9,11-methane-epoxy Prostaglandin F

Cayman Chemical Item Number 10007850

9,11-Epoxymethano PGH1 (CAS 72517-81-8)

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Description

Prostaglandin (PG) endoperoxides are intermediates in the biosynthesis of PGs, thromboxanes, and prostacyclin. The endoperoxides, PGH2 and PGG2, induce rapid and irreversible aggregation of human platelets.1 PGH1 and PGG1 are known to contract smooth muscle preparations, but are lacking in aggregatory effects. 9,11-methane-epoxy Prostaglandin F (9,11-methane-epoxy PGF) is a stable epoxymethano analog of PGH1 that produces a strong and dose-related aggregation of washed rabbit platelets (EC50 = 0.88 µM) and contraction of rabbit aortic strips (EC50 = 0.11 µM).1 9,11-methane-epoxy PGF induces contraction of guinea pig tracheas (EC50 = 3.4 µM) with a maximal contraction of about 60% of that caused by a submaximal dose of histamine.

1. Morita, A., Nishino, H., Hasegawa, K., et al. Biological activities of prostaglandin H1 analogs. Prostaglandins 18(4) 529-540 (1979).

Synonyms
  • 9,11-Epoxymethano PGH1
Formal Name 6-​(3-​hydroxy-​1-​octenyl)-​2-​oxabicyclo[2.2.1]heptane-​5-​heptanoic acid
CAS Number 72517-81-8
Molecular Formula C21H36O4
Formula Weight 352.5
Formulation A solution in methyl acetate
Purity >96%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CCCCC[C@H]​(O)​/C=C/[C@H]​1C2OCC(C2)​[C@@H]​1CCCCCCC(O)​=O
InCHI Code
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​1S/C21H36O4/c1-2-3-6-9-17(22)​12-13-19-18(16-14-20(19)​25-15-16)​10-7-4-5-8-11-21(23)​24/h12-13,16-20,22H,2-11,14-15H2,1H3,(H,23,24)​/b13-12+/t16-,17+,18-,19-,20-/m1/s1
InCHI Key
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VGRVXLWYKKBTNM-CQGVCJOOSA-N

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Background Reading

Morita, A., Nishino, H., Hasegawa, K., et al. Biological activities of prostaglandin H1 analogs. Prostaglandins 18(4) 529-540 (1979).

9,11-methane-epoxy Prostaglandin F is available in the following screening library:

Size Price Quantity Subtotal
100 µg $36.00 $0.00
500 µg $162.00 $0.00
1 mg $288.00 $0.00
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