Structure Database (LMSD)

Common Name
10-oxo-12Z-octadecenoic acid-d5
Systematic Name
10-oxooctadec-12Z-enoic-17,17,18,18,18-d5 acid
Synonyms
  • 12(Z)-10-oxoOME-d5
LM ID
LMFA02000459
Formula
Exact Mass
Calculate m/z
301.266529
Status
Curated

Classification

Biological Context

10-oxo-12(Z)-Octadecenoic acid-d5 is intended for use as an internal standard for the quantification of 10-oxo-12(Z)-octadecenoic acid by GC- or LC-MS. 10-oxo-12(Z)-Octadecenoic acid is a metabolite of linoleic acid and an activator of transient receptor potential vanilloid 1 (TRPV1).1,2 It is formed from linoleic acid by conjugated linoleic acid dehydrogenase (CLA-DH) via a 10-hydroxy-12(Z)-octadecenoic acid intermediate and can also be produced from linoleic acid by gut microbiota.1 10-oxo-12(Z)-Octadecenoic acid (100 µM) selectively increases calcium levels in HEK293 cells expressing TRPV1 over those expressing TRPV2, TRPV3, TRPV4, and TRP melastatin 8 (TRPM8).2 It also induces inward currents in HEK293 cells expressing TRPV1, an effect that can be blocked by the TRPV1 antagonist capsazepine. Dietary administration of 10-oxo-12(Z)-octadecenoic acid (0.1% w/w) reduces weight gain and adipose tissue weight and increases the expression of the gene encoding mitochondrial uncoupling protein 1 (Ucp1) in wild-type, but not Trpv1 knockout, mice fed a high-fat diet. It also decreases plasma glucose and triglyceride levels in diabetic KKAy mice fed a high-fat diet.

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic deuterated standard

String Representations

InChiKey (Click to copy)
IEQLMTRAAYQDSD-PJKSMEJXSA-N
InChi (Click to copy)
InChI=1S/C18H32O3/c1-2-3-4-5-8-11-14-17(19)15-12-9-6-7-10-13-16-18(20)21/h8,11H,2-7,9-10,12-16H2,1H3,(H,20,21)/b11-8-/i1D3,2D2
SMILES (Click to copy)
C(C(C/C=C\CCCC([2H])([2H])C([2H])([2H])[2H])=O)CCCCCCCC(O)=O

Other Databases

PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 21
Rings
Aromatic Rings
Rotatable Bonds 15
Van der Waals Molecular Volume 338.41
Topological Polar Surface Area 54.37
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 5.29
Molar Refractivity 87.48

Admin

Created at
3rd Dec 2024
Updated at
5th Dec 2024