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| Reference=<ref> at ]</ref> |
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| verifiedrevid = 412262064 |
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|ImageFile=Furaneol.svg |
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| Reference =<ref> at ]</ref> |
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|ImageSize=150px |
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| ImageFile =Furanol Grundstruktur V1.svg |
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|IUPACName=4-Hydroxy-2,5-dimethyl-3-furanone |
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| ImageSize =150px |
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|OtherNames={{•}}4-Hydroxy-2,5-dimethyl-3(2''H'')-furanone<br>{{•}}Alletone<br>{{•}}Pineapple ketone<br>{{•}}Strawberry furanone<br>{{•}}Dimethylhydroxy furanone |
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| IUPACName =4-Hydroxy-2,5-dimethyl-3-furanone |
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|Section1= {{Chembox Identifiers |
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| OtherNames ={{bulletedlist|4-Hydroxy-2,5-dimethyl-3(2''H'')-furanone|Alletone|Pineapple ketone|Strawberry furanone|Dimethylhydroxy furanone}} |
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| Abbreviations = DMHF |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Abbreviations = DMHF |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 18218 |
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| ChemSpiderID = 18218 |
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| StdInChIKey = INAXVXBDKKUCGI-UHFFFAOYSA-N |
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| StdInChIKey = INAXVXBDKKUCGI-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=3658-77-3 |
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| CASNo =3658-77-3 |
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| CASNo1 = 131222-82-7 |
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| PubChem=19309 |
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| SMILES = O=C1C(\O)=C(/OC1C)C |
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| CASNo1_Comment = (''R'')-(+) |
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| CASNo2 = 131222-81-6 |
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| CASNo2_Comment = (''S'')-(−) |
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| PubChem =19309 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 76247 |
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| SMILES = O=C1C(\O)=C(/OC1C)C |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=6|H=8|O=3 |
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| Formula=C<sub>6</sub>H<sub>8</sub>O<sub>3</sub> |
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| Appearance = |
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| MolarMass=128.13 g/mol |
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| MeltingPtC = 73 to 77 |
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| MeltingPt=73-77 °C |
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'''Furaneol''', or '''strawberry furanone''', is a natural ] used in the flavor and perfume industry because of its sweet ] aroma.<ref> at thegoodscentscompany.com</ref> It is actually found in strawberries<ref>Ulrich, D. et al. 1995. Analysis of strawberry flavour - Quantification of the volatile components of varieties of cultivated and wild strawberries. Z. Lebensm. UNters. Forsch. 200:217-220</ref> and a variety of other fruits and it is partly responsible for the smell of fresh ].<ref>{{cite journal |author=Tokitomo Y, Steinhaus M, Büttner A, Schieberle P |title=Odor-active constituents in fresh ] (Ananas comosus Merr.) by quantitative and sensory evaluation |journal=Biosci. Biotechnol. Biochem. |volume=69 |issue=7 |pages=1323–30 |year=2005 |pmid=16041138 |doi=10.1271/bbb.69.1323}}</ref> |
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'''Furaneol''', or '''strawberry furanone''', is an ] used in the flavor and perfume industry. It is formally a derivative of ]. It is a white or colorless solid that is soluble in water and organic solvents.<ref name= Zabetakis>{{cite journal|doi=10.1016/S0308-8146(98)00203-9|title=2,5-Dimethyl-4-hydroxy-2H-furan-3-one and its derivatives: analysis, synthesis and biosynthesis - a review |author=Zabetakis, I. |author2=Gramshaw, J. W. |author3=Robinson, D. S. |journal=Food Chemistry|year=1999|volume=65|pages=139–151}}</ref> |
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It is also important for odour of ],<ref>{{cite journal |
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==Odor and occurrence== |
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| author=Janes D, Kantar D, Kreft S, Prosen H |
