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463-40-1 molecular structure
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(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid

ChemBase ID: 18
Molecular Formular: C18H30O2
Molecular Mass: 278.4296
Monoisotopic Mass: 278.2245802
SMILES and InChIs

SMILES:
OC(=O)CCCCCCC/C=C\C/C=C\C/C=C\CC
Canonical SMILES:
CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O
InChI:
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-
InChIKey:
DTOSIQBPPRVQHS-PDBXOOCHSA-N

Cite this record

CBID:18 http://www.chembase.cn/molecule-18.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
IUPAC Traditional name
α-linolenic acid
α linolenic acid
Synonyms
(9Z,12Z,15Z)-Octadecatrienoic acid
9,12,15-Octadecatrienoic acid
ALA
alpha-Linolenate
linolenate
Alpha-Linolenic Acid
(9Z,12Z,15Z)-9,12,15-Octadecatrienoic Acid
(Z,Z,Z)-Octadeca-9,12,15-trienoic Acid
(all-Z)-9,12,15-Octadecatrienoic Acid
9,12,15-all-cis-Octadecatrienoic Acid
all-cis-9,12,15-Octadecatrienoic Acid
cis-Δ9,12,15-Octadecatrienoic acid
α-Linolenic Acid
Linolenic Acid
CAS Number
463-40-1
PubChem SID
160963481
46507620
PubChem CID
5280934

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
L467650 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.9881673  H Acceptors
H Donor LogD (pH = 5.5) 5.4320216 
LogD (pH = 7.4) 3.6783652  Log P 6.059955 
Molar Refractivity 89.6354 cm3 Polarizability 33.692265 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds 13 
Lipinski's Rule of Five false 
Log P 6.62  LOG S -6.02 
Solubility (Water) 2.66e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
0.000124 mg/mL at 25 oC [MEYLAN,WM et al. (1996)] expand Show data source
Chloroform expand Show data source
Methanol expand Show data source
Apperance
Colorless Oil expand Show data source
Hydrophobicity(logP)
5.8 expand Show data source
Storage Condition
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

TRC TRC DrugBank DrugBank
Toronto Research Chemicals - L467650 external link
An essential fatty acid. Occurs as the glyceride in most drying oils. Nutrient.
DrugBank - DB00132 external link
Item Information
Drug Groups approved; nutraceutical
Description Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. [Wikipedia]
Indication For nutritional supplementation and for treating dietary shortage or imbalance.
Pharmacology Alpha Linolenic Acid (ALA) is an 18-carbon polyunsaturated fatty acid with three double bonds. It is also called an omega-3 fatty acid, and is essential for all mammals. Alpha-linolenic acid (or omega 3 fatty acid) intake can decrease the risk of cardiovascular diseases by 1) preventing arrhythmias that can lead to sudden cardiac death, 2) decreasing the risk of thrombosis (blood clot formation) that can lead to heart attack or stroke, 3) decreasing serum triglyceride levels, 4) slowing the growth of atherosclerotic plaque, 5) improving vascular endothelial function, 6) lowering blood pressure slightly, and 7) decreasing inflammation. ALA deficiencies can lead to visual problems and sensory neuropathy. Scaly and hemorrhagic skin or scalp inflammations may also develop.
Affected Organisms
Humans and other mammals
References
Kris-Etherton PM, Harris WS, Appel LJ: Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation. 2002 Nov 19;106(21):2747-57. [Pubmed]
Connor WE: Importance of n-3 fatty acids in health and disease. Am J Clin Nutr. 2000 Jan;71(1 Suppl):171S-5S. [Pubmed]
Brouwer IA, Katan MB, Zock PL: Dietary alpha-linolenic acid is associated with reduced risk of fatal coronary heart disease, but increased prostate cancer risk: a meta-analysis. J Nutr. 2004 Apr;134(4):919-22. [Pubmed]
Cho E, Hung S, Willett WC, Spiegelman D, Rimm EB, Seddon JM, Colditz GA, Hankinson SE: Prospective study of dietary fat and the risk of age-related macular degeneration. Am J Clin Nutr. 2001 Feb;73(2):209-18. [Pubmed]
Lauritzen I, Blondeau N, Heurteaux C, Widmann C, Romey G, Lazdunski M: Polyunsaturated fatty acids are potent neuroprotectors. EMBO J. 2000 Apr 17;19(8):1784-93. [Pubmed]
External Links
Wikipedia

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Kris-Etherton PM, Harris WS, Appel LJ: Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease. Circulation. 2002 Nov 19;106(21):2747-57. Pubmed
  • • Connor WE: Importance of n-3 fatty acids in health and disease. Am J Clin Nutr. 2000 Jan;71(1 Suppl):171S-5S. Pubmed
  • • Brouwer IA, Katan MB, Zock PL: Dietary alpha-linolenic acid is associated with reduced risk of fatal coronary heart disease, but increased prostate cancer risk: a meta-analysis. J Nutr. 2004 Apr;134(4):919-22. Pubmed
  • • Cho E, Hung S, Willett WC, Spiegelman D, Rimm EB, Seddon JM, Colditz GA, Hankinson SE: Prospective study of dietary fat and the risk of age-related macular degeneration. Am J Clin Nutr. 2001 Feb;73(2):209-18. Pubmed
  • • Lauritzen I, Blondeau N, Heurteaux C, Widmann C, Romey G, Lazdunski M: Polyunsaturated fatty acids are potent neuroprotectors. EMBO J. 2000 Apr 17;19(8):1784-93. Pubmed
  • • Folch, J., et al.: J. Biol. Chem., 226, 497 (1957)
  • • Orban, E., et al.: J. Food Sci., 68, 128 (1957)
  • • Tritt, K., et al.: J. Agric. Food Chem., 53, 5304 (1957)
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PATENTS

PATENTS

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INTERNET

INTERNET

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