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Ochratoxin B

HCID 20966
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Basic information

CAS
4825-86-9
Standard SMILES
C[C@@H]1Cc2ccc(C(=O)N[C@@H](Cc3ccccc3)C(=O)O)c(O)c2C(=O)O1
InChIKey
DAEYIVCTQUFNTM-ABAIWWIYSA-N
Molecular formula
C20H19NO6
Average molar mass
369.4 g/mol
Monoisotopic mass
369.12123733

Overview

Crystals that exhibit blue fluorescence. (NTP, 1992)

Names & identifiers

Preferred name
Ochratoxin B
IUPAC
(2S)-2-[[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl]amino]-3-phenylpropanoic acid
English name
OCHRATOXIN B
Molecular formula
C20H19NO6
Molecular weight
369.37

Names & synonyms

OCHRATOXIN B4825-86-9CCRIS 5094ECJ5WS94N2BRN 1300160DTXSID1075301CHEBI:141524L-Phenylalanine, N-((3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl)-, (R)-Alanine, N-((8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenyl-, (-)-L-Phenylalanine, N-(((3R)-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl)-ALANINE, N-((8-HYDROXY-3-METHYL-1-OXO-7-ISOCHROMANYL)CARBONYL)-3-PHENYL-, L-Alanine, N-[(8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl]-3-phenyl-, (-)-
Show more names
(r)-carbonyl)ochratoxin b solutionOchratoxin B in MethanolOchratoxin B 10ug/ml in ACNOchratoxin B in acetonitrileOchratoxin B 10.0 μg/ml Acetonitrileochratoxin B from aspergillus ochraceusU-[13C20]- Ochratoxin B in Acetonitrile
L-Phenylalanine, N-[(3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl]-, (R)-L-Phenylalanine, N-[[(3R)-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]-RefChem:167487DTXCID10406132-((8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)formamido)-3-phenylpropanoic acid2-((hydroxy(8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)methylidene)amino)-3-phenylpropanoic acid(2S)-2-[[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl]amino]-3-phenylpropanoic acidOchratoxin B(OTB)

Properties

Computed structural properties

XLogP
4.1
Topological polar surface area
113 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
6
Rotatable bonds
5
Heavy atoms
27
Formal charge
0
Complexity
573

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Mycotoxins
Color/Form · 2 items

Crystals from methanol

Exhibits blue fluorescence

Melting Point · 2 items

430 °F (NTP, 1992)

221 °C ... also reported as 208-209 °C

Optical RotationSpecific optical rotation: -35 deg at 25 °C/D (concn = 0.15 in ethanol)
Physical Description · 2 items

Crystals that exhibit blue fluorescence. (NTP, 1992)

Solid with blue fluorescence; [Merck Index]

Physicochemical properties

Melting point
221 ° · 221° (van der Merwe)
alpha
-35 ° · D -35° (c = 0.15 in ethanol)
Boiling point
632.4 · 632.4±55.0 °C(Predicted)
Density
1.361 · 1.361±0.06 g/cm3(Predicted)
Flash point

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 · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

DOT LabelPoison
Fire HazardsFlash point data for this compound are not available. It is probably combustible. (NTP, 1992)
Health HazardsExcerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:
Hazards Summary · 1 item

Less toxic dechloro derivative of Ochratoxin A; [Merck Index] Ochratoxin B is about 1/10 as potent as Ochratoxin A and C; Ochratoxins are toxic to the kidneys in animal experiments and may cause Balkan endemic nephropathy in humans; [HSDB] An irritant; Targets the liver and kidneys; [MSDSonline] See Ochratoxin A.

