3-hydroxy-4,5-dimethyl-2(5H)-furanone, a burnt flavoring compound from aged sake.

Takahashi, Koichi; Tadenuma, Makoto; Sato, Shin

doi:10.1271/bbb1961.40.325

Cited by 53 publications

(36 citation statements)

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“…These data show that many concentrations in the samples were below the expected levels for contributing flavors based on assessment of individual compounds, but flavor interactions could readily affect contributions. The data also show that concentrations of compounds, especially the three produced through heat induced reactions involving sugars (maple lactone, sugar furanone, and Furaneol ;Shaw et al 1968;Belitz and Grosch, 1986;Takahashi, 1976), generally increased in parallel with intensity of color. These data support the views that syrups with darker colors possess stronger maple syrup flavors than those with light color, and that light amber syrup possesses very mild flavor intensity.…”

Section: Flavor Properties Of Individual Selected Volatile Flavor Commentioning

confidence: 73%

CONTRIBUTIONS OF SELECTED FLAVOR COMPOUNDS TO THE SENSORY PROPERTIES OF MAPLE SYRUP¹

Belford

Lindsay

Ridley

1991

Journal of Sensory Studies

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ABSTRACT. A base syrup formulation containing nonvolatile flavor compounds was used to systematically evaluate the sensory contributions of selected volatile compounds (Furaneol, 2,5–dimethyl‐4‐hydroxy‐3(2H)‐furanone; sugar furanone, 4,5‐dimethyl‐3‐hydroxy‐2(5H)‐furanone; guaiacol, 2‐methoxy phenol; vanillin, 4‐hydroxy‐3‐methoxy‐benzaldehyde) to maple syrup flavor. Descriptive sensory panels showed that all compounds contributed to maple flavor intensity, but sugar furanone was an exceptionally important determinant. Medium and dark amber syrups contained generally higher concentrations of the selected flavor compounds than the light amber syrup. 5′‐Inosine monophosphate was tentatively identified in maple syrup by HPLC analysis, and was found to contribute important taste characteristics to maple syrup. Consumer studies showed that more flavorful, darker grade A syrups were preferred over light amber grade A syrup.

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Section: Flavor Properties Of Individual Selected Volatile Flavor Commentioning

confidence: 73%

CONTRIBUTIONS OF SELECTED FLAVOR COMPOUNDS TO THE SENSORY PROPERTIES OF MAPLE SYRUP¹

Belford

Lindsay

Ridley

1991

Journal of Sensory Studies

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“…[12] While the precursor feedings suggested a bioconversion of L-isoleucine while maintaining the C6-carbon backbone, alternative routes to sotolon, such as the aldolization of 2-oxobutanonic acid and acetaldehyde as in wine, [5,16] or the formation from Maillard products, such as butane-2,3-dione and 2-hydroxyacetaldehyde [17] could not be ruled out in the fungal culture until now. Quantitative formation of sotolon and degradation of L-isoleucine did not correlate well.…”

Section: L-isoleucine Metabolism Of L Sulphureus Leading To Sotolonmentioning

confidence: 99%

“…The best-known hydroxyfuranone is 4-hydroxy-2,5-dimethyl-3 (2H)-furanone, with a strawberry-like aroma, which can be found in numerous fruits. In wine and sake, degradation products of L-threonine resulted in the formation of sotolon, [5] whereas ascorbic acid and ethanol were found to be the precursors in citrus soft drinks. Flavour threshold values of sotolon were often described in wine and vary between 2.5 μg/l (in model wine solution [2] ) and 19 μg/l (in port wine [3] ).…”

Section: Introductionmentioning

confidence: 99%

Isotope labelling experiments on the formation pathway of 3‐hydroxy‐4,5‐dimethyl‐2(5H)‐furanone from l‐isoleucine in cultures of Laetiporus sulphureus

Lanfermann

Krings

Schopp

et al. 2014

Flavour & Fragrance J

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Sotolon (3‐hydroxy‐4,5‐dimethyl‐2(5H)‐furanone) imparts a strong seasoning odour reminiscent of meat broth. Previous work indicated a formation via l‐4‐hydroxyisoleucine in surface cultures of the basidiomycete Laetiporus sulphureus grown on wheat gluten, but an enzymatic hydroxylation of l‐isoleucine was not proven. 13C‐Labelled l‐leucine, l‐isoleucine and 18O‐water were used to elucidate the metabolism of the amino acids and proved the existence of an oxygenase activity in the pathway to sotolon. l‐Isoleucine was converted into the corresponding α‐keto acid and then oxygenated in the C4‐position to give 4‐hydroxy‐3‐methyl‐2‐oxopentanoic acid, the direct precursor of sotolon. A similar biotransformation was not observed for l‐leucine. The results provide insight into the cold formation of a potent flavour compound previously associated with the thermal processing of food. Copyright © 2014 John Wiley & Sons, Ltd.

