Azaron

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of α-asarone     Structural formula of β-asarone
α-asarone β-asarone
General
Surname Azaron
other names

α-Asaron

  • ( E ) -1,2,4-trimethoxy-5- (1-propen-1-yl) benzene
  • trans -asarone

β-asarone

  • ( Z ) -1,2,4-trimethoxy-5- (1-propen-1-yl) benzene
  • cis -asaron

γ-Asaron

  • 1,2,4-trimethoxy-5- (2-propen-1-yl) benzene
  • 2,4,5-trimethoxy-1-allyl benzene
  • Isoasaron
  • Euasaron
Molecular formula C 12 H 16 O 3
Brief description
  • colorless and odorless needles (α-Asaron)
  • yellowish oil ( cis isomer)
External identifiers / databases
CAS number
  • 2883-98-9 (α-asaron)
  • 5273-86-9 (β-Asaron) * 5353-15-1 (γ-Asaron)
EC number 220-743-6
ECHA InfoCard 100,018,858
PubChem 636822
ChemSpider 552532
Wikidata Q419658
properties
Molar mass 208.25 g mol −1
Physical state

solid (α-Asaron)

Melting point

62 ° C (α-asaron)

boiling point
  • 296 ° C (α-asaron)
  • 281 ° C (β-asaron)
solubility

almost insoluble in water

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Under asarone one summarizes three naturally occurring in various plants, isomeric phenylpropanoids together, resulting in position and configuration of the double bond differing in the C3 side chain. These include the 1-propenylic compounds α-asarone ( trans -isomer) and β-asarone ( cis -isomer) as well as the allylic γ-asarone with a terminal double bond in the side chain (2-propenylic).

Occurrence

Sweet flag plant ( Acorus calamus )

In nature, α-, β- and γ-asaron often occur together. The essential oil of the rhizome of the Indian tetraploid calamus plant ( Acorus calamus ) contains 45-90% of the β-isomer, 1–2% of the α-isomer and traces of γ-asarone. The essential oils of the triploid European and diploid North American varieties of A. calamus contain significantly less asarone with a maximum of 10% and less than 1%, respectively. γ-Asarone is also found in various pepper plants .

use

Herbal medicines containing asarone are used in traditional medicine of many ethnic groups and in aromatherapy because of their possible spasmolytic effects . Natural fragrances , which may contain asarone, are also used in perfume production. Asarone can be found in home-grown or (with calamus and other plants) flavored bitters and liqueurs .

toxicity

α- and β-asarone (administered ip ) caused liver tumors in male mice. Both compounds were comparable (moderately) potent. β-asarone also caused leiomyosarcomas of the small intestine (rat, oral). Mutagenic effects, including in the Ames test with α- and β-asarone, have been reported (only after metabolic activation ). The toxicity and especially the carcinogenicity of γ-asarone have not yet been investigated. The mechanism of action of carcinogenesis is currently unknown. Asarones are most likely not activated by hydroxylation of the side chain (via cytochrome P450 enzymes) and subsequent sulfonation , unlike the structurally related compounds methyleugenol , safrole or estragole , since the inhibition of sulfotransferases in vivo had no influence on the incidence of hepatoma formation in mice . α-Asaron also showed a certain potential to be toxic to reproduction .

regulation

The asarone isomers could not yet be adequately evaluated toxicologically. The targeted addition of β-asarone to food is prohibited in the European Union . In the United States , the targeted addition of calamus in all forms to food is prohibited. For natural contents, maximum levels of 1.0 mg / kg for alcoholic beverages apply in the EU. According to chemicals law ( Regulation (EC) No. 1272/2008 (CLP) ), α- and β-asarone are classified as harmful to health.

