52744-22-6

Basic information

• Product Name: carminomycinone
• Synonyms: carminomycinone;8β-Acetyl-7,8,9,10-tetrahydro-1,6,8α,10α,11-pentahydroxy-5,12-naphthacenedione;4-Demethyl Daunomycinone;(8S,10S)-8-Acetyl-7,8,9,10-tetrahydro-1,6,8,10,11-pentahydroxy-5,12-naphthacenedione;4-DeMethoxy-4-hydroxydaunoMycinone;4-O-DeMethyldaunoMycinone
• CAS NO: 52744-22-6
• Molecular Formula: C₂₀H₁₆O₈
• Molecular Weight: 384.338
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 52744-22-6.mol

Chemical Properties

• Melting Point: 235-236 °C
• Boiling Point: 656.1°C at 760 mmHg
• Flash Point: 364.6°C
• Appearance: /
• Density: 1.709g/cm³
• Vapor Pressure: 4.17E-18mmHg at 25°C
• Refractive Index: 1.769
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, DMSO, Methanol
• PKA: 6.47±0.60(Predicted)
• CAS DataBase Reference: carminomycinone(CAS DataBase Reference)
• NIST Chemistry Reference: carminomycinone(52744-22-6)
• EPA Substance Registry System: carminomycinone(52744-22-6)

Safety Data

• Hazardous Substances Data: 52744-22-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Carminomycinone is used as an intermediate compound for the production of Daunorubicin, a widely used chemotherapeutic agent. Its role in the metabolic pathway of Daunorubicin highlights its importance in the development and synthesis of effective cancer treatments.
Used in Research and Development:
Carminomycinone serves as a valuable research tool for scientists and researchers working on the development of new drugs and therapies. Its unique chemical properties and metabolic role make it a promising candidate for further investigation and potential applications in the field of medicine.
Used in Quality Control and Analysis:
Due to its distinct chemical properties, carminomycinone can be utilized in the quality control and analysis of pharmaceutical products containing Daunorubicin. Its presence can be used as an indicator of the purity and effectiveness of these products, ensuring that they meet the required standards for patient use.

InChI:InChI=1/C20H16O8/c1-7(21)20(28)5-9-13(11(23)6-20)19(27)15-14(17(9)25)16(24)8-3-2-4-10(22)12(8)18(15)26/h2-4,11,22-23,25,27-28H,5-6H2,1H3/t11-,20-/m0/s1

Upstream product

• 21794-55-8 (+)-Daunomycinone 
• 138252-36-5 (1R,3R)-3-Acetyl-6-chloro-1,3,10,11-tetrahydroxy-1,2,3,4-tetrahydro-naphthacene-5,12-dione 
• 138252-34-3 (1S,3S,4aR,12aR)-6-Chloro-1,3,10,11-tetrahydroxy-3-trimethylsilanylethynyl-1,2,3,4,4a,12a-hexahydro-naphthacene-5,12-dione 
• 138252-35-4 (1R,3R,4aS,12aS)-3-Acetyl-6-chloro-1,3,10,11-tetrahydroxy-1,2,3,4,4a,12a-hexahydro-naphthacene-5,12-dione 
• 20830-81-3 DNR 
• 23541-50-6 daunomycin hydrochloride 
• 52794-97-5 carminomycin I hydrochloride 
• 144-62-7 oxalic acid 

Downstream Products

• 62152-30-1 (8S,10S)-1,6,8,10,11-Pentahydroxy-8-(1-hydroxy-ethyl)-7,8,9,10-tetrahydro-naphthacene-5,12-dione 
• 286010-04-6 C₂₆H₁₉BO₈ 
• 76203-82-2 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 
• 286010-11-5 C₂₆H₁₉BO₇ 

Relevant articles and documents

A Novel Synthesis of (+)-4-Demethoxydaunomycinone

(+)-4-Demethoxydaunomycinone (2) was obtained in five steps through the selective formation of the trifluormethanesulphonate (4) and its palladium-catalysed reduction.

Syntheses of idarubicin analogues containing a glucose or galactose moiety as a glycone

The new idarubicin analogues (12 and 13) with a glucose or galactoseas as a glycone were synthesized from daunomycin (2). (+)-4-Demethoxydaunomycinone (6) obtained from reaction of 2 with AlCl33 was converted to 4-trifluoromethanesulfonyl daunomycinone (7) through reaction with trifluoromethanesulfonic anhydride. The treatment of 7 with 1,1-bis- (diphenylphospino)ferrocene/Pd(OAc)22 in triethylamine/formic acid/dioxane provided the idarubicinone (5b). Glycosylation of 7-hydroxy group of 5b with two kinds of tetraacetyl pyranosyl halide (8 and 9) by a modified Koenigs-Knorr procedure and then deacetylation using aqueous 0.1 N LiOH solution and amberlite cationic resin gave the objective materials. The in vitro MTT assay of the analogues (12b and 13a) in comparison with idarubicin (5a) on peripheral blood human promyelocytic-leukemia cell line and human breast cancer cell line were also described.

5-deoxy, 12-deoxy, 5,12-bisdeoxy, and 4,5,12-trisdeoxy anthracyclines: Synthesis of new analogues of daunorubicin and doxorubicin by controlled deoxygenation of the C-ring

Hydrogenation of the anthracyclines daunorubicin (1) and doxorubicin (2) gave selective deoxygenation at position 5. Hydride reduction of (1) and (2) gave complementary regiocontrol, leading to 12-deoxygenation or 5,12-bisdeoxygenation. This chemistry all

A NEW SYNTHESIS OF ANTHRACYCLINES

Carminomycinone (1) has efficiently been synthesised in a five-staged sequence based on cycloaddition of a 1,3-dioxybutadiene to the 1,4-anthraquinone (3); (1) was then converted into daunomycinone (2), an established source of daunomycin, adriamycin and related antitumour anthracyclines.