| Identification | Back Directory | [Name]
PROSTAGLANDIN D2 | [CAS]
41598-07-6 | [Synonyms]
PGDS
PGD2
Prostaglandin D?
PROSTAGLANDIN D2
PROSTAGLANDINS D2
PGD2 (Prostaglandin D2)
RP23-47P18.11-006, 21kDa
11-dehydroprostaglandinf2-alpha
Prostaglandin D2 MaxSpecStandard
prostaglandin D2 synthase (brain)
prostaglandind2synthetichygroscopic
prostaglandin D2 cell culture tested
Anti-Ptgds antibody produced in goat
Prostaglandin D2 Lipid Maps MS Standard
Prostaglandin D - CAS 41598-07-6 - Calbiochem
9ALPHA,15S-DIHYDROXY-11-OXO-PROSTA-5Z,13E-DIEN-1-OIC ACID
(5Z,13E,15S)-9α,15-Dihydroxy-11-oxoprosta-5,13-dien-1-oic acid
(5z,9α,13e,15s)-9,15-dihydroxy-11-oxoprosta-5,13-dien-1-oic-acid
[5Z,9ALPHA,13E,15S]9,15-DIHYDROXY-11-OXOPROSTA-5,13-DIEN-1-OIC ACID
9,15-dihydroxy-11-oxo-,(5z,9-alpha,13e,15s)-prosta-13-dien-1-oicacid
Prosta-5,13-dien-1-oic acid, 9,15-dihydroxy-11-oxo-, (5Z,9α,13E,15S)-
PGD2, (5Z,9α,13E,15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dien-1-oic-acid
7-[(1R,2R,5S)-5-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-3-oxocyclopentyl]hept-5-enoic acid
Prostaglandin D2,(5Z,9α,13E,15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dien-1-oic-acid, PGD2
(Z)-7-((1R,2R,5S)-5-hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-3-oxocyclopentyl)hept-5-enoic acid | [EINECS(EC#)]
636-995-9 | [Molecular Formula]
C20H32O5 | [MDL Number]
MFCD00077857 | [MOL File]
41598-07-6.mol | [Molecular Weight]
352.47 |
| Chemical Properties | Back Directory | [Melting point ]
68°C | [alpha ]
+7.5°(D/21℃)(c=1,THF) | [Boiling point ]
406.07°C (rough estimate) | [density ]
1.0601 (rough estimate) | [refractive index ]
1.6120 (estimate) | [storage temp. ]
-20°C | [solubility ]
Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly), THF (Slightly) | [form ]
White solid | [pka]
4.76±0.10(Predicted) | [color ]
White to Light Orange | [biological source]
synthetic | [BRN ]
2170623 | [Stability:]
Light Sensitive |
| Hazard Information | Back Directory | [Description]
Prostaglandin D2 (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-synthase also known as β-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 of 6.8 μM. | [Uses]
Prostaglandin D2 is a fatty acid compound present in the human body. Elevated levels of localized Prostaglandin D2 has been linked to hair loss and growth inhibition. It has also been seen to contribute to the activity of allergic asthma. | [Definition]
ChEBI: A member of the class of prostaglandins D that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,9alpha,13E,15S- s
ereoisomer). | [Biochem/physiol Actions]
Primary prostaglandin in brain; induces inflammation; stimulates adenylyl cyclase. | [in vivo]
Prostaglandin D2 (PGD2; infused into the lateral ventricle; 5-50 pmol/min; for 6 hours between 20:00 and 2:00) induces sleep-wake profiles in A2AR KO mice[2]. | Animal Model: | Male WT and A2AR KO mice of the inbred C57BL/6 strain (weighing 23-27 g, 11-13 weeks old)[1] | | Dosage: | 5, 10, 20, or 50 pmol/min | | Administration: | Infused into the lateral ventricle; for 6 hours between 20:00 and 2:00 | | Result: | Induced sleep-wake profiles.
|
| [IC 50]
DP; Human Endogenous Metabolite | [storage]
Store at -20°C, stored under nitrogen | [References]
[1] L.JACKSON ROBERTS II Brian J S. Metabolic fate of endogenously synthesized prostaglandin D2 in a human female with mastocytosis[J]. Prostaglandins, 1985, 30 3: Pages 383-400. DOI: 10.1016/0090-6980(85)90114-5
[2] HAYAISHI O. Sleep-wake regulation by prostaglandins D2 and E2.[J]. The Journal of Biological Chemistry, 1988, 263 29: 14593-14596.
[3] H ONOE. Prostaglandin D2, a cerebral sleep-inducing substance in monkeys.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1988, 85 11: 4082-4086. DOI: 10.1073/pnas.85.11.4082
[4] Y KIKUCHI. Preclinical studies of antitumor prostaglandins by using human ovarian cancer cells.[J]. Cancer and Metastasis Reviews, 1994, 13 3-4: 309-315. DOI: 10.1007/bf00666101
[5] BRENDAN J. WHITTLE . Binding and activity of the prostacyclin receptor (IP) agonists, treprostinil and iloprost, at human prostanoid receptors: Treprostinil is a potent DP1 and EP2 agonist[J]. Biochemical pharmacology, 2012, 84 1: Pages 68-75. DOI: 10.1016/j.bcp.2012.03.012
[6] OYEBOLA O OYESOLA. The Prostaglandin D2 Receptor CRTH2 Promotes IL-33-Induced ILC2 Accumulation in the Lung.[J]. Journal of immunology, 2020, 204 4: 1001-1011. DOI: 10.4049/jimmunol.1900745
[7] AKIKO SUGANAMI. Human DP and EP2 prostanoid receptors take on distinct forms depending on the diverse binding of different ligands[J]. The FEBS journal, 2016, 283 21: 3931-3940. DOI: 10.1111/febs.13899
[8] D F WOODWARD. Pharmacological characterization of a novel antiglaucoma agent, Bimatoprost (AGN 192024).[J]. Journal of Pharmacology and Experimental Therapeutics, 2003, 305 2: 772-785. DOI: 10.1124/jpet.102.047837
[9] P. WAFFO-TéGUO. Potential Cancer-Chemopreventive Activities of Wine Stilbenoids and Flavans Extracted From Grape (Vitis vinifera) Cell Cultures[J]. Nutrition and Cancer-An International Journal, 2001, 40 1: 173-179. DOI: 10.1207/s15327914nc402_14 |
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