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
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-
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: O60427|||Q96SV3 Gene ID: 3992.0 Gene Symbol: FADS1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17409318 |
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Target ID: O95864 Gene ID: 9415.0 Gene Symbol: FADS2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17409318 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Intralipid Approved UseIntralipid® 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 Date8.3920323E11 |
PubMed
Title | Date | PubMed |
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[Biological effects on premature neonates of a milk formula enriched with alpha-linolenic acid: a multicenter study]. | 1994 Feb |
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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 |
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Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes. | 1995 Dec 1 |
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Nutritional attributes of traditional flaxseed in healthy young adults. | 1995 Jan |
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Supplementation with flaxseed oil versus sunflowerseed oil in healthy young men consuming a low fat diet: effects on platelet composition and function. | 1995 Mar |
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Importance of n-3 fatty acids in health and disease. | 2000 Jan |
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Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions. | 2000 Jun 20 |
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Identification of a fatty acid delta6-desaturase deficiency in human skin fibroblasts. | 2001 Apr |
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Prospective study of dietary fat and the risk of age-related macular degeneration. | 2001 Feb |
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Adipose tissue alpha-linolenic acid and nonfatal acute myocardial infarction in Costa Rica. | 2003 Apr 1 |
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A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs. | 2003 Feb 7 |
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Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40. | 2003 Mar 13 |
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Dietary alpha-linolenic acid reduces COX-2 expression and induces apoptosis of hepatoma cells. | 2004 Feb |
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Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120. | 2005 Jan |
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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 |
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Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes. | 2008 Jan |
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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 |
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Activation of the nuclear receptor PPARγ by metabolites isolated from sage (Salvia officinalis L.). | 2010 Oct 28 |
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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 |
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Discovery of a potent and selective GPR120 agonist. | 2012 May 10 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25889793
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28520897
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.
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Classification Tree | Code System | Code | ||
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DSLD |
2830 (Number of products:52)
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CFR |
21 CFR 357.210
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NCI_THESAURUS |
C493
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NCI_THESAURUS |
C68403
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DSLD |
1029 (Number of products:525)
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C997
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SUB21884
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595958
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27432
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207-334-8
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2042
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5280934
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SUB34619
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ALPHA-LINOLENIC ACID
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4618
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52071
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32387
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DTXSID7025506
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0RBV727H71
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D017962
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463-40-1
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0RBV727H71
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DB00132
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M6831
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PRIMARY | Merck Index |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)