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MedKoo Cat#: 146137 | Name: Sterigmatin

Description:

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

Sterigmatocystin is a toxic secondary metabolite produced by certain fungi, such as Aspergillus species. It is primarily known for its carcinogenic and mutagenic properties, and is used in scientific research to study mechanisms of DNA damage and cancer development. Sterigmatocystin functions by forming DNA adducts, leading to mutations and potentially triggering tumor formation. Its biological mechanism involves the alkylation of guanine bases in DNA, which disrupts cellular processes and contributes to its genotoxic effects.

Chemical Structure

Sterigmatin
Sterigmatin
CAS#55256-49-0

Theoretical Analysis

MedKoo Cat#: 146137

Name: Sterigmatin

CAS#: 55256-49-0

Chemical Formula: C17H10O6

Exact Mass: 310.0477

Molecular Weight: 310.26

Elemental Analysis: C, 65.81; H, 3.25; O, 30.94

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 #
No Data
Synonym
Sterigmatin;
IUPAC/Chemical Name
(3aS,12aR)-4,6-dihydroxy-3a,12a-dihydro-5H-furo[3',2':4,5]furo[3,2-b]xanthen-5-one
InChi Key
CWYJYLXZMAUSNI-BWKAKNAASA-N
InChi Code
1S/C17H10O6/c18-8-2-1-3-9-13(8)16(20)14-11(22-9)6-10-12(15(14)19)7-4-5-21-17(7)23-10/h1-7,17-19H/t7-,17+/m0/s1
SMILES Code
[H][C@]12OC=C[C@@]1([H])C3=C(O)C4=C(OC5=CC=CC(O)=C5C4=O)C=C3O2
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 310.26 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: Kawai K, Nakamaru T, Hisada K, Nozawa Y, Mori H. The effects of demethylsterigmatocystin and sterigmatin on ATP synthesis system in mitochondria: A comparison with sterigmatocystin. Mycotoxin Res. 1986 Mar;2(1):33-8. doi: 10.1007/BF03191960. PMID: 23604834. 2: Mori H, Sugie S, Yoshimi N, Kitamura J, Niwa M, Hamasaki T, Kawai K. Genotoxic effects of a variety of sterigmatocystin-related compounds in the hepatocyte/DNA-repair test and the Salmonella microsome assay. Mutat Res. 1986 Mar;173(3):217-22. doi: 10.1016/0165-7992(86)90039-4. PMID: 3081801. 3: Sana T, Khan M, Jabeen A, Shams S, Hadda TB, Begum S, Siddiqui BS. Urease and Carbonic Anhydrase Inhibitory Effect of Xanthones from Aspergillus nidulans, an Endophytic Fungus of Nyctanthes arbor-tristis. Planta Med. 2023 Apr;89(4):377-384. doi: 10.1055/a-1908-0935. Epub 2023 Jan 10. PMID: 36626924. 4: Zeng H, Cai J, Hatabayashi H, Nakagawa H, Nakajima H, Yabe K. verA Gene is Involved in the Step to Make the Xanthone Structure of Demethylsterigmatocystin in Aflatoxin Biosynthesis. Int J Mol Sci. 2020 Sep 2;21(17):6389. doi: 10.3390/ijms21176389. PMID: 32887494; PMCID: PMC7503927. 5: Yabe K, Nakamura M, Hamasaki T. Enzymatic formation of G-group aflatoxins and biosynthetic relationship between G- and B-group aflatoxins. Appl Environ Microbiol. 1999 Sep;65(9):3867-72. doi: 10.1128/AEM.65.9.3867-3872.1999. PMID: 10473388; PMCID: PMC99713. 6: Yabe K, Ando Y, Hashimoto J, Hamasaki T. Two distinct O-methyltransferases in aflatoxin biosynthesis. Appl Environ Microbiol. 1989 Sep;55(9):2172-7. doi: 10.1128/aem.55.9.2172-2177.1989. PMID: 2802602; PMCID: PMC203052.