73809-05-9

Basic information

• Product Name: 3-EPI-25-HYDROXYVITAMIN D3
• Synonyms: 3-EPI-25-HYDROXYVITAMIN D3;3-epi-25-Hydroxyvitamin D3 solution;(1R,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
• CAS NO: 73809-05-9
• Molecular Formula: C₂₇H₄₄O₂
• Molecular Weight: 400.643
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Metabolites & Impurities;Pharmaceuticals;Isolabel
• Mol File: 73809-05-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 60-62°C
• Boiling Point: 529.2±33.0 °C(Predicted)
• Flash Point: 14 °C
• Appearance: /
• Density: 1.01±0.1 g/cm3(Predicted)
• Storage Temp.: Amber Vial, -20?C Freezer, Under Inert Atmosphere
• PKA: 14.74±0.20(Predicted)
• CAS DataBase Reference: 3-EPI-25-HYDROXYVITAMIN D3(CAS DataBase Reference)
• NIST Chemistry Reference: 3-EPI-25-HYDROXYVITAMIN D3(73809-05-9)
• EPA Substance Registry System: 3-EPI-25-HYDROXYVITAMIN D3(73809-05-9)

Safety Data

• Hazard Codes: T+,F
• Statements: 24/25-26-48/25-11
• Safety Statements: 28-36/37-45-16-7
• RIDADR: UN1170 - class 3 - PG 2 - Ethanol, solution
• WGK Germany: 3
• Hazardous Substances Data: 73809-05-9(Hazardous Substances Data)

Usage

Description

3-EPI-25-HYDROXYVITAMIN D3, also known as 3-epi-25(OH)D3, is a metabolite of vitamin D3 produced in the liver. It is an epimer of 25-hydroxyvitamin D3, differing only at the C-3 position where the -OH group is in the α orientation instead of the β orientation. 3-EPI-25-HYDROXYVITAMIN D3 is a white to off-white solid and plays a significant role in determining the status of vitamin D in the body.

Uses

Used in Diagnostic Applications:
3-EPI-25-HYDROXYVITAMIN D3 is used as a biomarker to determine the status of vitamin D in the body. It helps in assessing the levels of vitamin D, which is crucial for maintaining overall health and preventing deficiencies.
Used in Analytical Chemistry:
3-EPI-25-HYDROXYVITAMIN D3 can be employed as an analytical standard for the quantification of 3-epi-25(OH)D3 molecules in human serum using the LC-MS/MS method. This application aids in accurate measurement and analysis of vitamin D levels in various research and clinical settings.
Used in Pharmaceutical Research:
The epimer metabolite of Calcifediol or 25-hydroxyvitamin D3 (C125700) has potential applications in the development of pharmaceuticals targeting vitamin D-related conditions. Understanding the role of 3-EPI-25-HYDROXYVITAMIN D3 in the body can contribute to the creation of novel treatments and therapies.
Used in Radiolabelled Compounds:
The labelled epimer metabolite of Calcifediol or 25-hydroxyvitamin D3 (C125700) can be utilized in the development of radiolabelled compounds for various medical imaging and diagnostic procedures. These compounds can help in visualizing and understanding the distribution and metabolism of vitamin D in the body.

Upstream product

• 100928-03-8 (S)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol 
• 100928-11-8 25,25-(ethylenedioxy)-27-norvitamin D₃ triisopropylsilyl ether 
• 100928-12-9 (R)-4-Methylene-3-[2-[(1R,3aS,7aR)-7a-methyl-1-[(R)-1-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-butyl]-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-cyclohexanol 
• 100928-10-7 (S,Z)-<2'-<5-((triisopropylsilyl)oxy)-2-methylenecyclohexylidene>ethyl>diphenylphosphine oxide 
• 84985-78-4 (4R,7aR)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-4-((R,Z)-1-hydroxy-2-((S)-5-hydroxy-2-methylenecyclohexylidene)ethyl)-7a-methyloctahydro-1H-inden-4-ol 
• 100928-06-1 (R)-6-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-3-trimethylsilanyl-heptan-2-one 
• 100938-73-6 {(R)-3-[2-Chloro-eth-(Z)-ylidene]-4-methylene-cyclohexyloxy}-triisopropyl-silane 
• 100928-01-6 (S,Z)-2'-<5-<(triisopropylsilyl)oxy>-2-methylenecyclohexylidene>ethanol 
• 100928-08-3 de-A,B-25,25-(ethylenedioxy)-27-norcholestan-8β-ol 
• 100928-05-0 {(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-yloxy}(tert-butyl)dimethylsilane 
• 100928-04-9 (S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 4-methylbenzenesulfonate 
• 100928-02-7 (24R,22E)-de-A,B-8β-<(tert-butyldimethylsilyl)oxy>ergost-22-ene 
• 100928-09-4 de-A,B-25,25-(ethylenedioxy)-27-norcholestan-8-one 
• 100928-07-2 8β-hydroxy-de-A,B-27-norcholestan-25-one 

Downstream Products

• 140710-90-3 (R)-6-{(1R,3aS)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol 
• 19356-17-3 (S)-3-[2-[(1R,3aS)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-4-methylene-cyclohexanol 
• 32222-06-3 1α,25-dihydroxycholecalciferol 
• 132054-64-9 (1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[2-[(1R,3aS)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-2-methylene-cyclohexanol 
• 132054-64-9 (1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[2-[(1R,3aS)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-2-methylene-cyclohexanol 
• 99447-30-0 C₂₇H₄₄O₅S 

Relevant articles and documents

Stereoselective Palladium-Catalyzed Approach to Vitamin D3 Derivatives in Protic Medium

We describe an efficient convergent synthesis of vitamin D3 metabolites and analogues. The synthetic strategy relies on a tandem Pd-catalyzed A-ring closure and Suzuki–Miyaura coupling to the CD-side chain component to set directly the vitamin D triene system under protic conditions. This strategy enables rapid access to vitamin D3 and 3-epi-vitamin D3 metabolites and analogues modified at the side chain for biological evaluation and structural and metabolic studies.

A direct, regio- and stereoselective 1α-hydroxylation of (5E)-calciferol derivatives

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