71204-89-2

Basic information

• Product Name: 1,3-dihydroxy-(1a,3b,5Z,7E)- 24-nor-9,10-secochola-5,7,10(19)-trien-23-oic acid
• Synonyms: 1,3-dihydroxy-(1a,3b,5Z,7E)- 24-nor-9,10-secochola-5,7,10(19)-trien-23-oic acid;Calcitroic acid (D3);calcitroic acid;(1α,3β,5Z,7E)-1,3-Dihydroxy-24-nor-9,10-secochola-5,7,10(19)-trien-23-oic Acid;(βR,1R,3aS,4E,7aR)-4-[(2Z)-2-[(3S,5R)-3,5-Dihydroxy-2-Methylenecyclohexylidene]ethylidene]octahydro-β,7a-diMethyl-1H-indene-1-propanoic Acid;1α-Hydroxycalcioi
• CAS NO: 71204-89-2
• Molecular Formula: C₂₃H₃₄O₄
• Molecular Weight: 374.51
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 71204-89-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 572.5°C at 760 mmHg
• Flash Point: 314.1°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 1.73E-15mmHg at 25°C
• Refractive Index: 1.568
• PKA: 4.71±0.10(Predicted)
• CAS DataBase Reference: 1,3-dihydroxy-(1a,3b,5Z,7E)- 24-nor-9,10-secochola-5,7,10(19)-trien-23-oic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dihydroxy-(1a,3b,5Z,7E)- 24-nor-9,10-secochola-5,7,10(19)-trien-23-oic acid(71204-89-2)
• EPA Substance Registry System: 1,3-dihydroxy-(1a,3b,5Z,7E)- 24-nor-9,10-secochola-5,7,10(19)-trien-23-oic acid(71204-89-2)

Safety Data

• Hazardous Substances Data: 71204-89-2(Hazardous Substances Data)

Usage

Uses

Calcitroic Acid is a major metabolite of Calcitriol (C144500).

Definition

ChEBI: A hydroxycalciol that is calcidiol in which the pro-S hydrogen of calcidiol is replaced by a hydroxy group and the C-23/C-27 unit is replaced by a carboxy group.

InChI:InChI=1/C23H34O4/c1-14(11-22(26)27)19-8-9-20-16(5-4-10-23(19,20)3)6-7-17-12-18(24)13-21(25)15(17)2/h6-7,14,18-21,24-25H,2,4-5,8-13H2,1,3H3,(H,26,27)/b16-6+,17-7-/t14-,18+,19-,20+,21-,23-/m1/s1

Upstream product

• 100928-04-9 (S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 4-methylbenzenesulfonate 
• 66774-80-9 (S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate 
• 64190-52-9 (8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol 
• 93489-71-5 (R)-3-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)butanal 
• 145223-29-6 (R)-3-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)butanenitrile 
• 75716-71-1 (R)-3-{(1R,3aS,7aR)-4-[2-[(3S,5R)-5-Acetoxy-3-hydroxy-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-butyric acid methyl ester 
• 75716-73-3 (R)-3-((3S,9S,10R,13R,14R,17R)-3-Acetoxy-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-butyric acid methyl ester 
• 75731-72-5 (R)-3-{(1R,3aS,7aR)-7a-Methyl-4-[2-[(S)-2-methylene-5-(toluene-4-sulfonyloxy)-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-yl}-butyric acid methyl ester 
• 75731-73-6 (R)-3-{(1R,3aS,7aR)-4-[(R)-2-((S)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hex-1-yl)-2-methoxy-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-butyric acid methyl ester 
• 75716-77-7 (R)-3-{(1R,3aS,7aR)-4-[(R)-2-Methoxy-2-(2-methylene-bicyclo[3.1.0]hex-1-yl)-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-butyric acid methyl ester 
• 75716-74-4 Methyl 3β-Hydroxy-24-norchola-5,7-dien-23-oate 
• 75716-76-6 (R)-methyl 3-((1R,3aS,7aR,E)-4-((Z)-2-((S)-5-hydroxy-2-methylenecyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)butanoate 
• 75716-75-5 (R)-3-{(1R,3aR,7aR)-4-[(Z)-2-((S)-5-Hydroxy-2-methyl-cyclohex-1-enyl)-vinyl]-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-1-yl}-butyric acid methyl ester 
• 33168-65-9 methyl 3β-acetoxy-24-norchol-5-en-23-oate 

Relevant articles and documents

Efficient and scalable total synthesis of calcitroic acid and its 13C-labeled derivative

Calcitroic acid, the deactivated form of the physiological active vitamin D3 metabolite calcitrol, and its 13C labeled derivative has been synthesized starting from the commercially available Inhoffen-Lythgoe diol in 11 steps with an

Unsaturated Steroids. Part 12. Synthesis of 1α,3β-Dihydroxy-24-nor-9,10-secochola-5,7,10(19)trien-23-oic (Calcitroic) Acid and of the Cholic- and 25-Homocholic Acid Analogues

The three title compounds were synthesized by the same general method.Thus, methyl 3β-hydroxy-24-nor-5α-chol-7-en-23-oate (3;R=CO2Me), derived from 3β-acetoxypregn-7-ene-22-carbaldehyde (2), gave methyl 3-oxo-24-nor-5α-chol-7-en-23-oate (4;R=H,R'=CH3).Bro