Structure Database (LMSD)

Common Name
9S-HODE-d4
Systematic Name
9S-hydroxy-10E,12Z-octadecadienoic acid-d4
Synonyms
LM ID
LMFA02000231
Formula
Exact Mass
Calculate m/z
300.260253
Status
Curated

Classification

Biological Context

9(S)-HODE-d4 is intended for use as an internal standard for the quantification of 9-HODE by GC- or LC-MS. (±)-9-HODE is formed via non-enzymatic oxidation of linoleic acid .1 9(S)-HODE and 9(R)-HODE are formed by lipoxygenase- and cyclooxygenase-mediated oxidation of linoleic acid, respectively.2,3,4 9(S)-HODE-d4 MaxSpec® standard is a quantitative grade standard of 9(S)-HODE-d4 that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. This 9(S)-HODE-d4 MaxSpec® standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.

This information has been provided by Cayman Chemical

References

1. Spiteller, P., and Spiteller, G. 9-Hydroxy-10,12-octadecadienoic acid (9-HODE) and 13-hydroxy-9,11-octadecadienoic acid (13-HODE): Excellent markers for lipid peroxidation. Chem. Phys. Lipids 89(2), 131-139 (1997).
2. Godessart, N., Camacho, M., López-Belmonte, J., et al. Prostaglandin H-synthase-2 is the main enzyme involved in the biosynthesis of octadecanoids from linoleic acid in human dermal fibroblasts stimulated with interleukin-1β. J. Invest. Dermatol. 107(5), 726-732 (1996).
3. Kühn, H., Belkner, J., and Wiesner, R. Subcellular distribution of lipoxygenase products in rabbit reticulocyte membranes. Eur. J. Biochem. 191(1), 221-227 (1990).
4. Gardner, H.W. Soybean lipoxygenase-1 enzymically forms both (9S)- and (13S)-hydroperoxides from linoleic acid by a pH-dependent mechanism. Biochim. Biophys. Acta 1001(3), 274-281 (1989).

References

Comments
Synthetic deuterated standard

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
NPDSHTNEKLQQIJ-VKLCZNAWSA-N
InChi (Click to copy)
InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+/t17-/m1/s1/i6D,8D,14D,17D
SMILES (Click to copy)
C(CCCCCCC[C@]([2H])(O)/C(/[2H])=C/C(/[2H])=C(/[2H])\CCCCC)(=O)O

Other Databases

KEGG ID
HMDB ID
PubChem CID
Cayman ID

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Created at
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Updated at
29th Jan 2021