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Details

Stereochemistry ACHIRAL
Molecular Formula C18H30O2
Molecular Weight 278.4303
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 3
Charge 0

SHOW SMILES / InChI
Structure of LINOLENIC ACID

SMILES

CC/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\CCCCCCCC(=O)O

InChI

InChIKey=DTOSIQBPPRVQHS-PDBXOOCHSA-N
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-

HIDE SMILES / InChI

Molecular Formula C18H30O2
Molecular Weight 278.4303
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 3
Optical Activity NONE

Alpha-linolenic acid (ALA), an 18-carbon omega-3 essential fatty acid, is the precursor of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). ALA cannot be synthesized by humans and therefore must be entirely acquired from exogenous sources. Evidence for the essentiality of ALA was first provided by a study showing that ALA supplementation reversed the abnormal neurologic signs observed in a 6-year-old girl who suffered from sensory loss and visual complications. Most of the ALA is catabolized via beta-oxidation for energy generation, and a small proportion of it undergoes conversion to produce another two potent members of omega-3 PUFA family: EPA and DHA. Delta 6 desaturase (D6D) enzyme is responsible the conversion of ALA to DHA. Although not conclusive, it was suggested, that the benefits associated with ALA seem to stem mainly from EPA and DHA, and as major consequence of ALA deficiency it appears that EPA and DHA are not adequately produced.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O60427|||Q96SV3
Gene ID: 3992.0
Gene Symbol: FADS1
Target Organism: Homo sapiens (Human)
Target ID: O95864
Gene ID: 9415.0
Gene Symbol: FADS2
Target Organism: Homo sapiens (Human)
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

8.3920323E11
PubMed

PubMed

TitleDatePubMed
Glucose, insulin and platelet fatty acids following myocardial infarction: an association with infarct size.
1987 Jul-Aug
[Biological effects on premature neonates of a milk formula enriched with alpha-linolenic acid: a multicenter study].
1994 Feb
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
Nutritional attributes of traditional flaxseed in healthy young adults.
1995 Jan
Supplementation with flaxseed oil versus sunflowerseed oil in healthy young men consuming a low fat diet: effects on platelet composition and function.
1995 Mar
Preferential uptake of long chain polyunsaturated fatty acids by isolated human placental membranes.
1996 Feb 9
Effect of linolenic acid/ethanol or limonene/ethanol and iontophoresis on the in vitro percutaneous absorption of LHRH and ultrastructure of human epidermis.
1999 Apr 15
Effects of butter oil blends with increased concentrations of stearic, oleic and linolenic acid on blood lipids in young adults.
1999 Jul
Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha.
1999 Jul 14
Polyunsaturated fatty acids are potent neuroprotectors.
2000 Apr 17
Importance of n-3 fatty acids in health and disease.
2000 Jan
Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions.
2000 Jun 20
Short-term supplementation of low-dose gamma-linolenic acid (GLA), alpha-linolenic acid (ALA), or GLA plus ALA does not augment LCP omega 3 status of Dutch vegans to an appreciable extent.
2000 Nov
Identification of a fatty acid delta6-desaturase deficiency in human skin fibroblasts.
2001 Apr
Prospective study of dietary fat and the risk of age-related macular degeneration.
2001 Feb
Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates.
2001 Jan 15
Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease.
2002 Nov 19
Adipose tissue alpha-linolenic acid and nonfatal acute myocardial infarction in Costa Rica.
2003 Apr 1
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
Dietary alpha-linolenic acid is associated with reduced risk of fatal coronary heart disease, but increased prostate cancer risk: a meta-analysis.
2004 Apr
Alpha-linolenic acid and the risk of prostate cancer. What is the evidence?
2004 Apr
Polyunsaturated fatty acids are FXR ligands and differentially regulate expression of FXR targets.
2004 Aug
Dietary alpha-linolenic acid reduces COX-2 expression and induces apoptosis of hepatoma cells.
2004 Feb
Effect of chemical penetration enhancer and iontophoresis on the in vitro percutaneous absorption enhancement of insulin through porcine epidermis.
2005
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
Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120.
2005 Jan
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
Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty Acyl-CoAs and insulin action in type 2 diabetic patients.
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
Prostate tissue and leukocyte levels of n-3 polyunsaturated fatty acids in men with benign prostate hyperplasia or prostate cancer.
2006 Feb
PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver.
2006 May
Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation.
2006 Nov
TRPV1 is a novel target for omega-3 polyunsaturated fatty acids.
2007 Jan 15
Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes.
2008 Jan
Cloning and characterization of the rat free fatty acid receptor GPR120: in vivo effect of the natural ligand on GLP-1 secretion and proliferation of pancreatic beta cells.
2008 Jun
Changing ratios of omega-6 to omega-3 fatty acids can differentially modulate polychlorinated biphenyl toxicity in endothelial cells.
2008 Mar 10
Cross-talk between vitamin D receptor (VDR)- and peroxisome proliferator-activated receptor (PPAR)-signaling in melanoma cells.
2009 Sep
Differential effects of steroids on the synthesis of polyunsaturated fatty acids by human neuroblastoma cells.
2009 Sep
Activation of the nuclear receptor PPARγ by metabolites isolated from sage (Salvia officinalis L.).
2010 Oct 28
PKC activation by resveratrol derivatives with unsaturated aliphatic chain.
2012
Studies on comparative efficacy of α-linolenic acid and α-eleostearic acid on prevention of organic mercury-induced oxidative stress in kidney and liver of rat.
2012 Mar
Discovery of a potent and selective GPR120 agonist.
2012 May 10
Alpha-linolenic acid is a potent neuroprotective agent against soman-induced neuropathology.
2012 Oct
Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice.
2013 Jul 5
Patents

