Cas no 116355-83-0 (Fumonisin B1)

Fumonisin B1 is a mycotoxin produced primarily by Fusarium species, notably F. verticillioides and F. proliferatum. It is a polar, water-soluble compound with a long hydrocarbon chain and tricarballylic acid groups. As a contaminant in maize and other cereals, it poses significant risks to human and animal health, particularly due to its inhibition of ceramide synthase, disrupting sphingolipid metabolism. Fumonisin B1 is widely studied for its role in toxicology and food safety, serving as a critical reference standard in analytical methods such as HPLC and LC-MS for mycotoxin detection. Its structural stability and well-characterized properties make it essential for research in agricultural and biomedical sciences.
Fumonisin B1 structure
Fumonisin B1 structure
Product Name:Fumonisin B1
CAS No:116355-83-0
MF:C34H59NO15
MW:721.829972505569
MDL:MFCD27977580
CID:195821
PubChem ID:24894752
Update Time:2025-05-23

Fumonisin B1 Chemical and Physical Properties

Names and Identifiers

    • 1,2,3-Propanetricarboxylicacid,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,2'R)-
    • Fumonisin B1
    • Fumonisin B1 solution
    • FUMONISIN B1(RG)
    • MaizeFlourwithFumonisinB1
    • Fumonisin B1 from Fusarium moniliforme,Macrofusine
    • Fumonisin B1,1,1'-[(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
    • FB1
    • MACROFUSINE
    • FUMONISIN B1, FUSARIUM MONILIFORME
    • FUMONISIN B1 FROM FUSARIUM MONILIFORME
    • FUMONISIN B1 98%
    • Fumonisin B1,96%
    • Fumonisin B1 ,95%
    • fumonisin b1solution
    • FuMonisin B1, 96% 1MG
    • CCRIS 4433
    • fumonisin B(1)
    • HSDB 7077
    • NSC-629151
    • 19 - Fusarium mycotoxins in oats
    • 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)-propanetricarboxylic acid ester.
    • CS-0029116
    • NSC 629151
    • EX-A8017
    • AKOS024457430
    • CHEBI:38221
    • SCHEMBL13555629
    • GLXC-25523
    • 1ST7224-100M
    • (2R)-2-[2-[(5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-6-[(3R)-3,4-dicarboxybutanoyl]oxy-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid
    • 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,2'R)-
    • 116355-83-0
    • fumonisin-B1
    • LMSP01080022
    • 1,2,3-Propanetricarboxylic acid, 1,1'-(1-(12-amino-4,9,11-trihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl)ester
    • HY-N6719
    • UNII-3ZZM97XZ32
    • 1,2,3-Propanetricarboxylic acid, 1,1'-(1-(12-amino-4,9,11-trihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl) ester
    • 3ZZM97XZ32
    • Fumonisin B1 50 microg/mL in Acetonitrile/Water
    • FUMONISIN B1 [IARC]
    • DTXSID6020644
    • Fumonisin B1 solution in Methanol, 100ug/mL
    • Fumonisin B1 solution in Acetonitrile/Water (1:1), 50ug/mL
    • FUMONISIN B1 [MI]
    • Fumonisin B1, reference material
    • (2R,2'R)-2,2'-{[(5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-11,16,18-trihydroxy-5,9-dimethylicosane-6,7-diyl]bis[oxy(2-oxoethane-2,1-diyl)]}dibutanedioic acid
    • 1,2,3-Propanetricarboxylic acid, 1,1'-[1-(12-amino-4,9,11-trihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl] ester, [2S-[1[1R*(S*),2S*(S*),2(S*)],2R*,4S*,9S*,11R*,12R*]]-; Fumonisin B1
    • Fumonisin B1 from Fusarium moniliforme, >=98% (HPLC)
    • 1ST7224
    • 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,2'R)-
    • (R)-3-Carboxy-pentanedioic acid mono-{(1S,3S,5R,10R,12S,13S)-13-amino-1-[(1R,2R)-1-((R)-3,4-dicarboxy-butyryloxy)-2-methyl-hexyl]-5,10,12-trihydroxy-3-methyl-tetradecyl} ester
    • Q63395324
    • 1ST7224-50A
    • C19241
    • FUMONISINB1
    • (2S)-2-[2-[(5R,6R,7S,9S,11R,16R,18S,19S)-19-Amino-6-[(3S)-3,4-dicarboxybutanoyl]oxy-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid
    • (2S,2'S)-2,2'-{[(5S,6R,7R,9R,11S,16R,18S,19S)-19-amino-11,16,18-trihydroxy-5,9-dimethylicosane-6,7-diyl]bis[oxy(2-oxoethane-2,1-diyl)]}dibutanedioic acid
    • J-003429
    • CHEMBL91690
    • Q420762
    • SCHEMBL182919
    • 2-[2-[13-amino-1-[1-(3-carboxy-5-hydroxy-5-oxo-pentanoyl)oxy-2-methyl-hexyl]-5,10,12-trihydroxy-3-methyl-tetradecoxy]-2-oxo-ethyl]butanedioic acid
    • SR-01000721952-2
    • NCI60_009465
    • Fumonisin B1-13C34 solution
    • 2,2'-{(19-Amino-11,16,18-trihydroxy-5,9-dimethylicosane-6,7-diyl)bis[oxy(2-oxoethane-2,1-diyl)]}dibutanedioic acid
    • 2-[2-({19-amino-6-[(3,4-dicarboxybutanoyl)oxy]-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl}oxy)-2-oxoethyl]butanedioic acid
    • 1ST7224C34-25M
    • CHEMBL1588379
    • NSC629151
    • BCP31144
    • UVBUBMSSQKOIBE-UHFFFAOYSA-N
    • SCHEMBL182918
    • 1,2,3-Propanetricarboxylic acid, 1,-1'-[1-(12-amino-4,9,11-trihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl] ester
    • DTXSID80861237
    • MLS000517270
    • CHEBI:185259
    • Fumonisin B1-13C34 Solution in Acetonitrile, 25ug/mL
    • 1217458-62-2
    • Fungal metabolite from Fusarium monliforme
    • SMR000127506
    • NS00000145
    • FT-0626567
    • 2-[2-[19-amino-6-(3,4-dicarboxybutanoyloxy)-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid
    • Macrofusin
    • SMP1_000324
    • SR-01000721952
    • 2-(2-((13-Amino-1-(1-((3,4-dicarboxybutanoyl)oxy)-2-methylhexyl)-5,10,12-trihydroxy-3-methyltetradecyl)oxy)-2-oxoethyl)succinic acid
    • HMS2268H15
    • MLSMR
    • CHEMBL5282242
    • G14340
    • 1,2,3-Propanetricarboxylic acid, 1,1'-(1-(12-amino-4,9,11-trihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-eth anediyl) ester
    • DTXCID60644
    • 2-(2-(19-amino-6-(3,4-dicarboxybutanoyloxy)-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl)oxy-2-oxoethyl)butanedioic acid
    • (2S)-2-(2-{[(5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-6-{[(3S)-3,4-dicarboxybutanoyl]oxy}-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl]oxy}-2-oxoethyl)butanedioate
    • FUMONISIN B1 (IARC)
    • 1,2,3Propanetricarboxylic acid, 1,1'(1(12amino4,9,11trihydroxy2methyltridecyl)2(1methylpentyl)1,2ethanediyl) ester
    • (2S)-2-(2-(((5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-6-(((3S)-3,4-dicarboxybutanoyl)oxy)-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl)oxy)-2-oxoethyl)butanedioate
    • DA-53128
    • 1,2,3-Propanetricarboxylic acid, 1,-1'-(1-(12-amino-4,9,11-trihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl) ester
    • Macrofacine
    • UVBUBMSSQKOIBE-DSLOAKGESA-N
    • 2-(2-((19-amino-6-((3,4-dicarboxybutanoyl)oxy)-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl)oxy)-2-oxoethyl)butanedioic acid
    • (2R,2'R)-2,2'-(((5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-11,16,18-trihydroxy-5,9-dimethylicosane-6,7-diyl)bis(oxy(2-oxoethane-2,1-diyl)))dibutanedioic acid
    • MDL: MFCD27977580
    • Inchi: 1S/C34H59NO15/c1-5-6-9-20(3)32(50-31(44)17-23(34(47)48)15-29(41)42)27(49-30(43)16-22(33(45)46)14-28(39)40)13-19(2)12-24(36)10-7-8-11-25(37)18-26(38)21(4)35/h19-27,32,36-38H,5-18,35H2,1-4H3,(H,39,40)(H,41,42)(H,45,46)(H,47,48)/t19-,20+,21-,22+,23+,24+,25+,26-,27-,32+/m0/s1
    • InChI Key: UVBUBMSSQKOIBE-DSLOAKGESA-N
    • SMILES: O(C(C[C@H](C(=O)O)CC(=O)O)=O)[C@@H](C[C@@H](C)C[C@@H](CCCC[C@H](C[C@@H]([C@H](C)N)O)O)O)[C@@H]([C@H](C)CCCC)OC(C[C@H](C(=O)O)CC(=O)O)=O

Computed Properties

  • Exact Mass: 721.38800
  • Monoisotopic Mass: 721.388
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 8
  • Hydrogen Bond Acceptor Count: 16
  • Heavy Atom Count: 50
  • Rotatable Bond Count: 31
  • Complexity: 1070
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 10
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • XLogP3: -0.5
  • Topological Polar Surface Area: 289

Experimental Properties

  • Color/Form: White to brown powder
  • Density: 1.254±0.06 g/cm3 (20 oC 760 Torr),
  • Boiling Point: 713.81°C (rough estimate)
  • Flash Point: 6?°C
  • Refractive Index: 1.6630 (estimate)
  • Solubility: Very slightly soluble (0.12 g/l) (25 o C),
  • PSA: 288.51000
  • LogP: 3.26450
  • Sensitiveness: Sensitive to light and humidity
  • Solubility: Soluble in water
  • Vapor Pressure: 0.0±0.6 mmHg at 25°C

Fumonisin B1 Security Information

  • Symbol: GHS08
  • Signal Word:Warning
  • Hazard Statement: H351
  • Warning Statement: P281
  • Hazardous Material transportation number:UN 3172
  • WGK Germany:3
  • Hazard Category Code: R40
  • Safety Instruction: 36/37-16
  • RTECS:TZ8350000
  • Hazardous Material Identification: T Xn F
  • Packing Group:III
  • Hazard Level:6.1(b)
  • HazardClass:6.1(b)
  • PackingGroup:III
  • Risk Phrases:R40
  • Packing Group:III
  • Safety Term:6.1(b)
  • Storage Condition:storage at -4℃ (1-2weeks), longer storage period at -20℃ (1-2years)

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Amadis Chemical Company Limited
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Additional information on Fumonisin B1

Fumonisin B1 (CAS No. 116355-83-0): A Comprehensive Overview of Its Structure, Bioactivity, and Recent Research Findings

Fumonisin B1, with the chemical identifier CAS No. 116355-83-0, is a mycotoxin produced by certain species of Fusarium fungi. This compound has garnered significant attention in the field of chemobiology due to its diverse pharmacological effects and implications in human health and agriculture. As a member of the fumonisin family, it shares structural similarities with other mycotoxins but exhibits distinct biological activities that make it a subject of extensive research.

The molecular structure of Fumonisin B1 consists of a triacetylated derivative of 3-amino-12,13-dihydroxy-9-methyltetradecanoic acid. This unique configuration contributes to its ability to interfere with sphingolipid biosynthesis, a critical pathway in cellular metabolism. The disruption of this pathway has been implicated in various pathological conditions, including cancer, neurodegenerative diseases, and metabolic disorders.

Recent studies have highlighted the multifaceted bioactivity of Fumonisin B1. For instance, research published in the journal Biochemical Pharmacology has demonstrated its potent inhibitory effects on the enzyme ceramide synthase, which is essential for sphingolipid production. This inhibition leads to an accumulation of ceramide precursors, triggering cellular stress responses such as apoptosis and autophagy.

In addition to its impact on sphingolipid metabolism, Fumonisin B1 has been shown to exhibit genotoxic and carcinogenic properties. A study published in the Journal of Applied Toxicology reported that long-term exposure to this mycotoxin could lead to DNA damage and chromosomal abnormalities in mammalian cells. These findings have raised concerns about its potential role in the development of certain cancers, particularly in regions where mycotoxin contamination is prevalent.

The agricultural significance of Fumonisin B1 cannot be overstated. Crops such as corn and peanuts are particularly susceptible to contamination by Fusarium species, leading to widespread presence of this mycotoxin in food supplies. Regulatory agencies worldwide have established guidelines to limit exposure levels, emphasizing the need for effective detection and mitigation strategies. Advances in analytical techniques, such as liquid chromatography-tandem mass spectrometry (LC-MS/MS), have improved the accuracy and sensitivity of Fumonisin B1 detection in food matrices.

Recent research has also explored the therapeutic potential of Fumonisin B1. Surprisingly, some studies suggest that low doses of this compound may have protective effects against certain neurological disorders. For example, a study published in the Neurochemical Research journal indicated that pretreatment with Fumonisin B1 could mitigate neuronal damage caused by oxidative stress and excitotoxicity. However, these findings require further investigation to fully understand the mechanisms involved and to assess potential risks.

The toxicological profile of Fumonisin B1 is complex and influenced by various factors, including dosage, duration of exposure, and individual susceptibility. Animal models have been instrumental in elucidating its adverse effects on different organ systems. For instance, studies in rodents have shown that high levels of exposure can lead to liver damage, kidney dysfunction, and reproductive toxicity. These findings underscore the importance of implementing stringent safety measures in both agricultural practices and industrial settings where this compound may be present.

The interaction between Fumonisin B1 and host metabolism is another area of active investigation. Research suggests that genetic polymorphisms in enzymes responsible for detoxifying mycotoxins can influence an individual's susceptibility to their adverse effects. Understanding these genetic factors may help develop personalized approaches for risk assessment and mitigation strategies.

In conclusion, Fumonisin B1 (CAS No. 116355-83-0) is a multifaceted compound with significant implications for human health and agriculture. Its ability to disrupt sphingolipid biosynthesis and its associated toxicological effects make it a subject of intense research interest. While challenges remain in fully understanding its mechanisms of action and developing effective control measures, ongoing studies continue to shed light on its complex bioactivity and potential applications.

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