OCHRATOXIN B Chemical Properties

Melting point:

221° (van der Merwe)

alpha 

D -35° (c = 0.15 in ethanol)

Boiling point:

632.4±55.0 °C(Predicted)

Density 

1.361±0.06 g/cm3(Predicted)

Flash point:

-11 °C

storage temp. 

2-8°C

solubility 

DMF: 10 mg/ml; DMSO: 15 mg/ml; Ethanol: 50 mg/ml; Ethanol:PBS (pH 7.2) (1:1): 0.50 mg/ml

form 

A crystalline solid

pka

3.40±0.10(Predicted)

color 

White to off-white

EPA Substance Registry System

L-Phenylalanine, N-[[(3R)-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]- (4825-86-9)

Safety Information

Hazard Codes 

Xn,T,F

Risk Statements 

22-36/37/38-65-48/23/24/25-36/38-11-46-45-36-20/21/22

Safety Statements 

26-36-45-16-53-36/37-62

RIDADR 

UN 3462 6.1/PG 3

WGK Germany 

3

RTECS 

AY6825000

HazardClass 

6.1(a)

PackingGroup 

I

HS Code 

39229000

Hazardous Substances Data

4825-86-9(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich

OCHRATOXIN B Usage And Synthesis

Description

Ochratoxins are mycotoxins produced by Aspergillus and Penicillium species of fungi that contaminate foods. Ochratoxin A (OTA, ) is a chlorinated form with toxicity that targets the kidneys, causing nephropathy and renal adenomas. OTB is a non-chlorinated analog of OTA that has cytotoxic effects on kidney and liver cells in vitro but only minor effects in vivo, due to its rapid metabolism and excretion. OTB inhibits cell proliferation of human liver HepG2 cells at doses as low as 1 μg/ml but lacks the genotoxic activity of OTA, even at higher concentrations.

Uses

Ochratoxins are toxic metabolites from Aspergillus orchraceus.

Uses

Ochratoxin B is the non-chlorinated analogue of the much more extensively studied ochratoxin A. It is co-produced by the same species of Aspergillus and Penicillium that are associated with food spoilage. Ochratoxin B has received little focused investigation and its mode of action and potential hazards have been inferred from ochratoxin A.

Definition

ChEBI: Ochratoxin B is a phenylalanine derivative resulting from the formal condensation of the amino group of L-phenylalanine with the carboxy group of (3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxylic acid. Ochratoxin B differs from the more naturally abundant ochratoxin A in the absence of the dihydroisocoumarin chlorine atom. It has cytotoxic effects on kidney and liver cells in vitro but only minor effects in vivo, due to its rapid metabolism and excretion. It inhibits cell proliferation of human liver HepG2 cells at doses as low as 1 mug/ ml but lacks the genotoxic activity of ochratoxin A, even at higher concentrations. It has a role as an Aspergillus metabolite, a Penicillium metabolite, a mycotoxin and a calcium channel blocker. It is a phenylalanine derivative, a N-acyl-L-phenylalanine, a member of isochromanes and a monocarboxylic acid. It is a conjugate acid of an ochratoxin B(1-).

General Description

Crystals that exhibit blue fluorescence.

Reactivity Profile

OCHRATOXIN B is incompatible with strong oxidizing agents, strong acids and strong bases. OCHRATOXIN B is a carboxylic acid derivative. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt.

Fire Hazard

Flash point data for OCHRATOXIN B are not available. OCHRATOXIN B is probably combustible.

References

[1] J VARGA. Ochratoxin production by Aspergillus species.[J]. Applied and Environmental Microbiology, 1996, 62 12: 4461-4464. DOI: 10.1128/aem.62.12.4461-4464.1996
[2] SIEGFRIED KNASMüLLER. Structurally related mycotoxins ochratoxin A, ochratoxin B, and citrinin differ in their genotoxic activities and in their mode of action in human-derived liver (HepG2) cells: implications for risk assessment.[J]. Nutrition and Cancer-An International Journal, 2004, 50 2: 190-197. DOI: 10.1207/s15327914nc5002_9
[3] E. O’BRIEN  Daniel R D  A Prietz. Investigation of the teratogenic potential of ochratoxin A and B using the FETAX system[J]. Birth defects research. Part B, Developmental and reproductive toxicology, 2005, 74 5: 417-423. DOI: 10.1002/bdrb.20054
[4] C N EZEKIEL. Fungal and bacterial metabolites in commercial poultry feed from Nigeria.[J]. Food Additives and Contaminants Part A-chemistry Analysis Control Exposure & Risk Assessment, 2012, 29 8: 1288-1299. DOI: 10.1080/19440049.2012.688878

OCHRATOXIN B(4825-86-9)Related Product Information

• Ochratoxin A-d5
• Ochratoxin A,B,C
• ochratoxin C
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• 3-METHYLHIPPURIC ACID
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• OCHRATOXIN A
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• 3-FORMYLSALICYLIC ACID, 97
• Salicyluric acid
• 4-ETHYLBENZAMIDE
• BZ-PHE-OH
• cresotamide
• N-(4-ETHYLBENZYL)-N-METHYLAMINE
• 3-Aminomethylbenzoic acid
• OCHRATOXIN A(RG)
• Methyl3-(aminomethyl)benzoate