| Identification | Back Directory | [Name]
FUMONISIN B1 | [CAS]
116355-83-0 | [Synonyms]
FB1
MACROFUSINE
FUMONISIN B1
FUMONISIN B1 98%
Fumonisin B1,96%
Fumonisin B1 ,95%
fumonisin b1solution
FuMonisin B1, 96% 1MG
FUMONISIN B1, FUSARIUM MONILIFORME
FUMONISIN B1 FROM FUSARIUM MONILIFORME
FUMONISIN B1 (MACROFUSINE) \ SPHINGOSINE
idecyl)-2-(1-methylpentyl)-1,2-ethanediyl)ester
FumonisinB1 from Fusarium moniliforme, Macrofusine
1,2,3-propanetricarboxylicacid,1,1’-(1-(12-amino-4,9,11-trihydroxy-2-methyltr
1,2,3-PROPANETRICARBOXYLIC ACID 1,1'-[12-AMINO-4,9,11-TRIHYDROXY-2-METHYLTRIDECYL)-2-(1-METHYLPENTYL)-1,2-ETHANEDIYL]ESTER
1,2,3-PROPANETRICARBOXYLIC ACID 1,1'-[1-(12-AMINO-4,9,11-TRIHYDROXY-2-METHYLTRIDECYL)-2-(1-METHYLPENTYL)-1,2-ETHANEDIYL] ESTER
1,2,3-Propanetricarboxylic acid, 1,1[1-(12-amino-4,9,11-trihydroxy-2-methyl-tridecyl)-2-(1-methylpentyl)-1,2-ethane-diyl]ester, Macrofusine
1,2,3-Propanetricarboxylic acid, 1,1-(1S,2R)-1-(2S,4R,9R,11S,12S)-12-amino-4,9,11-trihydroxy-2-methyltridecyl-2-(1R)-1-methylpentyl-1,2-ethanediyl ester, (2R,2R)-
1,1'-[(1S,2R)-1-[(2S,4R,9R,11S,12S)-12-Amino-4,9,11-trihydroxy-2-methyltridecyl]-2-[(1R)-1-methylpentyl]-1,2-ethanediyl-1,2,3-(2R,2'R)-propanetricarboxylicacidester.
(2R,2'R)-1,2,3-Propanetricarboxylic Acid 1,1'-[(1S,2R)-1-[(2S,4R,9R,11S,12S)-12-AMino-4,9,11-trihydroxy-2-Methyltridecyl]-2-[(1R)-1-Methylpentyl]-1,2-ethanediyl] Ester
Fumonisin B1 (2R,2'R)-1,2,3-Propanetricarboxylic acid 1,1'-[(1S,2R)-1-[(2S,4R,9R,11S,12S)-12-amino-4,9,11-trihydroxy-2-methyltridecyl]-2-[(1R)-1-methylpentyl]-1,2-ethanediyl] ester | [EINECS(EC#)]
201-067-0 | [Molecular Formula]
C34H59NO15 | [MDL Number]
MFCD00133349 | [MOL File]
116355-83-0.mol | [Molecular Weight]
721.83 |
| Chemical Properties | Back Directory | [Appearance]
white to tan powder | [Melting point ]
>60oC | [Boiling point ]
713.81°C (rough estimate) | [density ]
1.2207 (rough estimate) | [refractive index ]
1.6630 (estimate) | [Fp ]
6 °C | [storage temp. ]
2-8°C
| [solubility ]
Soluble in Water (up to 25 mg/ml). | [form ]
Powder | [pka]
3?+-.0.23(Predicted) | [color ]
White to tan | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months. | [CAS DataBase Reference]
116355-83-0 | [IARC]
2B (Vol. 56) 1993, 2B (Vol. 82) 2002 |
| Hazard Information | Back Directory | [Chemical Properties]
white to tan powder | [Uses]
A mycotoxin produced by mold associated with corn. Fungal metabolite believed to cause leukoencephalomalacia in horses. | [Uses]
A serine/threonine phosphatase inhibitor. | [Uses]
Fumonisin B1 is a major analogue of a family of potent mycotoxins produced by various Fusarium species, associated with animal toxicity worldwide. In vitro, fumonisin B1 inhibits sphingosine N-acyl-transferase (ceramide synthase) and blocks the growth of axons. | [Biological Activity]
Mycotoxin produced by Fusarium moniliforme . Potently inhibits sphingosine N-acyltransferase (ceramide synthase), causing an accumulation of sphingoid bases (IC 50 ~ 75 nM). Also inhibits protein phosphatases; IC 50 values are 80, 300, 400, 500 and 3000 μ M for PP5, PP2C α , PP2A, PP1 γ 2 and PP2B respectively. | [Description]
Fumonisin B1 (116355-83-0) inhibits ceramide synthesis (sphinganine N-acyltransferase), IC50 = 100 nM. Inhibits de novo sphingolipid biosynthesis (IC50 = 0.7 μM) thereby blocking glycosphingolipid production. | [Definition]
ChEBI: Fumonisin B1 is a diester that results from the condensation of the 1-carboxy groups of two molecules of propane-1,2,3-tricarboxylic acid with hydroxy groups at positions 14 and 15 of (2S,3S,5R,10R,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol. It has a role as a metabolite and a carcinogenic agent. It is a fumonisin, a primary amino compound, a diester and a triol. It is functionally related to a (2S,3S,5R,10R,12S,14S,15R,16R)-2-amino-12,16-dimethylicosane-3,5,10,14,15-pentol. It is a conjugate acid of a fumonisin B1(3-). | [General Description]
Fumonisin B1 is a neurotoxin and a phytotoxin. A cell-permeable mycotoxin that inhibits sphingolipid biosynthesis in rat kidney and in liver microsomes by inhibition of sphingosine N-acyltransferase (ceramide synthase) (IC50 = 100 nM). Cellular effects also appear to be induced by micromolar levels of FB1. Because it inhibits ceramide synthase activity, it elevates cellular levels of sphingoid bases, including sphinganine, resulting in overall inhibition of sphingolipid biosynthesis. Preferentially inhibits sphingomyelin biosynthesis in neuronal cells. Has carcinogenic properties. | [Biochem/physiol Actions]
Fumonisin B1 acts as a hepatocarcinogen and causes hepatotoxicity in rats. In horses, it causes leukoencephalitis, and in pigs, it causes pulmonary edema syndrome. In China and southern parts of Africa, it is linked with high incidence of esophageal cancer in humans. It acts as an inhibitor of sphingosine N-acyltransferase enzyme (ceramide synthase), related to structural similarities between fumonisin B1 and sphingoid bases like sphingosine. | [storage]
Store at -20°C, Keep away from moisture, Sealed | [References]
1) Merrill et al. (1993), Fumonisin B1 inhibits sphingosine (sphinganine) N-acyltransferase and de novo sphingolipid biosynthesis in cultured neurons in situ; J. Biol. Chem., 268 27299 |
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Spectrum Chemical Manufacturing Corp.
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