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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 Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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

1996
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
High susceptibility to paraquat-driven lipid peroxidation of cultured hepatocytes loaded with linolenic acid.
1995 Jul
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
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
Dietary alpha-linolenic acid is associated with reduced risk of fatal coronary heart disease, but increased prostate cancer risk: a meta-analysis.
2004 Apr
Effect of chemical penetration enhancer and iontophoresis on the in vitro percutaneous absorption enhancement of insulin through porcine epidermis.
2005
TRPV1 is a novel target for omega-3 polyunsaturated fatty acids.
2007 Jan 15
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
Discovery of a potent and selective GPR120 agonist.
2012 May 10
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 Fri Dec 15 18:39:45 GMT 2023
Edited
by admin
on Fri Dec 15 18:39:45 GMT 2023
Record UNII
I5OYY436YI
Record Status Validated (UNII)
Record Version
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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 Fri Dec 15 18:39:45 GMT 2023 , Edited by admin on Fri Dec 15 18:39:45 GMT 2023
PRIMARY
PUBCHEM
23676667
Created by admin on Fri Dec 15 18:39:45 GMT 2023 , Edited by admin on Fri Dec 15 18:39:45 GMT 2023
PRIMARY
CAS
822-18-4
Created by admin on Fri Dec 15 18:39:45 GMT 2023 , Edited by admin on Fri Dec 15 18:39:45 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE