Asarone

α-Asarone
IUPAC name 1,2,4-Trimethoxy-5-[(E)-prop-1-enyl]benzene
Other names alpha-Azaron cis-Isoelemicin 2,4,5-Trimethoxyphenyl-2-propene
Identifiers
CAS number	2883-98-9 N
PubChem	636822
ChemSpider	552532 Y
ChEMBL	CHEMBL333306 Y
Jmol-3D images	Image 1 Image 2
SMILES CC=CC1=CC(=C(C=C1OC)OC)OC O(c1cc(c(OC)cc1OC)/C=C/C)C
InChI InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+ Y Key: RKFAZBXYICVSKP-AATRIKPKSA-N Y InChI=1/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5+ Key: RKFAZBXYICVSKP-AATRIKPKBQ
Properties
Molecular formula	C12H16O3
Molar mass	208.254 g mol−1
Appearance	colorless solid substance
Density	1.028 g/cm−3 [1]
Melting point	62-63 °C [2]
Boiling point	296 °C [2]
Solubility in water	insoluble
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Asarone, which includes alpha (trans) and beta^[3] (cis) types, is an ether found in certain plants such as acorus and asarum.^[2] As a volatile fragrance oil, it is used in killing plant fungal^[4] pests and bacteria.^[5] The toxicity and carcinogenicity of asarone means that it may be difficult to develop practical anthelmintics and insecticides based on it.^[6]

Pharmacology

The main clinical symptom of asarone is prolonged vomiting that sometimes lasted more than 15 hours. Asarone is not metabolized to trimethoxyamphetamine as has been claimed by online vendors.^[7]

See also

• Elemicin
• Sweet Flag

Notes and references

1. ^ Data for α-Asarone at ChemSpider
2. ^ ^{a b c} "Asarone". The Merck Index. 14th edition. Merck Research Laboratories. 2006. pp. 135. ISBN 978-0-911910-00-1. 
3. ^ Beta asarone has CAS# 5273-86-9
4. ^ Suvarna Shenvi, Vinod, Rajendra Hegde, Anil Kush and G. Chandrasekara Reddy (2011). "A unique water soluble formulation of β-asarone from sweet flag (Acorus calamus L.) and its in vitro activity against some fungal plant pathogens". Journal of Medicinal Plants Research 5 (20): 5132–5137. http://www.academicjournals.org/JMPR/PDF/pdf2011/30Sept/Shenvi%20et%20al.pdf. 
5. ^ Asha DS, Ganjewala D (2009). "Antimicrobial activity of Acorus calamus (L.) rhizome and leaf extract". Act. Biol. Szeg. 53 (1): 45–49. 
6. ^ Perrett, Sheena; Whitfield, Philip J. (1995). "Anthelmintic and pesticidal activity ofAcorus gramineus (Araceae) is associated with phenylpropanoid asarones". Phytotherapy Research 9 (6): 405. doi:10.1002/ptr.2650090604. 
7. ^ Björnstad K, Helander A, Hultén P, Beck O (2009). "Bioanalytical investigation of asarone in connection with Acorus calamus oil intoxications". J Anal Toxicol 33 (9): 604–9. PMID 20040135. 

This article about an organic compound is a stub. You can help Wikipedia by expanding it.v · Categories: Phenylpropanoids Phenol ethers Organic compound stubs Wikimedia Foundation. 2010. Игры ⚽ Поможем решить контрольную работу Michael DeForest Wilson Abu Sankoh Look at other dictionaries: Asarone — As a*rone, n. [L. asarum hazelwort, wild spikenard, Gr. a saron] (Chem.) A crystallized substance, resembling camphor, obtained from the {Asarum Europ[ae]um}; called also {camphor of asarum}. [1913 Webster] …   The Collaborative International Dictionary of English asarone — noun An aromatic ether, 2,4,5 trimethoxyphenyl 2 propene, found in the essential oils of plants of the genus Asarum …   Wiktionary asarone — as·a·rone …   English syllables ašaronė — ãšaronė sf. (1) ašarojimas, verksmas: Tik dėl ãšaronių jos pasgailėjo Lš …   Dictionary of the Lithuanian Language asarone — noun see asaron …   Useful english dictionary Asarum Europaeum — Asarone As a*rone, n. [L. asarum hazelwort, wild spikenard, Gr. a saron] (Chem.) A crystallized substance, resembling camphor, obtained from the {Asarum Europ[ae]um}; called also {camphor of asarum}. [1913 Webster] …   The Collaborative International Dictionary of English camphor of asarum — Asarone As a*rone, n. [L. asarum hazelwort, wild spikenard, Gr. a saron] (Chem.) A crystallized substance, resembling camphor, obtained from the {Asarum Europ[ae]um}; called also {camphor of asarum}. [1913 Webster] …   The Collaborative International Dictionary of English Acorus calamus — Common Sweet Flag Sweet flag Scientific classification Kingdom: Plantae (unranked) …   Wikipedia Acore Odorant — Acore odorant …   Wikipédia en Français Acore odorant — Acorus calamus …   Wikipédia en Français 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”