Aristolochic acid
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aristolochic acid
(ə¦ris·tə¦läk·ik ′as·əd)
(organic chemistry) C17H11NO7 Crystals in the form of shiny brown leaflets that decompose at 281-286°C; soluble in alcohol, chloroform, acetone, ether, acetic acid, and aniline; used as an aromatic bitter. Also known as aristolochine.
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Aristolochic acid
| Aristolochic acid I | |
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8-methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acid |
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Other names
* Aristolochic acid
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| Identifiers | |
| CAS number | 313-67-7  |
| PubChem | 2236 |
| ChemSpider | 2149 |
| KEGG | C08469 |
| ChEMBL | CHEMBL93353 |
| Jmol-3D images | Image 1 |
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| 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 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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] and was linked to aristolochic acid-associated urothelial cancer in a Taiwanese study in 2012.[7]
Aristolochic acids are slightly soluble in water, have a melting point between 281 and 286 degrees celsius,[8] and have a bitter flavor.[9]
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Contents
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See also
References
- ^ Nolin, Thomas D. & Himmelfarb, Jonathan (2010). "Mechanisms of drug-induced nephrotoxicity". In Uetrecht, Jack. Adverse Drug Reactions. Springer. p. 123. ISBN 978-3-642-00662-3. http://books.google.com/books?id=0NhAFmL2Q08C&pg=PA123.
- ^ 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 978-0-444-52171-2. http://books.google.com/books?id=UBHng8FfwgIC&pg=PA863.
- ^ 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 978-0-8493-4086-4. http://books.google.com/books?id=eFQgSjZIu8EC&pg=PA75.
- ^ 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 978-3-527-32295-4. http://books.google.com/books?id=PueBA8SiPdAC&pg=PA7.
- ^ Wild, Chris et al., ed. (2008). Molecular epidemiology of chronic diseases. John Wiley & Sons. p. 113. ISBN 978-0-470-02743-1. http://books.google.com/books?id=w86iv6ib-zcC&pg=PA113.
- ^ Ronco, Claudio et al., ed. (2008). Critical care nephrology. Elsevier Health Sciences. p. 1699. ISBN 978-1-4160-4252-5. http://books.google.com/books?id=XkKn96HThzEC&pg=PA1699.
- ^ Chung-Hsin Chena, Kathleen G. Dickman, Masaaki Moriya et. al. Aristolochic acid-associated urothelial cancer in Taiwan. Proceedings of the National Academy of Sciences, April 2012.
- ^ 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 978-0-471-72761-3. http://books.google.com/books?id=HWUzlp_V6uIC&pg=PA384.
- ^ Offermanns, S. & Amara, Susan G., ed. (2006). Reviews of physiology, biochemistry and pharmacology, Volume 154. Birkhäuser. p. 56. ISBN 978-3-540-30384-8. http://books.google.com/books?id=2CgsRIL2lGAC&pg=PA56.
Further reading
- Aronson, J.K. (2008). "Aristolochicae". Meyler's side effects of herbal medicines. Elsevier. p. 55. ISBN 978-0-444-53269-5. http://books.google.com/books?id=ibxfK1l6oXoC&pg=PA55.
- Lai M., 2009. Journal of National Cancer Institute. doi:10.1093/jnci/djp467. (Short summary published as "Chinese herbal products containing aristolochic acid were associated with urinary tract cancer" in "HemOnc today", page 28, dated 2010-01-25.)
- Mills, Simon & Bone, Kerry (2005). "Aristolochic Acid Nephropathy". The essential guide to herbal safety. Elsevier Health Sciences. p. 15. ISBN 978-0-443-07171-3. http://books.google.com/books?id=85M0N8UioCcC&pg=PA15.
- Wing-Tat Poon, Chi-Kong Lai, Albert Yan-Wo Chan, 2007. "Aristolochic Acid Nephropathy: The Hong Kong Perspective." Hong Kong Journal of Nephrology, 9(1):7-14.
External links
- Complete list of warnings from the US Food and Drug Administration
- FDA Warns Consumers to Discontinue Use of Botanical Products that Contain Aristolochic acid. April 11, 2001.
- FDA Concerned About Botanical Products, Including Dietary Supplements, Containing Aristolochic Acid May 2000.
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