Asarone

Asarone is chemical compound of the phenylpropanoid class found in certain plants such as Acorus and Asarum.^[2] There are two isomers, α (or trans) and β (or cis).^[3] As a volatile fragrance oil, it is used in killing pests and bacteria.^[4]

Asarone

α-Asarone β-Asarone
Names
IUPAC names 1,2,4-Trimethoxy-5-[(E)-prop-1-enyl]benzene (α) 1,2,4-Trimethoxy-5-[(Z)-prop-1-enyl]benzene (β)
Other names alpha-Azaron cis-Isoelemicin 2,4,5-Trimethoxyphenyl-2-propene
Identifiers
CAS Number	2883-98-9 (α) Y 5273-86-9 (β) Y
3D model (JSmol)	(α): Interactive image (β): Interactive image
ChEMBL	ChEMBL333306 Y
ChemSpider	552532 (α) Y 4445072 (β) N
ECHA InfoCard	100.018.858
PubChem CID	636822 (α) 5281758 (β)
UNII	DQY9PNE5FK (α) Y IGA3MH6IUW (β) Y
CompTox Dashboard (EPA)	DTXSID00871878 DTXSID20197784, DTXSID00871878
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=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-WAYWQWQTSA-N Y
SMILES (α): O(c1cc(c(OC)cc1OC)/C=C/C)C (β): C/C=C\c1cc(c(cc1OC)OC)OC
Properties
Chemical formula	C12H16O3
Molar mass	208.257 g·mol−1
Appearance	Colorless solid
Density	α: 1.028 g/cm−3 [1]
Melting point	62 to 63 °C (144 to 145 °F; 335 to 336 K)[2] (α)
Boiling point	296 °C (565 °F; 569 K)[2] (α)
Solubility in water	Insoluble
Magnetic susceptibility (χ)	-131.4·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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.^[5]

The Council of Europe Committee of Experts on Flavouring Substances concluded that β-asarone is clearly carcinogenic^[6] and has proposed limits for its concentration in flavorings such as bitters made from Acorus calamus (sweet flag).^[7]

β-Asarone exhibits anti-fungal activity by inhibiting ergosterol biosynthesis in Aspergillus niger.^[8] However, the toxicity and carcinogenicity of asarone means that it may be difficult to develop any practical medication based on it.^[9]

See also

• Elemicin
• 2,4,5-Trimethoxypropiophenone

Notes and references

1. Data for α-Asarone at ChemSpider
2. "Asarone". The Merck Index. Vol. 14th edition. Merck Research Laboratories. 2006. p. 135. ISBN 978-0-911910-00-1.
3. Beta asarone has CAS# 5273-86-9
4. Asha DS, Ganjewala D (2009). "Antimicrobial activity of Acorus calamus (L.) rhizome and leaf extract". Acta Biol. Szeg. 53 (1): 45–49.
5. 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. doi:10.1093/jat/33.9.604. PMID 20040135.
6. Cartus, Alexander T.; Stegmüller, Simone; Simson, Nadine; Wahl, Andrea; Neef, Sylvia; Kelm, Harald; Schrenk, Dieter (2015-08-26). "Hepatic Metabolism of Carcinogenic β-Asarone". Chemical Research in Toxicology. 28 (9): 1760–1773. doi:10.1021/acs.chemrestox.5b00223. ISSN 0893-228X. PMID 26273788.
7. "Opinion of the Scientific Committee on Food on the presence of β-asarone in flavourings and other food ingredients with flavouring properties" (PDF). European Commission Scientific Committee on Food. 8 January 2002. {{cite journal}}: Cite journal requires |journal= (help)
8. Venkatesan, Ramya; Karuppiah, Prakash Shyam; Arumugam, Gnanamani; Balamuthu, Kadalmani (2017-11-10). "β-Asarone Exhibits Antifungal Activity by Inhibiting Ergosterol Biosynthesis in Aspergillus niger ATCC 16888". Proceedings of the National Academy of Sciences, India Section B: Biological Sciences. 89: 173–184. doi:10.1007/s40011-017-0930-4. ISSN 0369-8211. S2CID 46005148.
9. Perrett, Sheena; Whitfield, Philip J. (1995). "Anthelmintic and pesticidal activity of Acorus gramineus (Araceae) is associated with phenylpropanoid asarones". Phytotherapy Research. 9 (6): 405. doi:10.1002/ptr.2650090604. S2CID 84823162.