(3S,7R)-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione

• ChemBase ID: 132371
• Molecular Formular: C17H12O6
• Molecular Mass: 312.27358
• Monoisotopic Mass: 312.0633881
• SMILES: COc1cc2c(c3c1c1c(c(=O)o3)C(=O)CC1)[C@@H]1C=CO[C@@H]1O2
• Canonical SMILES: COc1cc2O[C@@H]3[C@H](c2c2c1c1CCC(=O)c1c(=O)o2)C=CO3
• InChI: InChI=1S/C17H12O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8,17H,2-3H2,1H3/t8-,17+/m0/s1
• InChIKey: OQIQSTLJSLGHID-WNWIJWBNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,7R)-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0^2,^9.0^3,^7.0^1^3,^1^7]nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione
• IUPAC Traditional name: aflatoxin B1
• Synonyms: Aflatoxin B1 from Aspergillus flavus; Aflatoxin B1; Aflatoxin B1 solution; (6aR,9aS)-2,3,6a,9a-Tetrahydro-4-methoxy-1H,11H-cyclopenta[c]furo[3’,2’:4,5]furo[2,3-h][1]benzopyran-1,11-dione; (-)-Aflatoxin B1; AFB1; NSC 529592; Aflatoxin B1; 黄曲霉素 B1 来源于黄曲霉; 黄曲霉素 B1; 黄曲霉素 B1 溶液

Database IDs

• CAS Number: 1162-65-8
• EC Number: 200-835-2; 214-603-3
• MDL Number: MFCD00869647
• Beilstein Number: 1269174
• PubChem SID: 162226648; 24860791; 24891116
• PubChem CID: 186907

CALCULATED PROPERTIES

• Acid pKa: 17.787313
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.5843809
• LogD (pH = 7.4): 1.5843809
• Log P: 1.5843809
• Molar Refractivity: 78.5851 cm^3
• Polarizability: 30.196644 Å^3
• Polar Surface Area: 71.06 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: crystalline; Light yellow Solid
• Melting Point: >255°C (dec.)
• Flash Point: 2 °C; 35.6 °F

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: GY1925000
• European Hazard Symbols: Flammable (F); Highly toxic (T+); Harmful (Xn)
• UN Number: 1648; 3462
• German water hazard class: 2; 3
• Hazard Class: 3; 6.1
• Packing Group: 1; 2
• Risk Statements: 11-20/21/22-36; 45-46-26/27/28
• Safety Statements: 16-36/37; 53-28-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H312-H319-H332; H300 +H310 + H330-H350; H300-H310-H330-H350
• GHS Precautionary statements: P201-P260-P264-P280-P284-P301 + P310; P210-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges; Eyeshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1648 3/PG 2; UN 3462 6.1/PG 1
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98% (TLC and HPLC)
• Concentration: 2 μg/mL in acetonitrile; 3.79 μg/g in acetonitrile
• Grade: analytical standard, for environmental analysis; BCR® certified Reference Material
• Biological Source: from Aspergillus flavus
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C17H12O6

DETAILS

Sigma Aldrich - A6636

Warning
可能致癌。
Application
Aflatoxin B1 is a carcinogenic compound that induces transversion of G to T at codon 249 of the p53 tumor suppressor gene. Aflatoxin B1 may be used as an internal standard when testing for aflatoxin contamination in food products.
Biochem/physiol Actions
Hepatocarcinogen. Food contaminant produced by Aspergillus flavus, a common soil fungus. Aflatoxin is biotransformed to genotoxic intermediates by P450 Phase I enzymes, mainly CYP3A4 via aflatoxin B1 3-hydroxylation. Detoxification depends on Phase II enzymes, such as Glutathione S-Transferase and AFB(1)-aldehyde reductase (AFAR).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A6636.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 856207

Application
This is the most toxic of the aflatoxins, a group of toxic metabolites of Aspergillus flavus. They are potent carcinogens, widely used as standards for contaminated food and feed assays. Aflatoxin B1 is often used in studies of metabolism and carcinogenesis. Goldblatt, A.L.1,2
Warning
Possibly carcinogenic.

Sigma Aldrich - 34029

General description
Certan Vial

Sigma Aldrich - ERMAC057

Legal Information
BCR is a registered trademark of European Commission

Toronto Research Chemicals - A357460

Aflatoxins B1, B2, G1, G2 as secondary metabolites of fungal species such as Aspergillus flavus or Aspergillus parasiticus growing on a variety of foods (peanuts, nuts, spices, cereals). Aflatoxins are a group of very carcinogenic mycotoxins with hepatot

REFERENCES

• Cifford, R., et al.: Nature, 209, 312 (1966)
• Wogan, et al.: Food Cosmet. Toxicol., 12, 681 (1966)
• Sinz, M.W., et al.: J. Toxicol. Toxin Rev., 10, 87 (1966)