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Anethole
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{{chembox | Watchedfields = changed | verifiedrevid = 443390450 | Name = | ImageFile = Anethole acsv.svg | ImageSize = 220 | ImageAlt = Skeletal formula of anethole | ImageFile1 = Anethole-3D-balls.png | ImageSize1 = 220 | ImageAlt1 = Ball-and-stick model of the anethole molecule | PIN = 1-Methoxy-4-[(1''E'')-prop-1-en-1-yl]benzene<!-- <ref>{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/637563#section=IUPAC-Name&fullscreen=true | title=Anethole }}</ref> --> | SystematicName = | OtherNames = (''E'')-1-Methoxy-4-(prop-1-en-1-yl)benzene<br />(''E'')-1-Methoxy-4-(1-propenyl)benzene<br />''para''-Methoxyphenylpropene<br />''p''-Propenylanisole<br />Isoestragole<br />''trans''-1-Methoxy-4-(prop-1-enyl)benzene | IUPACName = | Section1 = {{Chembox Identifiers | UNII_Ref = {{fdacite|correct|FDA}} | UNII = Q3JEK5DO4K | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D02377 | InChI = 1/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+ | InChIKey = RUVINXPYWBROJD-ONEGZZNKBR | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 452630 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = RUVINXPYWBROJD-ONEGZZNKSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo1 = 4180-23-8 | CASNo1_Comment = ''E'' isomer | CASNo2 = 104-46-1 | CASNo2_Comment = Unspecified stereochemistry (most commonly used CAS, implicitly ''E'') | CASNo3 = 25679-28-1 | CASNo3_Comment = ''Z'' isomer | PubChem = 637563 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 35616 | SMILES = O(c1ccc(\C=C\C)cc1)C | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID =553166 }} | Section2 = {{Chembox Properties | C =10|H=12|O=1 | MolarMassUnit = g/mol | Appearance = | Density = 0.998 g/cm<sup>3</sup> | MeltingPtC = 20 to 21 | BoilingPtC = 234 | BoilingPt_notes = <br/>{{cvt|81|Β°C|Β°F K|abbr=on}} at 2 mmHg | Solubility = | MagSus = {{val|-9.60e-5|u=cm<sup>3</sup>/mol}} }} | Section3 = {{Chembox Hazards | ExternalSDS = [https://web.archive.org/web/20010905233920/http://physchem.ox.ac.uk/MSDS/AN/anethole.html External MSDS] | FlashPt = | AutoignitionPt = }} | Section4 = | Section5 = | Section6 = | Section8 = {{Chembox Related | OtherCompounds = [[anisole]]<br>[[estragole]]}} }} '''Anethole''' (also known as '''anise camphor''')<ref>{{cite web|url=https://www.collinsdictionary.com/us/dictionary/english/anise-camphor|title=Anise camphor definition and meaning | Collins English Dictionary}}</ref> is an [[organic compound]] that is widely used as a [[flavoring]] substance. It is a derivative of the [[aromatic]] compound [[allylbenzene]] and occurs widely in the [[essential oil]]s of plants. It is in the class of [[phenylpropanoid]] organic compounds. It contributes a large component of the odor and flavor of [[anise]] and [[fennel]] (both in the botanical family [[Apiaceae]]), [[Syzygium anisatum|anise myrtle]] ([[Myrtaceae]]), [[liquorice]] ([[Fabaceae]]), magnolia blossoms, and [[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.{{clarify|reason=does this statement refer to anethole or estragole?|date=October 2023}}<ref name=Ullmann>{{Ullmann|first1=Karl-Georg|last1=Fahlbusch|first2=Franz-Josef|last2=Hammerschmidt|first3=Johannes|last3=Panten|first4=Wilhelm|last4=Pickenhagen|first5=Dietmar|last5=Schatkowski|first6=Kurt|last6=Bauer|first7=Dorothea|last7=Garbe|first8=Horst|last8=Surburg|title=Flavors and Fragrances|doi=10.1002/14356007.a11_141}}</ref> Anethole is only slightly soluble in [[water]] but exhibits high solubility in [[ethanol]]. This trait causes certain anise-flavored [[liqueur]]s to become opaque when diluted with water; this is called the [[ouzo effect]].
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