ADRIAMYCINONE

Base Information

• Chemical Name: ADRIAMYCINONE
• CAS No.: 24385-10-2
• Molecular Formula: C21H18 O9
• Molecular Weight: 414.369
• Hs Code.: 29147000
• Mol file: 24385-10-2.mol

Synonyms:5,12-Naphthacenedione,7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-,(8S,10S)- (9CI); 5,12-Naphthacenedione,7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(hydroxyacetyl)-1-methoxy-,(8S-cis)-; 5,12-Naphthacenedione,8-glycoloyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-, (8S,10S)-(8CI); Adriamycin aglycone; Adriamycinone; Doxorubicin aglycone;Doxorubicinone; Epirubicin aglycone

Chemical Property of ADRIAMYCINONE

Chemical Property:

• Vapor Pressure: 3.7E-22mmHg at 25°C
• Melting Point: 223-225oC
• Boiling Point: 726.6°C at 760 mmHg
• PKA: 7.45±0.60(Predicted)
• Flash Point: 260.4°C
• PSA: 161.59000
• Density: 1.671g/cm³
• LogP: 0.15390
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Doxorubicinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.
• Uses: A metabolite of Doxorubicin (Dx).

Technology Process of ADRIAMYCINONE

There total 9 articles about ADRIAMYCINONE 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: 95.0%

daunomycinone-14-bromide (29742-69-6) → adriamycinone (24385-10-2)

Guidance literature:

With silver tetrafluoroborate; In dimethyl sulfoxide; at 20 ℃;

DOI:10.1016/S0040-4039(02)00299-X

Reference yield: 90.0%

fac-triaquatricarbonyltechnetium-99m(1+) + C43H46N4O12 → adriamycinone (24385-10-2) + C46H46N4O15(99)Tc(1+) + C25H30N4O7(99)Tc(1+)

Guidance literature:

In water; Heating;

DOI:10.1021/acs.bioconjchem.5b00466

Reference yield: 85.0%

doxorubicin hydrochloride (25316-40-9) → adriamycinone (24385-10-2)

Guidance literature:

With hydrogenchloride; at 90 ℃; for 1h;

upstream raw materials:

doxorubicin hydrochloride

5,7-Dihydroxy-12-methoxy-5-[2-(4-methoxy-benzyloxy)-acetyl]-3a,4,5,6-tetrahydro-1,3-dioxa-benzo[de]naphthacene-8,13-dione

daunomycinone-14-bromide

doxorubicin

Downstream raw materials:

14-O-(p-anisyldiphenylmethyl)adriamycinone

Refernces

• 1、 Imstepf, Sebastian,Pierroz, Vanessa,Raposinho, Paula,Bauwens, Matthias,Felber, Michael,Fox, Thomas,Shapiro, Adam B.,Freudenberg, Robert,Fernandes, Célia,Gama, Sofia,Gasser, Gilles,Motthagy, Felix,Santos, Isabel R.,Alberto, Roger. "Nuclear Targeting with an Auger Electron Emitter Potentiates the Action of a Widely Used Antineoplastic Drug". . p. 2397 - 2407. Retrieved 2015.
• 2、 -. "Stable lyophilized anthracycline glycosides". Page/Page column 10. . Retrieved 2008/06/13.