carminomycinone

Base Information

• Chemical Name: carminomycinone
• CAS No.: 52744-22-6
• Molecular Formula: C20H16 O8
• Molecular Weight: 384.34
• Mol file: 52744-22-6.mol

Synonyms:5,12-Naphthacenedione,8-acetyl-7,8,9,10-tetrahydro-1,6,8,10,11-pentahydroxy-, (8S-cis)-;(+)-Carminomycinone; 4-Demethoxy-4-hydroxydaunomycinone;4-Demethyldaunomycinone; 4-O-Demethyldaunomycinone; Carminomycinone

Chemical Property of carminomycinone

Chemical Property:

• Vapor Pressure: 4.17E-18mmHg at 25°C
• Melting Point: 235-236 °C
• Boiling Point: 656.1°C at 760 mmHg
• PKA: 6.47±0.60(Predicted)
• Flash Point: 364.6°C
• PSA: 152.36000
• Density: 1.709g/cm³
• LogP: 0.87850
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, DMSO, Methanol

Purity/Quality:

98%Min ^*data from raw suppliers

4-Demethyl daunomycinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A metabolite Daunorubicin in liver microsomes. A metabolite Daunorubicin

Technology Process of carminomycinone

There total 16 articles about carminomycinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

DNR (20830-81-3) → cis-9-acetyl-4-hydroxy-7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-5,12-naphthacenedione (52744-22-6)

Guidance literature:

With aluminum (III) chloride; In dichloromethane; Inert atmosphere; Reflux;

DOI:10.5012/bkcs.2010.31.01.069

Reference yield: 88.0%

(+)-Daunomycinone (21794-55-8) → cis-9-acetyl-4-hydroxy-7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-5,12-naphthacenedione (52744-22-6)

Guidance literature:

With aluminium trichloride; In dichloromethane; for 2h; Heating;

DOI:10.1039/P19900000428

Reference yield: 70.0%

(1R,3R)-3-Acetyl-6-chloro-1,3,10,11-tetrahydroxy-1,2,3,4-tetrahydro-naphthacene-5,12-dione (138252-36-5) → (+/-)-Carminomycinone (52744-22-6,59433-02-2,138332-30-6) + (+/-)-7-Epicarminomycinone (52744-22-6,59433-02-2,138332-30-6)

Guidance literature:

In trifluoroacetic acid;

DOI:10.1016/0040-4039(91)80783-3

upstream raw materials:

(+)-Daunomycinone

oxalic acid

carminomycin I hydrochloride

daunomycin hydrochloride

Downstream raw materials:

Benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,7,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide

C₂₆H₁₉BO₇

C₂₆H₁₉BO₈

(8S,10S)-1,6,8,10,11-Pentahydroxy-8-(1-hydroxy-ethyl)-7,8,9,10-tetrahydro-naphthacene-5,12-dione

Refernces

• 1、 Pettit et al.. "". . p. 7387,7388. Retrieved 1975.
• 2、 Rho, Young S.,Park, Ran,Kim, Seon-Young,Yoo, Dong Jin. "Syntheses of idarubicin analogues containing a glucose or galactose moiety as a glycone". experimental part. p. 69 - 74. Retrieved 2010/08/06.
• 3、 Cameron, Donald W.,Feutrill, Geoffrey I.,Griffiths, Peter G.,O'Brien, David G.. "A NEW SYNTHESIS OF ANTHRACYCLINES". . p. 6179 - 6182. Retrieved 2007/10/02.