Individual evidence

  1. ↑ a b c d Entry on Asaron. In: Römpp Online . Georg Thieme Verlag, accessed on March 6, 2014.
  2. ↑ Fujita et al.: Yakugaku Zasshi 90 (1970) 1367, 1371 and Chem. Abstr. 74 (1971) # 34553.
  3. ↑ Asaron data sheet (PDF) from Carl Roth , accessed on February 19, 2010.
  4. ↑ a b Asaron data sheet at Sigma-Aldrich , accessed on March 9, 2011 ( PDF ).Template: Sigma-Aldrich / name not given
  5. ↑ K. Keller, E. Stahl: Composition of the essential oil from beta-Asarone free calamus. In: Planta Med. 47 (2), 1983, pp. 71-74.
  6. ↑ TS Rana, KS Mahar, MM Pandey, SK Srivastava, AK Rawat: Molecular and chemical profiling of 'sweet flag' (Acorus calamus L.) germplasm from India. In: Physiol Mol Biol Plants. 19 (2), 2013, pp. 231-237. doi: 10.1007 / s12298-013-0164-8
  7. ↑ P. Satyal, P. Paudel, A. Poudel, NS Dosoky, DM Moriarity, B. Vogler, WN Setzer: Chemical compositions, phytotoxicity, and biological activities of Acorus calamus essential oils from Nepal. In: Nat Prod Commun. 8 (8), 2013, pp. 1179-1181.
  8. ↑ PK Mukherjee, V. Kumar, M. Mal, PJ Houghton: In vitro acetylcholinesterase inhibitory activity of the essential oil from Acorus calamus and its main constituents. In: Planta Med. 73 (3), 2007, pp. 283-285.
  9. ^ W. Qin, S. Huang, C. Li, S. Chen, Z. Peng: Biological activity of the essential oil from the leaves of Piper sarmentosum Roxb. (Piperaceae) and its chemical constituents on Brontispa longissima (Gestro) (Coleoptera: Hispidae). In: Pesticide Biochem Physiol. 2010, pp. 132-139, doi: 10.1016 / j.pestbp.2009.10.006
  10. ↑ K. Matsui, K. Munakata, K. Wada: Insect antifeeding substances in Parabenzoin praecox and Piper futokadzura. In: Agr Biol Chem. 40, 1976, pp. 1045-1046.
  11. ↑ T. Masuda, A. Inazumi, Y. Yamada, WG Padolina, H. Kikuzaki, N. Nakatani: Antimicrobial phenylpropanoids from Piper sarmentosum. In: Phytochemistry. 30, 1991, pp. 3227-3228.
  12. ↑ Eliane Zimmermann : Aromatherapy for nursing and healing professions. Georg Thieme Verlag , 2006, ISBN 3-8304-9114-X .
  13. ↑ PK Mukherjee, V. Kumar, M. Mal, PJ Houghton: In vitro acetylcholinesterase inhibitory activity of the essential oil from Acorus calamus and its main constituents. In: Planta Med. 73 (3), 2007, pp. 283-285.
  14. ↑ RW Wiseman, EC Miller, JA Miller, A. Liem: Structure-activity studies of the hepatocarcinogenicities of alkenylbenzene derivatives related to estragole and safrole on administration to preweanling male C57BL / 6J x C3H / HeJ F1 mice. In: Cancer Res. 47 (9), 1987, pp. 2275-2283.
  15. ^ Joint FAO / WHO Expert Committee on Food Additives (JECFA), Monograph for β-Asarone , accessed on December 9, 2014.
  16. ↑ W. Göggelmann, O. glimmer mutagenicity testing of beta-Asarone and commercial calamus drugs with Salmonella typhimurium. In: Mutat Res. 121, 1983, pp. 191-194.
  17. ↑ G. Abel, W. Göggelmann: Genotoxic activity of β-asarone and commercial calamus drugs. In: Mutat Res / Environ Mutagen. 164, 4, 1986, p. 287.
  18. ^ BO Mohar, C. Espinoza-Aguirre, G. Cortinas dew NavChamorro: Determinación de la actividad mutagénica de alpha-asarona en ei sistema Salmonella typhimurium / microsomas. In: Proceedings of 1st Congress of the Mexican Association of Mutagenesis, Carcinogenesis and Teratogenesis. 1986; Referenced in: P. Morales-Ramírez, E. Madrigal-Bujaidar, J. Mercader-Martínez, M. Cassini, G. González, G. Chamorro-Cevallos, M. Salazar-Jacobo: Sister-chromatid exchange induction produced by in vivo and in vitro exposure to alpha-asarone. In: Mutat Res. 279, 1992, pp. 269-273.
  19. ↑ RW Wiseman, EC Miller, JA Miller, A. Liem: Structure-activity studies of the hepatocarcinogenicities of alkenylbenzene derivatives related to estragole and safrole on administration to preweanling male C57BL / 6J x C3H / HeJ F1 mice. In: Cancer Res. 47 (9), 1987, pp. 2275-2283.
  20. ^ Joint FAO / WHO Expert Committee on Food Additives (JECFA), Monograph for β-Asarone , accessed on December 9, 2014.
  21. ↑ M. Salazar, S. Salazar, V. Ulloa, T. Mendoza, N. Pages, G. Chamoro: Teratogenic action of alpha-asarone in the mouse. In: J Toxicol Clin Exp. 12, 3, 1992, pp. 149-154.
  22. ↑ G. Chamorro, L. Garduño, E. Martínez, E. Madrigal, J. Tamariz, M. Salazar: Dominant lethal study of alpha-asarone in male mice. In: Toxicol Lett. 99, 2, 1998, pp. 71-77.
  23. ↑ Regulation (EC) 1334/2008.
  24. ↑ Regulation (EC) 1334/2008.

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