Ein einfacher Zugang zu 4‐hydroxy‐2,5‐dimethyl‐3(2<i>H</i>)‐furanon (furaneol), einem Aromabestandteil von Ananas und Erdbeere

Re, Luciano; Maurer, Bruno; Ohloff, G.

doi:10.1002/hlca.19730560609

Cited by 106 publications

(26 citation statements)

References 20 publications

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“…The higher homologue (I-71), which exists in tautomeric forms and which was first only known as a synthetic product (374), was later found to be an important ingredient of soy sauce (377) and of roasted coffee (49). The sensory impression of 1-71, which is stronger than that of 1-70 (374), was described as sweet and reminiscent of shortcake.…”

Section: Flamentmentioning

confidence: 98%

“…Furaneol® is an aroma component which was also found to be present, for instance, in pineapple (373), strawberries (374), roasted almonds (375), and beef broth (376). The higher homologue (I-71), which exists in tautomeric forms and which was first only known as a synthetic product (374), was later found to be an important ingredient of soy sauce (377) and of roasted coffee (49). The sensory impression of 1-71, which is stronger than that of 1-70 (374), was described as sweet and reminiscent of shortcake.…”

Section: Flamentmentioning

confidence: 98%

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Coffee, cocoa, and tea

Flamen

1989

Food Reviews International

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This review deals with the chemistry of the odoriferous constituents of the volatile part of the flavors of coffee, cocoa, and tea. A general survey of the analytical studies which have been conducted on these aromas is presented. A list of identified compounds mentions the year of their first discovery and the reference of the corresponding publication. Comments are given on the structure, the origin, and the organoleptic properties of some typical constituents. In the last section the organoleptic characteristics of the three beverages are discussed on the basis of their distribution among the various functional classes.

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Section: Flamentmentioning

confidence: 98%

Section: Flamentmentioning

confidence: 98%

Coffee, cocoa, and tea

Flamen

1989

Food Reviews International

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“…g) Re et al 10 ) synthesized HMF starting from 2-pentyne-l,4-diol. Fisher and Hodge ll ) synthesized it from o-xylose.…”

Section: Please Scroll Down For Articlementioning

confidence: 98%

Isolation of 4-Hydroxy-5-methyl-3(2H)-furanone, a Flavor Component inShoyu(Soy Sauce)

Nunomura

Sasaki

Yokotsuka

1979

Agricultural and Biological Chemistry

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“…The common molecular feature of heated food aroma is a strictly planar enol-carbonyl moiety of alkyl-substituted five-or six-membered cyclic a-diketones, stabilized by strong hydrogen bonding [5] [6]. Thus, maltol (51) and FURANEOL~ (52) are typical representatives of burnt flavor [7].…”

Section: Fh 31mentioning

confidence: 99%

Stereochemistry‐Activity Relationships in Olfaction. Odorants containing a proton donor/proton acceptor unit

Ohloff

Giersch

1980

Helvetica Chimica Acta

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SummaryA novel class of odorants is described where the odor is associated with the interaction of two functional groups, one being an H-donor (AH function), and the other an H-acceptor (B function). Generally, odor occurs only if the distance between the two structural elements (AH/B system) is less than 3 A. Bifunctional derivatives of the p-menthane and iridane series served as models for deriving this rule. The stereospecificity of odor perception was an important prerequisite for its establishment.It is known that hydroxycarbonyl compounds having a molecular weight up to about 250 may possess a pronounced odor. In other cases, however, bifunctional compounds of this type are completely odorless. No molecular explanation for this contrasting behaviour has been offered. While engaged in work on structure-activity relationships in olfaction we have been able to account for this discrepancy by invoking the stereochemistry of the molecules giving rise to the effects, as illustrated by the formulas below. The compounds in red are odorants, whereas the uncolored molecules were found to be virtually odorless. Examination of Dreiding models shows the distance between the hydrogen atom of the hydroxyl group and the carbonyl group to be less than 3 A in the odoriferous compounds, but more than 3 A in the odorless molecules. A single exception to this rule has been found.In the bifunctional unit of compound 1 the distance between the functional groups is 2.2 A, assuming a chair conformation for the ring and an axial conformation for the aldehyde group. In the diequatorial conformation of compound 2 the distance between the functional groups is about 6 A. Base-catalyzed equilibration showed the equilibrium between 1 and 2 to be mainly (92%) on the side of 2 with concomitant disappearance of the odor. The required distance for this particular type of fragrance already reaches the limit of about 3 A in odoriferous compound 3.This value is largely exceeded in the odorless hydroxyaldhyde 4. We presume that in the cyclohexene derivatives 5-8 the carbonyl group occupies an axial position since only in this case -independent of whether the ring is in a half-chair or a half-twist conformation -the bifunctional unit can be adjusted to the required distance oO18-0l9X/80/ 1/oO76-l9$01.00/0 0 1980 Schweizerische Chemische Gesellschaft

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Ein einfacher Zugang zu 4‐hydroxy‐2,5‐dimethyl‐3(2H)‐furanon (furaneol), einem Aromabestandteil von Ananas und Erdbeere

Cited by 106 publications

References 20 publications

Coffee, cocoa, and tea

Coffee, cocoa, and tea

Isolation of 4-Hydroxy-5-methyl-3(2H)-furanone, a Flavor Component inShoyu(Soy Sauce)

Stereochemistry‐Activity Relationships in Olfaction. Odorants containing a proton donor/proton acceptor unit

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