View source for Anethole

{{chembox
| verifiedrevid = 321809583
| ImageFile = Anethole-structure-skeletal.png 
| ImageSize = 
| IUPACName = 1-methoxy-4-(1-propenyl)benzene
| OtherNames = 
| Section1 = {{Chembox Identifiers
|   InChI = 1/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+
| InChIKey = RUVINXPYWBROJD-ONEGZZNKBR
| CASNo_Ref = {{cascite}}
| CASNo = 104-46-1
|   PubChem = 637563
|   SMILES = O(c1ccc(\C=C\C)cc1)C
| ChemSpiderID=553166
  }}
| Section2 = {{Chembox Properties
|C=10|H=12|O=1
|   MolarMass = 
|   Appearance = 
|   Density = 0.998 g/cm<sup>3</sup>
|   MeltingPt = 20-21 °C
|   BoilingPt = 234 °C; 81 °C at 2 mmHg
|   Solubility = 
  }}
| Section3 = {{Chembox Hazards
|   ExternalMSDS = [http://physchem.ox.ac.uk/MSDS/AN/anethole.html External MSDS]
|   FlashPt = 
|   Autoignition = 
  }}
| Section8 = {{Chembox Related
|   OtherCpds = [[Anisole]]; [[Estragole]]}}
}}
'''Anethole''' (also ''' ''para''-methoxyphenylpropene''', ''' ''p''-propenylanisole''', and '''isoestragole''') is an [[aromatic compound]] that occurs widely in nature, in [[essential oil]]s.  It contributes a large component of the distinctive flavors of [[anise]] and [[fennel]] (both in the botanical family [[Apiaceae]]), [[Syzygium anisatum|anise myrtle]] ([[Myrtaceae]]), [[liquorice]] ([[Fabaceae]]), and [[star anise]] ([[Illiciaceae]]).  Closely related to anethole is its double-bond [[isomer]] [[estragole]], abundant in [[tarragon]] ([[Asteraceae]]) and [[basil]] ([[Lamiaceae]]), that has a flavor reminiscent of anise.  Anethole has numerous commercial uses in multiple industries, and high potential for additional uses.

==Structure and properties==
In chemical terms, anethole is an aromatic, [[saturation (chemistry)|unsaturated]] [[ether]].  It has two [[Cis-trans isomerism|''cis''-''trans'' isomer]]s (see also [[E-Z notation | ''E''-''Z'' notation]]), involving the double bond outside the ring.  The more abundant isomer, and the one preferred for use, is the ''[[Cis-trans isomerism|trans]]'' or ''E'' isomer:  '''''trans''-anethole''', '''''t''-anethole''', '''(''E'')-anethole''', '''''trans''-''para''-methoxyphenylpropene'''.  Its full [[chemical name]] is ''trans''-1-methoxy-4-(prop-1-enyl)benzene.

Anethole is less soluble in [[water]] than in [[ethanol]], which causes certain anise-flavored [[liquour]]s to become opaque when diluted with water (see [[Ouzo effect]]).  It is a clear, colorless liquid with [[boiling point]] 234 °C and [[congealing point]] ([[freezing point]]) 20 °C;<ref name="IFF">{{cite web
|title=Anethole USP
|publisher=International Flavors & Fragrances
|url=http://www.iff.com/Ingredients.nsf/0/025869D6ECC6B33180256990005F76F5
|accessdate=March 10, 2009
}}</ref>  below its congealing point, anethole forms white [[crystal]]s.  The crystals will precipitate from an aqueous solution, which causes a "[[snow globe]]" effect when certain anise-flavored liquours are chilled.  This effect is the basis of a patent for industrial purification of anethole from sources such as [[pine oil]].<ref>{{cite web
|title=United States Patent 4902850: Purification of anethole by crystallization 
|publisher=Free Patents Online
|url=http://www.freepatentsonline.com/4902850.html
|accessdate=March 10, 2009
}}</ref>  Anethole can be crystallized directly from a source essential oil by lowering the temperature of the oil;  adding a crystal of anethole helps to start the process.<ref>{{cite book
|title=Chopra's Indigenous Drugs of India
|author=Ram Nath Chopra and I. C. Chopra and K. L. Handa and L. D. Kapur
|publisher=Academic Publishers
|year=1958
|edition=2nd
|pages=178–179
|url=http://books.google.com/?id=2HyC4-GJ50YC&pg=PA178&dq=anethole
|isbn=9788185086804
}}</ref>  Historically, this was used to detect adulteration.<ref>{{cite journal
|title=Essential oils
|year=1920
|volume=14
|issue=17
|pages=3753–3755
|author=S. Waldbott
|journal=Chemical Abstracts
|url=http://books.google.com/?id=isq2AAAAIAAJ&pg=PA3753&dq=anethole+crystal
}}</ref>

==Production==
Commercial sources of anethole include some essential oils:<ref name="Ashurst">{{cite book
|title=Food Flavorings
|author=Philip R. Ashurst
|publisher=Springer
|year=1999
|pages=460
|url=http://books.google.com/?id=hrWuqmtwJiEC&dq=anethole&q=anethole#search_anchor
|isbn=9780834216211}}</ref><!-- pages 11, 33, 34-->
{| class="wikitable"
|-
!Essential oil
!World production
!''trans''-anethole
|-
|Anise
|8 tons (1999)
|95%
|-
|Star anise
|400 tons (1999), mostly from China
|87%
|-
|Fennel
|25 tons (1999), mostly from Spain
|70%
|}

==Uses==
Anethole is a [[flavoring]] substance of commercial value.  In addition, it is distinctly [[sweet]], measuring 13 times sweeter than [[sugar]]. It is perceived as being pleasant to the taste even at higher concentrations.  It is unrelated to [[glycyrrhizic acid]], which often co-occurs with it,{{Citation needed|date=September 2009}}<!-- "often" needs a reliable source --> and also is very sweet.  Anethole is used in alcoholic drinks, seasoning and confectionery applications, oral hygiene products, and in small quantities in natural berry [[flavor]]s.<ref name="Ashurst"/>

Anethole is an inexpensive chemical precursor for [[paramethoxyamphetamine]] (PMA),<ref name="pmid12742705">{{cite journal
| author = Waumans D, Bruneel N, Tytgat J
| title = Anise oil as para-methoxyamphetamine (PMA) precursor
| journal = Forensic Sci. Int.
| volume = 133
| issue = 1-2
| pages = 159–70
| year = 2003
| month = April
| pmid = 12742705
| doi = 
10.1016/S0379-0738(03)00063-X| url = http://linkinghub.elsevier.com/retrieve/pii/S037907380300063X
| issn = 
}}</ref> and used in its clandestine manufacture.<ref name="pmid15240033">{{cite journal
| author = Waumans D, Hermans B, Bruneel N, Tytgat J
| title = A neolignan-type impurity arising from the peracid oxidation reaction of anethole in the surreptitious synthesis of 4-methoxyamphetamine (PMA)
| journal = Forensic Sci. Int.
| volume = 143
| issue = 2-3
| pages = 133–9
| year = 2004
| month = July
| pmid = 15240033
| doi = 10.1016/j.forsciint.2004.02.033
| url = http://linkinghub.elsevier.com/retrieve/pii/S0379073804002075
| issn = 
}}</ref>  Anethole is present in the essential oil from [[guarana]], which is alleged to have has a psychoactive effect;  however, the absence of PMA or any other known psychoactive derivative of anethole leads to the conclusion that any purported psychoactive effect of guarana is not due to anethole.<ref name="pmid8765992">{{cite journal
| author = Benoni H, Dallakian P, Taraz K
| title = Studies on the essential oil from guarana
| journal = Z Lebensm Unters Forsch
| volume = 203
| issue = 1
| pages = 95–8
| year = 1996
| month = July
| pmid = 8765992
| doi = 
10.1007/BF01267777| url = 
| issn = 
}}</ref>  Anethole is also present in [[absinthe]], a [[liquor]] with a reputation for [[Psychedelics, dissociatives and deliriants|psychoactive]] effects;  these effects however are attributed to [[ethanol]]<ref name="pmid18429531">{{cite journal
| author = Lachenmeier DW
| title = [Thujone-attributable effects of absinthe are only an urban legend--toxicology uncovers alcohol as real cause of absinthism]
| language = German
| journal = Med Monatsschr Pharm
| volume = 31
| issue = 3
| pages = 101–6
| year = 2008
| month = March
| pmid = 18429531
| doi = 
| url = 
| issn = 
}}</ref> (see also [[Thujone]]).

