Phenylalanine-ochratoxin A

Base Information

• Chemical Name: Phenylalanine-ochratoxin A
• CAS No.: 303-47-9
• Molecular Formula: C20H18ClNO6
• Molecular Weight: 403.819
• Hs Code.: 29322985
• NCI Thesaurus Code: C44427
• Mol file: 303-47-9.mol

Synonyms:ochratoxin A

Chemical Property of Phenylalanine-ochratoxin A

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 7.3E-17mmHg at 25°C
• Melting Point: 169 °C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 632.4 °C at 760 mmHg
• PKA: 3.29±0.10(Predicted)
• Flash Point: 336.3 °C
• PSA: 112.93000
• Density: 1.425 g/cm³
• LogP: 2.96360
• Storage Temp.: 2-8°C
• Solubility.: ethanol: soluble
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 403.0822650
• Heavy Atom Count: 28
• Complexity: 608

Purity/Quality:

OchratoxinA(10μg/mLinAcetonitrile) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+, T, Xn, F
• Hazard Codes: T+,T,Xn,F
• Statements: 45-46-61-26/27/28-36-20/21/22-11-40-28-39/23/24/25-23/24/25-65-48/23/24/25-36/38
• Safety Statements: 53-22-36/37/39-45-36-26-16-36/37-28-62

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CC2=C(C=C(C(=C2C(=O)O1)O)C(=O)NC(CC3=CC=CC=C3)C(=O)O)Cl
• Isomeric SMILES: C[C@@H]1CC2=C(C=C(C(=C2C(=O)O1)O)C(=O)NC(CC3=CC=CC=C3)C(=O)O)Cl
• Uses: A nephrotoxic mycotoxin inhibitor of phenylalanyl-tRNA synthetases. Ochratoxins are toxic metabolites from Aspergillus orchraceus. Ochratoxin A is a chlorinated benzopyran coupled to phenylalanine, produced by several Aspergillus and Penicillium sp. associated with food spoilage. Ochratoxins are widely distributed in the environment and are known to be nephrotoxic, teratogenic and possibly carcinogenic. Ochratoxin A may act by inducing DNA strand breaks, sister chromatid exchanges, DNA adduct formation, or reactive oxygen but the mechanism of action as a toxin is not yet resolved. At the molecular level, ochratoxin A specifically inhibits NK cell activity, increases growth of transplantable tumour cells in mice, increases apoptosis, activates c-Jun N terminal kinase in human kidney epithelial cells, and blocks metaphase/anaphase transition. It also inhibits plasminogen activator inhibitor-2 production by human blood mononuclear cells.

Technology Process of Phenylalanine-ochratoxin A

There total 16 articles about Phenylalanine-ochratoxin A 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: 99.0%

tert-butyl N-(((3R)-5-chloro-8-hydroxy-3-methyl-1-oxoisochroman-7-yl)carbonyl)-L-phenylalaninate → ochratoxin A (303-47-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 22 ℃; for 6h; Inert atmosphere;

DOI:10.1021/jacs.6b13124

Reference yield: 46.0%

tert-butyl N-((5-chloro-8-hydroxy-3-methyl-1-oxoisochroman-7-yl)carbonyl)-L-phenylalaninate → ochratoxin A (303-47-9) + (+)-N-(((3S)-5-chloro-8-hydroxy-3-methyl-1-oxoisochroman-7-yl)carbonyl)-L-phenylalanine

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 6h; Inert atmosphere;

DOI:10.1055/s-0028-1088076

Reference yield:

C21H20ClNO6 → ochratoxin A (303-47-9) + (+)-N-(((3S)-5-chloro-8-hydroxy-3-methyl-1-oxoisochroman-7-yl)carbonyl)-L-phenylalanine

Guidance literature:

C₂₁H₂₀ClNO₆; With sodium hydroxide; In water; at 20 ℃; for 12h;

With hydrogenchloride; In water; for 2h; pH=1;

DOI:10.1016/j.bmc.2009.10.050

upstream raw materials:

5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-(1H)-2-benzopyran-7-carboxylic acid

L-phenylalanine tert-butyl ester

L-phenylalanine

ethyl 5-chloro-8-hydroxy-3-methyl-1-oxoisochroman-7-carboxylate

Downstream raw materials:

N-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl]-carbonyl}-L-phenylalanine

N-{[(3R)-5,8-dihydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl]carbonyl}-L-phenylalanine

Refernces

• 1、 Bouisseau, Anais,Roland, Aurelie,Reillon, Florence,Schneider, Remi,Cavelier, Florine. "First synthesis of a stable isotope of Ochratoxin A metabolite for a reliable detoxification monitoring". supporting information. p. 3888 - 3890. Retrieved 2013/09/02.
• 2、 Cramer, Benedikt,Harrer, Henning,Nakamura, Kazuhiko,Uemura, Daisuke,Humpf, Hans-Ulrich. "Total synthesis and cytotoxicity evaluation of all ochratoxin A stereoisomers". experimental part. p. 343 - 347. Retrieved 2010/04/05.