55721-11-4

Basic information

• Product Name: Secalciferol
• Synonyms: (24r)-hydroxycalcidiol;(3-beta,5z,7e,24r)-9,10-secocholesta-5,7,10(19)-triene-3,24,25-triol;24(r),25-dihydroxycholecalciferol;7,10(19)-triene-3,24,25-triol,(3-beta,5z,7e,24r)-10-secocholesta-5;k-dr;osteod;ro21-5816;Secalciferol
• CAS NO: 55721-11-4
• Molecular Formula: C₂₇H₄₄O₃
• Molecular Weight: 416.64
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals;Other APIs
• Mol File: 55721-11-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 63-65°C
• Boiling Point: 474.91°C (rough estimate)
• Flash Point: 241.5 ºC
• Appearance: /
• Density: 1.0362 (rough estimate)
• Vapor Pressure: 2.03E-15mmHg at 25°C
• Refractive Index: 1.4700 (estimate)
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• PKA: 14.67±0.29(Predicted)
• BRN: 4567039
• CAS DataBase Reference: Secalciferol(CAS DataBase Reference)
• NIST Chemistry Reference: Secalciferol(55721-11-4)
• EPA Substance Registry System: Secalciferol(55721-11-4)

Safety Data

• Hazard Codes: T+
• Statements: 28
• Safety Statements: 28-36/37-45
• RIDADR: 2811
• WGK Germany: 3
• RTECS: VS2895000
• Hazardous Substances Data: 55721-11-4(Hazardous Substances Data)

Usage

Description

Secalciferol, also known as a metabolite of Vitamin D, is a white solid with potential anti-inflammatory properties. It is recognized for its role in maintaining bone health and has been studied for its potential as an anti-inflammatory steroid.

Uses

Used in Pharmaceutical Industry:
Secalciferol is used as a therapeutic agent for promoting bone health and treating conditions related to bone metabolism. Its application is primarily due to its role as a metabolite of Vitamin D, which is essential for the regulation of calcium and phosphorus levels in the body.
Used in Anti-Inflammatory Applications:
Secalciferol is used as a potentially anti-inflammatory steroid, which may help in reducing inflammation and managing pain associated with various conditions. Its anti-inflammatory properties are attributed to its metabolite status of Vitamin D, which is known to modulate immune responses and inflammation.
Used in Research and Development:
Secalciferol is utilized as a research compound for studying the effects of Vitamin D metabolites on various biological processes, including bone metabolism, immune function, and inflammation. This application is valuable for understanding the underlying mechanisms of Vitamin D and its role in human health.
Brand Name:
Osteo D (Teva, Israel) is a brand name under which Secalciferol is marketed, specifically for its use in promoting bone health and managing conditions related to bone metabolism.

InChI:InChI=1/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19?,22-,23?,24?,25-,27-/m1/s1

Upstream product

• 55700-54-4 (24R)-24,25-dihydroxyprovitamin D₃ 
• 63840-62-0 3-acetate of (24R)-24,25-dihydroxyvitamin D₃ 
• 74041-33-1 (6RS,24R)-6-methoxy-9,10-seco-3,5-cyclocholesta-7,10⁽¹⁹⁾-dien-24,25-diol 
• 55700-55-5 25-hydroxycholesta-5,7-dien-3β,24-diyl diacetate 
• 77522-15-7 (2R)-2,3-dihydroxy-3-methylbutan-1-yl p-toluenesulfonate 
• 104729-36-4 3β-hydroxy-23,24-bisnorchola-5,7-dien-22-yl phenyl sulfone 
• 56006-76-9 C₃₂H₃₈N₂O₅ 
• 136463-16-6 C₃₈H₄₄N₂O₆S 
• 52092-79-2 (24R,6Z)-<25-hydroxy-9,10-secocholesta-5(10),6,8(9)-trien-3β,24-diyl> diacetate 
• 136463-26-8 (6RS,22RS,24RS)-<24,25-dihydroxy-6-methoxy-9,10-seco-3,5-cyclocholesta-7,10(19)-dien-22-yl> phenyl sulfone 
• 136463-14-4 C₃₂H₄₀N₂O₅ 
• 226569-00-2 (1R,3aR,4S,7aR)-1-[(1R,4R)-4,5-dihydroxy-1,5-dimethylhexyl]-7a-methyl-octahydro-1H-inden-4-ol 
• 239100-24-4 (8β,24R)-de-A,B-cholesta-8,24,25-triol cyclic 24,25-(1-methylethylidene acetal) 
• 474432-39-8 (24R)-de-A,B-24,25-dihydroxycholestan-8-one cyclic 24,25-(1-methylethylidene acetal) 

Downstream Products

• 50648-94-7 (1alpha,24R,25)-trihydroxy-Vitamin D₃ 

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.

Stereoselective convergent synthesis of 24,25-dihydroxyvitamin D3 metabolites: a practical approach.

Vitamin D3 active metabolites 24R,25-(OH)2-D3, 24S,25-(OH)2-D3, and 1 alpha, 24R,25-(OH)3-D3 were synthesized by a convergent and stereoselective approach. In the synthetic route, the stereogenic center at C-24 was generated through ultrasonically induced aqueous conjugate addition of iodide 6 to Seebach's dioxolanone 5, and the vitamin D triene system was constructed using the Lythgoe approach. The synthesis, which is both short (seven steps from iodide 6) and efficient (32-40% overall yield), allows the preparation of large quantities of the metabolites and provides a novel example of a highly stereoselective reaction promoted by the zinc-copper couple in aqueous media.

USE OF MALIC ACID AS A CHIRAL SYNTHON: 24,25-DIHYDROXYCHOLECALCIFEROL

A new chiral synthon prepared from malic acid is introduced and utilized in a synthesis of 24,25-dihydroxycholecalciferol.