Structure Database (LMSD)

Common Name
10E,12Z-octadecadienoic acid
Systematic Name
10E,12Z-octadecadienoic acid
Synonyms
  • trans-10, cis-12-octadecadienoic acid
  • C18:2n-6,8
  • 10(E),12(Z)-ODE
LM ID
LMFA01030125
Formula
C18H32O2
Exact Mass
Calculate m/z
280.24023
Sum Composition
FA 18:2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Octadecanoids [FA02]

Biological Context

Conjugated linoleic acid (CLA) refers to a family of 8 geometric isomers of linoleic acid in which the two double bonds are contiguous. (The predominant form of linoleic acid in nature, 18:ω6, has double bonds at 9 and 12, interrupted by a methylene carbon.) CLA is found in both meat and dairy products, but it is not found to any significant degree in plants. The predominant isomer of CLA in animal tissue is 9Z,11E; smaller amounts of 10E,12Z also occur. Various antioxidant and antitumor activities have been attributed to CLA or its downstream metabolites.1 Reported health benefits of dietary supplementation with CLA have been attributed variously to competitive inhibition of Δ6-desaturase and/or PPARγ activation.2 [Matreya, LLC. Catalog No. 1249]

This information has been provided by Cayman Chemical

References

1. Houseknecht, K.L., Vanden Heuvel, J.P., Moya-Camarena, S.Y., et al. Dietary conjugated linoleic acid normalizes impaired glucose tolerance in the Zucker diabetic fatty fa/fa rat. Biochem. Biophys. Res. Commun. 244(3), 678-682 (1998).
2. Shultz, T.D., Chew, B.P., Seaman, W.R., et al. Inhibitory effect of conjugated dienoic derivatives of linoleic acid and β-carotene on the in vitro growth of human cancer cells. Cancer Lett. 63(2), 125-133 (1992).

Reactions

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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Lactiplantibacillus plantarum (#1590)
Bacilli (#91061)
Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition.,
Proc Natl Acad Sci U S A, 2013
Pubmed ID: 24127592

String Representations

InChiKey (Click to copy)
GKJZMAHZJGSBKD-NMMTYZSQSA-N
InChi (Click to copy)
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-9H,2-5,10-17H2,1H3,(H,19,20)/b7-6-,9-8+
SMILES (Click to copy)
C(=C/C=C\CCCCC)\CCCCCCCCC(=O)O

Other Databases

CHEBI ID
44526
LIPIDBANK ID
DFA0164
PubChem CID
5282800
PlantFA ID
10783
Cayman ID
90145
PDB ID
ODD

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 329.62
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 5.88
Molar Refractivity 86.99

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Created at
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Updated at
5th Jan 2023