Anethole

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Anethole
Skeletal formula of anethole
Ball-and-stick model of the anethole molecule
Names
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
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.002.914 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+ checkY
    Key: RUVINXPYWBROJD-ONEGZZNKSA-N checkY
  • InChI=1/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+
    Key: RUVINXPYWBROJD-ONEGZZNKBR
  • O(c1ccc(\C=C\C)cc1)C
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
anisole
estragole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Anethole (also known as anise camphor)

star anise (Schisandraceae). Closely related to anethole is its isomer estragole, which is abundant in tarragon (Asteraceae) and basil (Lamiaceae), and has a flavor reminiscent of anise. It is a colorless, fragrant, mildly volatile liquid.[clarification needed][3] Anethole is only slightly soluble in water but exhibits high solubility in ethanol. This trait causes certain anise-flavored liqueurs to become opaque when diluted with water; this is called the ouzo effect
.

Structure and production

Anethole is an aromatic,

EZ notation), involving the double bond outside the ring. The more abundant isomer, and the one preferred for use, is the trans or E isomer.[4]

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

sweet, measuring 13 times sweeter than sugar. It is perceived as being pleasant to the taste even at higher concentrations. It is used in alcoholic drinks ouzo, rakı, anisette and absinthe, among others. It is also used in seasoning and confectionery applications, such as German Lebkuchen, oral hygiene products, and in small quantities in natural berry flavors.[8]

Precursor to other compounds

Because they

Research

Antimicrobial and antifungal activity

Anethole has potent

bactericidal action against Salmonella enterica[14] but not when used against Salmonella via a fumigation method.[15] Antifungal activity includes increasing the effectiveness of some other phytochemicals (such as polygodial) against Saccharomyces cerevisiae and Candida albicans;[16]

sheep gastrointestinal nematode Haemonchus contortus.[17] Anethole also has nematicidal activity against the plant nematode Meloidogyne javanica in vitro and in pots of cucumber seedlings.[18]

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

Diluting absinthe with water produces a spontaneous microemulsion (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

paramethoxyamphetamine (PMA),[31] and is used in its clandestine manufacture.[32] Anethole is present in the essential oil from guarana, which has psychoactive effects typically attributed to its caffeine content. The absence of PMA or any other known psychoactive derivative of anethole in human urine after ingestion of guarana leads to the conclusion that any psychoactive effect of guarana is not due to aminated anethole metabolites.[33]

Anethole is also present in

(ATT).)

Estrogen and prolactin

Anethole has

uterine weight in immature female rats.[38]

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

carcinogenicity, but there is currently insufficient data to support this.[44] At this time, the JECFA summary of these evaluations is that anethole has "no safety concern at current levels of intake when used as a flavoring agent".[45]

In large quantities, anethole is slightly

toxic and may act as an irritant.[46]

History

That an oil could be extracted from anise and fennel had been known since the

Jean Baptiste Dumas determined that the crystallizable components of anise oil and fennel oil were identical, and he determined anethole's empirical formula.[49] In 1845, the French chemist Charles Gerhardt coined the term anethol – from the Latin anethum (anise) + oleum (oil) – for the fundamental compound from which a family of related compounds was derived.[50] Although the German chemist Emil Erlenmeyer proposed the correct molecular structure for anethole in 1866,[51] it was not until 1872, that the structure was accepted as correct.[47]

See also

References

  1. ^ "Anethole".
  2. ^ "Anise camphor definition and meaning | Collins English Dictionary".
  3. ^ .
  4. ^ .
  5. ^ Waldbott, S. (1920). "Essential oils". Chemical Abstracts. 14 (17): 3753–3755.
  6. ^ US 4902850, Davis, Curry B., "Purification of anethole by crystallization", issued 1990-02-20 
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  27. PMID 16042427. Archived from the original
    (PDF) on 2009-03-18. Retrieved 2009-03-15.
  28. .
  29. . 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 ...
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  43. ^ Joint FAO/WHO Expert Committee on Food Additives. "trans-Anethole". WHO Food Additives Series. International Program on Chemical Safety (IPCS).
  44. ^ Joint FAO/WHO Expert Committee on Food Additives (1998). "trans-Anethole". WHO Food Additives Series. International Program on Chemical Safety (IPCS).
  45. ^ "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.
  46. ^ "Safety data for anethole". Physical & Theoretical Chemistry Laboratory Safety, Oxford University. Archived from the original on 2008-06-15. Retrieved 2009-03-10.
  47. ^ a b See:
  48. ^ 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.
  49. ^ 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.
  50. . 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.]
  51. ^ 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