publication . Article . 2013

Natural 4‐Hydroxy‐2,5‐dimethyl‐3(2H)‐furanone (Furaneol)

Wilfried Schwab;
Open Access English
  • Published: 01 Jun 2013 Journal: Molecules, volume 18, issue 6, pages 6,936-6,951 (eissn: 1420-3049, Copyright policy)
  • Publisher: MDPI
Abstract
4-Hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF, furaneol®) and its methyl ether 2,5-dimethyl-4-methoxy-3(2H)-furanone (DMMF) are import aroma chemicals and are considered key flavor compounds in many fruit. Due to their attractive sensory properties they are highly appreciated by the food industry. In fruits 2,5-dimethyl-3(2H)-furanones are synthesized by a series of enzymatic steps whereas HDMF is also a product of the Maillard reaction. Numerous methods for the synthetic preparation of these compounds have been published and are applied by industry, but for the development of a biotechnological process the knowledge and availability of biosynthetic enzymes are re...
Subjects
free text keywords: Review, 3(2H)-furanone, biosynthesis, Maillard reaction, D-fructose-1,6-diphosphate, QD241-441, Organic chemistry, Furaneol, chemistry.chemical_compound, chemistry, Ether, Biochemistry, Food industry, business.industry, business, Aroma, biology.organism_classification, biology, Biotechnological process, Flavor, symbols.namesake, symbols
Related Organizations
92 references, page 1 of 7

Hodge, J.E.. Novel reductones and methods of making them. U.S. Patent. 1960

Ledl, F., Schleicher, E.. New aspects of the Maillard reaction in foods and in the human body. Angew. Chem. Int. Ed.. 1990; 29: 565-594 [OpenAIRE] [DOI]

Cerny, C.. The aroma side of the Maillard reaction. Ann. N Y Acad. Sci.. 2008; 1126: 66-71 [PubMed]

Colin Slaughter, J.C.. The naturally occurring furanones: Formation and function from pheromone to food. Biol. Rev.. 1999; 74: 259-276 [PubMed] [DOI]

Schwab, W., Davidovich-Rikanati, R., Lewinsohn, E.. Biosynthesis of plant-derived flavor compounds. Plant J.. 2008; 54: 712-732 [OpenAIRE] [PubMed] [DOI]

Schwab, W., Roscher, R.. 4-Hydroxy-3(2H)-furanones: Natural and Maillard products. Rec. Res. Develop. Phytochem.. 1997; 1: 643-673

Roscher, R., Herderich, M., Steffen, J.P., Schreier, P., Schwab, W.. 2,5-Dimethyl-4-hydroxy-3[2H]-furanone 6'O-malonyl-β-D-glucopyranoside in strawberry fruit (Fragaria x ananassa, cv. Senga sengana). Phytochemistry. 1996; 43: 155-160 [PubMed]

Roscher, R., Steffen, J.P., Herderich, M., Schwab, W., Schreier, P.. Synthesis of phenyl 6'-O-malonyl-β-D-glucopyranoside. Facile preparation of malonylated glycoconjugates. J. Agric. Food Chem.. 1996; 44: 1626-1629 [OpenAIRE] [DOI]

Roscher, R., Schwab, W., Schreier, P.. Stability of naturally occurring 2,5-dimethyl-4-hydroxy-3[2H]-furanone derivatives. Z. Lebensm. Unters. Forsch.. 1997; 204: 438-441 [OpenAIRE] [DOI]

Emura, M., Yaguchi, Y., Nakahashi, A., Sugimoto, D., Miura, N., Monde, K.. Stereochemical studies of odorous 2-substituted-3(2H)-furanones by vibrational circular dichroism. J. Agric. Food Chem.. 2009; 57: 9909-9915 [OpenAIRE] [PubMed]

Yaguchi, Y., Nakahashi, A., Miura, N., Sugimoto, D., Monde, K., Emura, M.. Stereochemical study of chiral tautomeric flavorous furanones by vibrational circular dichroism. Org. Lett.. 2008; 10: 4883-4885 [OpenAIRE] [PubMed] [DOI]

Monde, K., Nakahashi, A., Miura, N., Yaguchi, Y., Sugimoto, D., Emura, M.. Stereochemical study of a novel tautomeric furanone: Homofuraneol. Chirality. 2009; 21 (Suppl. 1): E110-5 [OpenAIRE] [PubMed] [DOI]

Roscher, R., Schreier, P., Schwab, W.. Metabolism of 2,5-dimethyl-4-hydroxy-3(2H)-furanone in detached ripening strawberry fruits. J. Agric. Food Chem.. 1997; 45: 3202-3205 [OpenAIRE] [DOI]

Kitao, S., Matsudo, T., Sasaki, T., Koga, T., Kawamura, M.. Enzymatic synthesis of stable, odorless and powdered furanone glucosides by sucrose phosphorylase. Biosci. Biotechnol. Biochem.. 2000; 64: 134-141 [OpenAIRE] [PubMed] [DOI]

Haleva-Toledo, E., Naim, M., Zehavi, U., Rouseff, R.L.. Effects of L-cysteine and N-acetyl-L-cysteine on 4-hydroxy-2,5-dimethyl-3(2H)-furanone (furaneol), 5-(hydroxymethyl)furfural, and 5-methylfurfural formation and browning in buffer solutions containing either rhamnose or glucose and arginine. J. Agric. Food Chem.. 1999; 47: 4140-4145 [OpenAIRE] [PubMed] [DOI]

92 references, page 1 of 7
Powered by OpenAIRE Open Research Graph
Any information missing or wrong?Report an Issue
publication . Article . 2013

Natural 4‐Hydroxy‐2,5‐dimethyl‐3(2H)‐furanone (Furaneol)

Wilfried Schwab;