F3771

Fumonisin B₂ from Fusarium moniliforme

sphingosine N-acyltransferase inhibitor

• Synonym(s): FB₂, Fumonisin B₂
• Empirical Formula (Hill Notation): C₃₄H₅₉NO₁₄
• CAS Number: 116355-84-1
• Molecular Weight: 705.83
• MDL number: MFCD00133350
• UNSPSC Code: 12352202
• PubChem Substance ID: 24894857
• NACRES: NA.77

Properties

• biological source: Fusarium sp. (Fusarium moniliforme)
• Assay: ≥96% (TLC)
• form: powder
• solubility: methanol: 10 mg/mL, clear, colorless to faintly yellow
• storage temp.: −20°C
• SMILES string: CCCCC(C)C(OC(=O)CC(CC(O)=O)C(O)=O)C(CC(C)CCCCCCC(O)CC(O)C(C)N)OC(=O)CC(CC(O)=O)C(O)=O
• InChI: 1S/C34H59NO14/c1-5-6-12-21(3)32(49-31(43)18-24(34(46)47)16-29(40)41)27(48-30(42)17-23(33(44)45)15-28(38)39)14-20(2)11-9-7-8-10-13-25(36)19-26(37)22(4)35/h20-27,32,36-37H,5-19,35H2,1-4H3,(H,38,39)(H,40,41)(H,44,45)(H,46,47)
• InChI key: UXDPXZQHTDAXOZ-UHFFFAOYSA-N

Description

General description

Fumonisin B₂ (FB₂) is a diester of tricarballylic acid and polyhydric alcohols.. Fumonisins B₂ (FB₂) does not have one or more hydroxyl groups at the C5 or C10 positions.

Mycotoxin originally isolated from Fusarium sp, which grows on corn. Produces neural tube defects and craniofacial abnormalities in fetuses. Many strains of Aspergillus niger growing naturally on grapes are capable of producing fumonisin B₂, so it is now a concern for human consumption of grapes, raisins, and wine.

Application

Fumonisin B₂ (FB₂) from Fusarium moniliforme has been used:

• as a standard for the detection of FB₂ by high performance liquid chromatography (HPLC) in corn based food products
• used as standard in the determination of fumonisin B1 and B2 in corn and corn-based products by high-performance liquid chromatography
• as a standard in the determination of mycotoxins by HPLC

Biochem/physiol Actions

Inhibitor of sphingosine N-acyltransferase. Blocks the formation of ceramide from sphingosine.

Safety Information

• Pictograms: GHS08
• Signal Word: Warning
• Hazard Statements: H351
• Precautionary Statements: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Carc. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves