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P5640

Sigma-Aldrich

Prostaglandin E2

≥93% (HPLC), synthetic

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Synonym(s):
(5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid, Dinoprostone, PGE2
Empirical Formula (Hill Notation):
C20H32O5
CAS Number:
Molecular Weight:
352.47
Beilstein:
4709356
EC Number:
MDL number:
eCl@ss:
42020658
PubChem Substance ID:
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

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1 of 4

This Item
P6532P0409D2250000
Prostaglandin E2 ≥93% (HPLC), synthetic

Sigma-Aldrich

P5640

Prostaglandin E2

Prostaglandin E2 γ-irradiated, powder, BioXtra, suitable for cell culture

Sigma-Aldrich

P6532

Prostaglandin E2

Prostaglandin E2 synthetic, powder, BioReagent, suitable for cell culture

Sigma-Aldrich

P0409

Prostaglandin E2

Dinoprostone European Pharmacopoeia (EP) Reference Standard

D2250000

Dinoprostone

assay

≥93% (HPLC)

assay

-

assay

≥93% (HPLC)

assay

-

form

powder

form

powder

form

powder

form

-

functional group

carboxylic acid, hydroxyl

functional group

-

functional group

-

functional group

-

shipped in

ambient

shipped in

ambient

shipped in

ambient

shipped in

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

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

Exclamation markHealth hazard

Signal Word

Danger

Hazard Statements

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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International Union of Pharmacology classification of prostanoid receptors: properties, distribution, and structure of the receptors and their subtypes.
R A Coleman et al.
Pharmacological reviews, 46(2), 205-229 (1994-06-01)
Takayuki Nakagawa
Hearing research, 276(1-2), 27-33 (2011-02-08)
Prostaglandins are one of the major groups of chemical mediators in the mammalian body. Among prostaglandins, prostaglandin E2 (PGE2) is the most abundant prostanoid in humans and involved in regulating many different fundamental biological functions. PGE2 signaling is mediated by
Sanjiv Dhingra et al.
Circulation, 128(11 Suppl 1), S69-S78 (2013-10-18)
Allogeneic mesenchymal stem cells (MSCs) were immunoprivileged early after cardiac implantation and improved heart function in preclinical and clinical studies. However, long-term preclinical studies demonstrated that allogeneic MSCs lost their immunoprivilege and were rejected in the injured myocardium, resulting in
Katrin D Mayer-Barber et al.
Nature, 511(7507), 99-103 (2014-07-06)
Tuberculosis remains second only to HIV/AIDS as the leading cause of mortality worldwide due to a single infectious agent. Despite chemotherapy, the global tuberculosis epidemic has intensified because of HIV co-infection, the lack of an effective vaccine and the emergence
Yumeng Mao et al.
Cancer research, 73(13), 3877-3887 (2013-05-02)
Tumors can suppress the host immune system by employing a variety of cellular immune modulators, such as regulatory T cells, tumor-associated macrophages, and myeloid-derived suppressor cells (MDSC). In the peripheral blood of patients with advanced stage melanoma, there is an

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