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-
| Molecular Formula | C18H30O2 |
| Molecular Weight | 278.4296 |
| Charge | 0 |
| 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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: O60427|||Q96SV3 Gene ID: 3992.0 Gene Symbol: FADS1 Target Organism: Homo sapiens (Human) |
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Target ID: O95864 Gene ID: 9415.0 Gene Symbol: FADS2 Target Organism: Homo sapiens (Human) |
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 |
|---|---|---|
| Glucose, insulin and platelet fatty acids following myocardial infarction: an association with infarct size. | 1987 Jul-Aug |
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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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| High susceptibility to paraquat-driven lipid peroxidation of cultured hepatocytes loaded with linolenic acid. | 1995 Jul |
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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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| Preferential uptake of long chain polyunsaturated fatty acids by isolated human placental membranes. | 1996 Feb 9 |
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| Effects of butter oil blends with increased concentrations of stearic, oleic and linolenic acid on blood lipids in young adults. | 1999 Jul |
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| Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. | 1999 Jul 14 |
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| Polyunsaturated fatty acids are potent neuroprotectors. | 2000 Apr 17 |
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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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| 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 |
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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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| 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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| Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. | 2002 Nov 19 |
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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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| The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids. | 2003 Mar 28 |
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| Dietary alpha-linolenic acid is associated with reduced risk of fatal coronary heart disease, but increased prostate cancer risk: a meta-analysis. | 2004 Apr |
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| Alpha-linolenic acid and the risk of prostate cancer. What is the evidence? | 2004 Apr |
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| Polyunsaturated fatty acids are FXR ligands and differentially regulate expression of FXR targets. | 2004 Aug |
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| Dietary alpha-linolenic acid reduces COX-2 expression and induces apoptosis of hepatoma cells. | 2004 Feb |
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| Effect of chemical penetration enhancer and iontophoresis on the in vitro percutaneous absorption enhancement of insulin through porcine epidermis. | 2005 |
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| 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 |
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| Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120. | 2005 Jan |
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| Specificity of receptor-ligand interactions and their effect on dimerisation as observed by electrospray mass spectrometry: bile acids form stable adducts to the RXRalpha. | 2005 Nov |
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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 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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| Prostate tissue and leukocyte levels of n-3 polyunsaturated fatty acids in men with benign prostate hyperplasia or prostate cancer. | 2006 Feb |
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| PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver. | 2006 May |
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| Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation. | 2006 Nov |
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| The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. | 2006 Nov 25 |
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| TRPV1 is a novel target for omega-3 polyunsaturated fatty acids. | 2007 Jan 15 |
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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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| 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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| Cross-talk between vitamin D receptor (VDR)- and peroxisome proliferator-activated receptor (PPAR)-signaling in melanoma cells. | 2009 Sep |
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| Differential effects of steroids on the synthesis of polyunsaturated fatty acids by human neuroblastoma cells. | 2009 Sep |
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| Activation of the nuclear receptor PPARÎł by metabolites isolated from sage (Salvia officinalis L.). | 2010 Oct 28 |
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| PKC activation by resveratrol derivatives with unsaturated aliphatic chain. | 2012 |
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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 |
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| Alpha-linolenic acid is a potent neuroprotective agent against soman-induced neuropathology. | 2012 Oct |
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| Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice. | 2013 Jul 5 |
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| 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 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.
| Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 04:48:07 GMT 2023
by
admin
on
Sat Dec 16 04:48:07 GMT 2023
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| Record UNII |
0RBV727H71
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| Record Status |
Validated (UNII)
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| Record Version |
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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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C68403
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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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SUB34619
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ALPHA-LINOLENIC ACID
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4618
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DTXSID7025506
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0RBV727H71
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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 |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
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LIPID -> FATTY ACID |
MAY BE PRESENT
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LIPID -> FATTY ACID |
Value is fatty acid composition (%) for international corn oil w/std. deviation of 0.4%
LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
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PARENT -> CONSTITUENT ALWAYS PRESENT |
From Cannabis seed oil.
|
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LIPID -> FATTY ACID |
Values are % of total.
|
||
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LIPID -> FATTY ACID |
TURKISH SOURCE
|
||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
|
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SALT/SOLVATE -> PARENT |
|
||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
|
||
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LIPID -> FATTY ACID |
VARIES ACCORDING TO METHOD OF EXTRACTION
|
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
|
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LIPID -> FATTY ACID |
ALWAYS PRESENT
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LIPID -> FATTY ACID |
Values are % of weight of fatty acid composition.
O?Connor, RT, Herb, SF; J Am Oil Chem Soc 47, 186A, 195A, 197A(1970)(range)
Brignoli, CA et al: J Am Diet Assoc 68, 224(1976)(average)
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LIPID -> FATTY ACID |
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LIPID -> FATTY ACID |
Durkee Industrial Foods, Cleveland, Ohio(average value).
Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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LIPID -> FATTY ACID |
Values given are in undefined precent.
Average is typical for U.S. Sunflower oil.
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||
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LIPID -> FATTY ACID |
Value is fatty acid composition (%) for US corn oil w/std. deviation of 0.39%
LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
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ACTIVE MOIETY |
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