[[Pharmaceutical drug]]s derived from or related to anethole include [[anisyldithiolthione]],<ref name="pmid3964266">{{cite journal
| author = Mansuy D, Sassi A, Dansette PM, Plat M
| title = A new potent inhibitor of lipid peroxidation in vitro and in vivo, the hepatoprotective drug anisyldithiolthione
| journal = Biochem. Biophys. Res. Commun.
| volume = 135
| issue = 3
| pages = 1015–21
| year = 1986
| month = March
| pmid = 3964266
| doi = 
10.1016/0006-291X(86)91029-6| url = http://linkinghub.elsevier.com/retrieve/pii/0006-291X(86)91029-6
| issn = 
}}</ref>  [[anethole dithione]] (ADT), and [[anethole trithione]] (ATT).

==Research==
[[File:Preparing absinthe.jpg|thumb|Diluting [[absinthe]] with water produces a spontaneous microemulsion (ouzo effect)]]
Anethole is responsible for the "[[ouzo effect]]", the spontaneous formation of a [[microemulsion]]<ref name="Sitnikova+2005">{{cite journal |last=Sitnikova |first=Natalia L. |coauthors=Rudolf Sprik, Gerard Wegdam and Erika Eiser |month= |year=2005 |title=Spontaneously Formed trans-Anethol/Water/Alcohol Emulsions: Mechanism of Formation and Stability |journal=Langmuir |volume=21 |issue=16 |pages=7083–7089 |doi=10.1021/la046816l |url=http://www.science.uva.nl/~sprik/personal/pdf/05/la046816l.pdf |format=PDF|accessdate=2009--3-15 |pmid=16042427}}</ref><ref>{{cite journal
|title=The “Ouzo effect”: Following the spontaneous emulsification of trans-anethole in water by NMR
|journal=Comptes Rendus Chimie
|volume=11
|issue =4-5
|date=April-May 2008
|pages=493–498
|author=David Carteau, Dario Bassani, and Isabelle Pianet
|doi=10.1016/j.crci.2007.11.003    
}}</ref> that gives many alcoholic beverages containing anethole and water their cloudy appearance.  Such a spontaneous microemulsion has many potential commercial applications in the food and pharmaceutical industries.<ref name="pmid17229398">{{cite journal
| author = Spernath A, Aserin A
| title = Microemulsions as carriers for drugs and nutraceuticals
| journal = Adv Colloid Interface Sci
| volume = 128-130
| issue = 
| pages = 47–64
| year = 2006
| month = December
| pmid = 17229398
| doi = 10.1016/j.cis.2006.11.016
| url = 
| issn = 
}}</ref>  A derivative of anethole, [[anethole trithione]], is being investigated for use in [[self-microemulsifying drug delivery system]]s (SMEDDS).<ref name="pmid16824723">{{cite journal
| author = Jing Q, Shen Y, Ren F, Chen J, Jiang Z, Peng B, Leng Y, Dong J
| title = HPLC determination of anethole trithione and its application to pharmacokinetics in rabbits
| journal = J Pharm Biomed Anal
| volume = 42
| issue = 5
| pages = 613–7
| year = 2006
| month = November
| pmid = 16824723
| doi = 10.1016/j.jpba.2006.05.013
| url = http://linkinghub.elsevier.com/retrieve/pii/S0731-7085(06)00390-6
| issn = 
}}</ref>

