The opposite enantiomer of PGE2
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Isomer(s)
14010Prostaglandin E2
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ent-Prostaglandin E2

Item No. 10008294

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-oxo-11β,15R-dihydroxy-(8β,12α)-prosta-5Z,13E-dien-1-oic acid
CAS Number
65085-69-0
Synonyms
  • ent-PGE2
Molecular Formula
C20H32O5
Formula Weight
352.5
Purity
≥98%
Formulation (Request formulation change)
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 2 mg/ml
SMILES
O=C1[C@@H](C/C=C\CCCC(O)=O)[C@H](/C=C/[C@H](O)CCCCC)[C@@H](O)C1
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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m1/s1
InChi Key
XEYBRNLFEZDVAW-OBUVHCMGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Enzymatically-derived PGE2 is an optically pure compound whereas PGE2 derived from the free radical-catalyzed peroxidation of arachidonate is a racemic mixture. Ent-PGE2 is the opposite enantiomer of PGE2. Significant amounts of racemic PGE2 (rac-PGE2) are generated in vitro and in vivo in settings of oxidative stress via the isoprostane pathway. A proposed mechanism for the formation of rac-PGE2 involves the base catalyzed equilibration from 15-E2t-isoprostane (8-iso-PGE2), generated from the 15-H2t-isoprostane endoperoxide.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gao, L., Zackert, W.E., Hasford, J.J., et al. Formation of prostaglandin E2 and prostaglandin D2 via the isoprostane pathway: A mechanism for the generation of bioactive prostaglandins independent of the cyclooxygenase. The Journal of Biological Chemisty 278(31), 28479-28489 (2003).