Daunomycinone
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 598681

CAS#: 21794-55-8

Description: Daunomycinone is the aglycone of daunomycin.

Chemical Structure

img
Daunomycinone
CAS# 21794-55-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 598681
Name: Daunomycinone
CAS#: 21794-55-8
Chemical Formula: C21H18O8
Exact Mass: 398.10
Molecular Weight: 398.360
Elemental Analysis: C, 63.32; H, 4.55; O, 32.13

Price and Availability

Size Price Availability Quantity
100mg USD 325 2 Weeks
250mg USD 585 2 Weeks
1g USD 1350 2 Weeks
Bulk inquiry

Synonym: Daunomycinone; Daunomycinon; NSC 109351; NSC-109351; NSC109351; Leukaemomycinone C;

IUPAC/Chemical Name: (8S,10S)-8-acetyl-6,8,10,11-tetrahydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione

InChi Key: YOFDHOWPGULAQF-MQJDWESPSA-N

InChi Code: InChI=1S/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

SMILES Code: O=C(C1=C2C(O)=C3[C@@H](O)C[C@](O)(C(C)=O)CC3=C1O)C4=CC=CC(OC)=C4C2=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Daunorubicinone is an aglycone form of the antitumor antibiotic daunorubicin that has been used as a starting material in the synthesis of anticancer agents.
In vitro activity: TBD
In vivo activity: TBD

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 75.31
DMF 30.0 75.31

Preparing Stock Solutions

The following data is based on the product molecular weight 398.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: TBD
In vitro protocol: TBD
In vivo protocol: TBD

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Prikrylova V, Jizba J, Blumauerova M, Huk J, Sedmera P. Microbial transformation of semisynthetic derivatives of daunomycinone modified in ring A. Folia Microbiol (Praha). 1989;34(5):459-62. PubMed PMID: 2630409.

2: Yoshimoto A, Oki T, Umezawa H. Biosynthesis of daunomycinone from aklavinone and epsilon-rhodomycinone. J Antibiot (Tokyo). 1980 Oct;33(10):1199-201. PubMed PMID: 7451370.

3: Aligiannis N, Pouli N, Marakos P, Skaltsounis AL, Pratsinis H. Synthesis and cytotoxic activity of a new potent daunomycinone derivative. Bioorg Med Chem Lett. 2002 Dec 16;12(24):3505-7. PubMed PMID: 12443763.

4: Prikrylová V, Lipavská H, Jizba JV, Fuska J, Podojil M, Vanĕk Z. Synthesis and biological activity of (7S)-O-epoxyalkyl derivatives of daunomycinone. J Antibiot (Tokyo). 1985 Dec;38(12):1714-8. PubMed PMID: 3841537.

5: Karnetová J, Matĕjů J, Sedmera P, Vokoun J, Vanĕk Z. Microbial transformation of daunomycinone by Streptomyces aureofaciens B-96. J Antibiot (Tokyo). 1976 Nov;29(11):1199-202. PubMed PMID: 825496.

6: Ge P, Wang ZQ, Zhang CN. [Synthesis of the dipeptide derivatives of daunomycinone and adriamycinone]. Yao Xue Xue Bao. 1987 Apr;22(4):254-63. Chinese. PubMed PMID: 3687444.

7: Arcamone F, Penco S, Vigevani A, Redaelli S, Franchi G, DiMarco A, Casazza AM, Dasdia T, Formelli F, Necco A, Soranzo C. Synthesis and antitumor properties of new glycosides of daunomycinone and adriamycinone. J Med Chem. 1975 Jul;18(7):703-7. PubMed PMID: 168385.

8: Perchellet EM, Sperfslage BJ, McIlvain CJ, Aligiannis N, Pouli N, Marakos P, Skaltsounis AL, Perchellet JP. Antileukemic activity of synthetic daunomycinone derivatives bearing modifications in the glycosidic moiety. Anticancer Res. 2001 Nov-Dec;21(6A):3957-67. PubMed PMID: 11911277.

