2‐formylmethyl‐2‐methyl‐5‐(1‐hydroxy‐1‐methylethyl)‐tetrahydrofuran: Major volatile product of the water‐mediated oxidative decomposition of citral

Grein, Bertram.; Schmidt, Gertraut; Full, G.; Winterhalter, Peter; Schreier, Peter

doi:10.1002/ffj.2730090302

Cited by 4 publications

(5 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Becuase most chemical reactions of citral involve oxidative or free radical mechanisms (Clark and Chamblee, 1992;Grein et al, 1994), it was determined whether this was also true for the amino acid-catalyzed isomerization reaction. The isomerization catalyzed by glycine at neutral pH was performed in the absence of oxygen (N 2 atmosphere) or in the presence of 25 mM vitamin C, a well-known radical scavenger, respectively.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Amino Acid-Catalyzed Conversion of Citral: cis−trans Isomerization and Its Conversion into 6-Methyl-5-hepten-2-one and Acetaldehyde

Wolken

Have

Werf

2000

J. Agric. Food Chem.

View full text Add to dashboard Cite

Under alkaline conditions, amino acids or proteins catalyze the deacetylation of citral, a major aroma component, resulting in methylheptenone and acetaldehyde formation. 3-Hydroxycitronellal is an intermediate in this reaction. Amino acids also catalyze the cis-trans isomerization of the pure isomers of citral, geranial, and neral. Most likely the amino acids are involved in stabilizing intermediates of the isomerization and deacetylation reaction of citral. On the basis of the findings presented, some consequences for the application of citral, or its isomers, in food are discussed.

show abstract

Section: Resultsmentioning

confidence: 99%

“…3-Hydroxycitronellal was also described as an intermediate in the formation of a volatile cyclic compound from citral under oxygen atmosphere in aqueous acidic solution (Grein et al, 1994). They suggest the involvement of oxygen in the formation of 3-hydroxycitronellal from citral.…”

Section: Discussionmentioning

confidence: 96%

Amino Acid-Catalyzed Conversion of Citral: cis−trans Isomerization and Its Conversion into 6-Methyl-5-hepten-2-one and Acetaldehyde

Wolken

Have

Werf

2000

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…Compounds 10 and 11 were reported to be formed via the direct epoxidation of the 6,7-double bond of citral (13,14). Kimura et al, on the other hand, demonstrated the formation of R,p-dimethylstyrene (4), p-cymen-8-ol (7), and R-terpineol (9) using isolated p-menthadien-8-ols 5 and 8, respectively, under acidic aqueous conditions (4).…”

Section: Degradation Of Citral Under Acidic Aqueous Conditionsmentioning

confidence: 97%

“…b Retention index on DB-1 (60 m). c Identification methods: A, mass spectrum and retention index agree with those of authentic compounds; B and C, compounds were tentatively identified on the basis of the following criteria: (B) mass spectrum agrees with that of the Wiley mass spectral database (Agilent Technologies, 2000) and RI agrees with literature value (5) or (C) mass spectrum agrees with literature spectrum (13).…”

Section: Degradation Of Citral Under Acidic Aqueous Conditionsmentioning

confidence: 99%

“…In agreement with most published data, Oxidation reactions as well as the acid-catalyzed reactions would be involved in the formation of compounds 3, 4, 6, 7, 9-11, 14, and 17. Compounds 10 and 11 were reported to be formed via the direct epoxidation of the 6,7-double bond of citral (13,14). Kimura et al, on the other hand, demonstrated the formation of R,p-dimethylstyrene (4), p-cymen-8-ol (7), and R-terpineol (9) using isolated p-menthadien-8-ols 5 and 8, respectively, under acidic aqueous conditions (4).…”

Section: Degradation Of Citral Under Acidic Aqueous Conditionsmentioning

confidence: 99%

See 1 more Smart Citation

Formation Mechanism of p-Methylacetophenone from Citral via a tert-Alkoxy Radical Intermediate

Ueno

Masuda

2004

J. Agric. Food Chem.

View full text Add to dashboard Cite

The aim of this study was to clarify the formation mechanism of a potent off-odorant, p-methylacetophenone, from citral under acidic aqueous conditions. An acidic aqueous solution (pH 3.0) containing 10 mg/L of citral was stored at 40 degrees C for 2 weeks. Among the compounds detected in the stored citral solution, 4-(2-hydroxy-2-propyl)benzaldehyde was identified for the first time as a degradation product from citral. The formation of p-methylacetophenone and 4-(2-hydroxy-2-propyl)benzaldehyde behaved the same when antioxidants were added to the citral solution. In addition, both compounds were formed by the Fe(2+)-induced decomposition of 8-hydroperoxy-p-cymene, another compound identified in the stored citral solution. These results suggested that both p-methylacetophenone and 4-(2-hydroxy-2-propyl)benzaldehyde can be formed via the same radical intermediate [p-CH3C6H4C(CH3)2O*] that can be derived from the O-O bond homolysis of 8-hydroperoxy-p-cymene. On the other hand, the degradation of 8-hydroperoxy-p-cymene without Fe2+ under acidic aqueous conditions did not yield p-methylacetophenone and 4-(2-hydroxy-2-propyl)benzaldehyde, but the degradation of citral without Fe2+ did. Therefore, other than the decomposition of 8-hydroperoxy-p-cymene, a mechanism to generate the tert-alkoxy radical intermediate was proposed for the formation of p-methylacetophenone and 4-(2-hydroxy-2-propyl)benzaldehyde in the citral solution.

show abstract

Antioxidant activity of plant extracts on the inhibition of citral off‐odor formation

Liang

Wang

Simon

et al. 2004

Molecular Nutrition Food Res

View full text Add to dashboard Cite

Grape seed, pomegranate seed, green tea, and black tea extracts were used to inhibit the off-odor from citral degradation. A 0.1 M citrate buffer (pH 3), containing 100 ppm citral and 200 ppm gallic acid equivalent plant extract, was incubated at 40 degrees C. The reaction mixtures were analyzed by high-performance liquid chromatography (HPLC) at days 0, 6, 10, 13, and 16 to monitor degradation of citral and formation of alpha, p-dimethylstyrene, p-cymene-8-ol, and p-methylacetophenone. The addition of plant phenolic extracts could not inhibit citral degradation, however, all four plant extracts significantly inhibited p-methylacetophenone formation. The samples, with the addition of plant extracts, exhibited higher concentrations of alpha, p-dimethylstyrene and p-cymene-8-ol than the control. This is presumed to be due to the oxygen-scavenging effect of plant extracts blocking the pathway from p-cymene-8-ol to p-methylacetophenone. Our results suggest that these plant extracts act as general antioxidants inhibiting the generation ofp-methylacetophenone regardless of the types of water-soluble phenolic compounds existing in the plant extracts.

show abstract

2‐formylmethyl‐2‐methyl‐5‐(1‐hydroxy‐1‐methylethyl)‐tetrahydrofuran: Major volatile product of the water‐mediated oxidative decomposition of citral

Cited by 4 publications

References 14 publications

Amino Acid-Catalyzed Conversion of Citral: cis−trans Isomerization and Its Conversion into 6-Methyl-5-hepten-2-one and Acetaldehyde

Amino Acid-Catalyzed Conversion of Citral: cis−trans Isomerization and Its Conversion into 6-Methyl-5-hepten-2-one and Acetaldehyde

Formation Mechanism of p-Methylacetophenone from Citral via a tert-Alkoxy Radical Intermediate

Antioxidant activity of plant extracts on the inhibition of citral off‐odor formation

Contact Info

Product

Resources

About