Introduction：Basic information about Doxorubicinone CAS 24385-10-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Doxorubicinone Basic information
| Product Name: | Doxorubicinone |
| Synonyms: | Epirubicin aglycon;5,12-Naphthacenedione, 7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-;Ccris 7633;8-glycoloyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-5,12-Naphthacenedione;Doxorubicin aglycone;Doxorubicinone;Epirubicin aglycone;5,12-Naphthacenedione, 7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)- |
| CAS: | 24385-10-2 |
| MF: | C21H18O9 |
| MW: | 414.36 |
| EINECS: | |
| Product Categories: | Intermediates & Fine Chemicals;Pharmaceuticals;Metabolites & Impurities;Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals |
| Mol File: | 24385-10-2.mol |
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Doxorubicinone Chemical Properties
| Melting point | 223-225°C |
| Boiling point | 741.2±60.0 °C(Predicted) |
| density | 1.671±0.06 g/cm3(Predicted) |
| storage temp. | Amber Vial, -20°C Freezer |
| solubility | Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly) |
| pka | 7.45±0.60(Predicted) |
| form | Solid |
| color | Red to Very Dark Red |
| Stability: | Light Sensitive |
| Major Application | pharmaceutical (small molecule) |
| InChI | InChI=1S/C21H18O9/c1-30-11-4-2-3-8-14(11)20(28)16-15(17(8)25)18(26)9-5-21(29,12(24)7-22)6-10(23)13(9)19(16)27/h2-4,10,22-23,26-27,29H,5-7H2,1H3/t10-,21-/m0/s1 |
| InChIKey | IBZGBXXTIGCACK-CWKPULSASA-N |
| SMILES | C1(OC)=C2C(C(=O)C3=C(C2=O)C(O)=C2C(C[C@@](O)(C(CO)=O)C[C@@H]2O)=C3O)=CC=C1 |
| CAS DataBase Reference | 24385-10-2 |
Safety Information
| WGK Germany | WGK 3 |
| HS Code | 29147000 |
| Storage Class | 11 - Combustible Solids |
Doxorubicinone Usage And Synthesis
| Description | Doxorubicinone is a metabolite of the anthracycline antitumor antibiotic doxorubicin . Doxorubicinone inhibits mitochondrial succinoxidase from bovine heart and reduces the mitochondrial inner membrane potential in rat heart and liver mitochondria in a concentration-dependent manner. Doxorubicinone (40 μM) increases pentose phosphate pathway flux by 45% and reduces activity of glutathione peroxidase (GPx) and superoxide dismutase (SOD) by 17 and 60%, respectively, in human erythrocytes. It also induces cytotoxicity in patient-derived ovarian cancer colonies in a concentration-dependent manner. |
| Chemical Properties | Red Solid |
| Uses | A metabolite of Doxorubicin (Dx). |
| Definition | ChEBI: Adriamycinone is a member of tetracenes and a quinone. |
| General Description | Doxorubicinone (adriamycinone) is an aglycone. It is a metabolite of adriamycin converted in the body, and another metabolite is amycinol [1]. Adriamycin nephropathy (AN) is a rodent model of chronic kidney disease. AN is characterized by podocyte injury followed by glomerulosclerosis, tubulointerstitial inflammation and fibrosis. |
| References | [1] Emara S, et al. Effect of cyclodextrins on the stability of adriamycin,adriamycinol, adriamycinone and daunomycin. Talanta, 2008; 51: 359-364. |
Doxorubicinone Preparation Products And Raw materials
| Preparation Products | (7S,9S)-9-(1,2-dihydroxyethyl)-6,7,9,11-tetrahydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione |
