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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

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).

Biochem/physiol Actions

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

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

wgk_germany

WGK 2

flash_point_f

15.8 °F

flash_point_c

-9 °C

ppe

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

Certificates of Analysis (COA)

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EXTRACT FROM NETTLE SEEDS (URTICA DIOICA L.) DECREASES THE SYNTHESIS OF LIPOXIN Asub 4 THROUGH INHIBITION OF THE DEVELOPMENT OF FLUORIDE-INDUCED INFLAMMATION IN THP1 MONOCYTES/MACROPHAGES
Lukomska A, et al.
Fluoride null
Quantitation of sulfidopeptide leukotrienes by reversed-phase high-performance liquid chromatography.
M Müller et al.
Journal of chromatography, 343(1), 213-218 (1985-09-13)
S Tassin-Moindrot et al.
European journal of biochemistry, 267(4), 1117-1124 (2000-02-15)
The 3D solution structure of wheat nonspecific lipid transfer protein (ns-LTP) complexed with prostaglandin B2, a lipid with both vinyl and hydroxylated groups, has been determined by 1H 2D NMR. The global fold of the protein is close to the
R J Heaslip et al.
The Journal of pharmacology and experimental therapeutics, 250(1), 44-51 (1989-07-01)
The effects of prostaglandin (PG) F2 alpha and PGB2 on isolated rat aortic strips were studied in calcium-free 1 mM ethylene glycol bis(beta-aminoethyl ether)-N,N'-tetraacetic acid buffer to explore the mechanisms of PG-induced smooth muscle contraction. In the absence of extracellular
W S Powell et al.
The Journal of biological chemistry, 269(41), 25373-25380 (1994-10-14)
We have shown previously that human neutrophil microsomes contain a highly specific dehydrogenase which, in the presence of NADP+, converts 5S-hydroxy-6,8,11,14-eicosatetraenoic acid (5S-HETE) to its 5-oxo metabolite, 5-oxo-ETE, a potent agonist of these cells. However, intact neutrophils convert 5S-HETE principally
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