81738-09-2

Basic information

• Product Name: 23R,25-dihydroxyvitamin D₃
• CAS NO: 81738-09-2
• Molecular Weight: 416.645
• Mol File: 81738-09-2.mol

Chemical Properties

• CAS DataBase Reference: 23R,25-dihydroxyvitamin D₃(CAS DataBase Reference)
• NIST Chemistry Reference: 23R,25-dihydroxyvitamin D₃(81738-09-2)
• EPA Substance Registry System: 23R,25-dihydroxyvitamin D₃(81738-09-2)

Safety Data

• Hazardous Substances Data: 81738-09-2(Hazardous Substances Data)

Usage

Uses

Used in Healthcare Industry:
23R,25-Dihydroxyvitamin D₃ is used as a therapeutic agent for increasing plasma lactone concentration. This helps in maintaining calcium homeostasis and promoting bone health, making it beneficial for the treatment and prevention of osteoporosis and other bone-related disorders.
Additionally, research has shown that 23R,25-Dihydroxyvitamin D₃ has potential applications in the treatment of various diseases, such as cancer, autoimmune diseases, and infectious diseases, due to its immunomodulatory and anti-proliferative properties. However, further research is needed to fully understand its mechanisms of action and optimize its therapeutic potential.

Biochem/physiol Actions

Cholecalciferol is an inactive form of vitamin D3 which undergoes various levels of hydroxylation to form active vitamin D3 analogs. 1α-Hydroxyvitamin D3 (alfacalcidol) is a synthetic analog that is metabolized to 1,25-dihydroxycholecalciferol, the biologically active form of vitamin D3. Other analogues of cholecalciferol result from different hydroxylations. 23,25-Dihydroxyvitamin D3 is synthesized by the human placenta and by kidney cortex mitochondria.

Upstream product

• 93489-71-5 (R)-3-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)butanal 
• 81677-34-1 (23R)-cholest-5-ene-3β,23,25-triol 3,23-dibenzoate 
• 81677-30-7 (23R)-cholesta-5,25-diene-3β,23-diol dibenzoate 
• 81677-36-3 cholesta-5,7-diene-3β,23(R),25-triol 
• 81677-33-0 (23S)-cholest-5-ene-3β,23,25-triol 3,23-dibenzoate 
• 81677-29-4 (23S)-cholesta-5,25-diene-3β,23-diol dibenzoate 
• 81677-35-2 cholesta-5,7-diene-3β,23(S),25-triol 

Relevant articles and documents

Synthesis and Determination of the Configuration of 23,25-Dihydroxyvitamin D3; a New Metabolite of Vitamin D3; X-Ray Crystal Structure of a 3,23,25-Triol Precursor

The configuration at the C-23 position of 23,25-dihydroxyvitamin D3, a new metabolite of vitamin D3, was determined as S by comparison with the synthetically prepared C-23 S- and R-isomers and an X-ray crystallographic determination of the structure of the 3,23,25-triol (7b).

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.