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.
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 |
|||
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 Date8.3920323E11 |
PubMed
Title | Date | PubMed |
---|---|---|
Supplementation with flaxseed oil versus sunflowerseed oil in healthy young men consuming a low fat diet: effects on platelet composition and function. | 1995 Mar |
|
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 |
|
Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. | 1999 Jul 14 |
|
Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates. | 2001 Jan 15 |
|
Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. | 2002 Nov 19 |
|
Alpha-linolenic acid and the risk of prostate cancer. What is the evidence? | 2004 Apr |
|
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 |
|
Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120. | 2005 Jan |
|
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 |
|
Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation. | 2006 Nov |
|
TRPV1 is a novel target for omega-3 polyunsaturated fatty acids. | 2007 Jan 15 |
|
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 |
|
PKC activation by resveratrol derivatives with unsaturated aliphatic chain. | 2012 |
|
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
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 17 17:24:29 UTC 2022
by
admin
on
Sat Dec 17 17:24:29 UTC 2022
|
Record UNII |
0RBV727H71
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
DSLD |
2830 (Number of products:52)
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
||
|
CFR |
21 CFR 357.210
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
||
|
NCI_THESAURUS |
C493
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
||
|
NCI_THESAURUS |
C68403
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
||
|
DSLD |
1029 (Number of products:525)
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
C997
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
SUB21884
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
595958
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
ALTERNATIVE | |||
|
27432
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
207-334-8
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
2042
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
5280934
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
SUB34619
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
ALPHA-LINOLENIC ACID
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
4618
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
52071
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
32387
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
DTXSID7025506
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
0RBV727H71
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
D017962
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
463-40-1
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
0RBV727H71
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
DB00132
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | |||
|
M6831
Created by
admin on Sat Dec 17 17:24:32 UTC 2022 , Edited by admin on Sat Dec 17 17:24:32 UTC 2022
|
PRIMARY | Merck Index |
Related Record | Type | Details | ||
---|---|---|---|---|
|
LIPID -> FATTY ACID |
MAY BE PRESENT
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
|
||
|
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)
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
From Cannabis seed oil.
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
|
||
|
LIPID -> FATTY ACID |
TURKISH SOURCE
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
LIPID -> FATTY ACID |
ALWAYS PRESENT
|
||
|
LIPID -> FATTY ACID |
Values are % of total.
|
||
|
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)
|
||
|
LIPID -> FATTY ACID |
|
||
|
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)
|
||
|
LIPID -> FATTY ACID |
VARIES ACCORDING TO METHOD OF EXTRACTION
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
|
||
|
LIPID -> FATTY ACID |
Values given are in undefined precent.
Average is typical for U.S. Sunflower oil.
|
||
|
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)
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|