55721-11-4

Usage

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 
• 474432-39-8 (24R)-de-A,B-24,25-dihydroxycholestan-8-one cyclic 24,25-(1-methylethylidene acetal) 
• 63973-75-1 Acetic acid (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(R)-1-methyl-3-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-propyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 61949-44-8 Δ⁵-3β,24(R),25-trihydroxycholestene-3,24-diacetate 
• 113278-71-0 (R)-2-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-4-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-butyric acid ethyl ester 
• 1243679-35-7 C₂₆H₅₀O₄Si 
• 1243679-36-8 C₂₀H₃₆O₄ 
• 1243679-28-8 C₂₀H₃₄O₄ 
• 1243679-37-9 C₃₈H₆₆O₄Si 

Downstream Products

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

Relevant academic research and scientific papers

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.

A short practical approach to 24R,25-dihydroxyvitamin D3

A synthesis of the vitamin D3 metabolite 24R,25-dihydroxyvitamin D3 (1) by Lythgoe's Wittig-Horner approach is described. The key step of the synthesis is the stereocontrolled introduction of the 24-hydroxyl group by a palladium(0)-induced [3,3]-sigmatropic rearrangement on a 22R-allylic acetate (7).

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.

SYNTHESIS OF (24R)-24,25-DIHYDROXYVITAMIN D3

Two versions of the stereoselective synthesis of (24R)-24,25-dihydroxyvitamin D3 were realized.Vitamin D2 and ergosterol were used as starting materials.Methods are proposed for the production of the following key compounds: 6-Methoxy-23,24-bisnor-9,10-seco-3,5-cyclochola-7,10(19)-dien-22-yl phenyl sulfone; 3β-hydroxy-23,24-bisnorchola-5,7-dien-22-yl phenyl sulfone; (2R)-3-methylbutane-1,2,3-triol 1-p-toluenesulfonate.

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.

Stereoselective Introduction of Hydroxy Groups into the Cholesterol Side Chain. Preparation of (24R)- and (24S)-24,25-Dihydroxy- and (25R)- and (25S)-25,26-Dihydroxyvitamin D3 by Asymmetric Synthesis

24,25-Epoxy-26-hydroxy-3β-tetrahydropyranyloxycholest-5-enes (7a) and (8a), prepared by asymmetric epoxidation of the allylic alcohol (4), and 24-hydroxy-3β-tetrahydropyranyloxycholesta-5,25-dienes (11) and (12), synthesized by asymmetric reduction of the enone (6), were stereoselectively converted into 25,26-and 24,25-dihydroxycholesterol derivatives, which could be transformed into 25,26- and 24,25-dihydroxyvitamin D3.The highly stereoselective epoxide cleavage of 26-benzoyloxy-24,25-epoxides (7b), (8b), (25), and (26) was found to proceed with retention at C-24.

24,25-Dihydroxycholestans and process for preparing the same

A 24,25-dihydroxycholestane derivatives of the formula STR1 wherein A is a steroid residue and R is an aryl group and a process for preparation of the same are disclosed. The derivatives are an intermediate for synthesis of 24,25-dihydroxycholecalciferol having useful physicological activity like that of vitamin D3. 24,25-Dihydroxycholecalciferol can be produced in an industrially advantageous method via the intermediate which is easily prepared from commercially available starting compounds.

Syntheses of 24R,25- and 24S,25-dihydroxycholecalciferol

Syntheses of 24R,25- and 24S,25-dihydroxycholecalciferol, the biologically important metabolite and derivative, respectively, of vitamin D3, are described.