Anethole
Names | |
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Preferred IUPAC name
1-Methoxy-4-[(E)-prop-1-enyl]benzene[1] | |
Other names
(E)-1-Methoxy-4-(prop-1-en-1-yl)benzene
(E)-1-Methoxy-4-(1-propenyl)benzene para-Methoxyphenylpropene p-Propenylanisole Isoestragole trans-1-Methoxy-4-(prop-1-enyl)benzene | |
Identifiers | |
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3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.002.914 |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C10H12O | |
Molar mass | 148.205 g/mol |
Density | 0.998 g/cm3 |
Melting point | 20 to 21 °C (68 to 70 °F; 293 to 294 K) |
Boiling point | 234 °C (453 °F; 507 K) 81 °C (178 °F; 354 K) at 2 mmHg |
−9.60×10−5 cm3/mol | |
Hazards | |
Safety data sheet (SDS) | External MSDS |
Related compounds | |
Related compounds
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anisole estragole |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Anethole (also known as anise camphor)
Structure and production
Anethole is an aromatic,
Like related compounds, anethole is poorly soluble in water. Historically, this property was used to detect adulteration in samples.[5]
Most anethole is obtained from turpentine-like extracts from trees.[3][6] Of only minor commercial significance, anethole can also be isolated from essential oils.[7][8][9]
Essential oil | World production | Trans-anethole |
---|---|---|
Anise | 8 tonnes (1999) | 95% |
Star anise | 400 tonnes (1999), mostly from China | 87% |
Fennel | 25 tonnes (1999), mostly from Spain | 70% |
Currently Banwari Chemicals Pvt Ltd situated in Bhiwadi, Rajasthan, India is the leading manufacturer of anethole. It is prepared commercially from 4-methoxypropiophenone,[4][10] which is prepared from anisole.[3]
Uses
Flavoring
Anethole is distinctly
Precursor to other compounds
Because they
Research
Antimicrobial and antifungal activity
Anethole has potent
Insecticidal activity
Anethole also is a promising insecticide. Several essential oils consisting mostly of anethole have
As well as an insect pesticide, anethole is an effective insect repellent against mosquitos.[26]
Ouzo effect
Anethole is responsible for the "ouzo effect" (also "louche effect"), the spontaneous formation of a microemulsion[27][28] that gives many alcoholic beverages containing anethole and water their cloudy appearance.[29] Such a spontaneous microemulsion has many potential commercial applications in the food and pharmaceutical industries.[30]
Precursor to illicit drugs
Anethole is an inexpensive chemical precursor for
Anethole is also present in
Estrogen and prolactin
Anethole has
Fennel, which contains anethole, has been found to have a galactagogue effect in animals. Anethole bears a structural resemblance to catecholamines like dopamine and may displace dopamine from its receptors and thereby disinhibit prolactin secretion, which in turn may be responsible for the galactagogue effects.[39]
Safety
In the USA, anethole is
In large quantities, anethole is slightly
History
That an oil could be extracted from anise and fennel had been known since the
See also
- Category:Anise liqueurs and spirits
- List of liqueurs § Anise-flavored liqueurs
- Anol
- Chavicol
- Dianethole
- Fenchone
- Pseudoisoeugenol
- Safrole
References
- ^ "Anethole".
- ^ "Anise camphor definition and meaning | Collins English Dictionary".
- ^ ISBN 978-3527306732.
- ^ S2CID 49342669.
- ^ Waldbott, S. (1920). "Essential oils". Chemical Abstracts. 14 (17): 3753–3755.
- ^ US 4902850, Davis, Curry B., "Purification of anethole by crystallization", issued 1990-02-20
- ISBN 978-81-85086-80-4.
- ^ ]
- .
- S2CID 236342527.
- ^ PMID 11805095.
- PMID 16028980.
- S2CID 27196549.
- PMID 11743758.
- PMID 11307877.
- S2CID 9666596.
- PMID 17629623.
- PMID 18944489.
- PMID 17368893.
- PMID 15237942.
- S2CID 33429927.
- PMID 16786497.
- ^ PMID 15954709.
- PMID 11852640.
- PMID 11455661.
- PMID 12963152.
- PMID 16042427. Archived from the original(PDF) on 2009-03-18. Retrieved 2009-03-15.
- .
- ISBN 978-0-12-801758-6. Retrieved 2018-08-02.
O/W and W/O nano-emulsions can also be formed without a surfactant by self-emulsification, using the so-called Ouzo effect. The major components of Ouzo (a Greek drink) are trans-anethole, ethanol, and water. Anethole is almost insoluble ...
- PMID 17229398.
- PMID 12742705.
- PMID 15240033.
- S2CID 45636969.
- PMID 18429531.
- ISBN 978-0-299-10480-1.
- S2CID 28650422.
- PMID 6999244.
- ISBN 978-0-7020-5434-1.
- ISBN 978-0-443-06992-5.
- PMID 10496381.
- ^ PMID 2467866.
- PMID 12151622.
- ^ Joint FAO/WHO Expert Committee on Food Additives. "trans-Anethole". WHO Food Additives Series. International Program on Chemical Safety (IPCS).
- ^ Joint FAO/WHO Expert Committee on Food Additives (1998). "trans-Anethole". WHO Food Additives Series. International Program on Chemical Safety (IPCS).
- ^ "Summary of Evaluations Performed by the Joint FAO/WHO Expert Committee on Food Additives: trans-Anethole". International Program on Chemical Safety (IPCS). 2001-11-12. Archived from the original on 2009-03-11. Retrieved 2009-03-10.
- ^ "Safety data for anethole". Physical & Theoretical Chemistry Laboratory Safety, Oxford University. Archived from the original on 2008-06-15. Retrieved 2009-03-10.
- ^ a b See:
- Semmler, F. W. (1907). Die ätherischen Öle nach ihren chemischen Bestandteilen unter Berücksichtigung der geschichtlichen Entwicklung [The volatile oils according to their chemical components with regard to their historical development] (in German). Vol. 4. Leipzig: Veit & Co. p. 76.
- Lippmann, Edmund Oskar von (1921). "§ 339. Anethol". Zeittafeln zur Geschichte der Organischen Chemie [Timeline of the history of organic chemistry] (in German). Berlin: Springer-Verlag. p. 1. ISBN 9783662246665.
- Gildemeister, Eduard; Hoffmann, Friedrich (1900). "§ 307. Oil of anise". The Volatile Oils. Translated by Kremers, Edward. Milwaukee, Wisconsin: Review Publishing Co. pp. s558–s563.
- ^ De Saussure, N.-T. (1820). "Observations sur la combinaison de l'essence de citron avec l'acide muriatique, et sur quelques substances huileuses" [Observations on the combination of lemon essence with muriatic acid, and on several oily substances]. Annales de Chimie et de Physique. Série 2 (in French). 13: 259–284. See especially pp. 280–284.
- ^ See:
- Dumas, J. (1832). "Mémoire sur les substances végétales qui se rapprochent du camphre, et sur quelques huiles essentielles" [Memoir on plant substances that resemble camphor, and on several essential oils]. Annales de Chimie et de Physique. Série 2 (in French). 50: 225–240. On p. 234, Dumas provides an empirical formula C10H6O1/2 for anethol. If the subscripts are doubled and if the subscript for carbon is then halved (because Dumas, like many of his contemporaries, used the wrong atomic mass for carbon, 6 instead of 12), then Dumas' empirical formula is correct.
- Dumas' finding that the crystallizable components of anise oil and fennel oil were identical was confirmed in 1833 by the team of Rodolphe Blanchet (1807–1864) and Ernst Sell (1808–1854). See: Blanchet, Sell (1833). "Ueber die Zusammensetzung einiger organischer Substanzen" [On the composition of some organic substances]. Annalen der Pharmacie (in German). 6 (3): 259–313. . See especially pp. 287–288.
- Dumas' empirical formula for anethole was confirmed in 1841 by the French chemist Auguste Cahours. See: Cahours, A. A. T. (1841). "Sur les essences de fenouil, de badiane et d'anis" [On the essential oils of fennel, star anise, and anise]. Annales de Chimie et de Physique. Série 3 (in French). 2: 274–308. See pp. 278–279. Note that the subscripts of Cahours' empirical formula (C40H24O2) must be divided by 2 and then the subscript for carbon must be divided again by 2 (because, like many chemists of his time, Cahours used the wrong atomic mass for carbon, 6 instead of 12). If these changes are made, the resulting empirical formula is correct.
- .
Ich werde keinen neuen Namen für jede einzelne Art der folgenden physisch verschiedenen Arten annehmen. In meinem Werke bezeichne ich sie als Varietäten der Gattung „Anethol".
[I will adopt no new name for any individual species of the following physically different species. In my work, I designate them as varieties of the genus anethol.] - ^ Erlenmeyer, Emil (1866). "Ueber die Constitution des Anisols (Anethols)" [On the constitution of anisol (anethol)]. Zeitschrift für Chemie. 2nd Series (in German). 2: 472–474.
External links
- Media related to Anethole at Wikimedia Commons