MedKoo Cat#: 461546 | Name: Rubroskyrin

Description:

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

Rubroskyrin is a modified bis-anthraquinone pigment from Penicillium islandicum Sopp.

Chemical Structure

Rubroskyrin
Rubroskyrin
CAS#21884-47-9

Theoretical Analysis

MedKoo Cat#: 461546

Name: Rubroskyrin

CAS#: 21884-47-9

Chemical Formula: C30H22O12

Exact Mass: 574.1111

Molecular Weight: 574.49

Elemental Analysis: C, 62.72; H, 3.86; O, 33.42

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 #
No Data
Synonym
Rubroskyrin;
IUPAC/Chemical Name
(8S,8aS,9S,17S,17aR,19R)-1,4,6,8,11,14,19-heptahydroxy-2,12-dimethyl-7,8,8a,9-tetrahydro-9,17-methanonaphtho[2',3':5,6]cyclohepta[1,2-d]anthracene-5,10,15,16,18(17H)-pentaone
InChi Key
BLXAFSIUPZEETL-TWBHCDLESA-N
InChi Code
InChI=1S/C30H22O12/c1-6-3-8(31)12-16(22(6)35)25(38)14-15-19-10(33)5-11(34)20-26(39)13-9(32)4-7(2)23(36)18(13)29(42)30(19,20)21(27(15)40)28(41)17(14)24(12)37/h3-4,10,15,19,21,27,31-36,40H,5H2,1-2H3/t10-,15+,19-,21-,27+,30-/m0/s1
SMILES Code
O=C1C2=C(C(O)=C(C)C=C2O)C([C@@]3([C@]4([H])C(C(C5=O)=C(C(C6=C5C(O)=CC(C)=C6O)=O)[C@@]7([H])[C@H]4O)=O)[C@@]7([H])[C@@H](O)CC(O)=C13)=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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 574.49 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
1: Mori S, Kawai K, Nozawa Y, Ogihara Y. The redox reaction and biotransformation of rubroskyrin, a modified bis-anthraquione from Penicillium islandicum Sopp. Nat Toxins. 1998;6(2):85-90. PubMed PMID: 9888634. 2: KITAGAWA I, SHIBATA S. Metabolic products of fungi. X. The structure of rubroskyrin and its relation to the structure of luteoskyrin. Pharm Bull. 1956 Aug;4(4):309-13. PubMed PMID: 13378957. 3: Mori S, Kawai K, Nozawa Y, Ogihara Y. The interaction of rubroskyrin, a modified bis-anthraquinone pigment fromPenicillium islandicum Sopp, with respiratory chain of liver mitochondria. Mycotoxin Res. 1997 Mar;13(1):35-42. doi: 10.1007/BF02945060. PubMed PMID: 23604736. 4: HOWARD BH, RAISTRICK H. Studies in the biochemistry of micro-organisms. 92. The colouring matters of Penicillium islandicum Sopp. 4. Iridoskyrin, rubroskyrin and erythroskyrine. Biochem J. 1954 Jun;57(2):212-22. PubMed PMID: 13172171; PubMed Central PMCID: PMC1269734. 5: Mori S, Sugihara Y, Kitagawa A, Kawai K, Nozawa Y, Ogihara Y. The respiration-impairing effect of rubroskyrin, a toxic metabolite. Mycotoxin Res. 1996 Sep;12(2):91-8. doi: 10.1007/BF03192267. PubMed PMID: 23604656. 6: Mori H, Yoshimi N, Iwata H, Tanaka T, Kawai K, Sankawa U. Additional survey on genotoxicity of natural anthraquinones in the hepatocyte primary culture/DNA repair assay. J Toxicol Sci. 1988 Aug;13(3):161-6. PubMed PMID: 3193483. 7: Stark AA, Townsend JM, Wogan GN, Demain AL, Manmade A, Ghosh AC. Mutagenicity and antibacterial activity of mycotoxins produced by Penicillium islandicum Sopp and Penicillium rugulosum. J Environ Pathol Toxicol. 1978 Nov-Dec;2(2):313-24. PubMed PMID: 368283. 8: Ghosh AC, Manmade A, Kobbe B, Townsend JM, Demain AL. Production of luteoskyrin and isolation of a new metabolite, pibasterol, from Penicillium islandicum Sopp. Appl Environ Microbiol. 1978 Mar;35(3):563-6. PubMed PMID: 565188; PubMed Central PMCID: PMC242880. 9: Tikkanen L, Matsushima T, Natori S. Mutagenicity of anthraquinones in the Salmonella preincubation test. Mutat Res. 1983 Mar;116(3-4):297-304. PubMed PMID: 6339896.