81203-50-1

Basic information

• Product Name: (3R,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-[(2Z)-2-[(3S,5S)-3,5-dihydroxy-2-methylidene-cyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-hydroxy-3-methyl-oxolan-2-one
• Synonyms: (3R,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-[(2Z)-2-[(3S,5S)-3,5-dihydroxy-2-methylidene-cyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-hydroxy-3-methyl-oxolan-2-one;1,25-Dihydroxyvitamin D3-26,23-lactone;(1S,23S,25R)-1,25-Dihydroxy-23,26-epoxy-26-oxocholecalciferol;(23S,25R)-1α,25-(OH)2D3-26,23-Lactone;(23S,25R)-1α,25-DihydroxyvitaminD3 26,23-lactone;(5Z,7E,23S,25R)-1α,3β,23,25-Tetrahydroxy-9,10-secocholesta-5,7,10(19)-triene-26-oic acid γ-lactone;23S,25R-1α,25-(OH)2-D3-26,23-Lactone;Calcitriol lactone
• CAS NO: 81203-50-1
• Molecular Formula: C₂₇H₄₀O₅
• Molecular Weight: 444.6
• Mol File: 81203-50-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 624.1°C at 760 mmHg
• Flash Point: 204.8°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 3.41E-18mmHg at 25°C
• Refractive Index: 1.573
• PKA: 13.13±0.40(Predicted)
• CAS DataBase Reference: (3R,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-[(2Z)-2-[(3S,5S)-3,5-dihydroxy-2-methylidene-cyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-hydroxy-3-methyl-oxolan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-[(2Z)-2-[(3S,5S)-3,5-dihydroxy-2-methylidene-cyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-hydroxy-3-methyl-oxolan-2-one(81203-50-1)
• EPA Substance Registry System: (3R,5S)-5-[(2R)-2-[(1R,3aR,4E,7aR)-4-[(2Z)-2-[(3S,5S)-3,5-dihydroxy-2-methylidene-cyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]propyl]-3-hydroxy-3-methyl-oxolan-2-one(81203-50-1)

Safety Data

• Hazardous Substances Data: 81203-50-1(Hazardous Substances Data)

Usage

Uses

Calcitriol Lactone is a metabolite of Calcitriol (C144500), which is an active form of Vitamin D3. Calcitriol is also a calcium regulator.

InChI:InChI=1/C27H40O5/c1-16(12-21-15-27(4,31)25(30)32-21)22-9-10-23-18(6-5-11-26(22,23)3)7-8-19-13-20(28)14-24(29)17(19)2/h7-8,16,20-24,28-29,31H,2,5-6,9-15H2,1,3-4H3/b18-7+,19-8-/t16-,20-,21+,22-,23+,24+,26-,27-/m1/s1

Upstream product

• 32222-06-3 calcitriol 
• 161055-41-0 (3S,5R)-3,5-bis(t-butyldimethylsilyloxy)octa-1-en-7-yne 
• 144125-16-6 (3R,5S)-3-hydroxy-5-((R)-2-((1R,3αR,4S,7αR)-4-hydroxy-7α-methyloctahydro-1H-inden-1-yl)propyl)-3-methyldihydrofuran-2(3H)-one 
• 83685-54-5 (3R,5S)-3-Methyl-5-[(R)-2-((1R,3aR,7aR)-7a-methyl-4-oxo-octahydro-inden-1-yl)-propyl]-3-trimethylsilanyloxy-dihydro-furan-2-one 
• 83685-50-1 (2R,4R)-4-((3aR,4R,7aS)-4-Acetoxy-7a-methyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl)-2-bromo-pentanoic acid methyl ester 
• 95667-89-3 (3R,5S)-3-Hydroxy-3-methyl-5-[(R)-2-((1R,3aR,7aR)-7a-methyl-4-oxo-octahydro-inden-1-yl)-propyl]-dihydro-furan-2-one 
• 83685-53-4 (3R,5S)-3-Hydroxy-5-[(R)-2-((1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-octahydro-inden-1-yl)-propyl]-3-methyl-dihydro-furan-2-one 
• 87640-66-2 (3aR,4R,7aS)-1-((1R,3R)-3-Bromo-4-hydroxy-1-methyl-butyl)-7a-methyl-3a,4,5,6,7,7a-hexahydro-3H-inden-4-ol 
• 87640-67-3 (3aR,4R,7aS)-7a-Methyl-1-((R)-1-methyl-2-(S)-oxiranyl-ethyl)-3a,4,5,6,7,7a-hexahydro-3H-inden-4-ol 
• 83685-52-3 Trimethyl-[(1R,3aR,4R,7aR)-7a-methyl-1-((R)-1-methyl-2-(S)-oxiranyl-ethyl)-octahydro-inden-4-yloxy]-silane 
• 83685-51-2 (1R,3aR,4R,7aR)-7a-Methyl-1-((R)-1-methyl-2-(S)-oxiranyl-ethyl)-octahydro-inden-4-ol 
• 81506-36-7 Acetic acid (3aR,4R,7aS)-1-eth-(Z)-ylidene-7a-methyl-octahydro-inden-4-yl ester 
• 137649-21-9 (22S,23R,25R)-1α,3β,25-trihydroxy-22-(phenylseleno)-5,7-cholestadiene 26,23-lactone 4-phenyl-1,2,4-triazoline-3,5-dione adduct 
• 137649-19-5 (22S,23R,25R)-1α,3β,25-trihydroxy-22-iodo-5,7-cholestadiene 26,23-lactone 4-phenyl-1,2,4-triazoline-3,5-dione adduct 

Relevant articles and documents

Stereoselective Synthesis of Four Calcitriol Lactone Diastereomers at C23 and C25

(23S,25R)-Calcitriol lactone is a major metabolite of vitamin D3, but its synthesis has been far less well investigated than that of 1α,25(OH)2 vitamin D3, the active form of vitamin D3, even though the lactone

Facile Stereoselective Synthesis of (23S,25R)-1α,25-Dihydroxyvitamin D3 26,23-Lactone, a Major Metabolite of 1α,25-Dihydroxyvitamin D3

(23S,25R)-1α,25-Dihydroxyvitamin D3 26,23-lactone (1a), a major metabolite of 1α,25-dihydroxyvitamin D3 2, was synthesized efficiently and stereoselectively from 1α-hydroxydehydroepiandrosterone (3).The 17-oxosteroid 3 was first converted to C(22)-steroid aldehyde 9 with the natural stereochemistry at C(17) and C(20) using a stereoselective ene reaction as the key step.Then it was combined with the chiral C5 sulfone 4 having the correct stereochemistry for the lactone in 1a.Sulfone 4 was readily obtained from commercially available (R)-citramalic acid.The side-chain lactone with the natural stereochemistry at C(23) was constructed with high stereoselectivity (84percent) by iodo lactonization of the Δ22-26-carboxylic acid 16b under kinetically controlled conditions in the presence of γ-collidine.The stereoselectivity of the iodo lactonization of steroidal Δ22-25-hydroxy-26-carboxylic acids 16b, 24, and 25 was studied in detail, and a mechanism is proposed in which the configuration at C(25) and an added pyridine base play an important role.