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MedKoo Cat#: 461545 | Name: Rubratoxin B

Description:

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

Rubratoxin B is a mycotoxin that causes hypoglycemia and fatty liver and has shown anticancer activity.

Chemical Structure

Rubratoxin B
Rubratoxin B
CAS#21794-01-4

Theoretical Analysis

MedKoo Cat#: 461545

Name: Rubratoxin B

CAS#: 21794-01-4

Chemical Formula: C26H30O11

Exact Mass: 518.1788

Molecular Weight: 518.51

Elemental Analysis: C, 60.23; H, 5.83; O, 33.94

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
Rubratoxin B;
IUPAC/Chemical Name
4-hydroxy-10-(hydroxy(6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl)-5-(1-hydroxyheptyl)-5,9,10,11-tetrahydro-1H-cyclonona[1,2-c:5,6-c']difuran-1,3,6,8(4H)-tetraone
InChi Key
ZJTBTDVZNGBSNG-UHFFFAOYSA-N
InChi Code
InChI=1S/C26H30O11/c1-2-3-4-5-7-15(27)20-18-13(23(31)36-25(18)33)10-12(21(29)16-8-6-9-17(28)35-16)11-14-19(22(20)30)26(34)37-24(14)32/h6,9,12,15-16,20-22,27,29-30H,2-5,7-8,10-11H2,1H3
SMILES Code
O=C(C1=C2C(O)C(C(O)CCCCCC)C3=C(CC(C(C4CC=CC(O4)=O)O)C1)C(OC3=O)=O)OC2=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 518.51 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: Nagashima H. Rubratoxin-B-induced secretion of chemokine ligands of cysteine-cysteine motif chemokine receptor 5 (CCR5) and its dependence on heat shock protein 90 in HL60 cells. Environ Toxicol Pharmacol. 2015 Nov;40(3):997-1000. doi: 10.1016/j.etap.2015.10.012. Epub 2015 Nov 2. PubMed PMID: 26595743. 2: Iwashita K, Nagashima H. Rubratoxin B induces signs of fatty acid oxidation disorders (FAODs) in mice. Toxicol Lett. 2011 Oct 10;206(2):238-43. doi: 10.1016/j.toxlet.2011.07.027. Epub 2011 Jul 30. PubMed PMID: 21835235. 3: Nagashima H, Nakamura K, Goto T. Hepatotoxin rubratoxin B induced the secretion of TNF-alpha, IL-8, and MCP-1 in HL60 cells. Biochem Biophys Res Commun. 2001 Oct 5;287(4):829-32. PubMed PMID: 11573937. 4: Iwashita K, Nagashima H. Rubratoxin B induces interleukin-6 secretion in mouse white adipose tissues and 3T3-L1 adipocytes. Toxicol Lett. 2008 Nov 10;182(1-3):79-83. doi: 10.1016/j.toxlet.2008.08.008. Epub 2008 Aug 29. PubMed PMID: 18804154. 5: Nagashima H, Nakamura K, Goto T. Rubratoxin B induced the secretion of hepatic injury-related colony stimulating factors in human hepatoma cells. Toxicol Lett. 2003 Nov 30;145(2):153-9. PubMed PMID: 14581167. 6: Phillips TD, Hayes AW. Structural modification of polyfunctional rubratoxin B: effects on mammalian adenosine triphosphatase. J Environ Pathol Toxicol. 1979 Jan-Feb;2(3):853-60. PubMed PMID: 217944. 7: Nagashima H, Maeda-Nakamura K, Iwashita K, Goto T. Induced secretion of insulin-like growth factor binding protein-1 (IGFBP-1) in human hepatoma cell HepG2 by rubratoxin B. Arch Toxicol. 2007 May;81(5):347-51. Epub 2006 Nov 16. PubMed PMID: 17109117. 8: Unger PD, Hayes AW. High-pressure liquid chromatography of the mycotoxins, rubratoxins A and B, and its application to the analysis of urine and plasma for rubratoxin B. J Chromatogr. 1978 Jun 1;153(1):115-26. PubMed PMID: 580783. 9: Nagashima H, Nakamura K, Goto T. Stress-activated MAP kinases regulate rubratoxin B-caused cytotoxicity and cytokine secretion in hepatocyte-derived HepG2 cells. Toxicol Lett. 2005 Feb 15;155(2):259-67. PubMed PMID: 15603921. 10: Wang T, Zhang Y, Wang Y, Pei YH. Anti-tumor effects of Rubratoxin B on cell toxicity, inhibition of cell proliferation, cytotoxic activity and matrix metalloproteinase-2,9. Toxicol In Vitro. 2007 Jun;21(4):646-50. Epub 2007 Jan 11. PubMed PMID: 17306501. 11: Wada S, Usami I, Umezawa Y, Inoue H, Ohba S, Someno T, Kawada M, Ikeda D. Rubratoxin A specifically and potently inhibits protein phosphatase 2A and suppresses cancer metastasis. Cancer Sci. 2010 Mar;101(3):743-50. doi: 10.1111/j.1349-7006.2009.01438.x. Epub 2009 Nov 14. PubMed PMID: 20028386. 12: Engelhardt JA, Carlton WW, Hinsman EJ, Hayes AW. Rubratoxin B mycotoxicosis in the Syrian hamster: ultrastructural alterations. Exp Mol Pathol. 1989 Apr;50(2):193-204. PubMed PMID: 2707382. 13: Nagashima H, Maeda-Nakamura K, Iwashita K, Goto T. Induced secretion of tissue inhibitor of metalloproteinases-1 (TIMP-1) in vivo and in vitro by hepatotoxin rubratoxin B. Food Chem Toxicol. 2006 Jul;44(7):1138-43. Epub 2006 Mar 13. PubMed PMID: 16530906. 14: Nagashima H, Goto T. Calcium channel blockers verapamil and diltiazem impaired rubratoxin B-caused toxicity in HL60 cells. Toxicol Lett. 2000 Dec 20;118(1-2):47-51. PubMed PMID: 11137308. 15: Hood RD. Effects of concurrent prenatal exposure to rubratoxin B and T-2 toxin in the mouse. Drug Chem Toxicol. 1986;9(2):185-90. PubMed PMID: 3757826. 16: Kihara T, Surjono TW, Sakamoto M, Matsuo T, Yasuda Y, Tanimura T. Effects of prenatal rubratoxin-B exposure on behaviors of mouse offspring. Toxicol Sci. 2001 Jun;61(2):368-73. PubMed PMID: 11353145. 17: Aziz NH, Abdel-Aal SS. Regulation of rubratoxin-B biosynthesis: assessment of role of gamma-irradiation, pH and carbohydrates. Microbios. 1997;89(358):47-54. PubMed PMID: 9254332. 18: Engelhardt JA, Carlton WW, Carlson GP, Hayes AW. Reduction of hepatic and renal nonprotein sulfhydryl content and increased toxicity of rubratoxin B in the Syrian hamster and Mongolian gerbil. Toxicol Appl Pharmacol. 1988 Oct;96(1):85-92. PubMed PMID: 3188028. 19: Hayes AW. Effect of aflatoxin B and rubratoxin B on bacteriophage and rabbit cornea cells. Bull Environ Contam Toxicol. 1976 Jun;15(6):665-9. PubMed PMID: 947216. 20: Hayes AW. Action of rubratoxin B on mouse liver mitochondria. Toxicology. 1976 Aug-Sep;6(2):253-61. PubMed PMID: 989648.

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