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

Details

Stereochemistry ACHIRAL
Molecular Formula C18H30O2
Molecular Weight 278.4296
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 3
Charge 0

SHOW SMILES / InChI
Structure of LINOLENIC ACID

SMILES

CC\C=C/C\C=C/C\C=C/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 278.4296
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
Supplementation with flaxseed oil versus sunflowerseed oil in healthy young men consuming a low fat diet: effects on platelet composition and function.
1995 Mar
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
Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha.
1999 Jul 14
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
Alpha-linolenic acid and the risk of prostate cancer. What is the evidence?
2004 Apr
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
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
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
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
PKC activation by resveratrol derivatives with unsaturated aliphatic chain.
2012
Repeated systemic administration of the nutraceutical alpha-linolenic acid exerts neuroprotective efficacy, an antidepressant effect and improves cognitive performance when given after soman exposure.
2015 Dec
Association of serum aryl hydrocarbon receptor activity and RBC omega-3 polyunsaturated fatty acids with flow-mediated dilation in healthy, young Hispanic cigarette smokers.
2015 Jan 22
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 Dec 17 17:24:29 UTC 2022
Edited
by admin
on Sat Dec 17 17:24:29 UTC 2022
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
(9Z,12Z,15Z)-OCTADECA-9,12,15-TRIENOIC ACID
Systematic 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 [WHO-DD]
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
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 Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
CFR 21 CFR 357.210
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
NCI_THESAURUS C493
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
NCI_THESAURUS C68403
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
DSLD 1029 (Number of products:525)
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
Code System Code Type Description
NCI_THESAURUS
C997
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
EVMPD
SUB21884
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
RXCUI
595958
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
ALTERNATIVE
CHEBI
27432
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
ECHA (EC/EINECS)
207-334-8
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
NSC
2042
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
PUBCHEM
5280934
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
EVMPD
SUB34619
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
WIKIPEDIA
ALPHA-LINOLENIC ACID
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
DRUG CENTRAL
4618
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
RXCUI
52071
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
CHEBI
32387
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
EPA CompTox
DTXSID7025506
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
DAILYMED
0RBV727H71
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
MESH
D017962
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
CAS
463-40-1
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
FDA UNII
0RBV727H71
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
DRUG BANK
DB00132
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY
MERCK INDEX
M6831
Created by admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
PRIMARY Merck Index
Related Record Type Details
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)
PARENT -> CONSTITUENT ALWAYS PRESENT
From Cannabis seed oil.
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
TURKISH SOURCE
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
ALWAYS PRESENT
LIPID -> FATTY ACID
Values are % of total.
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
VARIES ACCORDING TO METHOD OF EXTRACTION
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 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)
Related Record Type Details
ACTIVE MOIETY