Back أوكراتوكسين أ Arabic Ocratoxina A Catalan Ocratoxina a Spanish اوکراتوکسین آ Persian Okratoksiini A Finnish Ochratoxine A French Ocratossina A Italian Ochratoxine A Dutch Ochratoksyna A Polish Ocratoxina A Portuguese

Ochratoxin A

Ochratoxin A
Names
IUPAC name
N-[(3R)-5-Chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]-L-phenylalanine
Systematic IUPAC name
(2S)-2-[(3R)-5-Chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxamido]-3-phenylpropanoic acid
Other names
(R)-N- [(5-Chloro- 3,4-dihydro- 8-hydroxy- 3-methyl- 1-oxo- 1H-2-benzopyran-7-yl) -carbonyl]- L- phenylalanine
(−)-N- [(5-Chloro- 8-hydroxy- 3-methyl- 1-oxo- 7-isochromanyl) carbonyl]- 3-phenylalanine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.586 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15+/m1/s1 checkY
    Key: RWQKHEORZBHNRI-BMIGLBTASA-N checkY
  • InChI=1/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15+/m1/s1
    Key: RWQKHEORZBHNRI-BMIGLBTABQ
  • O=C(O)[C@@H](NC(=O)c1c(O)c2c(c(Cl)c1)C[C@H](OC2=O)C)Cc3ccccc3
Properties
C20H18ClNO6
Molar mass 403.813
Melting point 169 °C (336 °F; 442 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Ochratoxin A—a toxin produced by different Aspergillus and Penicillium species — is one of the most-abundant food-contaminating mycotoxins.[1] It is also a frequent contaminant of water-damaged houses and of heating ducts.[2][3] Human exposure can occur through consumption of contaminated food products, particularly contaminated grain and pork products, as well as coffee, wine grapes, and dried grapes.[4][5][6] The toxin has been found in the tissues and organs of animals, including human blood and breast milk.[7] Ochratoxin A, like most toxic substances, has large species- and sex-specific toxicological differences.[5]

  1. ^ Al-Anati L, Petzinger E (2006). "Immunotoxic activity of ochratoxin A". J. Vet. Pharmacol. Ther. 29 (2): 79–90. doi:10.1111/j.1365-2885.2006.00718.x. PMID 16515661.
  2. ^ Polizzi V, et al. (2009). "Fungi, mycotoxins and volatile organic compounds in mouldy interiors from water-damaged buildings". Journal of Environmental Monitoring. 11 (10): 1849–1858. doi:10.1039/b906856b. PMID 19809708.
  3. ^ Richard JL, at al. (1999). "The occurrence of ochratoxin A in dust collected from a problem household". Mycopathologia. 146 (2): 99–103. doi:10.1023/A:1007056627296. PMID 10822509. S2CID 31557794.
  4. ^ Pfohl-Leszkowicz A, Manderville RA (2007). "Ochratoxin A: An overview on toxicity and carcinogenicity in animals and humans". Mol Nutr Food Res. 51 (1): 61–99. doi:10.1002/mnfr.200600137. PMID 17195275.
  5. ^ a b O'Brien E, Dietrich DR (2005). "Ochratoxin A: the continuing enigma". Crit. Rev. Toxicol. 35 (1): 33–60. doi:10.1080/10408440590905948. PMID 15742902. S2CID 15849038.
  6. ^ Blesa J, et al. (2006). "Factors affecting the presence of ochratoxin A in wines". Critical Reviews in Food Science and Nutrition. 46 (6): 473–8. doi:10.1080/10408390500215803. PMID 16864140. S2CID 45392770.
  7. ^ Clark HA, Snedeker SM (2006). "Ochratoxin A: its cancer risk and potential for exposure". Journal of Toxicology and Environmental Health Part B: Critical Reviews. 9 (3): 265–96. Bibcode:2006JTEHB...9..265C. doi:10.1080/15287390500195570. PMID 16621780. S2CID 41761053.
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