2,5-Dimethyl-4-hydroxy-3(2H)-furanone glucoside: Isolation from strawberries and synthesis

Mayerl, Friedrich; Näf, Regula; Thomas, Alan F.

doi:10.1016/0031-9422(89)80068-8

Cited by 67 publications

(46 citation statements)

References 5 publications

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“…The role of glucosides as precursors of important Ñavour components has been underestimated. However, recognition of their presence and role has grown (Mayerl et al 1989 ;Wu et al 1990aWu et al ,b, 1991Wintoch et al 1991 ;Zabetakis and Holden 1996). The derivatisation of glucosides renders them more volatile and more soluble in organic solvents.…”

Section: Identiðcation and Quantiðcation Of ñAvour Compoundsmentioning

confidence: 97%

“…In the elucidation and conÐrmation of the structure of an unknown compound, additional necessary information can be obtained by nuclear magnetic resonance (NMR) and UV-and IR-spectroscopic measurements Tridecan-2-ol 9, 10 trans-Hex-2-en-1-ol 1, 3, 11, 12 Pentadecan-2-ol 9, 10 cis-Hex-3-en-1-ol 3, 11, 12 (Mayerl et al 1989). The use of capillary gas chromatography/Fourier transformÈinfra red (GC/ FT-IR) to study food Ñavours (Schreier 1984) and strawberry aroma (Nikiforov et al 1994) has also been reported.…”

Section: Identiðcation and Quantiðcation Of ñAvour Compoundsmentioning

confidence: 99%

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Strawberry Flavour: Analysis and Biosynthesis

Zabetakis

Holden

1997

J. Sci. Food Agric.

201

137

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Section: Identiðcation and Quantiðcation Of ñAvour Compoundsmentioning

confidence: 97%

Section: Identiðcation and Quantiðcation Of ñAvour Compoundsmentioning

confidence: 99%

Strawberry Flavour: Analysis and Biosynthesis

Zabetakis

Holden

1997

J. Sci. Food Agric.

201

137

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“…It appears to be a degradation product of sugars in those products (Shaw et al, 1968). Furaneol exists in both free and glycosidically bound forms and its glucoside has been identified in strawberry (Mayerl et al, 1989) and tomato .…”

Section: Furaneolmentioning

confidence: 99%

Identification of Predominant Aroma Compounds in Muscadine Grape Juice

Baek

Cadwallader

Marroquin

et al. 1997

Journal of Food Science

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The aroma components of muscadine (Vitis rotundifolia Michx) grape juice were analyzed by gas chromatography (GC)/mass spectrometry and GC/olfactometry (aroma extract dilution analysis). 2,5-Dimethyl-4-hydroxy-3(2H)-furanone (furaneol), with a burnt sugar-like aroma, was the most intense aroma in the juice. Other predominant compounds included 2,3-butanedione, ethyl butanoate, ethyl 2-methylbutanoate, 2-phenylethanol, and o-aminoacetophenone. These compounds were described as buttery/cream cheese, bubble gum/fruity, green apple/fruity, rosy, and foxy, respectively. Furaneol and o-aminoacetophenone were thought to be responsible for characteristic candy and foxy-like aroma notes of muscadine grape juice. Flavor dilution chromatograms were similar for juices prepared from grapes harvested on different dates and from different locations.

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“…Recently, the occurrence of 2,5-dimethyl-4-hydroxy-2H-furan-3-one fi-D-glUCOpyranoside in strawberry fruit has been described. 6 In a number of previous studies carried out with different fruit species,'-' the importance of glycoconjugates as potential flavour precursors has been pointed out. This paper concerns the identification both of aglycons and glycoconjugates from wild (Fragaria vesca f: semperporens) and cultivated (Fragaria x ananassa, cv.…”

Section: Introductionmentioning

confidence: 99%

Glycosidically bound aroma compounds from two strawberry fruit species, Fragaria vesca f. semperflorens and Fragaria X ananassa, cv. Korona

Wintoch¹,

Krammer²,

Schreier³

1991

Flavour & Fragrance J

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Capillary gas chromatographic (HRGC) and on-line coupled HRGC-mass spectrometrical (HRGC-MS) identifications of bound aroma compounds from wild (Fragaria vescaJ semperjorens) and cultivated (Fragaria x ananassa, cv. Korona) strawberry fruit were achieved after isolation of extracts obtained by Amberlite XAD-2 adsorption and methanol elution followed by hydrolysis with a commercial pectinase enzyme. In E: vescaf: semperJrorens 37 and F. x ananassa 33 aglycons were identified. Among them (S)-2-methylbutanoic acid, benzyl alcohol, 2,5-dimethyl-4-hydroxy-2H-furan-3-one, benzoic acid and E-cinnamic acid were found as major components. After per-0-methylation of a glycosidic extract isolated from F. x ananassa, HRGC-MS revealed the occurrence of benzyl B-D-glucopyranoside, 2-(4-hydroxyphenyl)ethyl B-D-glucopyranoside, and the diastereomeric 2,5-dimethyl-4-hydroxy-2H-furan-3-one P-D-glucopyranosides. Chiral evaluation of enzymatically liberated 2,5-dimethyl-4-hydroxy-2H-furan-3-one carried out by on-line multidimensional capillary gas chromatography-mass spectrometry (MDGC-MS) revealed the presence of a racemic mixture. KEY WORDS Bound aroma compounds Enzymatic hydrolysis Fragaria x ananassaFragaria vesca J sernper-orens Strawberry fruit 2,5-Dimethyl-4-hydroxy-2H-furan-3-one 8-D-glucopyranoside

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2,5-Dimethyl-4-hydroxy-3(2H)-furanone glucoside: Isolation from strawberries and synthesis

Cited by 67 publications

References 5 publications

Strawberry Flavour: Analysis and Biosynthesis

Strawberry Flavour: Analysis and Biosynthesis

Identification of Predominant Aroma Compounds in Muscadine Grape Juice

Glycosidically bound aroma compounds from two strawberry fruit species, Fragaria vesca f. semperflorens and Fragaria X ananassa, cv. Korona

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