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Although malodorous at high concentrations, it exhibits a sweet ] aroma when dilute.<ref name= Zabetakis/> It is found in strawberries<ref>{{cite journal|last1=Ulrich|first1=D.|last2=Hoberg|first2=Edelgard|last3=Rapp|first3=Adolf|last4=Kecke|first4=Steffen|title=Analysis of strawberry flavour – discrimination of aroma types by quantification of volatile compounds|journal=Zeitschrift für Lebensmittel-Untersuchung und -Forschung A|volume=205|issue=3|year=1997|pages=218–223|url=https://www.researchgate.net/publication/226927264|doi=10.1007/s002170050154|s2cid=96680333}}</ref> and a variety of other fruits and it is partly responsible for the smell of fresh ].<ref>{{cite journal |vauthors=Tokitomo Y, Steinhaus M, Büttner A, Schieberle P |title=Odor-active constituents in fresh pineapple (''Ananas comosus'' Merr.) by quantitative and sensory evaluation |journal=Biosci. Biotechnol. Biochem. |volume=69 |issue=7 |pages=1323–30 |year=2005 |pmid=16041138 |doi=10.1271/bbb.69.1323|doi-access=free }}</ref> |
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| title=Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS |
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It is also an important component of the odours of ],<ref>{{cite journal |
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| journal=Food Chemistry |
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|vauthors=Janes D, Kantar D, Kreft S, Prosen H | title =Identification of buckwheat (''Fagopyrum esculentum'' Moench) aroma compounds with GC-MS |
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| volume=112 |
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| journal =Food Chemistry |
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| pages=120 |
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| volume =112 |
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| year=2008 |
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| issue = |
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| pages =120–124 |
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| doi=10.1016/j.foodchem.2008.05.048 |
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| year =2008 |
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}}</ref> and ].<ref>Buttery, R.G. et al. 2001. Analysis of furaneol in tomato using dynamic headspace sampling with sodium sulfate. J. Agric. Food Chem. 49:4349-4351</ref> |
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| doi =10.1016/j.foodchem.2008.05.048 |
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}}</ref> and ].<ref>{{cite journal|last1=Buttery|first1=Ron G.|last2=Takeoka|first2=Gary R.|last3=Naim|first3=Michael|last4=Rabinowitch|first4=Haim|last5=Nam|first5=Youngla|title=Analysis of Furaneol in Tomato Using Dynamic Headspace Sampling with Sodium Sulfate|journal=Journal of Agricultural and Food Chemistry|volume=49|issue=9|year=2001|pages=4349–4351|pmid=11559136|doi=10.1021/jf0105236}}</ref> Furaneol accumulation during ripening has been observed in strawberries and can reach a high concentration of 37 μg/g.<ref>{{cite book |
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| last = Pérez |
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| first = A. G. |
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| title = Fruit and Vegetable Flavour |
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| year = 2008 |
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| publisher = Woodhead Publishing |
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| language = en |
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| isbn = 978-1-84569-183-7 |
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}}</ref> |
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===Furaneol acetate=== |
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The ] of furaneol, also known as caramel acetate and strawberry acetate, is also popular with flavorists to achieve a fatty toffee taste and it is used in traces in perfumery to add a sweet gourmand note.<ref>{{cite web | url = https://www.thegoodscentscompany.com/data/rw1106051.html | title = Strawberry furanone acetate | website = thegoodscentscompany.com/ }}</ref> |
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==Stereoisomerism== |
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Furaneol has two ]s, (''R'')-(+)-furaneol and (''S'')-(−)-furaneol. The (''R'')-form is mainly responsible for the smell.<ref>Leffingwell,:John C. .</ref> |
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{| class="wikitable" style="text-align:center" |
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|+Stereoisomers of furaneol |
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| ]<br /><small>(''S'')-configuration</small> |
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| ]<br /><small>(''R'')-configuration</small> |
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==Biosynthesis== |
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It is one of several products from the dehydration of glucose. Its immediate biosynthetic precursor is the ], derived from dehydration of sucrose.<ref name= Zabetakis/> |
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==References== |
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