LIPID MAPS

Structure Database (LMSD)

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Common Name

(+/-)11,12-DiHETrE-d11

Systematic Name

(+-)11,12-dihydroxy-5Z,8Z,14Z-eicosatrienoic-16,16,17,17,18,18,19,19,20,20,20-d11 acid

Synonyms

11,12-DHET-d11

LM ID

LMFA03050033

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

(±)11(12)-DiHET-d11 is intended for use as an internal standard for the quantification of 11(12)-DiHET by GC- or LC-MS. 11(S),12(S)-DiHET and 11(R),12(R)-DiHET are vicinal diols formed via enzymatic hydration of 11(12)-EET by cytosolic or soluble epoxide hydrolases in a non-stereoselective manner.^1,2,3

This information has been provided by Cayman Chemical

References

1. Fang, X., Kaduce, T.L., Weintraub, N.L., et al. Functional implications of a newly characterized pathway of 11,12-epoxyeicosatrienoic acid metabolism in arterial smooth muscle. Circ. Res. 79(4), 784-793 (1996).

2. 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).

3. 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)

LRPPQRCHCPFBPE-KPONSFRYSA-N

InChi (Click to copy)

InChI=1S/C20H34O4/c1-2-3-4-5-9-12-15-18(21)19(22)16-13-10-7-6-8-11-14-17-20(23)24/h6,8-10,12-13,18-19,21-22H,2-5,7,11,14-17H2,1H3,(H,23,24)/b8-6-,12-9-,13-10-/i1D3,2D2,3D2,4D2,5D2

SMILES (Click to copy)

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