Structure Database (LMSD)
Common Name
9-elaidic acid
Systematic Name
9E-octadecenoic acid
Synonyms
- trans-9-octadecenoic acid
- C18:1n-9
- Elaidinic acid
- trans-Elaidic acid
- trans-Oleic acid
3D model of 9-elaidic 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
Elaidic acid is a monounsaturated trans fatty acid and the 9-trans isomer of oleic acid that has been found in partially hydrogenated cooking oils.1 It reduces HHT and HETE formation and increases synthesis of prostaglandin E2 (PGE2), PGF2α , PGD2 , and thromboxane B2 (TXB2) induced by arachidonic acid in isolated human platelets. Elaidic acid (0.1-5 mmol/L) induces apoptosis in human umbilical vein endothelial cells (HUVECs).2 In vivo, elaidic acid (100 mg/kg) reduces cardiac and hepatic autophagy induced by palmitic acid in mice.3
This information has been provided by Cayman Chemical
References
1. Srivastava, K.C., and Awasthi, K.K. A comparative study on the effect of cis (oleic, linoleic) and trans (elaidic, linoelaidic) fatty acids on the in vitro prostaglandin biosynthesis in human blood platelets from (1-14C) arachidonic acid. Prostaglandins Leukot. Med. 9(6), 669-684 (1982).
2. Zapolska-Downar, D., Kośmider, A., and Naruszewicz, M. Trans fatty acids induce apoptosis in human endothelial cells. J. Physiol. Pharmacol. 56(4), 611-625 (2005).
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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String Representations
InChiKey (Click to copy)
ZQPPMHVWECSIRJ-MDZDMXLPSA-N
InChi (Click to copy)
InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+
SMILES (Click to copy)
C(/CCCCCCCC)=C\CCCCCCCC(=O)O
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
DFA0112
PubChem CID
PlantFA ID
SwissLipids ID
Cayman ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
20
Rings
0
Aromatic Rings
0
Rotatable Bonds
15
Van der Waals Molecular Volume
332.26
Topological Polar Surface Area
37.30
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
2
logP
6.11
Molar Refractivity
87.09
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Created at
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Updated at
25th Apr 2022