2,5-Dimethyl-4-hydroxy-2H-furan-3-one and its derivatives: analysis, synthesis and biosynthesis—a review

Zabetakis, Ioannis; Gramshaw, J. W.; Robinson, Donald S.

doi:10.1016/s0308-8146(98)00203-9

Cited by 71 publications

(61 citation statements)

References 93 publications

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“…Compound 1 ) groups, suggesting the presence of a furanoid nucleus [16][17][18] as in the case of terrefuranone 18 . The presence of a conjugated carbonyl group was revealed by an IR absorption, along with a resonance signal in the 13 C-NMR spectrum at δ C 207.1.…”

Section: Resultsmentioning

confidence: 98%

“…The presence of a conjugated carbonyl group was revealed by an IR absorption, along with a resonance signal in the 13 C-NMR spectrum at δ C 207.1. Analysis of the 1 H NMR spectrum of 1 (Table 1) revealed a typical A 2 X 2 pattern signals at δ H 2.79 (2H, t, J = 6.2 Hz, H-6) and 3.96 (2H, t, J = 6.2 Hz, H-7), one 3H singlet at δ H 1.35 assigned to a methyl group on a quaternary carbon (C-2), one olefinic proton deshield by a conjugated carbonyl observed at δ H 5.48 (1H, s, H-4), a decyl moiety appeared at δ H 0.88 (3H, t, J = 6.8, Me-17), 1.23 (16H, br s, CH 2 -9~16), and 1.72 (2H, m, CH 2 -8), indicating that 1 was probably a furan derivative possessing a conjugated carbonyl group 16 . The 13 C-NMR and DEPT spectrum showed that 1 had a total of 17 carbons for two Me, eleven CH 2 (two for a CH 2 CH 2 OH moiety), one CH, and three quaternary C-atoms including one C=O (δ C 207.1) and a C=C bond (δ C 189.1).…”

Section: Resultsmentioning

confidence: 99%

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Secondary Metabolites Isolated From the Fungus Monascus Kaoliang-Fermented Rice

Cheng

Yang

et al. 2010

J. Chil. Chem. Soc.

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A chemical study of the EtOAc-soluble ethanolic extract of Monascus kaoliang BCRC 31506 (Eurotiaceae) fermented rice led to the isolation of a new furan-3-one derivative along with 9 known compounds, monascin (2), ankaflavin (3), N-trans-feruloyltyramine (4), vanillic acid (5), 4-acetonyl-3,5-dimethoxy-p-quinol (6), (+)-β-eudesmol (7), trans-phytol (8), aesculetin dimethyl ether (9) and (-)-matairesinol (10). Structure 1 is proposed for monascuskaoliaone on the basis of spectroscopic evidence (NMR, UV, IR, and HRMS). None of the compounds exhibited significant scavenging activity toward DPPH radical in bioautography or spectroscopic assays.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Secondary Metabolites Isolated From the Fungus Monascus Kaoliang-Fermented Rice

Cheng

Yang

et al. 2010

J. Chil. Chem. Soc.

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“…2,5-Dimethyl-4-hydroxy-3(2H)-furanone (DMHF, furaneol) is believed to be a key flavor constituent in many fruits and baked foods (Zabetakis et al 1999). DMHF (furaneol) is formed in stored citrus juice and has been reported to reduce juice quality.…”

Section: Furans and Furanonesmentioning

confidence: 99%

Non-enzymatic browning in citrus juice: chemical markers, their detection and ways to improve product quality

Bharate¹,

Bharate

2012

J Food Sci Technol

120

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Citrus juices are widely consumed due to their nutritional benefits and variety of pharmacological properties. Non-enzymatic browning (NEB) is one of the most important chemical reactions responsible for quality and color changes during the heating or prolonged storage of citrus products. The present review covers various aspects of NEB in citrus juice viz. chemistry of NEB, identifiable markers of NEB, analytical methods to identify NEB markers and ways to improve the quality of citrus juice. 2,5-Dimethyl-4-hydroxy-3(2H)-furanone (DMHF) is one of the promising marker formed during browning process with number of analytical methods reported for its analysis; therefore it can be used as an indicator for NEB process. Amongst analytical methods reported, RP-HPLC is more sensitive and accurate method, which can be used as analytical tool. NEB can be prevented by removal of amino acids/ proteins (via ion exchange treatment) or by targeting NEB reactions (e.g. blockage of furfural/ HMF by sulphiting agent).

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“…These furan derivatives may be formed due to sugar degradation. 15 Usually primary alcohols, especially straight-chain aliphatic alcohols, are present in volatile emissions of fruits. However, compared with other classes of compounds, such as ketones and aliphatic aldehydes, alcohols are less volatile in very diluted aqueous solutions, and higher molecular weight alcohols, such as octan-1-ol, are more volatile than methanol.…”

Section: Discussionmentioning

confidence: 99%

The aroma of jam prepared from fruits of mosphilla (Crataegus azarolus L.)

Hadjimitsi

Zabetakis

2005

Flavour Fragr. J.

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The volatile constituents of the jam of Crataegus azarolus (Rosaceae) were analysed using simultaneous distillation-extraction and identified by gas chromatography-mass spectroscopy. Forty-four volatile compounds were identified for the first time in this jam, while 12 peaks were not identified. The volatile compounds were quantitatively determined by the use of an internal standard. The major classes of compounds identified included aliphatic and aromatic aldehydes, ketones, alcohols, monoterpenes, sesquiterpenes and hydrocarbons. The major constituent identified was 2-furaldehyde.

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2,5-Dimethyl-4-hydroxy-2H-furan-3-one and its derivatives: analysis, synthesis and biosynthesis—a review

Cited by 71 publications

References 93 publications

Secondary Metabolites Isolated From the Fungus Monascus Kaoliang-Fermented Rice

Secondary Metabolites Isolated From the Fungus Monascus Kaoliang-Fermented Rice

Non-enzymatic browning in citrus juice: chemical markers, their detection and ways to improve product quality

The aroma of jam prepared from fruits of mosphilla (Crataegus azarolus L.)

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