Fumonisin B2
Basic information
- CAS
116355-84-1- Standard SMILES
CCCC[C@@H](C)[C@@H](OC(=O)C[C@@H](CC(=O)O)C(=O)O)[C@H](C[C@@H](C)CCCCCC[C@@H](O)C[C@H](O)[C@H](C)N)OC(=O)C[C@@H](CC(=O)O)C(=O)O- InChIKey
UXDPXZQHTDAXOZ-STOIETHLSA-N- Molecular formula
- C34H59NO14
- Average molar mass
- 705.8 g/mol
- Monoisotopic mass
- 705.39355556
Overview
Fumonisin B2 is a fumonisin that is (2S,3S,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,14,15-triol in which the hydroxy groups at positions 14 and 15 have each been esterified by condensation with the 1-carboxy group of 3-carboxyglutaric acid (giving a 3-carboxyglutarate ester group with R configuration in each case). It has a role as a carcinogenic agent and an Aspergillus metabolite. It is a diol, a fumonisin, a primary amino compound and a diester.
Names & identifiers
- Preferred name
- Fumonisin B2
- IUPAC
- (2R)-2-[2-[(5R,6R,7S,9S,16R,18S,19S)-19-amino-6-[(3R)-3,4-dicarboxybutanoyl]oxy-16,18-dihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid
- English name
- Fumonisin B2
- Molecular formula
- C34H59NO14
- Molecular weight
- 705.83
Names & synonyms
fumonisin b2116355-84-1fumonisin-B2UX4WHT4MKBCHEBI:38225DTXSID80891857(2R)-2-[2-[(5R,6R,7S,9S,16R,18S,19S)-19-amino-6-[(3R)-3,4-dicarboxybutanoyl]oxy-16,18-dihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid1,2,3-Propanetricarboxylic acid, 1,1'-(1-(12-amino-9,11-dihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl) ester1,2,3-Propanetricarboxylic acid, 1,1'-[(1S,2R)-1-[(2S,9R,11S,12S)-12-amino-9,11-dihydroxy-2-methyltridecyl]-2-[(1R)-1-methylpentyl]-1,2-ethanediyl] ester, (2R,2'R)-(2R)-2-(2-((5R,6R,7S,9S,16R,18S,19S)-19-amino-6-((3R)-3,4-dicarboxybutanoyl)oxy-16,18-dihydroxy-5,9-dimethylicosan-7-yl)oxy-2-oxoethyl)butanedioic acidRefChem:141698DTXCID201031278
Show more names
FUMONISIN B3FB2B2 Fumonisin B2FUMONISIN B2, 96+%Diquat-d4 DibromideFumonisin B2 (>90%)fumonisin b2solutionFumonisin B2 StandardFUMONISIN B2 SOLUTION (50&MU
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 268 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 15
- Rotatable bonds
- 31
- Heavy atoms
- 49
- Formal charge
- 0
- Complexity
- 1,040
Experimental & physicochemical properties
LipidsLipids -> Sphingolipids [SP] -> Sphingoid bases [SP01] -> Sphingoid base analogs [SP0108]
Collision Cross Section
258 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
259.85 Ų [M+H]+
Physicochemical properties
- Melting point
- 3200 · <3200(dec)
- Boiling point
- 705.92 °C · 705.92°C (rough estimate)
- Density
- 1.2044 · 1.2044 (rough estimate)
- refractive index
- 1.663 · 1.6630 (estimate)
- Flash point
- 6 °C · 6 °C
- storage temp.
- -20 °C · -20°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Off-white solid
- pka
- 3 · 3+-.0.23(Predicted)
- color
- Off-White to Beige
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (97.6%): Fatal if swallowed [Danger Acute toxicity, oral]
P203, P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
1,2,3-Propanetricarboxylic acid, 1,1'-[(1S,2R)-1-[(2S,9R,11S,12S)-12-amino-9,11-dihydroxy-2-methyltridecyl]-2-[(1R)-1-methylpentyl]-1,2-ethanediyl] ester, (2R,2'R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 1 (97.6%)
Toxicology
Treatment
There are no known antidotes to trichothecene mycotoxins. Treatments are directed at supporting hemopoietic abnormalities, gastrointestinal damage, and skin damage. Condiser activated charcoal if absorbed orally. Proceed with decontamination of the exposed region in case of eye or dermal contact. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. (A704)
Health Effects
Fumonisins are hepatotoxic and nephrotoxic, causing increased apoptosis followed by regenerative cell proliferation. Leukopenia, sepsis, bone marrow suppression, hemosiderosis, and multiple hemorrhages have all been reported. Contact with skin and eyes can cause coagulation necrosis. Angina, tachycardia, and hypotension may occur. Animals studies have also shown disturbed sphingolipid metabolism and cardiovascular dysfunction. (A704, L1937)
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationCarcinogenic substances that are found in the environment.
Uses & manufacturing
UsesFumonisin B2 is a fumonisin mycotoxin produced by the fungi Fusarium verticillioides and Fusarium moniliforme. Fumonisin B2 and other fumonisins frequently contaminate maize and other crops. (L1938)
Use ClassificationFood Contaminant -> MYCOTOXIN -> JECFA Functional Classes
Applications
DescriptionFumonisin B2 belongs to the family of toxins known as fumonisins. It is produced by several species of Fusarium molds primarily by Fusarium verticillioide. It is one of the major mycotoxin contaminant in corn and corn-based foods. Fumonisin B2 is a structural analog of fumonisin B1 but it is more cytotoxic than the latter and it inhibits sphinganine-N-acetyltransferase (ceramide synthase).Fumonisin B2 is a carcinogenic mycotoxin generally present on corn based food and feed-stuff, which is produced by the fungus Fusarium verticillioides and Fusarium moniliforme. Fumonisin B2 can also be detected in the industrially important fungi, Aspergillus niger.
UsesFumonisin B2 is a minor analogue of a family of potent mycotoxins produced by various Fusarium species, associated with animal toxicity worldwide. To date much of the research on the pharmacology of the fumonisins has focused on fumonisin B1. It is generally accepted that fumonisin B2 acts on ceramide biosynthesis, however, the pharmacology of the minor analogues is less well explored.
UsesA mycotoxin produced by mold associated with corn. Inhibitor of sphingosine N-acyltransferase. Blocks the formation of ceramide from sphingosine.
UsesContact herbicide used also to produce desiccation and defoliation
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.
Related reactions
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Compound notes
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