Aristolochic acid

Aristolochic acid
IUPAC name

8-methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acid
Other names

Aristolochic acid I

  • Aristinic acid
  • Aristolochia yellow
  • Aristolochic acid A
  • Aristolochin
  • Aristolochine
  • Descresept
  • Isoaristolochic acid
  • Tardolyt
  • TR 1736

Aristolochic acid II

  • Aristolochic acid B
Identifiers
CAS number 313-67-7 Y
PubChem 2236
ChemSpider 2149 Y
KEGG C08469 Y
ChEMBL CHEMBL93353 Y
Jmol-3D images Image 1
Properties
Molecular formula C17H11NO7
Molar mass 341.27 g mol−1
Density 1.571g/cm3
Melting point

260 - 265 °C
Boiling point

615.5°C @760mmHg
Solubility in water slightly soluble in water
Hazards
Flash point 326°C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Aristolochic acids are a family of carcinogenic, mutagenic, and nephrotoxic compounds commonly found in the Aristolochiaceae family of plants, including Aristolochia and Asarum, which are commonly used in Chinese herbal medicine.[1] Aristolochic acid I is the most abundant of the aristolochic acids and is found in almost all Aristolochia species.[2] Aristolochic acids are often accompanied by aristolactams.[3]

Aristolochic acids may be a causative agent in Balkan nephropathy.[4][5] Exposure to aristolochic acid is associated with a high incidence of uroepithelial tumorigenesis.[6]

Aristolochic acids are slightly soluble in water, have a melting point between 281 and 286 degrees celsius,[7] and have a bitter flavor.[8]

Contents

See also

References

  1. ^ Nolin, Thomas D. & Himmelfarb, Jonathan (2010). "Mechanisms of drug-induced nephrotoxicity". In Uetrecht, Jack. Adverse Drug Reactions. Springer. p. 123. ISBN 9783642006623. http://books.google.com/books?id=0NhAFmL2Q08C&pg=PA123. 
  2. ^ Wu, Tian-Shung et al. (2005). "Chemical constituents and pharmacology of Aristolochia species". In Rahman, Atta-ur. Studies in Natural Products Chemistry: Bioactive Natural Products (Part L). Gulf Professional Publishing. p. 863. ISBN 9780444521712. http://books.google.com/books?id=UBHng8FfwgIC&pg=PA863. 
  3. ^ Wink, Michael & Schimmer, Oskar (1999). "Modes of action of defensive secondary metabolites". In Wink, Michael. Functions of plant secondary metabolites and their exploitation in biotechnology. CRC Press. p. 75. ISBN 9780849340864. http://books.google.com/books?id=eFQgSjZIu8EC&pg=PA75. 
  4. ^ Geacintov, Nicholas E. & Broyde, Suse, ed (2010). "Introduction and perspectives on the Chemistry and Biology of DNA Damage". The Chemical Biology of DNA Damage. Wiley-VCH. p. 7. ISBN 9783527322954. http://books.google.com/books?id=PueBA8SiPdAC&pg=PA7. 
  5. ^ Wild, Chris et al., ed (2008). Molecular epidemiology of chronic diseases. John Wiley & Sons. p. 113. ISBN 9780470027431. http://books.google.com/books?id=w86iv6ib-zcC&pg=PA113. 
  6. ^ Ronco, Claudio et al., ed (2008). Critical care nephrology. Elsevier Health Sciences. p. 1699. ISBN 9781416042525. http://books.google.com/books?id=XkKn96HThzEC&pg=PA1699. 
  7. ^ Barceloux, Donald G. (2008). "Aristolochic acid and Chinese Herb nephropathy". Medical toxicology of natural substances: foods, fungi, medicinal herbs, plants, and venomous animals. John Wiley & Sons. p. 384. ISBN 9780471727613. http://books.google.com/books?id=HWUzlp_V6uIC&pg=PA384. 
  8. ^ Offermanns, S. & Amara, Susan G., ed (2006). Reviews of physiology, biochemistry and pharmacology, Volume 154. Birkhäuser. p. 56. ISBN 9783540303848. http://books.google.com/books?id=2CgsRIL2lGAC&pg=PA56. 

Further reading

External links