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MedKoo Cat#: 463286 | Name: Rhodomycinone

Description:

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

Rhodomycinone is a a major by-product of daunorubicin fermentations.

Chemical Structure

Rhodomycinone
Rhodomycinone
CAS#21288-60-8

Theoretical Analysis

MedKoo Cat#: 463286

Name: Rhodomycinone

CAS#: 21288-60-8

Chemical Formula: C22H20O9

Exact Mass: 428.1107

Molecular Weight: 428.39

Elemental Analysis: C, 61.68; H, 4.71; O, 33.61

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Rhodomycinone; E-Rhodomycinone; E Rhodomycinone; epsilon-Rhodomycinone; epsilon Rhodomycinone; NSC 196524; NSC196524; NSC-196524;
IUPAC/Chemical Name
methyl (1R,2R,4S)-2-ethyl-2,4,5,7,12-pentahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
InChi Key
PYFOXRACBORDCT-GOSXWKPOSA-N
InChi Code
InChI=1S/C22H20O9/c1-3-22(30)7-10(24)12-13(16(22)21(29)31-2)20(28)14-15(19(12)27)18(26)11-8(17(14)25)5-4-6-9(11)23/h4-6,10,16,23-24,27-28,30H,3,7H2,1-2H3/t10-,16-,22+/m0/s1
SMILES Code
CC[C@]1(C[C@@H](c2c([C@H]1C(OC)=O)c(O)c3c(C(c4c(C3=O)cccc4O)=O)c2O)O)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

Preparing Stock Solutions

The following data is based on the product molecular weight 428.39 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
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(RHODOMYCINONE, PYRROMYCINONE UND IHRE GLYKOSIDE.) [ANTHRACYCLINONES AND ANTHRACYCLINES. (RHODOMYCINONE, PYRROMYCINONE AND THEIR GLYCOSIDES)]. Fortschr Chem Org Naturst. 1963;21:121-82. German. PMID: 14287135. 6: Kiviharju K, Salonen K, Leisola M, Eerikäinen T. Modeling and simulation of Streptomyces peucetius var. caesius N47 cultivation and epsilon-rhodomycinone production with kinetic equations and neural networks. J Biotechnol. 2006 Nov 10;126(3):365-73. doi: 10.1016/j.jbiotec.2006.04.034. Epub 2006 May 6. PMID: 16797766. 7: Olano C, Lomovskaya N, Fonstein L, Roll JT, Hutchinson CR. A two-plasmid system for the glycosylation of polyketide antibiotics: bioconversion of epsilon-rhodomycinone to rhodomycin D. Chem Biol. 1999 Dec;6(12):845-55. doi: 10.1016/s1074-5521(00)80004-6. PMID: 10631513. 8: Yoshimoto A, Oki T, Umezawa H. Biosynthesis of daunomycinone from aklavinone and epsilon-rhodomycinone. J Antibiot (Tokyo). 1980 Oct;33(10):1199-201. doi: 10.7164/antibiotics.33.1199. 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Carbohydr Res. 2000 Dec 1;329(4):861-72. doi: 10.1016/s0008-6215(00)00257-3. PMID: 11125829. 13: Komatsu Y, Takahashi O, Hayashi H. Identification of the anthracycline antibiotic 4-O-(beta-D-glucopyranuronosyl)-epsilon-rhodomycinone, produced by Streptomyces ruber JCM3131, as an up-regulator of MHC class-I molecules in B16/BL6 cells. J Antibiot (Tokyo). 1998 Jan;51(1):85-8. doi: 10.7164/antibiotics.51.85. PMID: 9531993. 14: Dekleva ML, Strohl WR. Biosynthesis of epsilon-rhodomycinone from glucose by Streptomyces C5 and comparison with intermediary metabolism of other polyketide- producing streptomycetes. Can J Microbiol. 1988 Nov;34(11):1235-40. doi: 10.1139/m88-217. PMID: 3208200. 15: Blumauerová M, Královcová E, Matĕjů J, Jizba J, Vanĕk Z. Biotransformations of anthracyclinones in Streptomyces coeruleorubidus and Streptomyces galilaeus. Folia Microbiol (Praha). 1979;24(2):117-27. doi: 10.1007/BF02927295. PMID: 456946. 16: Yoshimoto A, Johdo O, Takatsuki Y, Ishikura T, Sawa T, Takeuchi T, Umezawa H. New anthracycline antibiotics obtained by microbial glycosidation of beta- isorhodomycinone and alpha 2-rhodomycinone. J Antibiot (Tokyo). 1984 Aug;37(8):935-8. doi: 10.7164/antibiotics.37.935. PMID: 6592162. 17: Brockmann H, Niemeyer J. Konfiguration and Konformation von alpha- Rhodomycinon, beta-Rhodomycinon and beta-Iso-rhodomycinon [Configuration and structure of alpha-rhodomycinone, beta-rhodomycinone and beta-iso- rhodomycinone]. Chem Ber. 1967;100(11):3578-87. German. doi: 10.1002/cber.19671001112. PMID: 6056217. 18: Nakagawa M, Kawai H, Hayakawa Y, Seto H, Otake N. 4-O-(beta-D- Glucopyranosyl)-epsilon-rhodomycinone, a new microbial transformation product of rhodomycinone. J Antibiot (Tokyo). 1985 Nov;38(11):1622-4. doi: 10.7164/antibiotics.38.1622. PMID: 4077740. 19: Brockmann H, Wimmer E. Rhodomycine, 8. Antibiotica aus Actinomyceten, LI. 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