ent-Prostaglandin E2

Cayman Chemical Item Number 10008294

ent-PGE2 (CAS 65085-69-0)

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Description

Enzymatically-derived prostaglandin E2 (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

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. J Biol Chem 278(31) 28479-28489 (2003).

Synonyms
  • ent-PGE2
Formal Name 9-​oxo-​11β,​15R-​dihydroxy-​(8β,​12α)-​prosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 65085-69-0
Molecular Formula C20H32O5
Formula Weight 352.5
Formulation A solution in methyl acetate
Purity >98%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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O=C1[C@@H]​(C/C=C\CCCC(O)​=O)​[C@H]​(/C=C/[C@H]​(O)​CCCCC)​[C@@H]​(O)​C1
InCHI Code
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​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
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XEYBRNLFEZDVAW-OBUVHCMGSA-N

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ent-Prostaglandin E2 is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $57.00 $0.00
5 mg $257.00 $0.00
10 mg $456.00 $0.00
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Cart Total $0.00

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Pricing updated 2015-03-30. Prices are subject to change without notice.

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Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

Upon receipt, it is important to check the storage requirements of your products and place them at the appropriate temperature. Products shipped without ice may require frozen storage for long term stability.

Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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1180 East Ellsworth Road

Ann Arbor, Michigan 48108 USA

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