A Probable Flavoring Principle in Vegetable‐Protein Hydrolysates

Sulser, H; DePIZZOL, J.; Bühi, W.

doi:10.1111/j.1365-2621.1967.tb00846.x

Cited by 70 publications

(33 citation statements)

References 20 publications

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“…The molar ratio of starting materials has an important effect on the yield of HDMF, and the highest yield was obtained from equal molar proportions of threonine and organic acid. In proportion to the decrease in the ratio of organic acid to threonine, the forma tion of 3-hydroxy-4-methyl-5-ethyl-2(5H)-fura none (HMEF) which has been isolated from vegetable-protein hydrolysates by Sulser et al 2) increased, while that of HDMF decreased.…”

Section: Properties Of Bfcmentioning

confidence: 99%

3-hydroxy-4,5-dimethyl-2(5H)-furanone, a burnt flavoring compound from aged sake.

Takahashi

Tadenuma

Sato

1976

Agricultural and Biological Chemistry

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Section: Properties Of Bfcmentioning

confidence: 99%

3-hydroxy-4,5-dimethyl-2(5H)-furanone, a burnt flavoring compound from aged sake.

Takahashi

Tadenuma

Sato

1976

Agricultural and Biological Chemistry

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“…20 The results were collected in Table 3. We pleasingly found that β-mono substituted 2-oxocarboxylic esters 1b-d behaved as suitable reactants for this process (Table 3, entries [3][4][5]. This demonstrated that the first homo-aldol reaction and the subsequent ring closure occurred for these substituted 2-oxocarboxylic esters without difficulty.…”

Section: Methodsmentioning

confidence: 92%

“…1,2 This kind of compounds have been isolated from a variety of natural sources, 1,2 and their properties leading to use as flavoring agents, 3 perfumes 4 and anti-depressants 5 have been evaluated, and analgesic 6 and antifungal 7 activities have been documented.…”

Section: Introductionmentioning

confidence: 99%

Approach to novel isotetronic acid derivatives: DBU-Et3N-mediated aldol/lactonization/O-protection sequence of 2-oxocarboxylic esters

Chen¹,

Ma²,

Li³

et al. 2009

Arkivoc

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An efficient synthesis of novel O-protected isotetronic acids is described. The method relies on DBU (1,8-diazabicyclo[5.4.0]-undec-7-ene) and triethylamine triggered homo-aldol reactions of 2-oxocarboxylic esters, followed by successful ring closure via lactonization and O-protection with various electrophiles. The unprotected isotetronic acids were also achieved with moderate to high yields if the free-OH group were pre-capped by the silylation agent TMSCl. All the three reaction steps were conducted in a sequential manner, without isolation of any intermediates.

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“…Several authors have investigated volatile substances responsible for the flavour of chemically hydrolyzed proteins. Sulser et al [7] found 2-hydroxy-3-methyl-4-ethyl-2-buten-4-olide to be the flavouring principle of this type of products. Many volatile substances were identified by MANLEY et al in basic [8], acidic and neutral [9] fractions from hydrolyzed soy protein.…”

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confidence: 98%

Flavour significant compounds in yeast autolysate Gistex X‐II powder. Part I. Acidic fraction

Davı́dek

Hajšlová

Kubelka

et al. 1979

Nahrung

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Basic informations about the composition of yeast autolysate GistexLX-11-powder were obtained. The representative sample of volatile flavour-significant compounds was isolated. There were 29 substances identified in the acidic fraction of the isolate and the odour of this fraction was organoleptically evaluated. The organoleptic properties were mainly influenced by the presence of lower fatty acids and phenylacetic and 3-phenylpropionic acids. Two sulphur-containing heterocyclic acids, i. e. 2-thiophenecarboxylic and 5-methyl-2-thiophenecarboxylic acids were identified for the first time as volatile constituents of foodstuffs. Flavour properties of these two and other 6 sulphur-and oxygen-containing heterocyclic acids were evaluated and their mass spectra are presented.Hydrolyzed vegetable proteins have been widely used for flavouring of many foodstuffs [l]. There are various types of these products that can be divided into 2 groups. First, chemical hydrolyzates produced mainly by hydrochloric acid hydrolysis, second, enzymic hydrolyzates (shoyu, yeast autolysates, etc.).A great number of studies has paid attention to flavour-significant compounds contributing to the typical flavour of Japanese shoyu [2-41. NONUMURA et al. HOUGH et al. [16] studied the biochemical changes occurring during yeast autolysis. They described the principle hydrolytic enzymes splitting the main components of yeast cells, i.e. proteins, saccharides and nucleic acids.This study was undertaken in order to receive some additional informations about flavoursignificant components of yeast autolysates. Experimental Material and rejerence compoundsYeast autolysate Gistex X-I1 powder (Koninklijke Netherlandsche Gist-en Spiritusfabriek N.V., Delft, Holland). The following heterocyclic acids were synthesized: 2-thiophenecarboxylic acid [17, 181, 5-methyl-2-thiophenecarboxylic acid [19, 201, 2-thienylacetic acid [21], 5-methyl-2-thienylacetic acid [2 I], 3-(2-thienyl) propionic acid [20,22],2-furylacetic acid [23-251, 5-methyl-2-furylacetic acid [23, 261. Other chemicals were obtained from Lachema n.p., Brno, Czechoslovakia. ApparatusA gas chromatograph Chrom 4 equipped with a flame ionization detector (Laboratorni piistroje n.p., Praha, Czechoslovakia), a LKB 9000 mass spectrometer (LKB Producter AB, Stockholm, Sweden). MethodsIsolation of flavour-signljkant compounds 8000 g of the yeast autolysate were mixed with sand and all the portions, 1000 g each, were extracted in a SOMLET apparatus with diethyl ether for 52 h. The combined extracts were dried over anhydrous sodium sulphate and concentrated to 100 ml using a Snyder column. Acidic fraction90 ml of the above mentioned diethyl ether solution were extracted with five 20 ml portions of 5 7; sodium bicarbonate, the extract was evaporated under vaccum nearly to dryness, acidified with hydrochloric acid to pH 0.5 and extracted again with five 20 ml portions of diethyl ether. The combined extracts were dried with anhydrous sodium sulphate and concentrated as above to 1 ml.One half of the obtained...

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A Probable Flavoring Principle in Vegetable‐Protein Hydrolysates

Cited by 70 publications

References 20 publications

3-hydroxy-4,5-dimethyl-2(5H)-furanone, a burnt flavoring compound from aged sake.

3-hydroxy-4,5-dimethyl-2(5H)-furanone, a burnt flavoring compound from aged sake.

Approach to novel isotetronic acid derivatives: DBU-Et3N-mediated aldol/lactonization/O-protection sequence of 2-oxocarboxylic esters

Flavour significant compounds in yeast autolysate Gistex X‐II powder. Part I. Acidic fraction

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