Daunomycinone

Base Information

• Chemical Name: Daunomycinone
• CAS No.: 21794-55-8
• Molecular Formula: C21H18 O8
• Molecular Weight: 398.369
• Hs Code.: 2914500000
• European Community (EC) Number: 680-667-8
• UNII: FN5680X78X
• DSSTox Substance ID: DTXSID50944400
• Nikkaji Number: J16.581F
• Wikidata: Q27278086
• Metabolomics Workbench ID: 111673
• ChEMBL ID: CHEMBL423953
• Mol file: 21794-55-8.mol

Synonyms:daunomycinone;daunorubicin aglycone;daunorubicinone;rubomycin aglycone

Chemical Property of Daunomycinone

Chemical Property:

• Vapor Pressure: 2.83E-19mmHg at 25°C
• Melting Point: 208-210°C
• Boiling Point: 677.4°C at 760 mmHg
• PKA: 7.48±0.60(Predicted)
• Flash Point: 243.4°C
• PSA: 141.36000
• Density: 1.59g/cm³
• LogP: 1.18150
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Very Slightly, Heated)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 398.10016753
• Heavy Atom Count: 29
• Complexity: 722

Purity/Quality:

99% ^*data from raw suppliers

Daunomycinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1(CC(C2=C(C1)C(=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4OC)O)O)O
• Isomeric SMILES: CC(=O)[C@]1(C[C@@H](C2=C(C1)C(=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4OC)O)O)O
• Uses: Daunomycinone is the main metabolite of Daunorubicin (D194500). A metabolite of Daunorubicin The main metabolite of Daunorubicin (DNR).

Technology Process of Daunomycinone

There total 55 articles about Daunomycinone 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) → (+)-Daunomycinone (21794-55-8)

Guidance literature:

With potassium hydroxide; In methanol; water; at 80 ℃; for 2h;

DOI:10.1039/c6cc00890a

Reference yield: 98.2%

C25H26O10 → (+)-Daunomycinone (21794-55-8)

Guidance literature:

With dimethylboron bromide; In dichloromethane; at 2 - 8 ℃; for 2h; Inert atmosphere;

Reference yield: 98.0%

daunomycin hydrochloride (23541-50-6) → (+)-Daunomycinone (21794-55-8)

Guidance literature:

With hydrogenchloride; at 90 - 95 ℃; for 3.5h;

DOI:10.1081/SCC-200030978

upstream raw materials:

daunomycin hydrochloride

DNR

2,2'-oxybis(acetaldehyde)

7-deoxydaunomycinnone quinone methide

Downstream raw materials:

7-O-<2,3,6-tridesoxy-4'-O-p-nitrobenzoyl-3-(trifluoroacetamido)-α-L-ribo-hexopyranosyl>daunomycinone

7-O-<2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-α-L-arabino-hexopyranosyl>daunomycinone

7-O-<2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-β-L-arabino-hexopyranosyl>daunomycinone

(2S,4S)-2-acetyl-4-tert-butyldimethylsilyloxy-2,5,12-trihydroxy-7-methoxy-1,2,3,4-tetrahydro-6,11-naphthacenedione