Anethole

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Structural formula
Structural formulas of anethole
cis -Anethol (top) and trans -Anethol (bottom)
General
Surname Anethole
other names
  • 4-propenyl anisole
  • cis -nethol
  • trans -Anethol
  • Parapropenyl anisole
  • 1- (4-methoxyphenyl) -1-propene
  • 1-methoxy-4- (1-propenyl) benzene
Molecular formula C 10 H 12 O
External identifiers / databases
CAS number 104-46-1 [( EZ ) -Anethol]
EC number 203-205-5
ECHA InfoCard 100.002.914
PubChem 7703
ChemSpider 7417
Wikidata Q27105777
properties
Molar mass 148.22 g mol −1
Physical state
  • liquid ( cis -nethol)
  • solid ( trans -Anethol)
density

0.99 g cm −3

Melting point
  • −22  ° C ( cis -nethol)
  • 22 ° C ( trans -Anethol)
boiling point
  • 79 ° C (3.07 hPa) ( cis -nethol)
  • 234–237 ° C ( trans -nethol)
Vapor pressure

1.33 h Pa (63 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 317-411
P: 273-280
Toxicological data
  • 93 mg kg −1 ( LD 50 ,  rat ,  ip , Z -isomer)
  • 900 mg kg −1 ( LD 50 ,  rat ,  ip , E isomer)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Anethole is an organic-chemical compound which, due to its biosynthetic pathway, belongs to the phenylpropanoids . It is a component of various essential oils e.g. B. Anise oil and occurs in various plants fennel , anise and star anise . Both isomers occur in nature, but there is more trans -amethol present. The smell of anethole is the cause of the typical aniseed aroma .

Isomerism

Because of the double bond contained in anethole, there are two isomers : cis - and trans - anethole. Both isomers have different physical properties.

Isomers of anethole
Surname cis -nethol trans -Anethol
other names ( Z ) -Anethol ( E ) -Anethol
CAS number 25679-28-1 4180-23-8
104-46-1 (undefined)
EC number 247-181-4 224-052-0
203-205-5 (undefined)
ECHA info card 100,042,878 100,021,866
100.002.914 (undefined)
PubChem 1549040 637563
7703 (undefined)
Wikidata Q27147814 Q255564
Q27105777 (undefined)

A structural isomer of anethole is estragole .

properties

500 ml of anethole are soluble in 1 liter of ethanol . In contrast, it is only very poorly soluble in water. The flash point is 90 ° C. trans -Anethol is a white, crystalline, sweet-tasting solid that melts at 21.4 ° C to form a colorless, oily liquid. The cis -nethol is liquid and solidifies at −22 ° C.

physiology

Anethole has an expectorant effect in the lungs ( secretolytic , secretomotor ) and weakly antibacterial . At the same time it shows a spasmolytic effect, which is why it can be used as an expectorant and carminative .

Anethole is a component of the aroma of anise oil (from Pimpinella anisum ).

use

Anethole is used as a fragrance and aromatic substance , especially in soaps and oral care products . It is also important to use it in the production of spirits as an aromatizer for spirits ( aniseed , anisette , ouzo , Pernod , Rakı ) and in food technology as a component of flavors, mainly in fruit flavor mixtures with the flavor raspberry and strawberry .

Web links

Individual evidence

  1. ↑ a b c d e f g Entry on anethole. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
  2. ↑ a b c data sheet trans-Anethole from Sigma-Aldrich , accessed on January 25, 2020 ( PDF ).
  3. ↑ Data sheet Anethol (PDF) from Carl Roth , accessed on February 19, 2010.
  4. ↑ a b Entry on anethole in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
  5. ^ Albert Gossauer: Structure and reactivity of biomolecules , Verlag Helvetica Chimica Acta, Zurich, 2006, p. 210, ISBN 978-3-906390-29-1 .