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.[2]
Although malodorous at high concentrations, it exhibits a sweet strawberry aroma when dilute.[2] It is found in strawberries[3] and a variety of other fruits and it is partly responsible for the smell of fresh pineapple.[4] It is also an important component of the odours of buckwheat,[5] and tomato.[6]
StereoisomerismEdit
Furaneol has two enantiomers, (R)-(+)-furaneol and (S)-(−)-furaneol. The (R)-form is mainly responsible for the smell.[7]
Stereoisomers of furaneol
(S)-configuration
(R)-configuration
BiosynthesisEdit
It is one of several products from the dehydration of glucose. Its immediate biosynthetic precursor is the glucoside, derived from dehydration of sucrose.[2]
^ abcZabetakis, I.; Gramshaw, J. W.; Robinson, D. S. (1999). "2,5-Dimethyl-4-hydroxy-2H-furan-3-one and its derivatives: analysis, synthesis and biosynthesis - a review". Food Chemistry. 65: 139–151. doi:10.1016/S0308-8146(98)00203-9.
^Ulrich, D.; Hoberg, Edelgard; Rapp, Adolf; Kecke, Steffen (1997). "Analysis of strawberry flavour – discrimination of aroma types by quantification of volatile compounds". Zeitschrift für Lebensmitteluntersuchung und -Forschung A. 205 (3): 218–223. doi:10.1007/s002170050154. S2CID 96680333.
^Tokitomo Y, Steinhaus M, Büttner A, Schieberle P (2005). "Odor-active constituents in fresh pineapple (Ananas comosus [L.] Merr.) by quantitative and sensory evaluation". Biosci. Biotechnol. Biochem. 69 (7): 1323–30. doi:10.1271/bbb.69.1323. PMID 16041138.
^Janes D, Kantar D, Kreft S, Prosen H (2008). "Identification of buckwheat (Fagopyrum esculentum Moench) aroma compounds with GC-MS". Food Chemistry. 112: 120–124. doi:10.1016/j.foodchem.2008.05.048.
^Buttery, Ron G.; Takeoka, Gary R.; Naim, Michael; Rabinowitch, Haim; Nam, Youngla (2001). "Analysis of Furaneol in Tomato Using Dynamic Headspace Sampling with Sodium Sulfate". Journal of Agricultural and Food Chemistry. 49 (9): 4349–4351. doi:10.1021/jf0105236. PMID 11559136.
^Leffingwell,:John C. Chirality & Odour Perception – The Furaneols.
August 25, 2023
furaneol, strawberry, furanone, organic, compound, used, flavor, perfume, industry, formally, derivative, furan, white, colorless, solid, that, soluble, water, organic, solvents, namesiupac, name, hydroxy, dimethyl, furanoneother, names, hydroxy, dimethyl, fur. 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 2 Furaneol 1 NamesIUPAC name 4 Hydroxy 2 5 dimethyl 3 furanoneOther names 4 Hydroxy 2 5 dimethyl 3 2H furanoneAlletonePineapple ketoneStrawberry furanoneDimethylhydroxy furanoneIdentifiersCAS Number 3658 77 3 Y131222 82 7 R 131222 81 6 S 3D model JSmol Interactive imageAbbreviations DMHFChEBI CHEBI 76247 NChemSpider 18218 YECHA InfoCard 100 020 826PubChem CID 19309UNII 20PI8YZP7A YCompTox Dashboard EPA DTXSID0041517InChI InChI 1S C6H8O3 c1 3 5 7 6 8 4 2 9 3 h3 8H 1 2H3 YKey INAXVXBDKKUCGI UHFFFAOYSA N YInChI 1 C6H8O3 c1 3 5 7 6 8 4 2 9 3 h3 8H 1 2H3Key INAXVXBDKKUCGI UHFFFAOYAHSMILES O C1C O C OC1C CPropertiesChemical formula C 6H 8O 3Molar mass 128 127 g mol 1Melting point 73 to 77 C 163 to 171 F 346 to 350 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Odor and occurrence 2 Stereoisomerism 3 Biosynthesis 4 ReferencesOdor and occurrence EditAlthough malodorous at high concentrations it exhibits a sweet strawberry aroma when dilute 2 It is found in strawberries 3 and a variety of other fruits and it is partly responsible for the smell of fresh pineapple 4 It is also an important component of the odours of buckwheat 5 and tomato 6 Stereoisomerism EditFuraneol has two enantiomers R furaneol and S furaneol The R form is mainly responsible for the smell 7 Stereoisomers of furaneol S configuration R configurationBiosynthesis EditIt is one of several products from the dehydration of glucose Its immediate biosynthetic precursor is the glucoside derived from dehydration of sucrose 2 References Edit 4 Hydroxy 2 5 dimethyl 3 2H furanone at Sigma Aldrich a b c Zabetakis I Gramshaw J W Robinson D S 1999 2 5 Dimethyl 4 hydroxy 2H furan 3 one and its derivatives analysis synthesis and biosynthesis a review Food Chemistry 65 139 151 doi 10 1016 S0308 8146 98 00203 9 Ulrich D Hoberg Edelgard Rapp Adolf Kecke Steffen 1997 Analysis of strawberry flavour discrimination of aroma types by quantification of volatile compounds Zeitschrift fur Lebensmitteluntersuchung und Forschung A 205 3 218 223 doi 10 1007 s002170050154 S2CID 96680333 Tokitomo Y Steinhaus M Buttner A Schieberle P 2005 Odor active constituents in fresh pineapple Ananas comosus L Merr by quantitative and sensory evaluation Biosci Biotechnol Biochem 69 7 1323 30 doi 10 1271 bbb 69 1323 PMID 16041138 Janes D Kantar D Kreft S Prosen H 2008 Identification of buckwheat Fagopyrum esculentum Moench aroma compounds with GC MS Food Chemistry 112 120 124 doi 10 1016 j foodchem 2008 05 048 Buttery Ron G Takeoka Gary R Naim Michael Rabinowitch Haim Nam Youngla 2001 Analysis of Furaneol in Tomato Using Dynamic Headspace Sampling with Sodium Sulfate Journal of Agricultural and Food Chemistry 49 9 4349 4351 doi 10 1021 jf0105236 PMID 11559136 Leffingwell John C Chirality amp Odour Perception The Furaneols Retrieved from https en wikipedia org w index php title Furaneol amp oldid 1163032892, wikipedia, wiki, book, books, library,
