LIPID MAPS

Structure Database (LMSD)

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Common Name

(+/-)8,9-DiHETrE-d11

Systematic Name

(+/-)8,9-dihydroxy-5Z,11Z,14Z-eicosatrienoic-16,16,17,17,18,18,19,19,20,20,20-d11

Synonyms

8,9-DiHET-d11

LM ID

LMFA03050035

Formula

C₂₀H₂₃D₁₁O₄

Exact Mass

Calculate m/z

349.314755

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View ion mobility data

View spectra on the LIPID MAPS® Standards Spectra Database

Classification

Biological Context

(±)8(9)-DiHET-d11 is intended for use as an internal standard for the quantification of 8(9)-DiHET by GC- or LC-MS. 8(S),9(S)-DiHET and 8(R),9(R)-DiHET are vicinal diols formed via enzymatic hydration of 8(9)-EET by cytosolic or soluble epoxide hydrolases.^1,2 8(S),9(S)-DiHET is produced at a greater proportion than 8(R),9(R)-DiHET by cytosolic epoxide hydrolase.¹

This information has been provided by Cayman Chemical

References

1. Zeldin, D.C., Kobayashi, J., Falck, J.R., et al. Regio- and enantiofacial selectivity of epoxyeicosatrienoic acid hydration by cytosolic epoxide hydrolase. The Journal of Biological Chemisty 268(9), 6402-6407 (1993).

2. Zhang, G., Kodani, S., and Hammock, B.D. Stabilized epoxygenated fatty acids regulate inflammation, pain, angiogenesis and cancer. Prog. Lipid Res. 53, 108-123 (2014).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

DCJBINATHQHPKO-BCEMLEMNSA-N

InChi (Click to copy)

InChI=1S/C20H34O4/c1-2-3-4-5-6-7-8-9-12-15-18(21)19(22)16-13-10-11-14-17-20(23)24/h6-7,9-10,12-13,18-19,21-22H,2-5,8,11,14-17H2,1H3,(H,23,24)/b7-6-,12-9-,13-10-/i1D3,2D2,3D2,4D2,5D2

SMILES (Click to copy)

C(C(O)C(O)C/C=C\CCCC(=O)O)/C=C\C/C=C\C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H]