Reactive GroupAcids, Carboxylic
Special ReportsWHO; Environmental Health Criteria 105: Selected Mycotoxins: Ochratoxins, Trichothecenes, Ergot (1990)
Reactivity Profile · 1 item

OCHRATOXIN B is incompatible with strong oxidizing agents, strong acids and strong bases. It 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.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 5 items

... Since little is known regarding biotransformation ... of OTB, the aim of this study was to investigate biotransformation of OTB in rats... Male F344 rats were administered either a single dose of OTB (10 mg/kg bw) or repeated doses (2 mg/kg bw, 5 days/week for 2 weeks) and euthanized 72 hr after the last dosing. ... Excretion of OTB and metabolites in urine and feces was analyzed using both HPLC with fluorescence detection and LC-MS/MS. Ochratoxin beta, which results from cleavage of the peptide bond, was the major metabolite excreted in urine in addition to small amounts of 4-hydroxy-OTB. In total, 19% of the administered dose was recovered as OTB and ochratoxin beta in urine and feces within 72 hr after a single dose. In contrast to OTA, no tissue-specific retention of OTB was evident after single and repeated administration. ... OTB is more extensively metabolized and more rapidly eliminated than OTA. ...

Ochratoxin B (0.13 mg/kg body wt) fed to pigs daily for 8 days was completely hydrolyzed to ochratoxin beta.

A metabolic product was formed from ochratoxin B by rat liver microsomal fractions in the presence of NADPH. It was isolated from the incubation mixture by extraction, thin-layer chromatography, high-pressure liquid chromatography, and crystallization. On the basis of mass and nuclear magnetic resonance spectroscopy, the structure is suggested to be 4-hydroxyochratoxin B. The Km for the formation of 4-hydroxyochratoxin B was determined, and the hydroxylation of ochratoxin A was not altered by the presence of ochratoxin B. Rats were given ochratoxin A or B, or a mixture of both intraperitoneally. The ratios of the three metabolites, ochratoxin A, (4R)-4-hydroxyochratoxin A, and ochratoxin alpha, excreted in the urine did not change in the presence of ochratoxin B. Ochratoxin B was metabolized to 4-hydroxyochratoxin B and ochratoxin beta, but in a different ratio than for the ochratoxin A metabolites. When given intraperitoneally, ochratoxin beta was excreted within 24 hr. In rats treated with ochratoxin A alone, the food intake was reduced by 50%, and histologically severe lesions, degeneration, and necrosis were observed in the proximal tubules. When ochratoxin A and B given in combination, the animals were clinically unaffected and histologically there was only slight damage of proximal tubules. These observations indicate that ochratoxin B considerably reduces the toxic effects of ochratoxin A.

The objectives of this study were to develop and evaluate procedures for the confirmation of ochratoxin A (OA), lactone opened OA (OP-OA), ochratoxin B (OB), hydroxy OA (OA-OH) and ochratoxin alpha (Oalpha) and metabolites formed in the rats from these toxins, and to demonstrate that many ochratoxin metabolites can be identified in the bile and urine of rats injected with the different ochratoxins. An esterification procedure in acidified methanol and a lactone hydrolysis procedure in strong base yielded two additional forms of most of the different ochratoxins. The esterification procedure provided a simple, fast and reliable method for the confirmation of the ochratoxins. A total of 20 different metabolites of OA, OP-OA, OB, OA-OH and Oalpha were detected in the urine and the bile of rats of which several were identified. Among these, OA and the recently discovered and toxic form of OA (OP-OA) were readily formed in vivo when either were injected. Procedures developed in this study can be used to confirm and isolate ochratoxins in biological samples and have shown that a new form of OA (OP-OA) along with many other metabolites are formed from OA and related ochratoxins in vivo.