9: Arcamone F, Bargiotii A, Cassinelli G, Redaelli S, Hanessian S, Di Marco A, Casazza AM, Dasdia T, Necco A, Reggiani P, Supino R. Stereocontrolled glycosidation of daunomycinone. Synthesis and biological evaluation of 6-hydroxy-L-arabino analogues of antitumor anthracyclines. J Med Chem. 1976 May;19(5):733-4. PubMed PMID: 1271420.

10: Sturdíková M, Fusková A, Prikrylová V, Podojil M, Fuska J. Cytotoxic and mutagenic in vitro effect of 7-O-epoxyalkyl derivatives of daunomycinone. Part IX. Neoplasma. 1986;33(3):297-305. PubMed PMID: 2426609.

11: Aligiannis N, Pouli N, Marakos P, Mitaku S, Skaltsounis AL, Leonce S, Pierre A, Atassi G. Design, synthesis and biological activity of 7-O-(4-O-acetyl-3-iodo-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl) daunomycinone and 7-O-(3-chloro-2,3,6-trideoxy-4-O-propanoyl-alpha-L-lyxo- hexopyranosyl)daunomycinone. Chem Pharm Bull (Tokyo). 2000 Jan;48(1):150-3. PubMed PMID: 10705494.

12: Nakai K, Takagi Y, Tsuchiya T. Synthesis and antitumor activity of 7-O-[2,6-dideoxy-2-fluoro-5-C-(trifluoromethyl)-alpha-L-talopyranosyl]- daunomycinone and -adriamycinone. Carbohydr Res. 1999 Mar 31;316(1-4):47-57. PubMed PMID: 10420587.

13: Blumauerová M, Pokorný V, Stastná J, Hostálek Z, Vanĕk Z. Improved yields of daunomycinone glycosides in developmental mutants of Streptomyces coeruleorubidus. Folia Microbiol (Praha). 1978;23(4):249-54. PubMed PMID: 689569.

14: Kende AS, Tsay YG, Mills JE. Letter: Total synthesis of (+/-)-daunomycinone and (+/-)-carminomycinone. J Am Chem Soc. 1976 Mar 31;98(7):1967-9. PubMed PMID: 1254856.

15: Takagi Y, Kobayashi N, Chang MS, Lim GJ, Tsuchiya T. Synthesis and antitumor activity of 7-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl) daunomycinone derivatives modified at C-3' or C-4'. Carbohydr Res. 1998 Feb;307(3-4):217-32. PubMed PMID: 9675364.

16: Takagi Y, Kobayashi N, Tsuchiya T, Umezawa S, Takeuchi T, Komuro K, Nosaka C. Syntheses and antitumor activities of 7-O-(6-deoxy-2-O-methyl-alpha-L-talopyranosyl)-daunomycinone and -adriamycinone. J Antibiot (Tokyo). 1989 Aug;42(8):1318-20. PubMed PMID: 2759915.

17: Kende AS, Belletire J, Bentley TJ, Hume E, Airey J. Letter: Regiospecif total synthesis of (plus or minus)-9-deoxy daunomycinone. J Am Chem Soc. 1975 Jul 23;97(15):4425-7. PubMed PMID: 1141604.

18: Kumar N, Seshadri R, Israel M. Adriamycin analogues. Preparation of 7-O-(D-ribofuranosyl)-daunomycinone and -adriamycinone. Carbohydr Res. 1986 Sep 15;153(1):171-80. PubMed PMID: 3779691.

19: Lee WW, Martinez AP, Smith TH, Henry DW. Daunomycinone analogues via the Diels-Alder reaction. Synthesis and chemistry of some 6,11-dihydroxy-5,12-naphthacenediones. J Org Chem. 1976 Jun 25;41(13):2296-303. PubMed PMID: 932859.

20: Takagi Y, Sohtome H, Tsuchiya T, Umezawa S, Takeuchi T. Synthesis of 7-O-[2,6-dideoxy-2-fluoro-4-O-(3-fluorotetrahydropyran-2-yl)- alpha-L-talopyranosyl]daunomycinone. J Antibiot (Tokyo). 1992 Mar;45(3):355-62. PubMed PMID: 1577663.