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P5640

Sigma-Aldrich

Prostaglandin E2

≥93% (HPLC), synthetic

Synonym(s):

(5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid, Dinoprostone, PGE2

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About This Item

Empirical Formula (Hill Notation):
C20H32O5
CAS Number:
363-24-6
Molecular Weight:
352.47
Beilstein/REAXYS Number:
4709356
EC Number:
206-656-6
MDL number:
MFCD00077861
UNSPSC Code:
12352401
eCl@ss:
42020658
PubChem Substance ID:
24898683
NACRES:
NA.77

biological source

synthetic

assay

≥93% (HPLC)

form

powder

functional group

carboxylic acid
hydroxyl

shipped in

ambient

storage temp.

−20°C

SMILES string

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

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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1

InChI key

XEYBRNLFEZDVAW-ARSRFYASSA-N

Gene Information

human ... PTGER1(5731) , PTGER2(5732) , PTGER3(5733) , PTGER4(5734) , PTGIR(5739)
mouse ... Ptger1(19216) , Ptger2(19217) , Ptger3(19218) , Ptger4(19219)

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Application


  • Post-resolution macrophages shape long-term tissue immunity and integrity in a mouse model of pneumococcal pneumonia.: Investigating the influence of prostaglandin E2 within the resolution phase of inflammation, this study demonstrates its essential role in macrophage-mediated tissue repair and immune memory following bacterial lung infections, providing insights into immune system regulation and recovery processes (Feehan et al., 2024).

Biochem/physiol Actions

Most biologically active prostaglandin. PGE2 induces cervical ripening and parturition; mediates bradykinin-induced vasodilation; regulates adenylyl cyclase. Tumor cells that over-express cyclooxygenase 2 display increased invasiveness, angiogenesis, and resistance to apoptosis that may be due to the PGE2-induced expression of angiogenic factors and stabilization of the anti-apoptotic protein, survivin.The effect of PGE2 on the immune system is mixed. It inhibits T cell activation in vitro, suggesting it is an immunosuppressant. However, in vivo, it appears to effect expansion of the Th17 subset and differentiation of the Th1 subset of T helper cells, marking it as an immunoactivator.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

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_germany

WGK 3

ppe

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

Certificates of Analysis (COA)

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