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Compound notes

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Database identifiers

CAS
4825-86-9
PubChem CID
20966
DTXSID
DTXSID1075301
ChEBI
CHEBI:141524
UNII
ECJ5WS94N2
EC Number
621-766-8
Nikkaji
J125.924E
-11 °C · -11 °C
storage temp.
2 · 2-8°C
solubility
10 mg/ml; · 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
3.4 · 3.40±0.10(Predicted)
color
White to off-white
Major Application
cleaning productscosmeticsfood and beveragespersonal care
InChI
1S/C20H19NO6/c1-11-9-13-7-8-14(17(22)16(13)20(26)27-11)18(23)21-15(19(24)25)10-12-5-3-2-4-6-12/h2-8,11,15,22H,9-10H2,1H3,(H,21,23)(H,24,25)/t11-,15+/m1/s1
InChIKey
DAEYIVCTQUFNTM-ABAIWWIYSA-N
SMILES
C[C@@H]1Cc2ccc(C(=O)N[C@@H](Cc3ccccc3)C(O)=O)c(O)c2C(=O)O1
FDA UNII
5 WS94N2 · ECJ5WS94N2
EPA Substance Registry System
3 R)-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]- · L-Phenylalanine, N-[[(3R)-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]- (4825-86-9)
UNSPSC Code
85151701 · 85151701
NACRES
24 · NA.24
Symbol(GHS)
2 · GHS02,GHS07
Signal word
Danger
Hazard statements
225 · H225-H302-H312-H319-H332
Precautionary statements
210 · P210-P280-P305+P351+P338
Hazard Codes
Xn,T,F
Risk Statements
22 · 22-36/37/38-65-48/23/24/25-36/38-11-46-45-36-20/21/22
Safety Statements
26 · 26-36-45-16-53-36/37-62
RIDADR
3462 · UN 3462 6.1/PG 3
WGK Germany
3 · 3
RTECS
6825000 · AY6825000
HazardClass
6.1 · 6.1(a)
PackingGroup
I
HS Code
39229000 · 39229000
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
Hazardous Substances Data
4825 · 4825-86-9(Hazardous Substances Data)
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
Hazard Classes and CategoriesAcute Tox. 3 (100%)

Safety & protection

Fire FightingFires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. You should then dampen the solid spill material with 60-70% ethanol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 item

SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Isolation and EvacuationExcerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:
Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Toxicology

TreatmentCare is symptomatic and supportive. (A704)
Health EffectsOchratoxin exposure has been associated with acute tubular necrosis and Balkan endemic nephropathy. Ochratoxin A has been shown to be nephrotoxic; might delay sexual maturation. (A704)
Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 300(SRC), determined from an estimated log Kow of 3.77(2) and a regression-derived equation(2), indicates that the neutral species of ochratoxin B is expected to have moderate mobility in soil(SRC). The estimated pKa values of ochratoxin B are 3.3 and 7.0(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Ochratoxin B is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.4X10-15 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2013).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 300(SRC), determined from an estimated log Kow of 3.77(2) and a regression-derived equation(2), indicates that the neutral species of ochratoxin B is expected to adsorb to suspended solids and sediment(SRC). Estimated pKa values of 3.3 and 7.0(3) indicate ochratoxin B will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from its estimated log Kow(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Ochratoxin B may undergo hydrolysis as it contains a cyclic ester functionality which can hydrolyze under environmental conditions (pH 5 to 9)(5). Biodegradation data in water were not available(SRC, 2013).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ochratoxin B, which has an estimated vapor pressure of 6.4X10-15 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase ochratoxin B may be removed from the air by wet and dry deposition(SRC). Ochratoxin B absorbs UV light at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 3 items

The presence of 34 mycotoxins in dietary supplements containing green coffee bean (GCB) extracts was determined. Ochratoxin B was found in 32% of tested products. The concentration of ochratoxin B ranged from <1.0-20.2 ug/kg(1).

Five independent episodes of ochratoxicosis in about 970,000 turkeys, two episodes in about 70,000 laying hens, and two episodes in about 12,000,000 broiler chickens were investigated. Ochratoxin A concentrations in suspect feed and ingredients ranged from <0.2 to 16 ppm. Feed samples tested for T-2 toxin, F-2 toxin, heavy metals, and polychlorinated biphenyls were negative. Minor amounts of aflatoxin (<60 ppb) were found in suspect feed from two episodes. ... Eight of the 9 episodes were traced to the corn supply and the ninth episode was traced to corn gluten meal that became contaminated during storage after manufacture. Evidence was obtained that the ochratoxin was unstable and declined in concentration during storage. ... The ochratoxin extracted from high potency samples consisted of ochratoxins A, B, and C in ratios of about 90:8:2(1).

