Synonym
Sterigmatocystin; Sterigmatocystine; NSC-201423; NSC 201423; NSC201423; NSC-204985; NSC 204985; NSC204985;
IUPAC/Chemical Name
(3aR,12cS)-8-hydroxy-6-methoxy-3a,12c-dihydro-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one
InChi Key
UTSVPXMQSFGQTM-DCXZOGHSSA-N
InChi Code
InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3/t8-,18+/m0/s1
SMILES Code
O=C1C2=C(OC3=C1C(O)=CC=C3)C4=C(O[C@@H]5[C@H]4C=CO5)C=C2OC
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
324.28
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.
| 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: Díaz Nieto CH, Granero AM, Zon MA, Fernández H. Sterigmatocystin: A mycotoxin to be seriously considered. Food Chem Toxicol. 2018 May 26;118:460-470. doi: 10.1016/j.fct.2018.05.057. [Epub ahead of print] Review. PubMed PMID: 29842907.
2: Gruber-Dorninger C, Novak B, Nagl V, Berthiller F. Emerging Mycotoxins: Beyond Traditionally Determined Food Contaminants. J Agric Food Chem. 2017 Aug 23;65(33):7052-7070. doi: 10.1021/acs.jafc.6b03413. Epub 2016 Sep 16. Review. PubMed PMID: 27599910.
3: Calvo AM, Cary JW. Association of fungal secondary metabolism and sclerotial biology. Front Microbiol. 2015 Feb 16;6:62. doi: 10.3389/fmicb.2015.00062. eCollection 2015. Review. PubMed PMID: 25762985; PubMed Central PMCID: PMC4329819.
4: Alkhayyat F, Yu JH. Upstream regulation of mycotoxin biosynthesis. Adv Appl Microbiol. 2014;86:251-78. doi: 10.1016/B978-0-12-800262-9.00005-6. Review. PubMed PMID: 24377857.
5: Levin RE. PCR detection of aflatoxin producing fungi and its limitations. Int J Food Microbiol. 2012 May 1;156(1):1-6. doi: 10.1016/j.ijfoodmicro.2012.03.001. Epub 2012 Mar 7. Review. PubMed PMID: 22445201.
6: Schwelm A, Bradshaw RE. Genetics of dothistromin biosynthesis of Dothistroma septosporum: an update. Toxins (Basel). 2010 Nov;2(11):2680-98. doi: 10.3390/toxins2112680. Epub 2010 Nov 5. Review. PubMed PMID: 22069571; PubMed Central PMCID: PMC3153176.
7: Versilovskis A, De Saeger S. Sterigmatocystin: occurrence in foodstuffs and analytical methods--an overview. Mol Nutr Food Res. 2010 Jan;54(1):136-47. doi: 10.1002/mnfr.200900345. Review. PubMed PMID: 19998385.
8: Zhang XH, Xue LY. [Carcinogenicity and biological effectiveness of sterigmatocystin]. Zhonghua Bing Li Xue Za Zhi. 2009 Feb;38(2):136-8. Review. Chinese. PubMed PMID: 19573367.
9: Paterson RR, Lima N. Mutagens manufactured in fungal culture may affect DNA/RNA of producing fungi. J Appl Microbiol. 2009 Apr;106(4):1070-80. doi: 10.1111/j.1365-2672.2008.04024.x. Review. PubMed PMID: 19291250.
10: Georgianna DR, Payne GA. Genetic regulation of aflatoxin biosynthesis: from gene to genome. Fungal Genet Biol. 2009 Feb;46(2):113-25. doi: 10.1016/j.fgb.2008.10.011. Epub 2008 Nov 5. Review. PubMed PMID: 19010433.
11: Tanaka K, Sago Y, Zheng Y, Nakagawa H, Kushiro M. Mycotoxins in rice. Int J Food Microbiol. 2007 Oct 20;119(1-2):59-66. Epub 2007 Aug 9. Review. PubMed PMID: 17913273.
12: van Egmond HP, Schothorst RC, Jonker MA. Regulations relating to mycotoxins in food: perspectives in a global and European context. Anal Bioanal Chem. 2007 Sep;389(1):147-57. Epub 2007 May 17. Review. PubMed PMID: 17508207.
13: Karlgren M, Ingelman-Sundberg M. Tumour-specific expression of CYP2W1: its potential as a drug target in cancer therapy. Expert Opin Ther Targets. 2007 Jan;11(1):61-7. Review. PubMed PMID: 17150034.
14: Bradshaw RE, Zhang S. Biosynthesis of dothistromin. Mycopathologia. 2006 Sep;162(3):201-13. Review. PubMed PMID: 16944287.
15: Cary JW, Ehrlich KC. Aflatoxigenicity in Aspergillus: molecular genetics, phylogenetic relationships and evolutionary implications. Mycopathologia. 2006 Sep;162(3):167-77. Review. PubMed PMID: 16944284.
16: Yu JH. Heterotrimeric G protein signaling and RGSs in Aspergillus nidulans. J Microbiol. 2006 Apr;44(2):145-54. Review. PubMed PMID: 16728950.
17: Kamei K, Watanabe A. Aspergillus mycotoxins and their effect on the host. Med Mycol. 2005 May;43 Suppl 1:S95-9. Review. PubMed PMID: 16110799.
18: Yu JH, Keller N. Regulation of secondary metabolism in filamentous fungi. Annu Rev Phytopathol. 2005;43:437-58. Review. PubMed PMID: 16078891.
19: Misumi J. [The mechanisms of gastric cancer development produced by the combination of Helicobacter pylori with Sterigmatocystin, a mycotoxin]. Nihon Rinsho. 2004 Jul;62(7):1377-86. Review. Japanese. PubMed PMID: 15283159.
20: Yabe K, Nakajima H. Enzyme reactions and genes in aflatoxin biosynthesis. Appl Microbiol Biotechnol. 2004 Jun;64(6):745-55. Epub 2004 Mar 12. Review. PubMed PMID: 15022028.
