| Identification | Back Directory | [Name]
STERIGMATOCYSTIN | [CAS]
10048-13-2 | [Synonyms]
NSC 201423
NSC 204985
,(3ar-cis)-
STERIGMATOCYSTIN
STERIGMATOCYSTINE
Sterigmatocystin,98%
Sterigmatocystin solution
STERIGMATOCYSTIN VIAL WITH 5 MG*
STERIGMATOCYSTIN, ASPERGILLUS VERSICOLOR
SterigMatocystin froM Aspergillus Versicolor
NSC 201423 NSC 204985 Sterigmatocystin
3a,12c-dihydro-8-hydroxy-6-methoxyfuro[3’,2’:4,5]furo[3,2-c]xanthen-7-one
2’:4,5)furo(2,3-c)xanthen-7-one,3a,12c-dihydro-8-hydroxy-6-methoxy-7h-furo(3
3a,12c-dihydro-8-hydroxy-6-methoxy-7h-furo(3’,2’:4,5)furo(2,3-c)xanthen-7-on
3a,12c-dihydro-8-hydroxy-6-methoxy-7h-furo(3’,2’:4,5)furo(2,3-c)xanthen-7-one
3A,12C-DIHYDRO-8-HYDROXY-6-METHOXY-7H-FUROL[3',2':4,5]FURO[2,3-C]XANTHEN-7-ONE
(3aR,12cS)-8-hydroxy-6-methoxy-3aH-furo[3',2':4,5]furo[2,3-c]xanthen-7(12cH)-one
(3aR)-3aβ,12cβ-Dihydro-8-hydroxy-6-methoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one
(3aR-cis)3a,12c-dihydro-8-hydroxy-6-methoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one
(3aR,12cS)-3a,12c-Dihydro-8-hydroxy-6-Methoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one | [EINECS(EC#)]
233-158-6 | [Molecular Formula]
C18H12O6 | [MDL Number]
MFCD00005084 | [MOL File]
10048-13-2.mol | [Molecular Weight]
324.28 |
| Chemical Properties | Back Directory | [Appearance]
yellow needles or powder | [Melting point ]
249-251℃ | [Boiling point ]
382.63°C (rough estimate) | [density ]
1.2842 (rough estimate) | [refractive index ]
1.4800 (estimate) | [Fp ]
6℃ | [storage temp. ]
2-8°C
| [solubility ]
Acetone: 5 mg/ml | [form ]
powder
| [pka]
6.92±0.20(Predicted) | [color ]
yellow
| [BRN ]
53259 | [LogP]
3.169 (est) | [CAS DataBase Reference]
10048-13-2 | [IARC]
2B (Vol. 10, Sup 7) 1987 | [EPA Substance Registry System]
Sterigmatocystin (10048-13-2) |
| Hazard Information | Back Directory | [Chemical Properties]
yellow needles or powder | [Uses]
Sterigmatocystin is a carcinogenic mycotoxin that is struturally related to Aflatoxin. Sterigmatocystin has been shown to inhibit RNA synthesis in rat liver nuclei. | [Uses]
Sterigmatocystin is a xanthone produced by several species of Aspergillus, isolated by a number of research groups in the 1950s as a mycotoxin associated with food and grain contamination. Sterigmatocystin is structurally related to the aflatoxins and, while it is considered to be mutagenic, teratogenic and carcinogenic, it is less widespread and potent than the aflatoxins. Sterigmatocystin, in the presence of microsomes, covalently binds to DNA. It uncouples oxidative phosphorylation but, unlike the aflatoxins, does not induce mitochondrial swelling or hinder Ca2+-induced swelling of mitochondria. Sterigmatocystin also inhibits acyl-CoA:cholesterol acyltransferase (ACAT) with selectivity for the ACAT2 isoenzyme. | [Definition]
ChEBI: An organic heteropentacyclic compound whose skeleton comprises a xanthene ring system ortho-fused to a dihydrofuranofuran moiety. The parent of the class of sterigmatocystins. | [Description]
Sterigmatocystin is a mycotoxin that has been found in Aspergillus.1,2 It is lethal to rats (LD50 = 60 mg/kg) and chick embryos (LD50s = 5-7 μg/embryo).2 Sterigmatocystin (100 and 1,000 ppb in drinking water) induces gastritis, as well as intestinal polyp formation and metaplasia in aged Mongolian gerbils.1 It induces formation of lung and liver adenomas and malignant lymphomas in newborn mice.3 | [Hazard]
Possible carcinogen; tumorigen; poison;
mutagen; causes necrosis of the liver and kidney,
and an inhibitory effect on orotic acid incorporation
into nuclear RNA. | [Biochem/physiol Actions]
Initiates lung and liver tumors under experimental conditions. | [storage]
4°C, protect from light | [Purification Methods]
It crystallises from amyl acetate, Me2CO or EtOH and sublimes in vacuo. It has UV max at 208, 235, 249 and 329nm (log 4.28, 4.39, 4.44 and 4.12). [UV: Bullock et al. J Chem Soc 4179, 1962, UV, IR: Holker & Mulheirn J Chem Soc, Chem Commun 1576, 1576 1968, Birkinshaw & Hammady Biochem J 65 162 1957.] This mycotoxin induces bone marrow changes in mice [Curry et al. Mutation Res 137 111 1984]. [Beilstein 19/10 V 575.] | [References]
[1] MASAHIRO KUSUNOKI. Long-term administration of the fungus toxin, sterigmatocystin, induces intestinal metaplasia and increases the proliferative activity of PCNA, p53, and MDM2 in the gastric mucosa of aged Mongolian gerbils.[J]. Environmental Health and Preventive Medicine, 2011, 16 4: 224-231. DOI: 10.1007/s12199-010-0190-x
[2] H. SCHROEDER W K. Production of sterigmatocystin by some species of the genus Aspergillus and its toxicity to chicken embryos.[J]. Applied microbiology, 1975, 26 1: 589-591. DOI: 10.1128/aem.30.4.589-591.1975
[3] K FUJII. Tumor induction by a single subcutaneous injection of sterigmatocystin in newborn mice.[J]. Cancer research, 1976, 36 5: 1615-1618.
|
| Safety Data | Back Directory | [Hazard Codes ]
T,Xn,F | [Risk Statements ]
25-40-36-20/21/22-11 | [Safety Statements ]
36/37-45-16 | [RIDADR ]
UN 3462 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
LV1750000
| [F ]
10 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29329990 | [Safety Profile]
Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Poison by ingestion and intraperitoneal routes. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. | [Hazardous Substances Data]
10048-13-2(Hazardous Substances Data) |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
parabiochem
|
| Telephone: |
025-83453382-8005 |
| Website: |
www.parabiochem.cn |
|