The effects of temperature and length of incubation on ochratoxin A production in various substrates were studied. The optimal temperature for toxin production by Aspergillus ochraceus NRRL-3174 was found to be around 28 C. Very low levels of ochratoxin A are produced in corn, rice, and wheat bran at 4 C. The optimal time for ochratoxin A production depends on the substrate, ranging from 7 to 14 days at 28 C. Ochratoxin B and dihydroisocoumaric acid, i.e., one of the hydrolysis products of ochratoxin A, were produced in rice but at levels considerably lower than ochratoxin A. No ochratoxin C was produced in rice at 28 C. When added to rice cereal or oatmeal, the toxin was found to be very stable over prolonged storage and even to autoclaving for 3 hr.

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity SummaryOchratoxin B is thought to inhibit the accumulation of cartilage proteoglycans and general protein synthesis in a concentration-related manner. (A2872)
Ecotoxicity Excerpts/AQUATIC SPECIES/ Ochratoxin B caused no deaths in Mt. Shasta strain of rainbow trout at dose of 66.7 mg/kg bw ip. Histophathological damage of liver and kidney occurred.
Signs and SymptomsMight cause respiratory irritation. (A704)
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of ochratoxin B can be estimated to be 300(SRC). According to a classification scheme(2), this estimated Koc value suggests that ochratoxin B is expected to have moderate mobility in soil. The estimated pKa values of ochratoxin B are 3.3 and 7.0(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

Natural Pollution Sources · 1 item

Ochratoxins are toxic metabolites from Aspergillus ochraceus, A. sulphureus, A. melleus and Penicillium viridicatum. As these molds occur widely, some toxins have been found as natural contaminants on corn, peanuts, storage grains, cottonseed, and other decaying vegetation. /Ochratoxins/

Human Toxicity Excerpts · 1 item

/GENOTOXICITY/ To elucidate the effects of three structurally related mycotoxins, namely, ochratoxin A (OTA), ochratoxin B (OTB), and citrinin (CIT), on human health, ...their acute toxic, mitogenic, and genotoxic effects in the human-derived liver cell line (HepG2) /were investigated/. These compounds are found in moldy foods in endemic areas of nephropathy, which is associated with urinary tract cancers. In agreement with previous experiments, /investigators/ found that OTA causes a dose-dependent induction of micronuclei (MN) and DNA migration in the single-cell gel electrophoresis (SCGE) assay, which was statistically significant at concentrations of > or =5 ug/mL. In contrast, OTB was devoid of genotoxic activity under identical conditions, but the compound caused pronounced inhibition of cell division even at doses lower than OTA (10 ug/mL). CIT caused an effect similar to that of OTA in MN assays (significant at dose levels of > or =2.5 ug/mL) but was negative in the SCGE test. All compounds failed to induce mutations in Salmonella/microsome assays in strains TA98 and TA100 after addition of HepG2-derived enzyme homogenate (S9-mix). By use of DNA-centromeric probes /investigators/ found that induction of MN by OTA involves chromosome breaking effects (55-60% of the MN were centromere negative), whereas CIT-induced MN were predominantly centromere positive (78-82%). /These/ findings indicate that OTB is devoid of genotoxic activity in human-derived cells and therefore probably not a genotoxic carcinogen in humans. In contrast, CIT was an equally potent inducer of MN in HepG2 cells as OTA, but this effect is caused by a different mechanism, namely, aneuploidy.

Safety data

wgk
3
rtecs
AY6825000
ridadr
UN 3462 6.1/PG 3
hs_code
39229000
risk_code
22-36/37/38-65-48/23/24/25-36/38-11-46-45-36-20/21/22
Signal word
Danger
Symbol(GHS)
GHS02,GHS07
hazard_code
Xn,T,F
safety_code
26-36-45-16-53-36/37-62
hazard_class
6.1(a)
Storage Class
3 - Flammable liquids
packing_group
I
Hazard statements
H225-H302-H312-H319-H332
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
Precautionary statements
P210-P280-P305+P351+P338
Hazardous Substances Data
4825-86-9(Hazardous Substances Data)

Ochratoxin B is metabolized to 4-hydroxyochratoxin B. (A2871)

