An analytical standard for detection and quantitation of a PGD2 impurity
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Diastereomer(s)
12010Prostaglandin D2
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5-trans Prostaglandin D2

Item No. 12210

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,15S-dihydroxy-11-oxo-prosta-5E,13E-dien-1-oic acid
CAS Number
2202725-84-4
Synonyms
  • 5,6-trans PGD2
Molecular Formula
C20H32O5
Formula Weight
352.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 100 mg/mlDMSO: 50 mg/mlEthanol: 75 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
O[C@@H](C1)[C@H](C/C=C/CCCC(O)=O)[C@@H](/C=C/[C@@H](O)CCCCC)C1=O
InChi Code
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4+,13-12+/t15-,16+,17+,18-/m0/s1
InChi Key
BHMBVRSPMRCCGG-IAVHXZOJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    PGD2 is one of the five primary enzymatic prostaglandins derived directly from PGH2. PGD2 is produced abundantly in the CSF by the lipocalin-type PGD synthase, and in the periphery by myeloid cells, including mast cells and basophils, by leukocyte-type PGD synthase.1,2 5-trans PGD2 is an isomer of PGD2 wherein the double bond between carbons 5 and 6 has been changed from cis (Z) to trans (E). The trans isomer of prostaglandin D2 (PGD2) occurs as an impurity between 2-5% in most commercial preparations of the bulk drug product. This compound was prepared primarily as an analytical standard for detection and quantitation of this impurity. From what can be inferred from the study of other trans isomers of F-type prostaglandins, the biological activity of 5-trans PGD2 is likely to be similar to that of the cis isomer. However, there are no specific published reports on the biological activity of 5-trans PGD2.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mahmud, I., Ueda, N., Yamaguchi, H., et al. Prostaglandin D synthase in human megakaryoblastic cells. The Journal of Biological Chemisty 272(45), 28263-28266 (1997).

    2. Ujihara, M., Urade, Y., Eguchi, N., et al. Prostaglandin D2 formation and characterization of its synthetases in various tissues of adult rats. Arch. Biochem. Biophys. 260(2), 521-531 (1988).