Sample Use Guides

It was examined the effect of the oral consumption of α-Linolenic acid (ALA) on blood levels of BDNF and Malondialdehyde (MDA) in healthy adult humans. 30 healthy volunteers, 15 men and 15 women, were selected randomly. During the experiment, each individual was given 3 oral capsules of flaxseed oil, containing 500mg of alpha linolenic acid, daily for one week. Then, plasma levels of brain-derived neurotrophic factors (BDNF) and MDA were tested.
Route of Administration: Oral
It was examined the effects of omega-3 alpha-linolenic acid (ALA) during in vitro oocyte maturation (IVM) in the presence of PSO on subsequent embryo development and quality, and the cellular mechanisms that might be involved. Bovine cumulus oocyte complexes (COCs) were supplemented during IVM with ALA (50 μM), PSO (425 μM), or PSO+ALA. Compared with FFA-free controls (P < 0.05), PSO increased embryo fragmentation and decreased good quality embryos on Day 2 post-fertilization. Day 7 blastocyst rate was also reduced. Day 8 blastocysts had lower cell counts and higher apoptosis but normal metabolic profile. It was found, that adding ALA in the presence of PSO normalised embryo fragmentation, cleavage, blastocyst rates and blastocyst quality compared to controls (P > 0.05). Combined treatment with ALA also reduced CC apoptosis, partially recovered CC expansion, abrogated the reduction in MMP in the CCs but not in the oocytes, and reduced BiP and HSP70 expression in CCs, compared with PSO only (P < 0.05). In conclusion, ALA supplementation protected oocyte developmental capacity under lipotoxic conditions mainly by protecting cumulus cell viability.
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:57:36 UTC 2021
Edited
by admin
on Sat Jun 26 13:57:36 UTC 2021
Record UNII
0RBV727H71
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LINOLENIC ACID
INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
LINOLENIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]
Common Name English
.ALPHA.-LINOLENIC ACID
Systematic Name English
(9Z,12Z,15Z)-OCTADECATRIENOIC ACID
Common Name English
ALPHA-LINOLENIC ACID
Systematic Name English
FEMA NO. 3380, LINOLENIC ACID-
Code English
CIS-9,CIS-12,CIS-15-OCTADECATRIENOIC ACID
Common Name English
UNIVOL U 316S
Brand Name English
LINOLENIC ACID [MI]
Common Name English
ALA
Common Name English
ALPHA LINOLENIC ACID
Common Name English
.ALPHA.-LINOLENIC ACID (C18:3) (CONSTITUENT OF KRILL OIL) [DSC]
Common Name English
LINOLENIC ACID [INCI]
Common Name English
LINOLENATE
Common Name English
VITAMIN F COMPONENT ALPHA LINOLENIC ACID
Common Name English
(Z,Z,Z)-9,12,15-OCTADECATRIENOIC ACID
Systematic Name English
NSC-2042
Code English
HYSTRENE 9014
Brand Name English
PRIFRAC 2942
Brand Name English
.ALPHA.-LINOLENIC ACID (CONSTITUENT OF FLAX SEED OIL) [DSC]
Common Name English
LINOLENIC ACID (CONSTITUENT OF EVENING PRIMROSE OIL) [DSC]
Common Name English
KORTACID 1499
Brand Name English
ALPHA-LINOLENIC ACID (C18:3 N3)
Common Name English
18:3(N-3)
Code English
LINOLENIC ACID [MART.]
Common Name English
LINOLENIC ACID [WHO-DD]
Common Name English
C18:3 (N-3)
Common Name English
LINOLENIC ACID [VANDF]
Common Name English
Classification Tree Code System Code
DSLD 2830 (Number of products:52)
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
CFR 21 CFR 357.210
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
NCI_THESAURUS C493
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
NCI_THESAURUS C68403
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
DSLD 1029 (Number of products:525)
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C997
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
PRIMARY
EVMPD
SUB21884
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
PRIMARY
RXCUI
595958
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
ALTERNATIVE
ECHA (EC/EINECS)
207-334-8
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
PRIMARY
PUBCHEM
5280934
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
PRIMARY
EVMPD
SUB34619
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
PRIMARY
WIKIPEDIA
ALPHA-LINOLENIC ACID
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
PRIMARY
DRUG CENTRAL
4618
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
PRIMARY
RXCUI
52071
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
PRIMARY
EPA CompTox
463-40-1
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
PRIMARY
MESH
D017962
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
PRIMARY
CAS
463-40-1
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
PRIMARY
FDA UNII
0RBV727H71
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
PRIMARY
DRUG BANK
DB00132
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
PRIMARY
MERCK INDEX
M6831
Created by admin on Sat Jun 26 13:57:36 UTC 2021 , Edited by admin on Sat Jun 26 13:57:36 UTC 2021
PRIMARY Merck Index
Related Record Type Details
LIPID -> FATTY ACID
Values are % of total.
LIPID -> FATTY ACID
MAY BE PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
Value is fatty acid composition (%) for international corn oil w/std. deviation of 0.4% LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
LIPID -> FATTY ACID
VARIES ACCORDING TO METHOD OF EXTRACTION
PARENT -> CONSTITUENT ALWAYS PRESENT
From Cannabis seed oil.
PARENT->INNOVATOR
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
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)
LIPID -> FATTY ACID
LIPID -> FATTY ACID
Durkee Industrial Foods, Cleveland, Ohio(average value). Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
LIPID -> FATTY ACID
Value is fatty acid composition (%) for US corn oil w/std. deviation of 0.39% LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
LIPID -> FATTY ACID
IOOC limits
Related Record Type Details
ACTIVE MOIETY