P5515

Prostaglandin E₁

≥98% (HPLC), synthetic

• Synonym(s): (11α,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid, Alprostadil, PGE₁
• Empirical Formula (Hill Notation): C₂₀H₃₄O₅
• CAS Number: 745-65-3
• Molecular Weight: 354.48
• Beilstein: 5294062
• EC Number: 212-017-2
• MDL number: MFCD00077860
• eCl@ss: 42020658
• PubChem Substance ID: 57654538
• NACRES: NA.77

Properties

• biological source: synthetic
• Quality Level: 200
• Assay: ≥98% (HPLC)
• form: powder
• solubility: ethanol: 5 mg/mL
• storage temp.: −20°C
• SMILES string: O=C1[C@H](CCCCCCC(O)=O)[C@@H](/C=C/[C@H](CCCCC)O)[C@H](O)C1
• InChI: 1S/C20H34O5/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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
• InChI key: GMVPRGQOIOIIMI-DWKJAMRDSA-N
• Gene Information: human ... PTGER1(5731) , PTGER2(5732) , PTGIR(5739) ; mouse ... Ptger1(19216) , Ptger2(19217) , Ptger3(19218) , Ptger4(19219)

Description

Application

Prostaglandin E1 has been used:

• as a platelet inhibitor to analyse its effect on autophagy
• in platelet adhesion assay
• to investigate its effect on cAMP production in thyroid glands of normal and growth-retarded mouse in vitro.

Biochem/physiol Actions

Prostaglandin E1 (PGE1) is a hormone synthesized from dihomo-γ-linolenic acid (DGLA) by the action of enzyme prostaglandin synthase. It is a vasodilator and activates adenylate cyclase. It is majorly present in human semen and is a potent platelet aggregation inhibitor. PGE1 infusions is effective in treating limb ischemia and peripheral vascular disease. It is unstable and is hydrolyzed to PGA1 in the lungs. Nanoparticle encapsulation of PGE1 is essential for its delivery at the vascular injury site. It elicits vasodilator effects on the retinal artery and vein in central retinal artery occlusion (CRAO). PGE1 and its synthetic analog misoprostol interact with E-prostanoid receptor 4 (EP4) and elicits protection in chronic myelogenous leukemia (CML).

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301
• Precautionary Statements: P301 + P310 + P330
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class Code: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves