The volatile organic compounds generated from the Maillard reaction between l-ascorbic acid and l-cysteine in hot compressed water.

BACKGROUND: Hot compressed water (HCW), also known as subcritical water (SCW), refers to high-temperature compressed water in a special physical and chemical state. It is an emerging technology for natural product extraction. The volatile organic compounds (VOCs) generated from the Maillard reaction between l-ascorbic acid (ASA) and l-cysteine (Cys) have attracted significant interest in the flavor and fragrance industry. This study aimed to explore the formation mechanism of VOCs from ASA and Cys and examine the effects of reaction parameters such as temperature, time, and pH in HCW. RESULTS: The identified VOCs were predominantly thiophene derivatives, polysulfides, and pyrazine derivatives in HCW. The findings indicated that thiophene derivatives were formed under various pH conditions, with polysulfide formation favored under acidic conditions and pyrazine derivative formation preferred under weak alkaline conditions, specifically at pH 8.0. CONCLUSION: The Maillard reaction between ASA and Cys mainly produced thiophene derivatives, polysulfides, and pyrazine derivatives in HCW. The generation mechanism was significantly dependent on the surrounding pH conditions. © 2024 Society of Chemical Industry.

The study of volatile products formation from the self-degradation of l-ascorbic acid in hot compressed water.

The volatile products (VPs) formation from the self-degradation of l-ascorbic acid (ASA) in hot compressed water (HCW) was investigated with different reaction parameters, such as time, temperature, pH and ratio of ASA/water. The results showed that various reaction parameters had varying degrees of influence on the reaction, while the most significant effect factor was the initial pH of the solution. Furfural was the major product under acidic conditions, while furan derivatives were the main products under alkaline conditions. The above results showed that pH played the dominant role for yields and distribution of VPs in HCW. In the HCW system, the yields and classifications of VPs and conversion rate of ASA were not the same as those of VPs and ASA under traditional conditions. Based on the experimental results, the possible formation mechanism of VPs from the self-degradation of ASA was proposed in HCW.

Kinetics of L-ascorbic acid degradation and non-enzymatic browning development in hot-compressed water.

The effect of reaction conditions, which comprised the reaction temperature (150-190°C), processing time (0.50, 0.75, 1.00, 1.25, 1.50, 2.00, and 2.50 h), pH (5.0, 7.0, and 9.5), and concentration (0.03-0.07 mol/L) of L-ascorbic acid (ASA), on the degradation of ASA was investigated in hot-compressed water (HCW). The degradation kinetics of ASA and generation kinetics of browning products (BPs) were studied. The results showed that ASA degradation conformed to the pseudo-first-order kinetics, and the formation of BPs was closely related to the concentration of H3O+ in HCW. The acidic condition (pH = 5.0) and lower concentration of ASA (0.03 mol/L) were more favorable for ASA degradation. In HCW, the average apparent activation energy (Ea) of ASA was 15.77, 31.70, and 47.53 kJ/mol at pH 5.0, 7.0, and 9.5, respectively. The possible degradation mechanisms of ASA and the generation of BPs in HCW were proposed based on the experimental results.

Free and Bound Aroma Compounds of Turnjujube (Hovenia acerba Lindl.) during Low Temperature Storage.

Free and bound aroma volatiles from turnjujube during low temperature storage were extracted by headspace solid-phase microextraction. They were then characterized and identified using gas chromatography-mass spectrometry. Turnjujube was harvested and stored for 7, 14, and 21 days at 7 °C, the common temperature of display refrigerators in grocery stores. The results showed that 41 free and 24 bound aroma compounds were detected for the first time in turnjujube in both freshly harvested and stored turnjujube. The free and bound aroma compounds of turnjujube were markedly influenced by the storage time. The major free aroma compounds in turnjujube included esters, alcohols, aliphatic aldehydes, and aliphatic ketones. The major bound aroma compounds included borneol, eugenol, and isoeugenol, which contributed to sweet, floral, and herbaceous aroma after their hydrolysis. Freshly harvested turnjujube mostly had a fruity and herbaceous aroma, which diminished after storage at 7 °C. In contrast, the fatty aroma enhanced gradually over storage, and the floral aroma enhanced noticeably after storage for seven days. Foul odor was not detected even after storage at 7 °C for 21 days. The formation mechanisms of some aroma compounds were proposed.

Free and bound volatile compounds in the Rubus coreanus fruits of different ripening stages.

The aim of the present study was to investigate the free and bound volatiles in the Rubus coreanus (RC) fruits of different ripening stages. Thirty-seven free volatiles and 28 bound volatiles were identified in RC fruit for the first time. The contents of free (E)-2-hexen-1-ol, 1-hexanol, 2-heptanol, ß-myrcene, (E), (Z)-ß-ocimene, allo-ocimene, linalool, cosmene, α-terpineol, methyl salicylate, eugenol, and ß-damascenone remain high, and increased with the ripening of RC fruit. The contents of 11 bound volatiles decreased during the ripening, and became lower than the contents of their free volatiles in the ripe fruit. The ripe black fruit is closely correlated to the free nonanal, sulcatone, (E)-2-hexen-1-ol, 1-hexanol, 2-heptanol, 1-heptanol, 1-nonanol, (E)-linalool oxide (furanoid), and ß-damascenone, and bound (E)-2-hexen-1-ol and (E)- ß-ocimene. The ripe RC fruit is more fruity and floral than unripe fruit. The gradually hydrolyzed bound volatiles can enhance the fruity, floral, and herbaceous odors. PRACTICAL APPLICATIONS: Rubus coreanus (RC) fruit is a functional natural fruit. Both fresh and processed Rubus coreanus fruits including jams, confitures, wine, yogurt, vinegar, and beverages, as well as ingredients in functional foods or cosmetics have been extensively consumed. However, the free and bound aroma compounds in RC fruit have not been well understood. This work illustrates the contributions of free and bound volatiles to the flavor of RC fruit.

Changes of the free and bound volatile compounds in Rubus corchorifolius L. f. fruit during ripening.

The changes of free and bound volatile compounds in Rubus corchorifolius fruit during ripening were determined with a headspace SPME-GC-MS method. The results suggest that the free aldehydes, alcohols, esters and phenols increases, while that of free terpenoids decreases, with the ripening of the fruit. The bound aldehydes, alcohols, terpenoids, esters and phenols gradually decreases during ripening because these bound compounds are hydrolyzed to their free form. The characteristic free aroma compounds of ripened red fruit were found to be hexanal, 2-heptanone, ethyl hexanoate, 4-terpineol, geranial and methyleugenol. The free aroma compounds in red and yellow fruits exhibit similar odor profiles, and both of them are much sweeter, more floral and greener than the green fruit. The overall aroma of the fruits all ripening stages are mainly attributed to the free aroma compounds including ß-damascenone, hexanal, 2-hexenal and linalool. The formation mechanisms of some volatile compounds were proposed.

Kinetics of browning and correlations between browning degree and pyrazine compounds in l-ascorbic acid/acidic amino acid model systems.

The kinetics of browning and the correlation between browning products (BPs) and pyrazine compounds were investigated by heating equimolar l-ascorbic acid (ASA)/acidic amino acids under weak alkaline conditions at 120-150°C for 10-120min. The formations of BPs and pyrazine compounds from the reaction were monitored by UV-vis and SPME-GC-FID, respectively. The formation of BPs in both ASA/l-glutamic acid and ASA/l-aspartic acid model reaction systems followed zero order reaction kinetics with activation energies (Ea) of 90.13 and 93.38kJ/mol, respectively. ASA/l-aspartic acid browned at a slightly higher rate than ASA/l-glutamic acid. The total concentration of pyrazine compounds was highly and positively correlated with that of BPs. Based on the observed kinetic data, the formation mechanisms of BPs and pyrazine compounds were proposed.

Effects of reaction parameters on self-degradation of L-ascorbic acid and self-degradation kinetics.

The degradation behavior of L-ascorbic acid (ASA) was investigated under different parameters of temperature, time, and pH. Higher temperatures and longer times accelerated the ASA degradation. Degradation product distributions changed with different pH values. As solution pH of 4.5 was beneficial for formation of uncolored intermediate products with an absorbance maximum at 294 nm. Formation of brown products was promoted at pH values from 5.8 to 6.8 with an absorbance maximum at 420 nm. Under different pH conditions, volatile products formation varied. Furfural and derivatives of furan were primary products due to the effects of pH. The non-enzymatic selfdegradation behavior of ASA was characteristic of first-order kinetics based on a classic dynamic model. Activation energy values varied under different pH values. An ASA degradation mechanism and pathway are proposed.

Mechanism of formation of sulphur aroma compounds from l-ascorbic acid and l-cysteine during the Maillard reaction.

The sulphur aroma compounds produced from a phosphate-buffered solution (pH 8) of l-cysteine and l-, l-[1-13C] or l-[4-13C] ascorbic acid, heated at 140±2°C for 2h, were examined by headspace SPME in combination with GC-MS. MS data indicated that C-1 of l-ascorbic acid was not involved in the formation of sulphur aroma compounds. The sulphur aroma compounds formed by reaction of l-ascorbic acid with l-cysteine mainly contained thiophenes, thiazoles and sulphur-containing alicyclic compounds. Among these compounds, 1-butanethiol, diethyl disulphide, 5-ethyl-2-methylthiazole, cis and trans-3,5-dimethyl-1,2,4-trithiolane, thieno[2,3-b]thiophene, thieno[3,2-b]thiophene, cis and trans-3,5-diethyl-1,2,4-trithiolane, 1,2,5,6-tetrathiocane, 2-ethylthieno[2,3-b]thiophene, 2,4,6-trimethyl-1,3,5-trithiane and cyclic octaatomic sulphur (S8) were formed solely by l-cysteine degradation, and the rest by reaction of l-ascorbic acid degradation products, such as hydroxybutanedione, butanedione, acetaldehyde, acetol, pyruvaldehyde and formaldehyde with l-cysteine or its degradation products, such as H2S and NH3. A new reaction pathway from l-ascorbic acid via its degradation products was proposed.

[Analysis of the chemical constituents of volatile oil from Asarum insigne by GC-MS].

OBJECTIVE: To analyse the chemical constituents of volatile oil from Asarum insigne. METHODS: The volatile oil from Asarum insigne was isolated with steam distillation and identified by capillary GC/MS method. RESULTS: 68 Volatile components were identified and determined, accounting for 92.18% of the total peak area. The main volatile compounds and their relative contents are camphene (13.48%), alpha-pinene (12.44%), beta-pinene (11.07%), borneol (8.12%), trans-beta-farnesene (5.91%), elemicin (5.38%), 1,3-benzodioxole-5-(2-propenyl) (3.06%), myristicin (2.95%), ledene (2.47%), eucalyptol (2.33%), patchouli alcohol (2.25%), alpha-bisabolene (2.04%) and bornyl acetate (1.36%) etc. CONCLUSION: The study provided solid and scientific proof for the exploitation and utilization of Asarum insigne.

Top note compounds of Chinese traditional bacteria-fermented soybean.

Top note compounds of Chinese traditional bacteria-fermented soybean were analysed by using headspace sampler, GC and GC-MS. Thirty-three note compounds were identified in Chinese traditional bacteria-fermented soybean. Among them, 28 compounds are responsible for the Chinese traditional bacteria-fermented soybean top note. 3-Methylbutanal (6.690%), amyl nitrite (12.976%), 2-methylpropanoic acid (4.014%), 2,3-butanediol (2.171%), 3-methylbutanoic acid (14.273%), 2-methylbutanoic acid (11.866%), benzeneacetaldehyde (1.422%), nonadecane (3.195%), eicosane (5.331%), heneicosane (23.418%) and docosane (5.011%) were all found in concentrations higher than 1.0% (calculated as % peak area of GC analysis using a DB-5 column).

Analysis of volatile compounds in traditional smoke-cured bacon(CSCB) with different fiber coatings using SPME.

The volatile compounds of Chinese traditional smoke-cured bacon (CSCB) were studied using SPMS-GC/MS. There were 48 volatile compounds identified and quantified, which belonged to several classes of chemical: 1 alkane, 16 aldehydes, 5 ketones, 9 alcohols, 4 thioethers and thiols, 3 furans and 10 phenols compounds. All the volatile compounds except for alkane was responsible for CSCB characteristic flavor. The major volatile compounds of CSCB came from smoking, oxidation and Maillard reaction, etc. Many volatile compounds were not reported in previous paper isolated by steam distillation method or nitrogen purge-and-steam distillation method on CSCB. It should be because of different method of isolating volatile substances from CSCB. Among the fibers tested, CAR/PDMS (carboxen/polydimethylsiloxane) fiber coating showed the highest area counts for most volatile compounds. CAR/PDMS coating extracted better those compounds whose linear retention indices (LRI) was lower than 926 (on average) and DVB/CAR/PDMS (divinylbenzene/carboxen/polydimethylsiloxane) those with higher LRI.

[Studies on the chemical constituents of the volatiles of Clerodendron bungei].

OBJECTIVE: To analyse chemical constituents of the volatiles of Clerodendron bungei. METHOD: The volatiles of C. bungei were extracted through steam distillation, and then the constituents were separated by GC and identified by MS. RESULT AND CONCLUSION: 33 Compounds were identified. The principal chemical constituents of the volatiles of C. bungei are ethanol, acetone, 1-penten-3-ol,2-pentanol, (Z)-2-penten-1-ol, 3-furaldehyde, 3-hexen-1-ol, 4-hexen-1-ol, 1-hexanol, 1-octen-3-ol, 3-octanol, benzenemethanol, linal-ool oxide, trans-Linalool oxide, linalool,2,5-dimethylcyclohexanol, phenylethyl alcohol, etc.