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“…Sotolon (3‐hydroxy‐4,5‐dimethyl‐2(5 H )‐furanone) is a flavour substance widely utilized in tobacco flavourings, artificial maple syrup, and curry. It contributes significantly to the burnt note of cane sugar, aged sake, as well as the curry odour of fenugreek seeds . Also, sotolon is found in coffee, lovage, condiments, dry white wines, and other foodstuffs .…”

Section: Introductionmentioning

confidence: 99%

Resolution of racemic 3‐hydroxy‐4,5‐dimethyl‐2(5H)‐furanone (sotolon) by packed column supercritical fluid chromatography

Xie

Han

Sun

et al. 2012

Flavour & Fragrance J

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The resolution of racemic 3‐hydroxy‐4,5‐dimethyl‐2(5H)‐furanone (sotolon) by packed column supercritical fluid chromatography was studied. On an analytical scale, the chiral stationary phases of Chiralpak AD‐H, Chiralcel OB‐H, Chiralcel OD‐H, and Chiralcel OJ‐H along with methanol, ethanol, isopropanol and acetonitrile as organic modifiers were tested. The effect on resolution of the modifier content in mobile phase, column temperature, column pressure, and flow rate of mobile phase was investigated through single‐factor experiment and orthogonal experiment. The optimum conditions found were Chiralpak AD‐H, column temperature 28°C, column pressure 8 MPa, 2.5% (v/v) methanol in the mobile phase, and a flow rate of 1.5 ml/min for the mobile phase, whereby the resolution achieved was 2.98. Several milligrams of enantiomers, with an optical purity of S‐100% and R‐93%, were obtained by scaling up the analytical method to preparative separation using Chiralpak AD (250 × 10 mm I.D. 10 µm ps). Copyright © 2012 John Wiley & Sons, Ltd.

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3-hydroxy-4,5-dimethyl-2(5H)-furanone, a burnt flavoring compound from aged sake.

Cited by 53 publications

References 1 publication

CONTRIBUTIONS OF SELECTED FLAVOR COMPOUNDS TO THE SENSORY PROPERTIES OF MAPLE SYRUP¹

CONTRIBUTIONS OF SELECTED FLAVOR COMPOUNDS TO THE SENSORY PROPERTIES OF MAPLE SYRUP¹

Isotope labelling experiments on the formation pathway of 3‐hydroxy‐4,5‐dimethyl‐2(5H)‐furanone from l‐isoleucine in cultures of Laetiporus sulphureus

Resolution of racemic 3‐hydroxy‐4,5‐dimethyl‐2(5H)‐furanone (sotolon) by packed column supercritical fluid chromatography

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3-hydroxy-4,5-dimethyl-2(5H)-furanone, a burnt flavoring compound from aged sake.

Cited by 53 publications

References 1 publication

CONTRIBUTIONS OF SELECTED FLAVOR COMPOUNDS TO THE SENSORY PROPERTIES OF MAPLE SYRUP1

CONTRIBUTIONS OF SELECTED FLAVOR COMPOUNDS TO THE SENSORY PROPERTIES OF MAPLE SYRUP1

Isotope labelling experiments on the formation pathway of 3‐hydroxy‐4,5‐dimethyl‐2(5H)‐furanone from l‐isoleucine in cultures of Laetiporus sulphureus

Resolution of racemic 3‐hydroxy‐4,5‐dimethyl‐2(5H)‐furanone (sotolon) by packed column supercritical fluid chromatography

Contact Info

Product

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About

CONTRIBUTIONS OF SELECTED FLAVOR COMPOUNDS TO THE SENSORY PROPERTIES OF MAPLE SYRUP¹

CONTRIBUTIONS OF SELECTED FLAVOR COMPOUNDS TO THE SENSORY PROPERTIES OF MAPLE SYRUP¹