65445-14-9

Basic information

• Product Name: BRN 4715875
• Synonyms: BRN 4715875;(1R,3S,E)-5-((E)-2-((3aS,7aR)-7a-Methyl-1-((R)-6-Methylheptan-2-yl)dihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-4-Methylenecyclohexane-1,3-diol;1α-Hydroxy-5,6-trans-vitamin D3;Alfacalcidol EP impurity A;(1R,3S,E)-5-((E)-2-((1R,3aS,7aR)-7a-methyl-1-((R)-6-methylheptan-2-yl)hexahydro-1H-inden-4(2H)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol;Alfacalcidol Impurity A
• CAS NO: 65445-14-9
• Molecular Formula: C₂₇H₄₄O₂
• Molecular Weight: 400.6371
• Mol File: 65445-14-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 531.5°Cat760mmHg
• Flash Point: 222.6°C
• Appearance: /
• Density: 1.01g/cm³
• Vapor Pressure: 1.62E-13mmHg at 25°C
• Refractive Index: 1.534
• PKA: 14.43±0.40(Predicted)
• CAS DataBase Reference: BRN 4715875(CAS DataBase Reference)
• NIST Chemistry Reference: BRN 4715875(65445-14-9)
• EPA Substance Registry System: BRN 4715875(65445-14-9)

Safety Data

• Hazardous Substances Data: 65445-14-9(Hazardous Substances Data)

Usage

General Description

BRN 4715875, also known as 2'-Hydroxy-4-methoxyacetophenone, is a chemical compound with the molecular formula C9H10O3. It is a white to off-white crystalline substance that is commonly used as a fragrance and flavoring agent in the food and cosmetic industry. This chemical has a sweet, floral odor and is often used in perfumes, soaps, and lotions. It is also used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. BRN 4715875 is considered to be relatively safe for use in these applications when handled and stored properly, but caution should still be taken to prevent exposure and ingestion.

InChI:InChI=1/C27H44O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h11-12,18-19,23-26,28-29H,4,6-10,13-17H2,1-3,5H3/b21-11+,22-12-/t19-,23+,24-,25+,26-,27-/m1/s1

Upstream product

• 67657-77-6 5,6-trans-1α-Acetoxyvitamin D₃ 
• 73809-40-2 5,6-trans-1α-Hydroxyvitamin D₃ 3-acetate 
• 86307-24-6 (1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[2-[(1R,3aS)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-2-methylene-cyclohexanol 
• 87649-55-6 tert-Butyl-{(S)-3-[2-[(1R,3aS)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-4-methylene-cyclohexyloxy}-dimethyl-silane 
• 67-97-0 (5E)-cholecalciferol 
• 67-97-0 cholecalciferol 
• 71726-02-8 (S)-3-[(R)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-ol 
• 86307-24-6 (1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[2-[(1R,3aS)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-2-methylene-cyclohexanol 
• 57733-78-5 Vitamin D₃ tosylate 
• 67657-75-4 1α-Acetoxy-3,5-cyclovitamin D₃ 
• 67657-73-2 1α-Hydroxy-3,5-cyclovitamin D₃ 
• 67710-68-3 3,5-Cyclovitamin D₃ 
• 67-97-0 Vitamin D₃ 
• 67657-73-2 (1S,6R)-3-deoxy-1-hydroxy-6-methoxy-3,5-cyclo-5,6-dihydrovitamin D₃ 

Downstream Products

• 41294-56-8 1α-hydroxyvitamin D3 
• 112670-85-6 (1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-indene 

Relevant articles and documents

Improved preparation method of alfacalcidol

The invention discloses an improved preparation method of alfacalcidol. The preparation method is characterized by comprising the following steps: starting from 1 alpha-OH-3,5-cyclized vitamin D3, directly carrying out ring-opening hydrolysis without an acetate intermediate to obtain alfacalcidol and a trans-isomer thereof, carrying out a Diels-Alder reaction, selectively reacting with the trans-isomer, and carrying out column chromatography separation or methyl formate recrystallization to obtain a pure alfacalcidol product. The method is simple and convenient to operate, mild in reaction condition and high in total yield, and is suitable for large-scale synthesis of products.

A modified synthesis of the antiosteoporosis drug alfacalcidol via a key photochemical transformation of 1α-5,6-Trans-Vitamin D3

Alfacalcidol (1α-hydroxyvitamin D3) is an important clinical drug for the treatment of osteoporosis. Its practical synthesis has been intensively pursued across academia. The difficulties of separating 5,6-cis and 5,6-trans isomers in the current process was avoided by photochemical transformation of the 5,6-trans isomer into the 5,6-cis isomer. Employing vitamin D3 as a starting material, alfacalcidol was obtained by a five-step reaction sequence of esterification, cyclization, oxidation, solvolysis ring-opening, and subsequent photochemical reaction. The overall yield has been greatly improved from 17% to 31%. Georg Thieme Verlag Stuttgart New York.

Direct C(1) Hydroxylation of Vitamin D3 and Related Compounds

A direct synthesis of C(1) hydroxylated vitamin D analogues from the corresponding vitamin D precursors has been developed.Allylic oxidation of 3,5-cyclovitamin D derivatives, readily obtained from the buffered solvolysis of vitamin D tosylates, with selenium dioxide yields 1α-hydroxylated 3,5-cyclovitamin D compounds which are smoothly converted to the desired 1α-hydroxyvitamin D derivatives by acid-catalyzed cycloreversion.Application of this scheme to vitamin D3 (1a), 25-hydroxyvitamin D3 (1b), and vitamin D2 (1c) affords the 1α-hydroxy products in ca.20 percent overall yield.