71183-99-8

Basic information

• Product Name: 24,25-dihydroxyvitamin D2
• Synonyms: 24,25-dihydroxyvitamin D2;24,25-HYDROXYVITAMIND;(5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetrene-3β,24,25-triol;24,25-Dihydroxyergocalciferol
• CAS NO: 71183-99-8
• Molecular Formula: C₂₈H₄₄O₃
• Molecular Weight: 428.65
• Mol File: 71183-99-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 582.2°C at 760 mmHg
• Flash Point: 244.8°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 5.59E-16mmHg at 25°C
• Refractive Index: 1.555
• PKA: 14.53±0.29(Predicted)
• CAS DataBase Reference: 24,25-dihydroxyvitamin D2(CAS DataBase Reference)
• NIST Chemistry Reference: 24,25-dihydroxyvitamin D2(71183-99-8)
• EPA Substance Registry System: 24,25-dihydroxyvitamin D2(71183-99-8)

Safety Data

• Hazardous Substances Data: 71183-99-8(Hazardous Substances Data)

Usage

General Description

24,25-dihydroxyvitamin D2, also known as 24,25-(OH)2D2, is a metabolite of vitamin D2 that is produced in the liver. It plays a crucial role in regulating calcium and phosphorus levels in the body, as well as bone metabolism. 24,25-(OH)2D2 helps to maintain bone health and prevent conditions such as rickets and osteomalacia. It also has anti-inflammatory properties and may be involved in immune function. In addition, this chemical has been studied for its potential role in the treatment of various diseases, including cancer and autoimmune disorders. Overall, 24,25-dihydroxyvitamin D2 is an important compound for maintaining overall health and well-being.

InChI:InChI=1/C28H44O3/c1-19-9-12-23(29)18-22(19)11-10-21-8-7-16-27(5)24(13-14-25(21)27)20(2)15-17-28(6,31)26(3,4)30/h10-11,15,17,20,23-25,29-31H,1,7-9,12-14,16,18H2,2-6H3/b17-15+,21-10+,22-11-/t20-,23-,24-,25+,27-,28-/m1/s1

Upstream product

• 95511-44-7 (22E,24S)-3β,24,25-trihydroxyergosta-5,7,22-triene 
• 60283-66-1 3-hydroxy-3-methyl-2-butanone tetrahydropyranyl ether 
• 95511-44-7 (24R,S)-ergosta-5,7,22-triene-3β,24,25-triol 
• 60283-67-2 (22E)-3β-acetoxy-25-hydroxy-5α,8α-(3,5-dioxo-4-phenyl-1,2,4-triazolidino)cholesta-6,22-dien-24-one 
• 95511-43-6 (22E)-3β,24,25-trihydroxy-5α,8α-(3,5-dioxo-4-phenyl-1,2,4-triazolidino)ergosta-6,22-diene 
• 28421-57-0 3-acetoxy-2'-phenyl-[1,2,4]triazolo[1',2':6,7](6,7-diaza-5,8-etheno-23,24-dinor-cholane)-21,3',5'-trione 
• 28421-56-9 3-acetoxy-2'-phenyl-[1,2,4]triazolo[1',2':6,7](6,7-diaza-5,8-etheno-ergost-22-ene)-3',5'-dione 
• 107717-75-9 3β-acetoxy-22,25-dihydroxy-5α,8α-(3,5-dioxo-4-phenyl-1,2,4-triazolidino)cholesta-6-en-24-one 
• 95586-93-9 (22E,24R)-3β,24,25-trihydroxyergosta-5,7,22-triene 
• 50-14-6 Calciferol 
• 21343-40-8 ercalcidiol 

Relevant articles and documents

Highly regio- and stereoselective hydroxylation of vitamin D2 by CYP109E1

Vitamin D2 is a form of vitamin D derived from mushrooms and plants which is structurally modified in the body due to the action of several enzymes. The resulting metabolites represent important compounds with potential bioactive properties. However, they are poorly studied and their availability is mostly limited. In order to identify new enzymes capable of producing vitamin D2 metabolites, we investigated a bacterial P450 monooxygenase, CYP109E1, which was previously shown to be a vitamin D3 hydroxylase. It was found that CYP109E1 catalyzes a vitamin D2 two-step hydroxylation at positions C24 and C25 resulting in the generation of 24(R),25-diOH VD2. Interestingly, the enzyme showed high selectivity towards vitamin D2, whereas it showed an unselective product pattern for the structurally similar vitamin D3. Our docking results for vitamin D2 and D3 revealed favorable hydroxylation positions for both substrates and suggested an explanation for the high selectivity of CYP109E1 towards vitamin D2. In addition, we established a whole-cell biocatalyst expressing CYP109E1 in Bacillus megaterium to produce 24(R),25-diOH VD2 and a production yield of 12.3 ± 1.2 mg/L was obtained after 48 h. To the best of our knowledge, this is the first report on the generation of 24(R),25-diOH VD2 by a microbial biocatalyst allowing a low-cost and eco-friendly production of this pharmaceutically interesting and expensive metabolite from the relatively cheap substrate, VD2.

Synthesis of diastereomeric 24,25-dihydroxyvitamin D2 and separation of its (24R)- and (24S)-isomers

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