CAS 21794-55-8

(+)-Daunomycinone

Description:

(+)-Daunomycinone, with the CAS number 21794-55-8, is a naturally occurring anthracycline antibiotic derived from the bacterium Streptomyces peucetius. It is characterized by its complex polycyclic structure, which includes a tetracyclic ring system and a sugar moiety, contributing to its biological activity. This compound exhibits potent antitumor properties, primarily by intercalating into DNA and inhibiting topoisomerase II, leading to disruption of DNA replication and transcription. (+)-Daunomycinone is known for its red-orange color and is soluble in organic solvents such as methanol and dimethyl sulfoxide (DMSO), but has limited solubility in water. Its pharmacological profile includes a range of side effects, such as cardiotoxicity, which necessitates careful monitoring during therapeutic use. The compound is utilized in the treatment of various cancers, including leukemia and solid tumors, highlighting its significance in oncology. Overall, (+)-Daunomycinone serves as an important model for the development of new anticancer agents and continues to be a subject of research in medicinal chemistry.

Formula: C₂₁H₁₈O₈

InChI: InChI=1/C21H18O8/c1-8(22)21(28)6-10-13(11(23)7-21)19(26)16-15(18(10)25)17(24)9-4-3-5-12(29-2)14(9)20(16)27/h3-5,11,23,25-26,28H,6-7H2,1-2H3/t11-,21-/m0/s1

InChI key: InChIKey=YOFDHOWPGULAQF-MQJDWESPSA-N

SMILES: O=C1C=2C(=C(O)C3=C(C2O)[C@@H](O)C[C@@](C(C)=O)(O)C3)C(=O)C=4C1=C(OC)C=CC4

Synonyms:

• (+)-Daunomycinone
• (8S,10S)-8-Acetyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-5,12-naphthacenedione
• 5,12-Naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-, (8S-cis)-
• 5,12-naphthacenedione, 8-acetyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-, (8S,10S)-
• Daunomycin aglicone
• Daunomycinon
• Daunomycinone derivative
• Daunorubicin aglycone
• Daunorubicinone
• Leukaemomycinone C
• NSC 109351
• (8S,10S)-8-Acetyl-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
• 5,12-naphthacenedione,8-acetyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-me
• Epirubicin Impurity B (Daunomycinone)
• Epirubicin Hydrochloride EP Impurity B
• (8s,10s)-thoxy
• leukaemomycinonec
• daunomycinaglicone
• Daunorubicinone CRS
• 8-acetyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-, (8S-cis)-5,12-Naphthacenedione
• 8-acetyl-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-1-methoxy-,(8s,10s)-12-naphthacenedione

Daunorubicinone ((8S,10S)-8-Acetyl-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione)

CAS: 21794-55-8

Ketone-phenols and ketones with other oxygen function

Formula: C₂₁H₁₈O₈

Color and Shape: Orange Red Powder

Molecular weight: 398.10017

Ref: 45-1164697

DAUNOMYCINONE

CAS: 21794-55-8

Formula: C₂₁H₁₈O₈

Purity: 98%

Color and Shape: Solid

Molecular weight: 398.3628

Ref: IN-DA00BBTF

Epirubicin EP Impurity B (Daunorubicin EP Impurity A, Daunomycinone)

CAS: 21794-55-8

Formula: C₂₁H₁₈O₈

Molecular weight: 398.37

Ref: 4Z-E-144003

Daunomycinone

CAS: 21794-55-8

Daunomycinone (NSC-109351), a cancer-fighting antibiotic glycan, is derived from daunomycin and inhibits tumors.

Formula: C₂₁H₁₈O₈

Purity: 98.9%

Color and Shape: Solid

Molecular weight: 398.36

Ref: TM-T20699

Daunomycinone

CAS: 21794-55-8

Daunomycinone

Purity: ≥98%

Molecular weight: 398.36g/mol

Ref: 54-BUP14520

Daunomycinone

CAS: 21794-55-8

Applications Daunomycinone is the main metabolite of Daunorubicin (D194500).
References Hjelle, J.T., et al.: J. Pharmacol. Exp. Therap., 229, 372 (1984); Prikrylova, V., et al.: J. Antibiotics, 38, 1714 (1985)

Formula: C₂₁H₁₈O₈

Color and Shape: Red

Molecular weight: 398.36

Ref: TR-D193850

Daunomycinone

CAS: 21794-55-8

Daunomycinone is a chemical compound that belongs to the group of antitumor agents. It is used in cancer therapy and has been shown to inhibit protein synthesis, leading to cell death. Daunomycinone can be synthesized by reacting adriamycin with trifluoroacetic acid in the presence of an organic base. This reaction produces a daunomycinone molecule that has a hydroxyl group at one end and a carbonyl group at the other. The binding constants between daunomycinone and human serum proteins have been determined experimentally using molecular modeling techniques. Hydrogen bonding interactions are also present in this complex, which may account for its high affinity for proteins found in human serum.

Formula: C₂₁H₁₈O₈

Purity: Min. 95%

Color and Shape: Red Powder

Molecular weight: 398.36 g/mol

Ref: 3D-FD20803

Epirubicin EP Impurity B

CAS: 21794-55-8

Formula: C₂₁H₁₈O₈

Molecular weight: 398.37

Ref: ST-EA-CP-E117002

Daunorubicin EP Impurity A

CAS: 21794-55-8

Formula: C₂₁H₁₈O₈

Molecular weight: 398.37

Ref: ST-EA-CP-D104001