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Asarone - Wikipedia

From Wikipedia, the free encyclopedia

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).

verify (what is ^YN ?)

Infobox references

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]

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]

Notes and references

^ Data for α-Asarone at ChemSpider
^ ^a ^b ^c "Asarone". The Merck Index. Vol. 14th edition. Merck Research Laboratories. 2006. p. 135. ISBN 978-0-911910-00-1.
^ Beta asarone has CAS# 5273-86-9
^ Asha DS, Ganjewala D (2009). "Antimicrobial activity of Acorus calamus (L.) rhizome and leaf extract". Acta Biol. Szeg. 53 (1): 45–49.
^ 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.
^ 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.
^ "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)
^ 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.
^ 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.

Categories:

Hidden categories:

Pharmacology

See also

Notes and references