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P5172

Sigma-Aldrich

Prostaglandin D2

≥95%, synthetic

Synonym(s):

(5Z,9α,13E,15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dien-1-oic-acid, PGD2

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About This Item

Empirical Formula (Hill Notation):
C20H32O5
CAS Number:
41598-07-6
Molecular Weight:
352.47
Beilstein:
2170623
MDL number:
MFCD00077857
UNSPSC Code:
12352211
eCl@ss:
42020658
PubChem Substance ID:
24898605
NACRES:
NA.77

biological source

synthetic

Assay

≥95%

form

powder

storage temp.

−20°C

SMILES string

[H][C@]1(C\C=C/CCCC(O)=O)[C@@H](O)CC(=O)[C@]1([H])\C=C\[C@@H](O)CCCCC

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

InChI key

BHMBVRSPMRCCGG-OUTUXVNYSA-N

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Biochem/physiol Actions

Primary prostaglandin in brain; induces inflammation; stimulates adenylyl cyclase.

Features and Benefits

This compound is featured on the Prostanoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H360

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Roy Pettipher et al.
Nature reviews. Drug discovery, 6(4), 313-325 (2007-03-31)
Immunological activation of mast cells is an important trigger in the cascade of inflammatory events leading to the manifestation of allergic diseases. Pharmacological studies using the recently discovered DP(1) and CRTH2 antagonists combined with genetic analysis support the view that
S O'Sullivan et al.
The Journal of allergy and clinical immunology, 98(2), 421-432 (1996-08-01)
Prostaglandin (PG)D2 is a major product of arachidonic acid metabolism in pulmonary mast cells. We therefore attempted to determine whether measurement of the stable urinary metabolite of PGD2, 9 alpha, 11 beta-PGF2, could serve as a marker of mast cell
Takahisa Murata et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(13), 5205-5210 (2013-03-13)
We investigated the role of prostaglandin D2 (PGD2) signaling in acute lung injury (ALI), focusing on its producer-effector interaction in vivo. Administration of endotoxin increased edema and neutrophil infiltration in the WT mouse lung. Gene disruption of hematopoietic PGD synthase
E E Nishizawa et al.
Prostaglandins, 9(1), 109-121 (1975-01-01)
Prostaglandin D2 was found to be a potent inhibitor of platelet aggregation. Aggregation of human platelets by ADP, collagen and prostaglandin G2 was inhibited more strongly by PGD2 than by PGE1. Although ADP-induced aggregation of rabbit platelets was inhibited more
Hana Sarashina et al.
Journal of immunology (Baltimore, Md. : 1950), 192(1), 459-465 (2013-12-04)
The effects of PGD2 are extremely context dependent. It can have pro- or anti-inflammatory effects in clinically important pathological conditions. A greater mechanistic insight into the determinants of PGD2 activity during inflammation is thus required. In this study, we investigated
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