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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 of LINOLEIC ACID

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

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

1921
1413
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1343
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
Primary
Phase I
409
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Fatty acids and derivatives as antimicrobial agents.
1972 Jul
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
Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes.
1995 Dec 1
Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha.
1999 Jul 14
Plasma saturated and linoleic fatty acids are independently associated with blood pressure.
1999 Sep
Low-saturated fat, low-cholesterol diet in 3-year-old children: effect on intake and composition of trans fatty acids and other fatty acids in serum phospholipid fraction-The STRIP study. Special Turku coronary Risk factor Intervention Project for children.
2000 Jan
Essential fatty acid metabolism and its modification in atopic eczema.
2000 Jan
Zinc protects against apoptosis of endothelial cells induced by linoleic acid and tumor necrosis factor alpha.
2000 Jan
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
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
Linoleic acid both enhances activation and blocks Kv1.5 and Kv2.1 channels by two separate mechanisms.
2001 Oct
Topical peroxisome proliferator activated receptor-alpha activators reduce inflammation in irritant and allergic contact dermatitis models.
2002 Jan
Protective action of CLA against oxidative inactivation of paraoxonase 1, an antioxidant enzyme.
2003 Jun
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
Binding analyses between Human PPARgamma-LBD and ligands.
2004 Jan
Omega-3 fatty acids inhibit an increase of proinflammatory cytokines in patients with active Crohn's disease compared with omega-6 fatty acids.
2005 Dec
Specificity of receptor-ligand interactions and their effect on dimerisation as observed by electrospray mass spectrometry: bile acids form stable adducts to the RXRalpha.
2005 Nov
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
Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes.
2008 Jan
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
New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors.
2012 Nov
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
Inhibition of matrix metalloproteinase-9 expression by docosahexaenoic acid mediated by heme oxygenase 1 in 12-O-tetradecanoylphorbol-13-acetate-induced MCF-7 human breast cancer cells.
2013 May
Patents

Patents

JP2000247965A
4
JP2001081026A
4
JP2002146382A
4
JP2002501019A
7
JP2002533379A
51
JP2002536075A
14
JP2002536412A
7
JP2003508487A
8
JP2003533978A
5
JP2004236605A
5
JP2004256496A
4
JP2004531543A
5
JP2005194222A
4
JP2005314576A
4
JP2006230373A
4
JP2006282650A
4
JP2006321718A
4
JP2006326886A
4
JP2007135591A
4
JP2007176837A
4
JP2007504443A
9
JP2007514727A
4
JP2008113586A
4
JP2008540795A
5
JP2009051755A
4
JP2009084286A
4
JP2009132721A
4
JP2009184990A
4
JP2009256645A
4
JP2010195825A
4
JP2010502769A
10
JP2010535563A
8
JP2010538142A
5
JP2011103906A
4
JP2011503287A
5
JP2011508668A
16
JP2011524393A
6
JP2014195425A
4
JP2014201554A
4
JP3120091B2
9
JP4213205B2
14
JP4634804B2
4
JP4707659B2
4
JP4838936B2
15
JPH00491788A
4
JPH01135797A
4
JPH01186811A
8
JPH01300897A
4
JPH02113850A
4
JPH02178338A
7
JPH02191213A
4
JPH02283798A
4
JPH023498A
4
JPS56138111A
4
JPS6351486A
8
US2894909
4

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
  • 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 [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
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
LOINC 35165-0
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
LOINC 2564-3
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
LOINC 90917-6
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
LOINC 75117-2
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
NCI_THESAURUS C2563
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
CFR 21 CFR 357.210
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
CFR 21 CFR 184.1065
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
LOINC 90915-0
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
LOINC 47686-1
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
DSLD 1537 (Number of products:578)
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
Code System Code Type Description
WIKIPEDIA
LINOLEIC ACID
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
HSDB
5200
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
MESH
D019787
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
FDA UNII
9KJL21T0QJ
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
CAS
60-33-3
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
DRUG CENTRAL
3323
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
DRUG BANK
DB14104
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
MERCK INDEX
M6830
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C615
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
PUBCHEM
5280450
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
RXCUI
6400
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-470-9
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
RXCUI
70611
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
ALTERNATIVE
EPA CompTox
60-33-3
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
EVMPD
SUB14359MIG
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
Related Record Type Details
PALM OIL
LIPID -> FATTY ACID
Values are % of total.
COD LIVER OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
COCONUT OIL
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
SAFFLOWER OIL
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.
CORN OIL
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)
Structure of MANGANESE LINOLEATE
SALT/SOLVATE -> PARENT
CANOLA OIL
LIPID -> FATTY ACID
KRILL OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Structure of AMMONIUM LINOLEATE
SALT/SOLVATE -> PARENT
RICE BRAN OIL
LIPID -> FATTY ACID
U.S produced rice oil. Values are % of composition.
Structure of POTASSIUM LINOLEATE
SALT/SOLVATE -> PARENT
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
OLIVE OIL
LIPID -> FATTY ACID
TURKISH SOURCE
SOYBEAN OIL
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)
Structure of ZINC LINOLEATE
SALT/SOLVATE -> PARENT
CORN OIL
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)
COTTONSEED OIL
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)
Structure of ALUMINIUM TRILINOLEATE
SALT/SOLVATE -> PARENT
AVOCADO OIL
LIPID -> FATTY ACID
varies depending of method of extraction
ELYMUS REPENS ROOT
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.
ARCTIUM LAPPA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
CANNABIS SATIVA SUBSP. INDICA TOP
PARENT -> CONSTITUENT ALWAYS PRESENT
From Cannabis seed oil.
PHYLLANTHUS AMARUS TOP
PARENT->INNOVATOR
FISH OIL
LIPID -> FATTY ACID
USP
Structure of SODIUM LINOLEATE
SALT/SOLVATE -> PARENT
Structure of COPPER LINOLEATE
SALT/SOLVATE -> PARENT
Structure of COBALTOUS LINOLEATE
SALT/SOLVATE -> PARENT
SESAME OIL
LIPID -> FATTY ACID
Value is % of total fatty acids. Goden VJ, Spensley PC; Oils and Oilseeds, TPI, London, 1971, p.151
BORAGE SEED OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
SUNFLOWER OIL
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
PEANUT OIL
LIPID -> FATTY ACID
Values are % of total.
Structure of MERCURIC LINOLEATE
SALT/SOLVATE -> PARENT
Structure of CALCIUM LINOLEATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of LINOLEIC ACID
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