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P5172

Prostaglandin D₂

Name: Prostaglandin D<SUB>2</SUB>
Brand: SIGMA

synthetic, ≥95%, adenylyl cyclase stimulator, powder

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

UNSPSC Code:

12352211

eCl@ss:

42020658

PubChem Substance ID:

24898605

NACRES:

NA.77

Beilstein/REAXYS Number:

2170623

MDL number:

MFCD00077857

Assay:

≥95%

Form:

powder

Quality level:

100

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Product Name

Prostaglandin D₂, ≥95%, synthetic

biological source

synthetic

Quality Level

100

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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Related Categories

Bioactive Small Molecules

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

GHS08,GHS07

signalword

Danger

hcodes

H302,H360

pcodes

P202 - P264 - P280 - P301 + P312 - P308 + P313 - P405

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B

Storage Class

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

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Prostaglandin D2 activates group 2 innate lymphoid cells through chemoattractant receptor-homologous molecule expressed on TH2 cells.

Luzheng Xue et al.

The Journal of allergy and clinical immunology, 133(4), 1184-1194 (2014-01-07)

Activation of the group 2 innate lymphoid cell (ILC2) population leads to production of the classical type 2 cytokines, thus promoting type 2 immunity. Chemoattractant receptor-homologous molecule expressed on TH2 cells (CRTH2), a receptor for prostaglandin D₂ (PGD₂), is expressed

Aldo-keto reductase 1C3 is expressed in differentiated human epidermis, affects keratinocyte differentiation, and is upregulated in atopic dermatitis.

Alon Mantel et al.

The Journal of investigative dermatology, 132(4), 1103-1110 (2011-12-16)

Aldo-keto reductase 1C3 (AKR1C3) has been shown to mediate the metabolism of sex hormones and prostaglandin D(2) (PGD(2)), a lipid mediator that promotes skin inflammation in atopic dermatitis (AD). As both have a role in skin function and pathology, we

Metabolism of prostaglandin D2 by human cerebral cortex into 9 alpha, 11 beta-prostaglandin F2 by an active NADPH-dependent 11-ketoreductase.

L S Wolfe et al.

Journal of neurochemistry, 53(1), 64-70 (1989-07-01)

In homogenates of rat cerebral neocortex prostaglandin D2 (PGD2) was found to be quantitatively the main PG biosynthesized by a cytosolic PGD synthetase from endogenously released arachidonic acid. Amounts of 628 ng/g wet weight were found after 30-min incubation periods

Serum albumin enhances the impairment of platelet aggregation with thromboxane synthase inhibition by increasing the formation of prostaglandin D2.

P Gresele et al.

Biochemical pharmacology, 33(13), 2083-2088 (1984-07-01)

Dazoxiben, a thromboxane synthase inhibitor, inhibits arachidonic acid induced aggregation in platelet-rich plasma from some donors only ("responders"). We have studied the effect of dazoxiben in vitro on platelet aggregation and prostaglandin (PG) metabolism and the influence of the incubation

Opposing immunomodulatory roles of prostaglandin D2 during the progression of skin inflammation.

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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Global Trade Item Number

SKU	GTIN
P5172-10MG	04061832785851
P5172-1MG	04061834376750
P5172-5MG	04061832785868

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