Bacterial strains capable of using trans-anethole as the sole carbon source include JYR-1 (''[[Pseudomonas putida]]'')<ref name="pmid16028980">{{cite journal
| unused_data = DUPLICATE DATA: doi = 10.1021/jf040445x
| author = Ryu J, Seo J, Lee Y, Lim Y, Ahn JH, Hur HG
| title = Identification of syn- and anti-anethole-2,3-epoxides in the metabolism of trans-anethole by the newly isolated bacterium ''Pseudomonas putida'' JYR-1
| journal = J. Agric. Food Chem.
| volume = 53
| issue = 15
| pages = 5954–8
| year = 2005
| month = July
| pmid = 16028980
| doi = 10.1021/jf040445x
| issn = 
}}</ref> and TA13 (''[[Arthrobacter]] aurescens'').<ref name="pmid11805095">{{cite journal
| author = Shimoni E, Baasov T, Ravid U, Shoham Y
| title = The trans-anethole degradation pathway in an ''Arthrobacter'' sp
| journal = J. Biol. Chem.
| volume = 277
| issue = 14
| pages = 11866–72
| year = 2002
| month = April
| pmid = 11805095
| doi = 10.1074/jbc.M109593200
| url = http://www.jbc.org/cgi/pmidlookup?view=long&pmid=11805095
| issn = 
}}</ref>  Because they [[Metabolism|metabolize]] anethole into several [[aromatic chemical compound]]s, these bacteria are candidates for use in commercial [[bioconversion]] of these valuable compounds from anethole and other [[phenylpropanoid]]s.  Compared to other industrial processes, such bioconversion may be less costly and more friendly to the environment.<ref name="pmid11805095"/>

Anethole has potent [[antimicrobial]] properties, against [[bacteria]], [[yeast]], and [[fungi]].<ref name="pmid11807977">{{cite journal
| author = De M, De AK, Sen P, Banerjee AB
| title = Antimicrobial properties of star anise (''Illicium verum'' Hook f)
| journal = Phytother Res
| volume = 16
| issue = 1
| pages = 94–5
| year = 2002
| month = February
| pmid = 11807977
| doi = 10.1002/ptr.989
| issn = 
}}</ref>  Reported antibacterial properties include both [[bacteriostatic]] and [[bactericidal]] action against ''[[Salmonella enterica]]''<ref name="pmid11743758">{{cite journal
| author = Kubo I, Fujita K
| title = Naturally occurring anti-Salmonella agents
| journal = J. Agric. Food Chem.
| volume = 49
| issue = 12
| pages = 5750–4
| year = 2001
| month = December
| pmid = 11743758
| doi = 10.1021/jf010728e
| issn = 
}}</ref> but not when used against ''Salmonella'' via a [[fumigation]] method.<ref name="pmid11307877">{{cite journal
| author = Weissinger WR, McWatters KH, Beuchat LR
| title = Evaluation of volatile chemical treatments for lethality to ''Salmonella'' on alfalfa seeds and sprouts
| journal = J. Food Prot.
| volume = 64
| issue = 4
| pages = 442–50
| year = 2001
| month = April
| pmid = 11307877
| doi = 
| url = 
| issn = 
}}</ref>  Antifungal activity includes increasing the effectiveness of some other [[phytochemical]]s (eg [[polygodial]]) against ''[[Saccharomyces cerevisiae]]'' and ''[[Candida albicans]]'';<ref name="pmid17078111">{{cite journal
| unused_data = DUPLICATE DATA: doi = 10.1002/ptr.2016
| author = Fujita K, Fujita T, Kubo I
| title = Anethole, a potential antimicrobial synergist, converts a fungistatic dodecanol to a fungicidal agent
| journal = Phytother Res
| volume = 21
| issue = 1
| pages = 47–51
| year = 2007
| month = January
| pmid = 17078111
| doi = 10.1002/ptr.2016
| issn = 
}}</ref>  this synergistic effect has potential medical uses.<ref name="pmid16412035">{{cite journal
| author = Marotta F, Barreto R, Kawakita S, Minelli E, Pavasuthipaisit K, Lorenzetti A, Nishiwaki M, Gelosa F, Fesce E, Okura R
| title = Preventive strategy for Candida gut translocation during ischemia-reperfusion injury supervening on protein-calorie malnutrition
| journal = Chin J Dig Dis
| volume = 7
| issue = 1
| pages = 33–8
| year = 2006
| pmid = 16412035
| doi = 10.1111/j.1443-9573.2006.00241.x
| url = http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=1443-9611&date=2006&volume=7&issue=1&spage=33
| issn = 
}}</ref>

