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Chemical Compound Review:

Alletone 4-hydroxy-2,5-dimethyl-furan- 3-one

Synonyms: Furaneol, HDMF, PubChem6962, SureCN57008, ACMC-1CK6Y, ...

Sung, W.S. et al., Ong, P.K. et al., Lunkenbein, S. et al., Ferreira, V. et al., Sasaki, T. et al., et al.

Ferreira, Jarauta, López, Cacho,

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Psychiatry related information on Pineapple ketone

Sensory experiments confirmed that the complexed forms found in white wines are not perceived by orthonasal olfaction, and that the furaneol determined by the method can be considered as the free and odor-active fraction [1].

High impact information on Pineapple ketone

FaQR, required for the biosynthesis of the strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone, encodes an enone oxidoreductase [2].
Of these, 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) is regarded as the most important, but it is methylated further by FaOMT (Fragaria x ananassa O-methyltransferase) to 2,5-dimethyl-4-methoxy-3(2H)-furanone (DMMF) during the ripening process [3].
2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF); antimicrobial compound with cell cycle arrest in nosocomial pathogens [4].
The formation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) by Zygosaccharomyces rouxii was studied in yeast-peptone-dextrose medium containing d-fructose 1,6-diphosphate under various culture conditions [5].
It is suggested that Furaneol methylation is mediated by an O-methyltransferase activity and that this activity increases during fruit ripening [6].

Biological context of Pineapple ketone

4-Hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) and 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone (EHMF) exhibited a higher suppression effect on lipid peroxidation in human plasma than the other furanones did [7].

Associations of Pineapple ketone with other chemical compounds

However, on the basis of calculated odor activity values (OAVs), cis-rose oxide, beta-damascenone, linalool, furaneol, ethyl isobutyrate, (E)-2-nonenal, ethyl isohexanoate, geraniol, and delta-decalactone were determined to be the main contributors of canned lychee aroma [8].
2,5-Dimethyl-4-hydroxy-3(2H)-furanone as a secondary metabolite from D-fructose-1,6-diphosphate metabolism by Zygosaccharomyces rouxii [9].
Some components were present only in the SPME extracts, including norfuraneol, furaneol, and cyclotene, which are key Maillard reaction intermediates [10].

Analytical, diagnostic and therapeutic context of Pineapple ketone

2,5-Dimethyl-4-hydroxy-3(2H)-furanone (DMHF), an aroma compound found in a number of fruits and foods, has shown various biological properties in animal models, but its antimicrobial effect remains poorly understood [4].

References

Quantitative determination of sotolon, maltol and free furaneol in wine by solid-phase extraction and gas chromatography-ion-trap mass spectrometry. Ferreira, V., Jarauta, I., López, R., Cacho, J. Journal of chromatography. A. (2003) [Pubmed]
FaQR, required for the biosynthesis of the strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone, encodes an enone oxidoreductase. Raab, T., López-Ráez, J.A., Klein, D., Caballero, J.L., Moyano, E., Schwab, W., Muñoz-Blanco, J. Plant Cell (2006) [Pubmed]
Up- and down-regulation of Fragaria x ananassa O-methyltransferase: impacts on furanone and phenylpropanoid metabolism. Lunkenbein, S., Salentijn, E.M., Coiner, H.A., Boone, M.J., Krens, F.A., Schwab, W. J. Exp. Bot. (2006) [Pubmed]
2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF); antimicrobial compound with cell cycle arrest in nosocomial pathogens. Sung, W.S., Jung, H.J., Park, K., Kim, H.S., Lee, I.S., Lee, D.G. Life Sci. (2007) [Pubmed]
4-hydroxy-2,5-dimethyl-3(2H)-furanone formation by Zygosaccharomyces rouxii: effect of the medium. Hauck, T., Brühlmann, F., Schwab, W. J. Agric. Food Chem. (2003) [Pubmed]
Aroma biosynthesis in strawberry: s-adenosylmethionine:furaneol o-methyltransferase activity in ripening fruits. Lavid, N., Schwab, W., Kafkas, E., Koch-Dean, M., Bar, E., Larkov, O., Ravid, U., Lewinsohn, E. J. Agric. Food Chem. (2002) [Pubmed]
Antioxidative activities of 4-hydroxy-3(2H)-furanones and their anti-cataract effect on spontaneous cataract rat (ICR/f). Sasaki, T., Yamakoshi, J., Saito, M., Kasai, K., Matsudo, T., Koga, T., Mori, K. Biosci. Biotechnol. Biochem. (1998) [Pubmed]
Similarities in the aroma chemistry of Gewürztraminer variety wines and lychee (Litchi chinesis sonn.) fruit. Ong, P.K., Acree, T.E. J. Agric. Food Chem. (1999) [Pubmed]
2,5-Dimethyl-4-hydroxy-3(2H)-furanone as a secondary metabolite from D-fructose-1,6-diphosphate metabolism by Zygosaccharomyces rouxii. Dahlen, T., Hauck, T., Wein, M., Schwab, W. J. Biosci. Bioeng. (2001) [Pubmed]
A comparison of headspace entrainment on Tenax with solid phase microextraction for the analysis of the aroma volatiles of cooked beef. Elmore, J.S., Papantoniou, E., Mottram, D.S. Adv. Exp. Med. Biol. (2001) [Pubmed]

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