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82475 Sigma-Aldrich

Prostaglandin E2

≥99.0% (TLC)

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

  • CAS Number 363-24-6

  • Empirical Formula (Hill Notation) C20H32O5

  • Molecular Weight 352.47

  •  Beilstein/REAXYS Number 4709356

  •  EC Number 206-656-6

  •  MDL number MFCD00077861

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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 & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
UK8000000

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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