[[In vitro]], anethole has [[antihelmintic]] action on eggs and larvae of the [[domestic sheep|sheep]] [[gastrointestinal nematode]] ''[[Haemonchus contortus]]''.<ref name="pmid17629623">{{cite journal
| author = Camurça-Vasconcelos AL, Bevilaqua CM, Morais SM, Maciel MV, Costa CT, Macedo IT, Oliveira LM, Braga RR, Silva RA, Vieira LS
| title = Anthelmintic activity of Croton zehntneri and Lippia sidoides essential oils
| journal = Vet. Parasitol.
| volume = 148
| issue = 3-4
| pages = 288–94
| year = 2007
| month = September
| pmid = 17629623
| doi = 10.1016/j.vetpar.2007.06.012
| url = http://linkinghub.elsevier.com/retrieve/pii/S0304-4017(07)00290-7
| issn = 
}}</ref>  Anethole also has nematicidal activity against the plant nematode ''[[Meloidogyne javanica]]'' in vitro and in pots of cucumber seedlings.<ref name="pmid18944489">{{cite journal
| author = Oka Y, Nacar S, Putievsky E, Ravid U, Yaniv Z, Spiegel Y
| title = Nematicidal activity of essential oils and their components against the root-knot nematode
| journal = Phytopathology
| volume = 90
| issue = 7
| pages = 710–5
| year = 2000
| month = July
| pmid = 18944489
| doi = 10.1094/PHYTO.2000.90.7.710
| url = http://apsjournals.apsnet.org/doi/abs/10.1094/PHYTO.2000.90.7.710?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%3dncbi.nlm.nih.gov
| issn = 
}}</ref>