Absorption, Distribution and Excretion · 3 items

Methods for preparation of labelled ochratoxin A and B are described. The method for preparation of labelled ochratoxin B involves the synthesis of the azide of ochratoxin beta via the mixed anhydride and subsequent conjugation to labelled phenylalanine to yield (14)C-ochratoxin B. The labelled ochratoxins were injected into male Wistar rats and after different survival times they were sacrificed and subjected to whole body autoradiography. The distribution pattern of ochratoxin A in the rat did not differ from that earlier registered for mouse. The previously known, high susceptibility of rats (and not mice) to ochratoxin A-induced cancer could thus not be explained by an accumulation of the toxin in specific cells or organs. The distribution patterns of ochratoxin A and B were almost congruent--the only apparent difference being a much longer retention of the labelled ochratoxin A in the blood compared to ochratoxin B, which was much faster excreted. When analyzing tissue extracts for labelled metabolites only the extracts from the rats injected with ochratoxin B were found to contain easily detectable concentrations, while no metabolites of ochratoxin A were seen.

Mixture of ochratoxins A and B (0.38 and 0.13 mg/kg body wt) was fed to pigs daily for 8 days during early pregnancy. Ochratoxin B was poorly absorbed and preferentially hydrolyzed in intestinal tract.

... Since little is known regarding biotransformation ... of OTB, the aim of this study was to investigate biotransformation of OTB in rats... Male F344 rats were administered either a single dose of OTB (10 mg/kg bw) or repeated doses (2 mg/kg bw, 5 days/week for 2 weeks) and euthanized 72 hr after the last dosing. ... Excretion of OTB and metabolites in urine and feces was analyzed using both HPLC with fluorescence detection and LC-MS/MS. Ochratoxin beta, which results from cleavage of the peptide bond, was the major metabolite excreted in urine in addition to small amounts of 4-hydroxy-OTB. In total, 19% of the administered dose was recovered as OTB and ochratoxin beta in urine and feces within 72 hr after a single dose. In contrast to OTA, no tissue-specific retention of OTB was evident after single and repeated administration. ... OTB is more extensively metabolized and more rapidly eliminated than OTA. ...

Uses & manufacturing

Uses · 3 items

A toxic metabolite of Aspergillus ochraceus, Aspergillus sulphureus, Aspergillus melleus, and Penicillium viridicatum molds. Ochratoxins are natural contaminants of corn, peanuts, storage grains, cottonseed, and other decaying vegetables; Used as an experimental teratogen and carcinogen; [Merck Index]

Experimentally as teratogen and carcinogen /Ochratoxins/

Human exposure occurs mainly through consumption of improperly stored food products, particularly contaminated grain and pork products, as well as coffee, wine grapes and dried grapes. (L1939)

General Manufacturing Information · 5 items

Dichlorvos at 1 mg/100 mL of yeast extract-sucrose medium decreased production of ochratoxin b in cultures of Aspergillus ochraceus by 50%, but growth of culture was not affected. Concentrations of 10-30 mg/100 mL, dichlorvos decreased production of ochratoxin b 50-90%; growth was decreased 9-21%.

Isolations: van Walbeek et al, Can J Microbiol 14, 131 (1968); Shotwell et al, Appl Microbiol 17, 765 (1969); Nesheim, J Assoc Offic Anal Chem 52, 975 (1969); Natori et al, Chem Pharm Bull 18, 2259 (1970). /Ochratoxins/

As these molds occur widely, some toxins have been found as natural contaminants on corn, peanuts, storage grains, cottonseed, and other decaying vegetation. /Ochratoxins/

Ochratoxion B ... /is/ the less toxic ... /non-chlorinated/ derivative of ochratoxin A.

Two strains of Aspergillus ochraceus isolated from country cured hams produced ochratoxin B on rice, defatted peanut meal, and country cured ham.

Applications · 4 items

DescriptionOchratoxins 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.

UsesOchratoxins are toxic metabolites from Aspergillus orchraceus.

UsesOchratoxin 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.

General DescriptionCrystals that exhibit blue fluorescence.

Upstream & downstream products

Upstream raw materials

OCHRATOXIN AL-Phenylalanine, N-[[(3R)-3,4-dihydro-5,8-dihydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]-2'-Deoxyguanosine
Additional notes · 1 item

DefinitionChEBI: 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-).