Prostaglandin D2

• CAT Number: R023854
• CAS Number: 41598-07-6
• Molecular Formula: C20H32O5
• Molecular Weight: 352.471
• Purity: ≥95%
• Synonyms: (5Z,9α,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-oic Acid;?11-Dehydroprostaglandin F2α; PGD2
• Storage: -20°C
• IUPAC Name: (Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-3-oxocyclopentyl]hept-5-enoic acid
• InChI: 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
• InChIKey: BHMBVRSPMRCCGG-OUTUXVNYSA-N
• SMILES: CCCCCC(C=CC1C(C(CC1=O)O)CC=CCCCC(=O)O)O

Prostaglandin D2 (CAS 41598-07-6; PGD2 ) is the major eicosanoid product of mast cells and is released in large quantities during allergic and asthmatic anaphylaxis. Mastocytosis patients produce excessive amounts of PGD2, which causes vasodilation, flushing, hypotension, and syncopal episodes. PGD2 is also produced in the brain via an alternative pathway involving a soluble, secreted PGD-<wbr />synthase also known as β-<wbr />trace. In the brain, PGD2 produces normal physiological sleep and lowering of body temperature. Further pharmacological actions include inhibition of platelet aggregation and relaxation of vascular smooth muscle. PGD2 inhibits human ovarian tumor cell proliferation with an IC50 value of 6.8 µM.

Reference

1.Roberts II, L. Jackson, and Brian J. Sweetman. "Metabolic fate of endogenously synthesized prostaglandin D2 in a human female with mastocytosis." Prostaglandins 30.3 (1985): 383-400.
2.Hayaishi, Osamu. "Sleep-wake regulation by prostaglandins D2 and E2." Journal of Biological Chemistry 263.29 (1988): 14593-14596.
3.Onoe, Hirotaka, et al. "Prostaglandin D2, a cerebral sleep-inducing substance in monkeys." Proceedings of the National Academy of Sciences 85.11 (1988): 4082-4086.
4.Giles, H., and P. Leff. "The biology and pharmacology of PGD2." Prostaglandins 35.2 (1988): 277-300.
5.Kikuchi, Yoshihiro, et al. "Preclinical studies of antitumor prostaglandins by using human ovarian cancer cells." Cancer and Metastasis Reviews 13.3-4 (1994): 309-315.