Volatile Flavor and Aroma Components of Pineapple. l. Isolation and Tentative Identification of 2,5‐Dimethyl‐4‐Hydroxy‐3(2H)‐Furanone

Rodin, J. O.; Himel, Chester M.; Silverstein, Robert M.; Leeper, Robert W.; Gortner, Willis A.

doi:10.1111/j.1365-2621.1965.tb00302.x

Cited by 160 publications

(82 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…EMHF arises similarly, but with the addition of a C 2 fragment arising from alanine 18 . DMHF also occurs naturally in fruits, for example strawberries 17 and pineapples 11 and in the fermented products soy sauce 10 and miso 4 which also contain high levels of EMHF 4,10 . During fermentation yeast is thought to transform Maillard intermediates to DMHF and EMHF rather than make direct use of sugars and amino acids 5,12 .…”

Section: -2863(9'8-32mentioning

confidence: 99%

Formation of 4-Hydroxyfuranones and their Precursors during Production of Worts and Beers

Mackie

Slaughter

2002

Journal of the Institute of Brewing

View full text Add to dashboard Cite

Laboratory beers and samples taken at each stage of production, were analysed for the flavour active 4-hydroxyfuranones; 5-methyl-4-hydroxy-3(2H)-furanone (MHF), 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) and 5-(or 2)-ethyl-2(or 5)-methyl-4-hydroxy-3(2H)-furanone (EMHF). The length and temperature of mashing, the length of boiling, the rate of cooling the worts and the effects of grist composition were investigated to identify the 4-hydroxyfuranone content of worts and subsequent beers. Fermentation temperature and the use of the stabilising agents, PVPP and Lucilite PC5, on the 4-hydroxyfuranone content of the beer was also investigated. The results demonstrated that several aspects of beer production procedures affect the furanone content of the beer, but in practice the important factors are grist composition, the rate at which the boiled wort is cooled and fermentation temperature. Fermentation has a major effect on final furanone content as yeast produces both DMHF and EMHF. The results suggest that malt levels of precursor compounds, which can be converted to 4-hydroxyfuranones by the Maillard reaction or by yeast, may prove to be more important than the quantities of the furanones found in malt in determining the final furanone content of beer. A clearer understanding of the nature of the precursors should allow manipulation of their production and beer furanone content.

show abstract

Section: -2863(9'8-32mentioning

confidence: 99%

Formation of 4-Hydroxyfuranones and their Precursors during Production of Worts and Beers

Mackie

Slaughter

2002

Journal of the Institute of Brewing

View full text Add to dashboard Cite

show abstract

“…HDMF was first reported as a product of the Maillard reaction (Hodge et al, 1963), and it was then isolated from pineapple (Ananas comosus) (Rodin et al, 1965), strawberry (Ohloff, 1969), and a number of different fruits . The methyl ether DMMF, first detected in pineapple (Willhalm et al, 1965), was also identified as an aroma component of a multitude of fruits, such as overripe strawberry, mango (Mangifera indica), and arctic bramble (Rubus arcticus) Schwab and Roscher, 1997).…”

Section: Introductionmentioning

confidence: 99%

FaQR, Required for the Biosynthesis of the Strawberry Flavor Compound 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone, Encodes an Enone Oxidoreductase

Raab

López‐Ráez

Klein³

et al. 2006

Plant Cell

161

159

View full text Add to dashboard Cite

The flavor of strawberry (Fragaria 3 ananassa) fruit is dominated by an uncommon group of aroma compounds with a 2,5-dimethyl-3(H)-furanone structure. We report the characterization of an enzyme involved in the biosynthesis of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF; Furaneol), the key flavor compound in strawberries. Protein extracts were partially purified, and the observed distribution of enzymatic activity correlated with the presence of a single polypeptide of ;37 kD. Sequence analysis of two peptide fragments showed total identity with the protein sequence of a strongly ripeninginduced, auxin-dependent putative quinone oxidoreductase, Fragaria 3 ananassa quinone oxidoreductase (FaQR). The open reading frame of the FaQR cDNA consists of 969 bp encoding a 322-amino acid protein with a calculated molecular mass of 34.3 kD. Laser capture microdissection followed by RNA extraction and amplification demonstrated the presence of FaQR mRNA in parenchyma tissue of the strawberry fruit. The FaQR protein was functionally expressed in Escherichia coli, and the monomer catalyzed the formation of HDMF. After chemical synthesis and liquid chromatography-tandem mass spectrometry analysis, 4-hydroxy-5-methyl-2-methylene-3(2H)-furanone was confirmed as a substrate of FaQR and the natural precursor of HDMF. This study demonstrates the function of the FaQR enzyme in the biosynthesis of HDMF as enone oxidoreductase and provides a foundation for the improvement of strawberry flavor and the biotechnological production of HDMF.

show abstract

“…Due to the keto-enol tautomerism which obstructs asymmetric synthetic approach or chemical derivatization, neither absolute configuration nor optical rotation has yet been clarified for over 40 years since its first discovery. 13,14 Very recently, we have succeeded in the determination of the absolute configurations of the DMHF (furaneol, 2) and its methyl ether, DMMF (mesifuran, 3) by utilizing the vibrational circular dichroism (VCD) technique. 15 VCD measures the differential absorption of left versus right circularly polarized infrared radiation by molecular vibrational transition.…”

Section: Introductionmentioning

confidence: 99%

Stereochemical study of a novel tautomeric furanone, homofuraneol

et al. 2009

View full text Add to dashboard Cite

A mixture of tautomers with unique keto-enol structures, 5-ethyl-4-hydroxy-2-methylfuran-3(2H)-one and 2-ethyl-4-hydroxy-5-methylfuran-3(2H)-one (EHMF, homofuraneol, 1a and 1b), comprises four structural isomers including their enantiomers. The four isomers were successfully separated by chromatographic optical resolution, and their odor evaluation was performed. Determination of the absolute chemistry of 1a and 1b were accomplished for the first time by direct measurement of the VCD spectra of their methyl ether derivatives 4a and 4b compared with the calculated ones as well as chemical relay reaction. The relationship between odor characteristics and stereochemistry was also examined.

show abstract

Volatile Flavor and Aroma Components of Pineapple. l. Isolation and Tentative Identification of 2,5‐Dimethyl‐4‐Hydroxy‐3(2H)‐Furanone

Abstract: SUMMARY An unstable compound with an intense odor of “burnt pineapple” was isolated as a major component of a pineapple flavor concentrate. This compound was tentatively identified as 2,5‐dimethyl‐P‐hydroxy‐3(2H)‐furanone (I).

Cited by 160 publications

References 10 publications

Formation of 4-Hydroxyfuranones and their Precursors during Production of Worts and Beers

Formation of 4-Hydroxyfuranones and their Precursors during Production of Worts and Beers

FaQR, Required for the Biosynthesis of the Strawberry Flavor Compound 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone, Encodes an Enone Oxidoreductase

Stereochemical study of a novel tautomeric furanone, homofuraneol

Contact Info

Product

Resources

About