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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.

related product

Product No.
Description
Pricing

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H351

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

F3771-10MG-PW:
F3771-5MG:
F3771-1MG-PW:
F3771-BULK:
F3771-10MG:
F3771-1MG:
F3771-VAR:

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)
Determination of fumonisin B1 and B2 in corn and corn-based products in Turkey by high-performance liquid chromatography
OMURTAG GZ
Journal of Food Protection, 64, 1072-1075 (2001)
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%.
Pranitha Dawlal et al.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment, 36(2), 296-307 (2019-01-25)
Consumption of fumonisin-contaminated foods has a negative influence on the health of humans (carcinogen; oesophageal cancer in Eastern Cape in South Africa). Lactic acid bacteria (LAB) have emerged as a promising natural detoxification agent against mycotoxins. The aim of this
View All Related Papers

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