903-67-3

Basic information

• Product Name: 3-BETA,17-ALPHA,20-ALPHA-TRIHYDROXY-5-PREGNENE
• Synonyms: 5-PREGNEN-3-BETA, 17,20-ALPHA-TRIOL;5-PREGNEN-3BETA,17ALPHA,20ALPHA-TRIOL;3-BETA,17-ALPHA,20-ALPHA-TRIHYDROXY-5-PREGNENE;5-pregnene-3B,17A,20A-triol;5-pregnene-3 beta,17 alpha,20 alpha-triol;3B,17ALPHA,20ALPHA-Trihydroxy-5-p;(3S,8R,9S,10R,13S,14S,17R)-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol;(3β,17α,20S)-Pregn-5-ene-3,17,20-triol
• CAS NO: 903-67-3
• Molecular Formula: C₂₁H₃₄O₃
• Molecular Weight: 334.49
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids
• Mol File: 903-67-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 482.7°Cat760mmHg
• Flash Point: 216.1°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 2.42E-11mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: 3-BETA,17-ALPHA,20-ALPHA-TRIHYDROXY-5-PREGNENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BETA,17-ALPHA,20-ALPHA-TRIHYDROXY-5-PREGNENE(903-67-3)
• EPA Substance Registry System: 3-BETA,17-ALPHA,20-ALPHA-TRIHYDROXY-5-PREGNENE(903-67-3)

Safety Data

• Hazardous Substances Data: 903-67-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H34O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,13,15-18,22-24H,5-12H2,1-3H3/t13-,15-,16+,17-,18-,19-,20-,21-/m0/s1

Upstream product

• 3517-42-8 17α-hydroxy-3β,21-diacetoxy-5-pregnen-20-one 
• 3517-38-2 3β,17α-diacetoxypregn-5-en-20-one 
• 39946-41-3 Δ⁵-pregnene-3β,17α,20(S)-triol 20-O-β-D-canaropyranoside (periplocoside N) 
• 116709-67-2 Δ⁵-pregnene-3β,17α,20(S)-triol 3-O-(4',6'-dideoxy-3-O-methyl-Δ^3'-D-2'-hexosuloside) 20-O-(3-O-methoxymethyl-β-D-canaropyranoside) 
• 119902-16-8 Δ⁵-pregnene-3β,17α,20(S)-triol 3-O-(4',6'-dideoxy-3'-O-methyl-Δ^3'-D-2'-hexosuloside) 20-O-β-D-digitalopyranosyl-(1->4)-β-D-cymaropyranosyl-(1->4)-β-D-canaropyranosyl-(1->4)-β-D-digitoxopyranosyl-(1->5)-3,7-dideoxy-4-O-methyl-α-D-gluco-2-... 
• 119902-17-9 Δ⁵-pregnene-3β,17α,20(S)-triol 20-O-(β-D-digitalopyranosyl-(1->4)-β-D-cymaropyranosyl-(1->4)-β-D-cymaropyranosyl-(1->4)-β-D-cymaropyranosyl-(1->5)-3,7-dideoxy-4-O-methyl-α-D-gluco-2-heptulopyranosyl-(2-4)-dideoxy-(1->3)-β-D-canaropyranoside) 
• 119902-15-7 Δ⁵-pregnene 3β,17α,20(S)-triol 20-O-β-D-digitalopyranosyl-(1->4)-β-D-cymaropyranosyl-(1->4)-β-D-canoropyranosyl-(1->4)-β-D-digitoxopyranosyl-(1->5)-3,7-dideoxy-4-O-methyl-α-D-gluco-2-heptulopyranosyl-(2-4)-dideoxy-(1->3)-β-D-canaropyranoside 
• 1863-39-4 3β-acetoxy-17α-hydroxy-5-pregnen-20-one 

Downstream Products

• 53-43-0 dehydroepiandrosterone 

Relevant articles and documents

Chemical synthesis of 7- and 8-dehydro derivatives of pregnane-3,17α,20-triols, potential steroid metabolites in Smith-Lemli-Opitz syndrome

Pregnane-3,17α,20-triols bearing unsaturation at Δ7, Δ8, Δ5,7, or Δ5,8 have been tentatively identified as steroid metabolites in Smith-Lemli-Opitz syndrome (SLOS). Starting with 17α-hydroxypregnenolone diacetate, we have synthesized 13 unsaturated C21 triols by four different routes in one to four steps. These multifunctional steroids were prepared by a series of regio- and stereoselective transformations chosen to minimize facile olefin isomerization and 17-deoxygenation. The results include a study of stereoselectivity in the reduction of 17α-hydroxy-20-ketosteroids, an alternative method for reducing diethyl azodicarboxylate adducts of Δ5,7 steroids, and an efficient oxidation-isomerization of a Δ5,7 steroid using cholesterol oxidase. The 13 triols and their synthetic precursors were fully characterized by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. The NMR data, together with molecular modeling, indicated unanticipated conformational heterogeneity for two synthetic intermediates, 17α-hydroxypregna-4,7-diene-3,20-dione and 17α-hydroxy-5β-pregn-7-ene-3,20-dione. The unsaturated C21 triols are useful as reference standards to study adrenal steroid production in SLOS and to develop methods for pre- and postnatal diagnosis of this congenital disorder.