Anethole also is a promising insecticide.  Several essential oils consisting mostly of anethole have [[insecticide|insecticidal]] action against [[larva]]e of the [[mosquito]]s ''[[Ochlerotatus]] caspius''<ref name="pmid17368893">{{cite journal
| author = Knio KM, Usta J, Dagher S, Zournajian H, Kreydiyyeh S
| title = Larvicidal activity of essential oils extracted from commonly used herbs in Lebanon against the seaside mosquito, ''Ochlerotatus caspius''
| journal = Bioresour. Technol.
| volume = 99
| issue = 4
| pages = 763–8
| year = 2008
| month = March
| pmid = 17368893
| doi = 10.1016/j.biortech.2007.01.026
| url = http://linkinghub.elsevier.com/retrieve/pii/S0960-8524(07)00102-2
| issn = 
}}</ref> and [[Aedes aegypti]].<ref name="pmid15237942">{{cite journal
| unused_data = DUPLICATE DATA: doi = 10.1021/jf0497152
| author = Cheng SS, Liu JY, Tsai KH, Chen WJ, Chang ST
| title = Chemical composition and mosquito larvicidal activity of essential oils from leaves of different ''Cinnamomum osmophloeum'' provenances
| journal = J. Agric. Food Chem.
| volume = 52
| issue = 14
| pages = 4395–400
| year = 2004
| month = July
| pmid = 15237942
| doi = 10.1021/jf0497152
| issn = 
}}</ref><ref name="pmid16646345">{{cite journal
| author = Morais SM, Cavalcanti ES, Bertini LM, Oliveira CL, Rodrigues JR, Cardoso JH
| title = Larvicidal activity of essential oils from Brazilian ''Croton'' species against ''Aedes aegypti'' L
| journal = J. Am. Mosq. Control Assoc.
| volume = 22
| issue = 1
| pages = 161–4
| year = 2006
| month = March
| pmid = 16646345
| doi = 
10.2987/8756-971X(2006)22[161:LAOEOF]2.0.CO;2| url = 
| issn = 
}}</ref>  In similar manner, anethole itself is effective against the [[fungus gnat]] ''Lycoriella ingenua'' ([[Sciaridae]])<ref name="pmid16786497">{{cite journal
| unused_data = DUPLICATE DATA: doi = 10.1002/ps.1228
| author = Park IK, Choi KS, Kim DH, Choi IH, Kim LS, Bak WC, Choi JW, Shin SC
| title = Fumigant activity of plant essential oils and components from horseradish (''Armoracia rusticana''), anise (''Pimpinella anisum'') and garlic (''Allium sativum'') oils against ''Lycoriella ingenua'' (Diptera: Sciaridae)
| journal = Pest Manag. Sci.
| volume = 62
| issue = 8
| pages = 723–8
| year = 2006
| month = August
| pmid = 16786497
| doi = 10.1002/ps.1228
| issn = 
}}</ref> and the [[mold mite]] ''Tyrophagus putrescentiae''.<ref name="pmid15954709">{{cite journal
| author = Lee HS
| title = Food protective effect of acaricidal components isolated from anise seeds against the stored food mite, ''Tyrophagus putrescentiae'' (Schrank)
| journal = J. Food Prot.
| volume = 68
| issue = 6
| pages = 1208–10
| year = 2005
| month = June
| pmid = 15954709
| doi = 
| url = 
| issn = 
}}</ref>  Against the mite, anethole is a slightly more effective [[pesticide]] than [[DEET]] but [[anisaldehyde]], a related natural compound that occurs with anethole in many essential oils, is 14 times more effective.<ref name="pmid15954709"/>  The insecticidal action of anethole is greater as a [[fumigation|fumigant]] than as a contact agent.  (E)-anethole is highly effective as a [[fumigant]] against the [[cockroach]] ''[[Blattella germanica]]''<ref name="pmid11852640">{{cite journal
| unused_data = DUPLICATE DATA: doi = 10.1002/ps.435
| author = Chang KS, Ahn YJ
| title = Fumigant activity of (E)-anethole identified in ''Illicium verum'' fruit against ''Blattella germanica''
| journal = Pest Manag. Sci.
| volume = 58
| issue = 2
| pages = 161–6
| year = 2002
| month = February
| pmid = 11852640
| doi = 10.1002/ps.435
| issn = 
}}</ref> and against adults of the [[weevil]]s ''[[Sitophilus oryzae]]'', ''[[Callosobruchus chinensis]]'' and [[beetle]] ''[[Lasioderma serricorne]]''.<ref name="pmid11455661">{{cite journal
| unused_data = DUPLICATE DATA: doi = 10.1002/ps.274
| author = Kim DH, Ahn YJ
| title = Contact and fumigant activities of constituents of ''Foeniculum vulgare'' fruit against three coleopteran stored-product insects
| journal = Pest Manag. Sci.
| volume = 57
| issue = 3
| pages = 301–6
| year = 2001
| month = March
| pmid = 11455661
| doi = 10.1002/ps.274
| issn = 
}}</ref>

As well as an insect pesticide, anethole is an effective [[insect repellent]] against
mosquitos.<ref name="pmid12963152">{{cite journal
| author = Padilha de Paula J, Gomes-Carneiro MR, Paumgartten FJ
| title = Chemical composition, toxicity and mosquito repellency of ''Ocimum selloi'' oil
| journal = J Ethnopharmacol
| volume = 88
| issue = 2-3
| pages = 253–60
| year = 2003
| month = October
| pmid = 12963152
| doi = 
10.1016/S0378-8741(03)00233-2| url = http://linkinghub.elsevier.com/retrieve/pii/S0378874103002332
| issn = 
}}</ref>

