71118-02-0

Basic information

• Product Name: 15,17-dihydroxyprogesterone
• Synonyms: 15,17-dihydroxyprogesterone
• CAS NO: 71118-02-0
• Molecular Formula: C₂₁H₃₀O₄
• Molecular Weight: 346.46
• Mol File: 71118-02-0.mol

Chemical Properties

• Melting Point: 213-215 °C
• Boiling Point: 523.9°C at 760 mmHg
• Flash Point: 284.7°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 3.64E-13mmHg at 25°C
• Refractive Index: 1.576
• PKA: 12.67±0.70(Predicted)
• CAS DataBase Reference: 15,17-dihydroxyprogesterone(CAS DataBase Reference)
• NIST Chemistry Reference: 15,17-dihydroxyprogesterone(71118-02-0)
• EPA Substance Registry System: 15,17-dihydroxyprogesterone(71118-02-0)

Safety Data

• Hazardous Substances Data: 71118-02-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H30O4/c1-12(22)21(25)11-17(24)18-15-5-4-13-10-14(23)6-8-19(13,2)16(15)7-9-20(18,21)3/h10,15-18,24-25H,4-9,11H2,1-3H3/t15-,16+,17-,18-,19+,20+,21+/m1/s1

Upstream product

• 68-96-2 17-hydroxyprogesterone 
• 57-83-0 Progesterone 
• 2484-49-3 15β-acetoxy-17α-hydroxy-4-pregnen-3,20-dine 
• 128947-84-2 15β,17α,21-trihydroxy-4-pregnen-3,20-dione 
• 152-58-9 Cortexolone 
• 171980-18-0 3β,15β-diacetoxy-17α-hydroxy-5-pregnen-20-one 
• 171980-19-1 15β-acetoxy-3β,17α-dihydroxy-5-pregnen-20-one 

Downstream Products

• 2484-50-6 15-oxo-17-hydroxyprogesterone 
• 80380-40-1 3β,15β,17α-trihydroxy-5-pregnen-20-one 

Relevant articles and documents

15β-hydroxysteroids (Part VII). Steroids of the human perinatal period: The synthesis of steroid markers and their radioactive tracers

We report the synthesis of 10 novel steroids obtained from 3β,15β- diacetoxy-17α-hydroxy-5-pregnen-20-one (1c) as intermediates in the synthesis of 15β-acetoxy-20,20-ethylenedioxy-17α-hydroxy-4-pregnen-3-one (6a) and its tritiated tracer 15β-acetoxy-20-20-ethylenedioxy-17α-hydroxy- 1,2,6,7-3-pregn-4-en-3-one (6d). The one pot interconversion of intermediate (6a) to 3β,15β,17α-trihydroxy-5-pregnen-20-one (1a) and 3α,15β,17α- trihydroxy-5β-pregnan-20-one (2a) provides a new and efficient approach to the synthesis of diagnostically important metabolites of the human neonate and a possible route in the synthesis of the tritated tracers 3β,15β,17α- trihydroxy-1,2,7-3H-pregn-5-en-20-one (1d) and 3α,15β,17α-trihydroxy- 1,2,6,7-3H-5β-pregnan-20-one (2b) for the development of new immunoassays. We also report in this investigation an alternative route in the synthesis of 15β,17α-dihydroxy-4-pregnen-3,20-dione (7a) an intermediate in the synthesis of human 15β-hydroxysteroid metabolites.

15β-Hydroxysteroids (part V). Steroids of the human perinatal period: The synthesis of 3β, 15β, 17α-trihydroxy-5-pregnen-20- one from 15β, 17α-dihydroxy-4-pregnen-3,20-dione

A simple three-step synthetic method is reported on the conversion of Δ4-3-ketosteroids to the corresponding 3β- hydroxy-Δ5-steroid analogues. 17α-Hydroxy-4-pregnen-3,20-dione (10a) was used as a model to develop a method for the synthesis of 3β,17α-dihydroxy-5-pregnen-20-one (16). The major problem being the synthesis of 3,17α-diacetoxy-3,5-pregnadien-20-one (14) was solved by acetylating using a mixture of acetic anhydride and perchloric acid. The conversion of 15β,17α-dihydroxy-4-pregnen- 3,20-dione (8), product of Penicillium citrinum fermentation, to the desired 3β, 15β, 17α-trihydroxy-5-pregnen-20-one (1), is described using a modification of this method. Reaction of 8 with acetic anhydride and perchloric acid in ethyl acetate gave 3,15β,17α-triacetoxy-3,5-pregnadien-20-one (17) which on reduction with sodium borohydrice gave 5-pregnen-3β,15β,17α, 20(S + R)-tetrols (18a and 18b); however, reduction of 17 with a mixture of sodium borohydride and potassium bicarbonate gave after basic hydrolysis with metanolic sodium hydroxide the desired product 3β,15β,17α-trihydroxy-5-pregnen-20-one (1) in good yield (54%).