Ochratoxin B

Base Information

• Chemical Name: Ochratoxin B
• CAS No.: 4825-86-9
• Molecular Formula: C20H19NO6
• Molecular Weight: 369.374
• Hs Code.: 39229000
• European Community (EC) Number: 621-766-8
• UN Number: 3462
• UNII: ECJ5WS94N2
• DSSTox Substance ID: DTXSID1075301
• Nikkaji Number: J125.924E
• Wikidata: Q3880769
• Mol file: 4825-86-9.mol

Synonyms:ochratoxin B

Chemical Property of Ochratoxin B

Chemical Property:

• Vapor Pressure: 7.33E-17mmHg at 25°C
• Melting Point: 221oC
• Boiling Point: 632.4°Cat760mmHg
• PKA: 3.40±0.10(Predicted)
• Flash Point: 336.2°C
• PSA: 112.93000
• Density: 1.361g/cm³
• LogP: 2.31020
• Storage Temp.: 2-8°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 369.12123733
• Heavy Atom Count: 27
• Complexity: 573
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Ochratoxin B ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T,F
• Hazard Codes: Xn,T,F
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Mycotoxins
• Canonical SMILES: CC1CC2=C(C(=C(C=C2)C(=O)NC(CC3=CC=CC=C3)C(=O)O)O)C(=O)O1
• Isomeric SMILES: C[C@@H]1CC2=C(C(=C(C=C2)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)O)O)C(=O)O1
• 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: 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.

Technology Process of Ochratoxin B

There total 5 articles about Ochratoxin B which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

8-hydroxy-3-methyl-1-oxo-isochroman-7-carboxylic acid L-phenyl alanine tert-butyl ester amide → C20H19NO6 + N-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl]-carbonyl}-L-phenylalanine (4825-86-9)

Guidance literature:

With trifluoroacetic acid; In chloroform; for 15 - 18h;

Reference yield:

ochratoxin A (303-47-9) → N-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl]-carbonyl}-L-phenylalanine (4825-86-9)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; for 0.5h; Yield given; Ambient temperature;

Reference yield:

ochratoxin A (303-47-9) + 2'-Deoxyguanosine (961-07-9) → N-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl]-carbonyl}-L-phenylalanine (4825-86-9) + N-{[(3R)-5,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl]carbonyl}-L-phenylalanine (205034-32-8) + (S)-2-({(R)-5-[2-Amino-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-8-yl]-8-hydroxy-3-methyl-1-oxo-isochroman-7-carbonyl}-amino)-3-phenyl-propionic acid

Guidance literature:

With phosphate buffer; In dimethyl sulfoxide; for 0.133333h; pH=7.4; UV-irradiation;

DOI:10.1021/ja034221r

upstream raw materials:

ochratoxin A

2'-Deoxyguanosine

GLUTATHIONE

Downstream raw materials:

L-phenylalanine

(-)-3,4-dihydro-8-hydroxy-3-methyl-7-isocoumarincarboxylic acid

Refernces

• 1、 -. "COMPOUNDS AND COMPOSITIONS USEFUL IN THE TREATMENT OF NEOPLASIA". Page/Page column 98-99. . Retrieved 2008/06/13.
• 2、 Brow, Mark E.,Dai, Jian,Park, Gyungse,Wright, Marcus W.,Gillman, Ivan G.,Manderville, Richard A.. "Photochemically catalyzed reaction of ochratoxin a with D- and L-cysteine". . p. 649 - 656. Retrieved 2007/10/03.