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 |
|---|---|---|---|
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 |
|---|---|---|---|---|
| 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 Date1996 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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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| Preferential uptake of long chain polyunsaturated fatty acids by isolated human placental membranes. | 1996 Feb 9 |
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| Importance of n-3 fatty acids in health and disease. | 2000 Jan |
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| Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates. | 2001 Jan 15 |
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| A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs. | 2003 Feb 7 |
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| 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 |
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| The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. | 2006 Nov 25 |
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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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| Changing ratios of omega-6 to omega-3 fatty acids can differentially modulate polychlorinated biphenyl toxicity in endothelial cells. | 2008 Mar 10 |
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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 ÎĽM), PSO (425 ÎĽM), 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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100000088243
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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)