42737-58-6

Basic information

• Product Name: (24R)-24,25-dihydroxyvitamin D₃
• Synonyms: (24R)-24,25-dihydroxyvitamin D₃
• CAS NO: 42737-58-6
• Molecular Weight: 416.645
• Mol File: 42737-58-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (24R)-24,25-dihydroxyvitamin D₃(CAS DataBase Reference)
• NIST Chemistry Reference: (24R)-24,25-dihydroxyvitamin D₃(42737-58-6)
• EPA Substance Registry System: (24R)-24,25-dihydroxyvitamin D₃(42737-58-6)

Safety Data

• Hazardous Substances Data: 42737-58-6(Hazardous Substances Data)

Upstream product

• 88099-49-4 (25S)-25,26-dihydroxyvitamin D₃ 3β,26-diacetate 
• 5255-17-4 3β-hydroxy-5-cholenoic acid 
• 66414-43-5 3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol 
• 66414-44-6 3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-al 
• 88156-14-3 (24E)-26-hydroxy-3β-tetrahydropyranyloxycholesta-5,24-diene 
• 78191-96-5 3β-tetrahydropyranyloxycholesta-5,25-dien-24-one 
• 88099-49-4 Acetic acid (S)-3-[2-[(1R,7aR)-1-((1R,5R)-6-acetoxy-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester 
• 57651-43-1 (R)-1,2-O-isopropylidene-2-methyl-1,2,5-pentanetriol 
• 69401-17-8 (25R)-3β,25,26-trihydroxycholest-5-ene 
• 82182-39-6 Toluene-4-sulfonic acid (R)-2-[(3S,8S,9S,10R,13S,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]-5-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-pentyl ester 
• 21461-88-1 (R)-2-methyl-pentane-1,2,5-triol 
• 77518-18-4 (R)-4-(3-Iodo-propyl)-2,2,4-trimethyl-[1,3]dioxolane 
• 57651-45-3 Toluene-4-sulfonic acid 3-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-propyl ester 
• 21461-86-9 (5R)-γ-valerolactone γ-carboxylic acid 

Downstream Products

• 56009-11-1 (1R,3aS,7aR)-1-((1R,5R)-1,5-Dimethyl-5,6-bis-trimethylsilanyloxy-hexyl)-7a-methyl-4-[2-[(S)-2-methylene-5-trimethylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-indene 

Relevant articles and documents

Chemical Synthesis of Side-Chain-Hydroxylated Vitamin D3 Derivatives and Their Metabolism by CYP27B1

1α,25-Dihydroxyvitamin D3 (abbreviated here as 1,25D3) is a hormonally active form of vitamin D3 (D3), and is produced from D3 by CYP27 A1-mediated hydroxylation at C25, followed by CYP27B1-mediated hydroxylation at C1. Further hydroxylation of 25D3 and 1,25D3 occurs at C23, C24 and C26 to generate corresponding metabolites, except for 1,25R,26D3. Since the capability of CYP27B1 to hydroxylate C1 of side-chain-hydroxylated metabolites other than 23S,25D3 and 24R,25D3 has not been examined, we have here explored the role of CYP27B1 in the C1 hydroxylation of a series of side-chain-hydroxylated D3 derivatives. We found that CYP27B1 hydroxylates the R diastereomers of 24,25D3 and 25,26D3 more effectively than the S diastereomers, but shows almost no activity towards either diastereomer of 23,25D3. This is the first report to show that CYP27B1 metabolizes 25,26D3 to the corresponding 1α-hydroxylated derivative, 1,25,26D3. It will be interesting to examine the physiological relevance of this finding.

Synthesis and Structure Proof of a Vitamin D3 Metabolite, 25(S),26-Dihydroxycholecalciferol

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