Structure Database (LMSD)

Common Name
EPA (d5)
Systematic Name
5Z,8Z,11Z,14Z,17Z-eicosapentaenoic acid (d5)
Synonyms
LM ID
LMFA01030761
Formula
Exact Mass
Calculate m/z
307.255965
Status
Curated

Classification

Biological Context

Eicosapentaenoic acid-d5 (EPA-d5) is intended for use as an internal standard for the quantification of EPA by GC- or LC-MS. EPA is an ω-3 fatty acid abundantly available in marine organisms. It is oxygenated by COX-1 and COX-2 at rates of about 5% and 30%, respectively, compared to arachidonic acid.1 EPA has been shown to offer protection against coronary heart disease, thrombosis, ischemic brain injury, scaly dermatitis, and some inflammatory diseases.2,3 EPA-d5 MaxSpec® standard is a quantitative grade standard of EPA-d5 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 EPA-d5 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. Wada, M., DeLong, C.J., Hong, Y.H., et al. Enzymes and receptors of prostaglandin pathways with arachidonic acid-derived versus eicosapentaenoic acid-derived substrates and products. The Journal of Biological Chemisty 282(31), 22254-22266 (2007).
2. Yerram, N.R., Moore, S.A., and Spector, A.A. Eicosapentaenoic acid metabolism in brain microvessel endothelium: Effect on prostaglandin formation. J. Lipid Res. 30(11), 1747-1757 (1989).
3. Takeuchi, H., Inoue, J., Yoshida, M., et al. Dietary effects of n-3 eicosapentaenoic acid on essential fatty acid-deficiency symptoms of rats. Agric. Biol. Chem. 53(12), 3225-3232 (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)
JAZBEHYOTPTENJ-YSTLBCQOSA-N
InChi (Click to copy)
InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-/i1D3,2D2
SMILES (Click to copy)
OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C([2H])([2H])C([2H])([2H])[2H]

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID

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Created at
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Updated at
29th Jan 2021