82475

Prostaglandin E₂

≥99.0% (TLC)

• Synonym(s): (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid, Dinoprostone, PGE₂
• Empirical Formula (Hill Notation): C₂₀H₃₂O₅
• CAS Number: 363-24-6
• Molecular Weight: 352.47
• Beilstein: 4709356
• EC Number: 206-656-6
• MDL number: MFCD00077861
• UNSPSC Code: 12352200

Properties

• Assay: ≥99.0% (TLC)
• solubility: acetone: 10 mg/mL, clear, colorless to faintly yellow
• 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

Description

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.

Other Notes

Differential effect of PGE₂ on transforming growth factor-β, and insulin-induced collagen formation in lung fibroblasts

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H302,H360FD
• Precautionary Statements: P202 - P264 - P280 - P301 + P312 - P308 + P313 - P405
• 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