131801-98-4

Basic information

• Product Name: (3S,5Z,7E)-3,25-dihydroxy-23,26-epoxy-9,10-secocholesta-5,7,10-trien-26-one
• CAS NO: 131801-98-4
• Molecular Formula: C₂₇H₄₀O₄
• Molecular Weight: 428.6041
• Mol File: 131801-98-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 586°C at 760 mmHg
• Flash Point: 190.9°C
• Density: 1.13g/cm³
• Vapor Pressure: 3.59E-16mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: (3S,5Z,7E)-3,25-dihydroxy-23,26-epoxy-9,10-secocholesta-5,7,10-trien-26-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5Z,7E)-3,25-dihydroxy-23,26-epoxy-9,10-secocholesta-5,7,10-trien-26-one(131801-98-4)
• EPA Substance Registry System: (3S,5Z,7E)-3,25-dihydroxy-23,26-epoxy-9,10-secocholesta-5,7,10-trien-26-one(131801-98-4)

Safety Data

• Hazardous Substances Data: 131801-98-4(Hazardous Substances Data)

Upstream product

• 76719-32-9 5-{2-[(3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl}-3-hydroxy-3-methyl-dihydro-furan-2-one 
• 81305-33-1 (R)-5-{2-[(3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propyl}-3-methyl-dihydro-furan-2-one 
• 76719-33-0 Acetic acid (3S,8S,9S,10R,13R,14S,17R)-17-[2-(4-hydroxy-4-methyl-5-oxo-tetrahydro-furan-2-yl)-1-methyl-ethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 76719-34-1 3-Hydroxy-5-[2-((3S,9S,10R,13R,14R,17R)-3-hydroxy-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-propyl]-3-methyl-dihydro-furan-2-one 
• 78109-04-3 C₃₇H₄₈IN₃O₇ 
• 78109-06-5 C₃₇H₄₈BrN₃O₇ 
• 78109-10-1 C₃₅H₄₅N₃O₆ 
• 82079-13-8 (23R,25R)-cholest-5-ene-3β-tetrahydropyranyloxy-26,23-lactone 
• 82033-28-1 (23R)-cholest-5-ene-3β-tetrahydropyranyloxy-26,23-lactone 
• 81305-14-8 (23R,25R)-cholest-5-ene-3β,25-dihydroxy-26,23-lactone 
• 81305-25-1 (22E)-cholest-5,22-diene-3β,25-dihydroxy-26-oic acid 
• 76719-26-1 cholest-5-ene-3β-hydroxy-26,23-lactone 
• 76719-24-9 (E)-(R)-6-((3S,8S,9S,10R,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-hept-4-enoic acid 
• 81305-24-0 (22E)-cholest-5,22-diene-25-hydroxy-3β-tetrahydropyranyloxy-26-oic acid methyl ester 

Relevant articles and documents

Elucidation of metabolic pathways of 25-hydroxyvitamin D3 mediated by CYP24A1 and CYP3A using Cyp24a1 knockout rats generated by CRISPR/Cas9 system

CYP24A1-deficient (Cyp24a1 KO) rats were generated using the CRISPER/Cas9 system to investigate CYP24A1-dependent or -independent metabolism of 25(OH)D3, the prohormone of calcitriol. Plasma 25(OH)D3 concentrations in Cyp24a1 KO rats were approximately twofold higher than in wild-type rats. Wild-type rats showed five metabolites of 25(OH)D3 in plasma following oral administration of 25(OH)D3, and these metabolites were not detected in Cyp24a1 KO rats. Among these metabolites, 25(OH)D3-26,23-lactone was identified as the second major metabolite with a significantly higher Tmax value than others. When 23S,25(OH)2D3 was administered to Cyp24a1 KO rats, neither 23,25,26(OH)3D3 nor 25(OH)D3- 26,23-lactone was observed. However, when 23S,25R,26(OH)3D3 was administered to Cyp24a1 KO rats, plasma 25(OH)D3-26,23-lactone was detected. These results suggested that CYP24A1 is responsible for the conversion of 25(OH)D3 to 23,25,26(OH)3D3 via 23,25(OH)2D3, but enzyme( s) other than CYP24A1 may be involved in the conversion of 23,25,26(OH)3D3 to 25(OH)D3-26,23-lactone. Enzymatic studies using recombinant human CYP species and the inhibitory effects of ketoconazole suggested that CYP3A plays an essential role in the conversion of 23,25,26(OH)3D3 into 25(OH)D3-26,23-lactone in both rats and humans. Taken together, our data indicate that Cyp24a1 KO rats are valuable for metabolic studies of vitamin D and its analogs. In addition, long-term administration of 25(OH)D3 to Cyp24a1 KO rats at 110 μg/kg body weight/day resulted in significant weight loss and ectopic calcification. Thus, Cyp24a1 KO rats could represent an important model for studying renal diseases originating from CYP24A1 dysfunction.

Structure and synthesis of 25-hydroxycholecalciferol-26,23-lactone, a metabolite of vitamin D

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Stereoselective synthesis and structure proof of a metabolite of vitamin D3, (23S, 25R)-25-hydroxyvitamin D3 26,23-lactone (calcidiol lactone)

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