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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

Description

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.

Originator

Approval Year

1994
155
Targets

Targets

Primary TargetPharmacologyConditionPotency
Fatty acid desaturase 1
4
Target ID: O60427|||Q96SV3
Gene ID: 3992.0
Gene Symbol: FADS1
Target Organism: Homo sapiens (Human)
Substrate
643
Fatty acid desaturase 2
5
Target ID: O95864
Gene ID: 9415.0
Gene Symbol: FADS2
Target Organism: Homo sapiens (Human)
Substrate
643
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8307
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
[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
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
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
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
Dietary alpha-linolenic acid reduces COX-2 expression and induces apoptosis of hepatoma cells.
2004 Feb
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
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
Activation of the nuclear receptor PPARγ by metabolites isolated from sage (Salvia officinalis L.).
2010 Oct 28
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
Patents

Patents

04297292
9
04704393
2
JP1075290A
2
JP2000282080A
5
JP2000512663A
45
JP2002315593A
2
JP2002537070A
15
JP2002538219A
9
JP2003522787A
12
JP2003526539A
2
JP2004329204A
2
JP2005179211A
2
JP2005509588A
19
JP2008035743A
2
JP2008142082A
2
JP2008289490A
2
JP2009149599A
9
JP2009522777A
13
JP2011507695A
19
JP2012500628A
4
JPH02188510A
2
JPH02226517A
2
JPH03167105A
3
JPH0398559A
2
JPH04108711A
4
JPH04341180A
2
JPH05194250A
6
JPH05213772A
2
JPH0570332A
2
JPH0625084A
3
JPH08277355A
2
JPH083069A
2
JPH09201176A
2
JPH09208435A
4
JPH10140010A
2
JPH1036899A
2
JPH1060358A
2
JPH11116503A
2
JPH11181234A
2
JPH11221091A
3
JPH1136140A
2
JPS57125273A
2
JPS5736944A
2
JPS61103826A
3
JPS61185571A
2
JPS6135763A
2
JPS62138411A
2
JPS6222569A
2
JPS6447701A
2

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
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
ACTIVE MOIETY
Structure of LINOLENIC ACID
SALT/SOLVATE (PARENT)
Structure of SODIUM LINOLENATE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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