==Safety==
Formerly [[generally recognized as safe]] (GRAS), after a hiatus anethole was reaffirmed by [[Flavor and Extract Manufacturers Association]] (FEMA) as GRAS.<ref name="pmid10496381">{{cite journal
| author = Newberne P, Smith RL, Doull J, Goodman JI, Munro IC, Portoghese PS, Wagner BM, Weil CS, Woods LA, Adams TB, Lucas CD, Ford RA
| title = The FEMA GRAS assessment of trans-anethole used as a flavouring substance. Flavour and Extract Manufacturer's Association
| journal = Food Chem. Toxicol.
| volume = 37
| issue = 7
| pages = 789–811
| year = 1999
| month = July
| pmid = 10496381
| doi = 
| url = http://linkinghub.elsevier.com/retrieve/pii/S027869159900037X
| issn = 
}}</ref>  The hiatus was due to concerns about liver toxicity and possible carcinogenic activity, reported in rats.<ref name="pmid2467866">{{cite journal
| author = Newberne PM, Carlton WW, Brown WR
| title = Histopathological evaluation of proliferative liver lesions in rats fed trans-anethole in chronic studies
| journal = Food Chem. Toxicol.
| volume = 27
| issue = 1
| pages = 21–6
| year = 1989
| month = January
| pmid = 2467866
| doi = 
10.1016/0278-6915(89)90087-2| url = 
| issn = 
}}</ref>  Anethole is associated with a slight increase in [[liver cancer]] in rats,<ref name="pmid2467866"/> although the evidence is scant and generally regarded as evidence that anethole is ''not'' a [[carcinogen]].<ref name="pmid2467866"/><ref name="pmid12151622">{{cite journal
| author = Waddell WJ
| title = Thresholds of carcinogenicity of flavors
| journal = Toxicol. Sci.
| volume = 68
| issue = 2
| pages = 275–9
| year = 2002
| month = August
| pmid = 12151622
| doi = 
10.1093/toxsci/68.2.275| url = http://toxsci.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=12151622
| issn = 
}}</ref>  An evaluation of anethole by the [[Joint FAO/WHO Expert Committee on Food Additives]] (JECFA) found its notable [[pharmacology|pharmacologic]] properties to be reduction in [[motor activity]], lowering of [[Normal human body temperature|body temperature]], and [[hypnotic]], [[analgesic]], and [[anticonvulsant]] effects.<ref name="JECFA466">{{Cite document
|title=Trans-anethole
|publisher=International Program on Chemical Safety (IPCS)
|author-link=Joint FAO/WHO Expert Committee on Food Additives
|issue=466
|series=WHO Food Additives Series
|volume=14
|url=http://www.inchem.org/documents/jecfa/jecmono/v14je02.htm
}}</ref>  A subsequent evaluation by JECFA found some reason for concern re [[carcinogenicity]] but insufficient data.<ref name="JECFA717">{{Cite document
|title=Trans-anethole
|publisher=International Program on Chemical Safety (IPCS)
|author-link=Joint FAO/WHO Expert Committee on Food Additives
|year=1998
|issue=717
|series=WHO Food Additives Series
|volume=28
|url=http://www.inchem.org/documents/jecfa/jecmono/v28je10.htm
}}</ref>  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''.<ref name="JECeval">{{cite web
|title=Summary of Evaluations Performed by the Joint FAO/WHO Expert Committee on Food Additives:  Trans-anethole
|publisher=International Program on Chemical Safety (IPCS)
|date=November 12, 2001
|url=http://www.inchem.org/documents/jecfa/jeceval/jec_137.htm
|accessdate=March 10, 2009
}}</ref>

In large quantities, anethole is slightly [[toxic]] and may act as an irritant.<ref>{{cite web
|title=Safety data for anethole
|publisher=Physical & Theoretical Chemistry Laboratory Safety, Oxford Universtiy
|url=http://msds.chem.ox.ac.uk/AN/anethole.html
|accessdate=March 10, 2009
}}</ref>  <!-- It can stimulate hepatic regeneration in rats, and can also produce spasmolytic activity in high doses.{{Fact|date=March 2009}} -->

==See also==
*[[:Category:Anise liqueurs and spirits]]
*[[List of liqueurs#Anise-flavored liqueurs]]
*[[Chavicol]]
*[[Safrole]]
*[[Fenchone]]

==References==
{{reflist|2}}

== External links ==
*[http://people.ouc.bc.ca/woodcock/molecule/modelfiles/anethole.html Molecular Models from OUC: anethole]

[[Category:Flavors]]
[[Category:Sweeteners]]
[[Category:Essential oils]]
[[Category:Phenylpropanoids]]
[[Category:Aromatic compounds]]
[[Category:Alkenes]]
[[Category:Phenol ethers]]

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[[ja:アネトール]]
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[[Category:2Fix]]