2012
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
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 Fri Dec 16 16:03:02 UTC 2022
Edited
by admin
on Fri Dec 16 16:03:02 UTC 2022
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 Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
LOINC 35165-0
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
LOINC 2564-3
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
LOINC 90917-6
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
LOINC 75117-2
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
NCI_THESAURUS C2563
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
CFR 21 CFR 357.210
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
CFR 21 CFR 184.1065
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
LOINC 90915-0
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
LOINC 47686-1
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
DSLD 1537 (Number of products:578)
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
Code System Code Type Description
CHEBI
17351
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
WIKIPEDIA
LINOLEIC ACID
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
HSDB
5200
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
MESH
D019787
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
FDA UNII
9KJL21T0QJ
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
CAS
60-33-3
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
DRUG CENTRAL
3323
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
DRUG BANK
DB14104
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
MERCK INDEX
M6830
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY Merck Index
NCI_THESAURUS
C615
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
NSC
281243
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
PUBCHEM
5280450
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
RXCUI
6400
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
DAILYMED
9KJL21T0QJ
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
ECHA (EC/EINECS)
200-470-9
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
RXCUI
70611
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
ALTERNATIVE
EPA CompTox
DTXSID2025505
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
EVMPD
SUB14359MIG
Created by admin on Fri Dec 16 16:03:03 UTC 2022 , Edited by admin on Fri Dec 16 16:03:03 UTC 2022
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
varies depending of method of extraction
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
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)
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
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
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.
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
PARENT -> CONSTITUENT ALWAYS PRESENT
From Cannabis seed oil.
LIPID -> FATTY ACID
USP
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
U.S produced rice oil. Values are % of composition.
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
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values are % of total.
LIPID -> FATTY ACID
EUROPEAN SOURCE
PARENT -> CONSTITUENT ALWAYS PRESENT
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
LIPID -> FATTY ACID
Values are % of total.
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY