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Daunomycinone (CAS 21794-55-8)

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Alternate Names:
Daunomycin Aglicone; Daunomycinon
Application:
Daunomycinone is a Daunorubicin primary metabolite
CAS Number:
21794-55-8
Molecular Weight:
398.36
Molecular Formula:
C21H18O8
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Daunomycinone is an anthracycline aglycone that is studied extensively in organic chemistry and biochemistry research. It serves as a key intermediate in the synthesis of anthracycline antibiotics. Research on daunomycinone primarily focuses on its role in the structure-activity relationship of anthracycline compounds. As an aglycone, it lacks the glycosidic moiety present in full anthracycline antibiotics, which allows scientists to study the contributions of the sugar group to the overall biological activity of these compounds. Chemists are interested in daunomycinone for its potential to be modified chemically and create semi-synthetic anthracycline derivatives. Such derivatives are synthesized to enhance their properties or to better understand the molecular basis of their action. Moreover, daunomycinone is investigated for its chromophore properties, as the compound′s planar structure and conjugated system contribute to its strong interaction with light, making it useful in photophysical studies. Researchers also explore its role in DNA intercalation studies due to the structural similarities it shares with other intercalative agents.


Daunomycinone (CAS 21794-55-8) References

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  2. Stereocontrolled glycosidation of daunomycinone. Synthesis and biological evaluation of 6-hydroxy-L-arabino analogues of antitumor anthracyclines.  |  Arcamone, F., et al. 1976. J Med Chem. 19: 733-4. PMID: 1271420
  3. Synthesis and antitumor properties of new glycosides of daunomycinone and adriamycinone.  |  Arcamone, F., et al. 1975. J Med Chem. 18: 703-7. PMID: 168385
  4. Cytotoxic and mutagenic in vitro effect of 7-O-epoxyalkyl derivatives of daunomycinone. Part IX.  |  Sturdíková, M., et al. 1986. Neoplasma. 33: 297-305. PMID: 2426609
  5. Microbial transformation of semisynthetic derivatives of daunomycinone modified in ring A.  |  Prikrylova, V., et al. 1989. Folia Microbiol (Praha). 34: 459-62. PMID: 2630409
  6. Synthesis of antitumor-active 7-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl)-daunomycinone and -adriamycinone.  |  Ok, K., et al. 1987. Carbohydr Res. 169: 69-81. PMID: 3427590
  7. Biotransformations of anthracyclinones in Streptomyces coeruleorubidus and Streptomyces galilaeus.  |  Blumauerová, M., et al. 1979. Folia Microbiol (Praha). 24: 117-27. PMID: 456946
  8. New daunorubicin analogs. 3-Amino-2,3,6-trideoxy-alpha- and beta-D-arabino- and 3,6-diamino-2,3,6-trideoxy- alpha-D-ribo-hexopyranosides of daunomycinone.  |  Fuchs, EF., et al. 1979. J Antibiot (Tokyo). 32: 223-38. PMID: 457582
  9. 7-(Aminoethyl) ether and thioether of daunomycinone.  |  Acton, EM., et al. 1979. J Med Chem. 22: 922-6. PMID: 490537
  10. Chemical modification of anthracycline antibiotics IV. Synthesis of new anthracyclines with trisaccharide.  |  Tanaka, H., et al. 1982. J Antibiot (Tokyo). 35: 312-20. PMID: 6951827
  11. Adriamycin analogues. Preparation and antitumor evaluation of 7-O-(beta-D-glucosaminyl)daunomycinone and 7-O-(beta-D-glucosaminyl)adriamycinone and their N-trifluoroacetyl derivatives.  |  Israel, M. and Murray, RJ. 1982. J Med Chem. 25: 24-8. PMID: 7086817
  12. Biosynthesis of daunomycinone from aklavinone and epsilon-rhodomycinone.  |  Yoshimoto, A., et al. 1980. J Antibiot (Tokyo). 33: 1199-201. PMID: 7451370
  13. Microbial transformation of daunomycinone by Streptomyces aureofaciens B-96.  |  Karnetová, J., et al. 1976. J Antibiot (Tokyo). 29: 1199-202. PMID: 825496
  14. Daunomycinone analogues via the Diels-Alder reaction. Synthesis and chemistry of some 6,11-dihydroxy-5,12-naphthacenediones.  |  Lee, WW., et al. 1976. J Org Chem. 41: 2296-303. PMID: 932859

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Daunomycinone, 5 mg

sc-211212
5 mg
$245.00