furaneol
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 412262064
| Reference =[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/W317403 4-Hydroxy-2,5-dimethyl-3(2H)-furanone] at Sigma-Aldrich
| ImageFile =Furanol Grundstruktur V1.svg
| ImageSize =150px
| IUPACName =4-Hydroxy-2,5-dimethyl-3-furanone
| OtherNames ={{bulletedlist|4-Hydroxy-2,5-dimethyl-3(2H)-furanone|Alletone|Pineapple ketone|Strawberry furanone|Dimethylhydroxy furanone}}
|Section1={{Chembox Identifiers
| Abbreviations = DMHF
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 18218
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 20PI8YZP7A
| InChI = 1/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3
| InChIKey = INAXVXBDKKUCGI-UHFFFAOYAH
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = INAXVXBDKKUCGI-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =3658-77-3
| CASNo1 = 131222-82-7
| CASNo1_Comment = (R)-(+)
| CASNo2 = 131222-81-6
| CASNo2_Comment = (S)-(−)
| PubChem =19309
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 76247
| SMILES = O=C1C(\O)=C(/OC1C)C
}}
|Section2={{Chembox Properties
| C=6|H=8|O=3
| Appearance =
| Density =
| MeltingPtC = 73 to 77
| MeltingPt_notes =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Furaneol, or strawberry furanone, is an organic compound used in the flavor and perfume industry. It is formally a derivative of furan. It is a white or colorless solid that is soluble in water and organic solvents.{{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}}
Odor and occurrence
Although malodorous at high concentrations, it exhibits a sweet strawberry aroma when dilute. It is found in strawberries{{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}} and a variety of other fruits and it is partly responsible for the smell of fresh pineapple.{{cite journal |vauthors=Tokitomo Y, Steinhaus M, Büttner A, Schieberle P |title=Odor-active constituents in fresh pineapple (Ananas comosus [L.] 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 }}
It is also an important component of the odours of buckwheat,{{cite journal
|vauthors=Janes D, Kantar D, Kreft S, Prosen H | title =Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS
| journal =Food Chemistry
| volume =112
| issue =
| pages =120–124
| year =2008
| doi =10.1016/j.foodchem.2008.05.048
}} and tomato.{{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}} Furaneol accumulation during ripening has been observed in strawberries and can reach a high concentration of 37 μg/g.{{cite book
| last = Pérez
| first = A. G.
| title = Fruit and Vegetable Flavour
| year = 2008
| publisher = Woodhead Publishing
| language = en
| isbn = 978-1-84569-183-7
}}
=Furaneol acetate=
The acetate ester 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.{{cite web | url = https://www.thegoodscentscompany.com/data/rw1106051.html | title = Strawberry furanone acetate | website = thegoodscentscompany.com/ }}
Stereoisomerism
Furaneol has two enantiomers, (R)-(+)-furaneol and (S)-(−)-furaneol. The (R)-form is mainly responsible for the smell.Leffingwell,:John C. [http://www.leffingwell.com/chirality/furaneol.htm Chirality & Odour Perception – The Furaneols].
| class="wikitable" style="text-align:center"
|+Stereoisomers of furaneol |
| File:(S)-Furanol V1.svg (S)-configuration | File:(R)-Furanol V1.svg |
Biosynthesis
It is one of several products from the dehydration of glucose. Its immediate biosynthetic precursor is the glucoside, derived from dehydration of sucrose.