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Ochratoxin A

Ochratoxin A structure

CAS No:
303-47-9
Formula:
C20H18ClNO6
Chemical Name:
Ochratoxin A
Synonyms:
L-Phenylalanine,N-[[(3R)-5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]-;Alanine,N-[(5-chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl]-3-phenyl-,(-)-;Ochratoxin A;L-Phenylalanine,N-[(5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl]-,(R)-;N-[[(3R)-5-Chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]-L-phenylalanine;Phe-OTA;Phenylalanine-ochratoxin A;NSC 201422;NSC 221991;(R)-N-[(5-Chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-benzo[c]pyran-7-yl)carbonyl]-3-phenylalanine;3R,14S-Ochratoxin A;19850-84-1;26153-09-3

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Description

white to off-white crystalline powder White crystalline solid or powder.

Ochratoxin A Basic Attributes

Molecular Weight：

403.813

Exact Mass：

403.81

EC Number：

206-143-7

HScode：

29322985

Characteristics

PSA：

112.93000

XLogP3：

4.31

Appearance：

Ochratoxin a is a white crystalline powder. (NTP, 1992)

Density：

1.4±0.1 g/cm3

Melting Point：

169 °C

Boiling Point：

632.4±55.0 °C at 760 mmHg

Flash Point：

336.3±31.5 °C

Refractive Index：

1.628

Water Solubility：

The sodium salt is soluble in water.

Storage Conditions：

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should b

Vapor Pressure：

3.11X10-14 mm Hg at 25 deg C (est)

Toxicity：

LD50 orally in rats: 20-22 mg/kg (Purchase, Theron)

Specific rotation：

Specific optical rotation: -118 deg at 25 °C/D (concn = 1.1 in chloroform)

Safety Information

Hazard category：

6.1(a)

Transport codes：

UN 3462 6

wgk germany：

hazard class code：

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 instructions：

53-22-36/37/39-45-36-26-16-36/37-28-62

RTECS Number：

AY4375000

Marks：

T: Toxic;T+: Very toxic;Xn: Harmful;F: Flammable;

Stability/Shelf Life：

Fairly stable in cereal products; up to 35% survives autoclaving for up to 3 hr

Precautionary statement(s)：

P264-P281-P301 + P310

Hazard Statements：

H300-H351-H413

Ochratoxin A Use and Manufacturing

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.

Computed Properties

Molecular Weight:403.8
XLogP3:4.7
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:5
Exact Mass:403.0822650
Monoisotopic Mass:403.0822650
Topological Polar Surface Area:113
Heavy Atom Count:28
Complexity:608
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes