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P5390

Sigma-Aldrich

Prostaglandin B2

≥98%, synthetic

Synonym(s):

(5Z,13E,15S)-15-Hydroxy-9-oxoprosta-5,8(12),13-trien-1-oic acid, PGB2

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About This Item

Empirical Formula (Hill Notation):
C20H30O4
CAS Number:
13367-85-6
Molecular Weight:
334.45
Beilstein/REAXYS Number:
2153006
MDL number:
MFCD00065730
UNSPSC Code:
12352211
PubChem Substance ID:
24898630
NACRES:
NA.77
Pricing and availability is not currently available.

biological source

synthetic

Quality Level

100

assay

≥98%

form

solution

solubility

ethanol: ~100 mg/mL
PBS, pH 7.2: ~2 mg/mL
DMSO: ~50 mg/mL

storage temp.

−20°C

SMILES string

CCCCC[C@H](O)\C=C\C1=C(C\C=C/CCCC(O)=O)C(=O)CC1

InChI

1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12,14,17,21H,2-3,5-6,8-11,13,15H2,1H3,(H,23,24)/b7-4-,14-12+/t17-/m0/s1

InChI key

PRFXRIUZNKLRHM-HKVRTXJWSA-N

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Application

Prostaglandin B2 has been used as an internal standard in high-performance liquid chromatography (HPLC).[1]

Biochem/physiol Actions

Prostaglandin B2 (PGB2) is an eicosanoid and a lipid mediator. It is synthesized by the dehydration of PGE2.[2] It is a primary prostaglandin associated with the osteoblasts[3] and may induce pulmonary hypertension.[4] PGB2 is also reported to inhibit glucagon stimulated glycogenolysis and forskolin-stimulated adenylate cyclase activity in plasma membranes.[5]

Physical form

Prostaglandin B2 is supplied as a solution in methyl acetate

Preparation Note

PGB2 is provided as a solution in methyl acetate. To change the solvent, evaporate the methyl acetate under a gentle stream of nitrogen and immediately add the solvent of choice. PGB2, purged with an inert gas, is soluble in ethanol at ~100 mg/mL, DMSO at ~50 mg/mL and in dimethyl formamide at ~ 75 mg/mL.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

target_organs

Central nervous system

supp_hazards

EUH066

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

15.8 °F

flash_point_c

-9 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW9915
MKCM6897
MKCF8460
MKBZ3355V
MKBZ3378V

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Yurika Otoki et al.
Lipids, 55(1), 7-22 (2019-11-07)
In the brain, approximately 90% of oxylipins are esterified to lipids. However, the significance of this esterification process is not known. In the present study, we (1) validated an aminopropyl solid phase extraction (SPE) method for separating esterified lipids using
L O Eriksson et al.
Acta physiologica Scandinavica, 139(3), 393-404 (1990-07-01)
The prostaglandin E2 (PGE2) binding site in human kidney was characterized in membrane preparations from cortex, outer medulla and inner medulla using radioligand binding techniques. The localization of the binding sites for [3H]PGE2 was visualized autoradiographically. In the membrane suspensions
George Binh Lenon et al.
Evidence-based complementary and alternative medicine : eCAM, 4(2), 209-217 (2007-06-06)
Herbal therapies are being used increasingly for the treatment of allergic rhinitis. The aim of this study was to investigate the possible pharmacological actions and cellular targets of a Chinese herbal formula (RCM-101), which was previously shown to be effective
S Kjellström et al.
Journal of chromatography. A, 823(1-2), 489-496 (1998-11-18)
An automated on-line sampling method was developed using microdialysis as the simultaneous sampling and sample pre-treatment technique. The extraction fraction values of microdialysis probes sampling different eicosanoids were investigated. The impact of cyclodextrins in the perfusion liquid used for sampling
T A Haas et al.
Journal of chromatography, 430(1), 1-9 (1988-08-19)
A number of methods have been used to measure various lipoxygenase metabolites in aqueous samples. These methods, however, suffer from three major limitations: first, they require extensive extraction and isolation from protein-containing media; second, mainly due to the first limitation
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