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F3771

Sigma-Aldrich

Fumonisin B2 from Fusarium moniliforme

sphingosine N-acyltransferase inhibitor

Synonym(s):

FB2, Fumonisin B2

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About This Item

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

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

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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.

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hcodes

H351

Hazard Classifications

Carc. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Selected mycotoxins affecting animal and human health
Handbook of Toxicologic Pathology, 699 (2002)
Elena Bernal-Algaba et al.
Toxins, 13(8) (2021-08-27)
In the last decades, the aquaculture industry has introduced plant-based ingredients as a source of protein in aquafeeds. This has led to mycotoxin contaminations, representing an ecological, health and economic problem. The aim of this study was to determine in
Zearalenone, deoxynivalenol and fumonisins in mixed-feed for laying hens
Martins HM, et al.
Mycotoxin Research, 22(4), 206-210 (2006)
Fumonisins and deoxynivalenol in corn-based food products in Portugal
Martins HM, et al.
Food And Chemical Toxicology, 46(7), 2585-2587 (2008)
I Benlashehr et al.
Poultry science, 90(8), 1671-1675 (2011-07-15)
Two extraction steps combined with HPLC with fluorescence detection were developed to determine the toxicokinetics of fumonisin B(2) (FB(2)) in ducks and turkeys. The limit of quantification of the method was 25 ng of FB(2)/mL. The mean extraction was 63%.
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