Structure Database (LMSD)
Common Name
alpha-Linolenic acid
Systematic Name
9Z,12Z,15Z-octadecatrienoic acid
Synonyms
- cis-9, cis-12, cis-15-octadecatrienoic acid
- C18:3n-3,6,9
3D model of alpha-Linolenic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
α-Linolenic acid is an essential ω-3 polyunsaturated fatty acid found in plants.1 In vivo, it is converted to the longer-chain fatty acids eicosapentaenoic , docosapentaenoic , or docosahexaenoic acid .2 It is also catabolized via fatty acid β-oxidation for energy or the synthesis of saturated and monounsaturated fatty acids, or stored in adipose tissue. Dietary consumption of α-linolenic acid-containing foods is positively associated with a moderately lower risk of cardiovascular disease.1 α-Linolenic Acid MaxSpec® standard is a quantitative grade standard of α-linolenic acid that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. The verified concentration is provided on the certificate of analysis. This α-linolenic acid MaxSpec® standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.
This information has been provided by Cayman Chemical
References
2. Burdge, G.C. Metabolism of α-linolenic acid in humans. Prostaglandins Leukot. Essent. Fatty Acids 75(3), 161-168 (2006).
Reactions
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Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Homo sapiens
(#9606)
Mammalia
(#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
J Lipid Res, 2010
Pubmed ID:
20671299
DOI:
10.1194/jlr.M009449
String Representations
InChiKey (Click to copy)
DTOSIQBPPRVQHS-PDBXOOCHSA-N
InChi (Click to copy)
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-
SMILES (Click to copy)
C(CCCCCCC(=O)O)/C=C\C/C=C\C/C=C\CC
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
DFA0191
PubChem CID
PlantFA ID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
20
Rings
0
Aromatic Rings
0
Rotatable Bonds
13
Van der Waals Molecular Volume
326.98
Topological Polar Surface Area
37.30
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
2
logP
5.66
Molar Refractivity
86.90
Admin
Created at
-
Updated at
25th Apr 2022