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

Details

Stereochemistry ACHIRAL
Molecular Formula C18H29O2.Na
Molecular Weight 300.4114
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 3
Charge 0

SHOW SMILES / InChI
Structure of SODIUM LINOLENATE

SMILES

[Na+].CC\C=C/C\C=C/C\C=C/CCCCCCCC([O-])=O

InChI

InChIKey=UNZSHUCNBUBSGW-IFNWOZJISA-M
InChI=1S/C18H30O2.Na/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);/q;+1/p-1/b4-3-,7-6-,10-9-;

HIDE SMILES / InChI

Molecular Formula C18H29O2
Molecular Weight 277.4217
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 3
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
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
[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
Preferential uptake of long chain polyunsaturated fatty acids by isolated human placental membranes.
1996 Feb 9
Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha.
1999 Jul 14
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
Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates.
2001 Jan 15
Adipose tissue alpha-linolenic acid and nonfatal acute myocardial infarction in Costa Rica.
2003 Apr 1
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
Polyunsaturated fatty acids are FXR ligands and differentially regulate expression of FXR targets.
2004 Aug
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
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
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
Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes.
2008 Jan
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
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
Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice.
2013 Jul 5
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 Thu Jul 06 01:51:42 UTC 2023
Edited
by admin
on Thu Jul 06 01:51:42 UTC 2023
Record UNII
I5OYY436YI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM LINOLENATE
Common Name English
SODIUM .ALPHA.-LINOLENATE
Systematic Name English
9,12,15-OCTADECATRIENOIC ACID, SODIUM SALT, (9Z,12Z,15Z)-
Common Name English
LINOLENIC ACID, SODIUM SALT
Common Name English
Code System Code Type Description
FDA UNII
I5OYY436YI
Created by admin on Thu Jul 06 01:51:42 UTC 2023 , Edited by admin on Thu Jul 06 01:51:42 UTC 2023
PRIMARY
PUBCHEM
23676667
Created by admin on Thu Jul 06 01:51:42 UTC 2023 , Edited by admin on Thu Jul 06 01:51:42 UTC 2023
PRIMARY
CAS
822-18-4
Created by admin on Thu Jul 06 01:51:42 UTC 2023 , Edited by admin on Thu Jul 06 01:51:42 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE