CH623568A5 - Process for the preparation of novel perfumes and/or flavourings - Google Patents

Description

The invention relates to a method for producing new fragrances and / or flavors. These are the compounds of the formula

Ri— (Y) n-S-S — R2 (I)

in which Rt optionally substituted phenyl, furyl or a nitrogen and / or sulfur and optionally additionally containing oxygen as ring members, optionally substituted monocyclic radical, R2 lower alkyl or lower alkenyl and Y optionally mono- or di-substituted methylene and n = 0 Is -5, or 2-5 if Ra is phenyl or furyl,

with the exception of 2-thienyl ethyl disulfide, 2-pyridyl methyl disulfide, 4-chlorophenyl methyl disulfide and 3-nitrophenyl isopropyl disulfide.

The enumerated asymmetric disulfides (and their production) are from US Pat. 2,610,968 (Velsicol Corp.).

The process is characterized in that a compound of the formula

A-S-N-NH-COOR (II)

or COOR

A-S-SCN (III)

or

S

II

A-S-S-COCH3 (IV)

or

A-S-S-A (V)

or

A-S-N ^ X (VI)

or

® ^ A

A-S-S ^ 7ß> (VII)

R

with a mercaptan of the formula

A-SH (VIII)

implements

where in one reactant A represents a radical Rj (Y) n and in the other reactant A represents a radical R2, Y and n are as defined above, but n should only be 1-4 in the case of formulas II, III and V, R represents lower alkyl, X is the diacyl radical of an aliphatic or aromatic dicarboxylic acid and Z® represents an anion.

Heterocyclic radicals containing nitrogen and / or sulfur and optionally additionally oxygen as ring members are in particular 5- or 6-membered heterocycles which contain one or more nitrogen atoms and / or one or more sulfur atoms. Examples of heterocycles on which these heterocyclic radicals are based are: pyrrole, pyridine, pyrazine, imidazole, pyrazole, pyrimidine, thiophene, thiazole, isothiazole, oxazole, triazole, etc., which substituted heterocycles, for example lower alkyl-substituted, could be.

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The position at which the heterocyclic residue is attached to the rest of the molecule is not critical. Lower alkyl or lower alkenyl radicals represented by the radical R2 (or R) are in particular straight-chain or branched, with 1-6 carbon atoms, such as, for example, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, Isobutyl, amyl, hexyl, etc.

Y may represent mono- or di-substituted methylene, in addition to unsubstituted methylene (—CH2—), in particular residues of the formulas

-CHR ° -, -CR ° R °° -

wherein R ° and R0Ü represent lower alkyl or lower alkenyl radicals.

The reaction of the compound II with the mercaptan VIII can by known methods, for. B. according to Mukajyama et al., Tetrahedron Letters (1968), 5907 or Boekelheide et al., Tetrahedron Letters (1970), 1203.

The reaction is conveniently carried out in the presence of a base. Particularly suitable bases are weakly inorganic bases, such as ammonia, sodium bicarbonate, sodium carbonate, etc., or organic bases, e.g. B. aliphatic or aromatic amines. A particularly preferred amine is N, N-diisopropylethylamine. The reaction can be carried out in the presence or absence of an organic solvent. Suitable solvents are hydrocarbons, especially aromatic hydrocarbons such as benzene, toluene etc., halogenated hydrocarbons such as chloroform, dichloromethane etc., ethers such as diethyl ether, alcohols such as alkanols, e.g. As methanol, ethanol, etc., esters such as alkane carboxylic acid esters, for. B. ethyl acetate. The reaction temperature is not critical. It is expediently between about −20 ° C. and the reflux temperature of the reaction mixture. It is preferable to work at approximately 20 ° -10 ° C.

The reaction product can be isolated from the reaction mixture by methods known per se, e.g. B. by concentrating the raction mixture, taking up the residue in an organic solvent such as, for example, a chlorinated hydrocarbon, if appropriate, an ether or ester, etc., washing the organic phase with saturated aqueous sodium bicarbonate solution, drying the organic phase and concentrating. The product of the formula I can be obtained in pure form by distillation or chromatography, for example on silica gel. The hydra-derivative II is conveniently obtained by reacting the azodicarboxylic acid ester of the formula

ROOC-N = N — COOR (IX)

where R has the above meaning,

obtained with the corresponding mercaptan VIII. For this purpose, the mercaptan is preferably in the presence of catalytic amounts of a strong acid such as a mineral acid, e.g. B. sulfuric acid or hydrochloric acid, or p-toluenesulfonic acid.

It is convenient to work in an inert solvent. Suitable solvents are e.g. B. hydrocarbons such as hexane, aromatic hydrocarbons such as benzene, halogenated hydrocarbons such as chloroform. Dichloromethane etc., ether, e.g. B. Diethyl ether. The reaction temperature is not critical, but it is expediently between approximately -20 and 100 ° C. It is preferred to work between room temperature and the reflux temperature of the solvent. The hydrazoderivate II obtained in this way can then be isolated according to methods known per se, for example those mentioned above, or can also be reacted directly.

The reaction of the compound of formula III with mercaptan VIII can also be carried out according to methods known per se [Meijer et al., Ree. Trav. Chim. Pays Bas 93, 242 (1974)]. Appropriately, the mercaptan in the form of a metal salt, e.g. B. an alkali metal salt, especially the lithium salt. It is convenient to do this in a solvating medium, e.g. B. an ether such as diethyl ether, dimethoxyethane, etc., dimethyl sulfoxide, dimethylformamide, hexamethylphosphoric triamide, etc. A preferred solvent is dimethoxyethane. The reaction temperature is not critical, but it is conveniently between about -50 ° and about + 50 ° C. A preferred temperature range is between about -20 ° C and room temperature. The reaction product of the formula I obtained in this way can be prepared by methods known per se, e.g. according to one of the above, cleaned and isolated.

The preparation of compound III can be accomplished by reacting the corresponding mercaptan VIII using dirhodan. For this purpose, the mercaptan VIII is expediently reacted with dirhodane generated in situ. Dirhodan is expediently made from a heavy metal rhodanide, for example lead rhodanide, with the aid of an oxidizing agent, such as. As bromine, etc., in an inert solvent. Suitable solvents are hydrocarbons, for example those mentioned above, or ethers, for example those mentioned above.

The reaction temperature is not critical, but it is expediently between about -30 ° and 80 ° C. It is preferable to work between about -20 ° C. and room temperature. The product of the formula III obtained in this way can now be isolated by methods known per se, such as, for example, those given above. But it can also be implemented directly with the Mercaptan VIII.

For the purpose of reacting the compound IV with the mercaptan VIII, the compound of the formula IV is preferably initially prepared “in situ”, namely from dimethyldithiobis (thioformate) [E.I. Stout et al., J. Org. Chem. 39, 562 (1974)] and the corresponding mercaptan VIII:

S S

I! II

A-SH + CH3OC-S-S-COCH3 -> IV (VIII) (X)

In practice, one proceeds by presenting the compound of formula X, e.g. B. in an inert solvent in a temperature range from for example -30 ° C to room temperature, and then the first mercaptan of the formula VIII added dropwise. This dropping is done together with an equivalent of a base, e.g. B. an organic base such as an amine, preferably pyridine. The dissolved, neutralized mercaptan is expediently added dropwise. After complete reaction, for example after 5 to 30 minutes, the second mercaptan VIII with a second equivalent of base is now added dropwise in the same way according to the invention and is thus reacted with the compound of the formula IV.

For the purpose of working up, the reaction mixture is expediently mixed with an organic solvent, for. B. one of the above, extracted or, in the case of less volatile disulfides I, z. B. those boiling point of about 100 ° C or higher, simply concentrated. The following cleaning can be done according to known methods, such as. B. the above, take place.

The reaction of the compound of the formula V with the compound of the formula VIII is based on the fact that the compound VIII is oxidized by the compound V [Reid, Orga-

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never Chemistry of bivalent Sulfur III, 372 (I960)]. The reaction is conveniently carried out in the presence of a catalyst. Bases are particularly suitable as catalysts, e.g. B. inorganic bases such as alkali metal hydroxides, e.g. As sodium hydroxide or potassium hydroxide, metal hydrides such as NaH or organic bases, for. B. aliphatic or aromatic amines, such as triethylamine, pyridine, etc. The reaction can be carried out in the presence or absence of a solvent. As a solvent comes e.g. B. question one of the above. It is convenient to work at an elevated temperature. The reaction can be brought to completion by various measures, for example by excess disulfide component V or, if appropriate, by continuous removal of component I or the free mercate pan formed in the reaction, for example by distillation. The workup of the reaction mixture is conveniently carried out by removal, for. B. filtering, or neutralization of the catalyst with acid and concentration of the crude product. This can be worked up according to methods known per se.

The reaction of the sulfenimide VI with the mercaptan VIII can also be carried out according to methods known per se, see e.g. K.S. Boustani et al., Tetrahedron Letters 1970 (3547); D.N. Harpp et al., Tetrahedron Letters 1970 (3551) or D.N. Harpp et al., J. Org. Chem. 36, 3828 (1971), Büchel et al., Chem. Ber. 100, 1248 (1967), Behfo-rouz et al., J. org. Chem. 34, 51 (1969).

The diacyl radical X of the aliphatic or aromatic dicarboxylic acid is, for example, the rest of the glutaric acid, succinic acid, phthalic acid etc.

Appropriately, approximately equivalent amounts of mercaptan VIII and sulfenimide VI are reacted. The reaction can be carried out in an inert organic solvent, for example a hydrocarbon such as an aliphatic hydrocarbon such as hexane or an aromatic hydrocarbon such as benzene etc., a chlorinated hydrocarbon such as methylene chloride etc. The reaction temperature is not critical, but is expediently between approximately 0 ° and 150 ° C. A preferred range is that between approximately room temperature and the reflux temperature of the reaction mixture.

For the purpose of reacting the sulfonium salt VII with the mercaptan VIII, the former is preferably prepared in situ. For this purpose, the - preferably symmetrical - disulfide A-S-S-A is first mixed with an alkylating agent. As alkylating agents such. B. tri-lower alkyl-oxonium salts, such as especially the tetrafluoroborates, in question. Other suitable salts may include hexa-chloroantimonate, perchlorate, nitrate, sulfonate (aryl or alkyl), etc., as the anion. It is essential for achieving optimal yields that the anion Z © used in the alkylating agent reacts less rapidly than the anion A-S © with the cation of VII.

The reaction is conveniently carried out in an inert solvent, e.g. An aliphatic or aromatic hydrocarbon such as hexane, heptane, benzene, toluene etc., a chlorinated hydrocarbon such as chloroform, dichloromethane etc., a nitro compound such as a nitroalkane e.g. Nitromethane, nitroethane, etc., a sulfoxide, e.g. Dimethyl sulfoxide, etc. Chlorinated hydrocarbons such as dichloromethane or nitro compounds such as nitromethane are preferred. The molar ratio of disulfide to alkylating agent is preferably 1: 1, but an excess of disulfide can also be used.

The reaction temperature is not critical, it is expediently between about -20 ° and 50 ° C. But higher or lower temperatures can also be considered. Temperatures of approximately 0 ° C. are preferred for nitromethane. The alkylated disulfide can be isolated, but it is conveniently reacted directly with the mercaptan VIII. The latter is preferably - as such or in salt form, e.g. B. as ammonium, alkali or alkaline earth metal salt - in one of the above solvents, especially nitromethane, added to the dissolved salt. The temperature range is expediently that specified above.

The reaction mixture can be worked up by the methods given above, eg. B. chromatography and / or distillation.

The starting materials used in the different process variants are either known or can be prepared by methods known per se.

The disulfides I produced according to the invention are notable for special odor and / or flavor properties. The spectrum of flavors in particular is very broad. There are fruity, spicy (e.g. mustard-like) vegetable notes, e.g. B. for leeks, celery, cauliflower, chives, onions, etc., mushroom and cheese and meat notes. The roasted and meat notes are of particular interest.

The compounds I can accordingly be used, for example, for perfuming or aromatizing products such as cosmetics (soaps, ointments, powders, etc.), detergents or foods, luxury foods and beverages, the compounds I preferably not alone, but in the form of compositions with other fragrances or flavors are used. Such fragrance or flavoring compositions containing compounds of the formula I [they can be prepared in a manner known per se, namely by adding the new compounds to known fragrance or Flavor compositions or mixtures of compounds I with natural or synthetic compounds or mixtures suitable as a component of fragrance or flavor compositions as active components also form the subject of the invention.

Due to their natural notes, the new disulfides are particularly suitable as odoriferous substances for modifying known compositions, e.g. B. Chypre type or floral notes.

The concentration of the new compounds can vary within wide limits depending on the intended use, for example between about 0.001 (detergents) and about 10% by weight (alcoholic solutions). The concentrations in perfume bases or concentrates can of course also be higher.

As flavorings, the compounds I can be used, for example, to produce or improve, reinforce, increase or modify fruit, meat or roasted notes in foods (meat, meat substitutes, sauces, bouillons, soups, vegetables, seasonings, snack foods, roasted products such as coffee or Cocoa, milk products such as cheese, curd cheese, yogurt, etc.), in luxury foods (tobacco, crackers, etc.) and beverages (lemonades, etc.).

The pronounced taste qualities enable the use in low concentrations. A suitable dosage ranges from about 0.001-10 ppm, preferably from about 0.1-10 ppm in the finished product, i.e. the flavored food, luxury food or drink.

The new disulfides can be mixed in the usual way with the ingredients used for flavoring compositions or added to such flavors. The aromas used according to the invention are understood to mean flavoring compositions which can be diluted in a manner known per se or distributed in edible materials.

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They can be converted into the usual forms of use, such as solutions, pastes or powders, by methods known per se. The products can be spray dried, vacuum dried or lyophilized.

Suitable carrier materials, thickeners, taste improvers, spices and auxiliary ingredients, etc., are suitable for the production of such customary use forms, for example:

Gum arabic, tragacanth, salts or brewer's yeast, Algi-nate. Carrageenan or similar absorbents; Maltol, dienale, spice oleoresins, smoke flavors; Cloves, diacetyl, sodium citrate; Monosodium glutamate, disodium inosine 5'-monophosphate (IMP), disodium guanosine 5-phosphate (GMP); or special flavors, water, ethanol, propylene glycol, glycerin.

In the following examples, the temperatures are given in degrees Celsius.

example 1

8.66 g (0.0429 mol) of diisopropyl azodicarboxylic acid are dissolved in 40 ml of chloroform. 6 g (0.0429 mol) of 2- (2-pyrazinylethyl) mercaptan are then added dropwise, followed by 4 drops of concentrated sulfuric acid. The reaction mixture is kept at the reflux temperature for 4 hours. The mixture is allowed to cool to room temperature, 20 ml of saturated sodium bicarbonate solution are added and the mixture is extracted 4 times with 50 ml of chloroform. The organic phases are combined, dried over anhydrous sodium sulfate and concentrated on a rotary evaporator at 40 ° / 12 mm Hg. The yield of crude N- [r-TTiia-3'-pyrazin-2-yl-propyl] -N, N-diisopropoxycarbonyl hydrazine is 16.6 g.

The product has the following analytical data: NMR (CDC13): 8.60-833 (m, 3H), 6.60 (s, broad, 1H), 5.22 (septet, J = 6Hz, 1H), 4. 96 (septet, J = 6Hz, 1H), 3.15 (s, 4H), 1.43 (d, J = 6Hz, 6H), 1.27 (d, J = 6Hz, 6H) ppm. IR (left): gangs etc. at 3350.1730, 1240, 1105, 755 cm-1.

The hydrazine derivative obtained above is dissolved in 160 ml of iso-propanol and mixed with 7.5 g (1,2-mol equivalent) of diisopropylethylamine. The reaction mixture is then cooled to 0 ° and excess methyl mercaptan is introduced. After the addition is complete, stirring is continued for 2 hours. It is extracted with 50 ml of saturated sodium bicarbonate solution and 4 times with 100 ml of chloroform. The combined organic phases are dried over anhydrous sodium sulfate and then concentrated on a rotary evaporator at 40 ° / 12 mm Hg. The crude product obtained is chromatographed on a chromatography column (150 g of silica gel), a mixture of hexane and ether in a ratio of 1: 4 being used as the eluent. The fractions are pooled and subjected to short path distillation in a Kugelrohr. In this way, 1.2 g of pure 2- (2-pyrazinylethyl) methyl disulfide are obtained. nD20 = 1.5863; Boiling point 85-95 ° / 0.035 mg Hg.IR (liq.): Bands etc. at 1520, 1470, 1430, 1400, 1300, 1160, 1110, 1060, 1020, 850, 830 cm-1.

Smell and taste: sulphurous, meaty, vegetable-like (leek, chives, garlic, onions, cauliflower).

Example 2

3 ml of bromine are added to 120 ml of diethyl ether precooled to 0 °, followed by 22.5 g (0.0696 mol) of crystallized lead rhodanide under an argon atmosphere. The reaction mixture is stirred until the color of the bromine has completely disappeared, which takes 2 hours. The lead salt is then filtered off, the filtrate is cooled to -5 ° and then 7.0 g (0.05 mol) of 2- (2-pyrazinylethyl) mercaptan, dissolved in 30 ml of ether, are added dropwise. After the addition has ended, the reaction mixture is stirred at 0 to -5 ° for 15 minutes, then poured onto ice and extracted 4 times with 50 ml of ether each time. The organic phases are combined, washed with 50 ml of water, dried over anhydrous sodium sulfate and concentrated on a rotary evaporator at 0 to 20 ° / 12 mm Hg. The crude 2- (2-pyrazinyI) ethylthiorhodanide (12 g) thus obtained is immediately further processed. [IR band (left) of the crude product 2080 cm-1].

Methyl mercaptan is introduced into 60 ml of freshly distilled dimethoxyethane cooled to −20 °. 27.5 ml (110% based on mercaptan) of a 2.8% n-butyl-lithium / hexane solution are added dropwise, a white suspension being formed. 12 g of the rhodanide obtained above, dissolved in 50 ml of dimethoxyethane, are now added dropwise at -20 to -30 °. The reaction mixture is allowed to assume room temperature. It is poured onto ice and extracted 4 times with 125 ml ether. The organic phases are combined, dried over anhydrous sodium sulfate and concentrated on a rotary evaporator at 40 ° / 12 mm Hg. The crude product is chromatographed on 150 g of silica gel, a mixture of hexane / ether in a ratio of 1: 4 being used as the eluent. The fractions are concentrated and subjected to short path distillation in a bulb tube at 90-92 ° / 0.03 mm Hg. In this way, 2.5 g (26.9% based on the mercaptan used) of pure 2- (2-pyrazinylethyl) methyl disulfide are obtained. nD20 = 1.5905.

Example 3

a) A solution of 8.15 g (0.055 mol) of trimethyloxonium tetrafluoroborate in 20 ml of nitromethane is added to a solution of 5.17 g (0.055 mol) of freshly distilled dimethyl disulfide in 10 ml of nitromethane, cooled to 0 °. After the addition has ended, the reaction mixture is stirred at this temperature for 90 minutes. A solution of 7 g (0.05 mol) of 2- (2-pyrazinethyl) -mer-captan and 6.45 g (0.05 mol) of diisopropylamine in 10 ml of nitromethane are then added dropwise at 0.degree. The reaction mixture is allowed to reach room temperature, 50 ml of saturated sodium bicarbonate solution and ice are added, and the mixture is extracted 4 times with 100 ml of chloroform. The organic phases are combined, dried over anhydrous sodium sulfate and then concentrated on a rotary evaporator at 40 ° / 12 mm Hg. The crude product obtained is chromatographed on 150 g of silica gel, a mixture of hexane: ether in a ratio of 1: 4 being used as the eluent. The fractions are combined and subjected to short path distillation in a bulb tube at 85-88 ° / 0.03 mm Hg. 4.25 g (45.7%) of pure 2- (2-pyrazinethyl) methyl disulfide are obtained.

Using the same method, dimethyl disulfide and l- (2-thiazolyl) -2-methylpropyl-mercaptan are used to obtain [l- (2-thiazolyl) -2-methylpropyl] methyl disulfide. nD20 = 1.5770. IR (left): gangs etc. at 1500, 1470, 1430, 1420, 1390, 1370, 1195, 1140, 1055, 730 cm-1.

Smell and taste: earthy, fruity (cassis), sulphurous, vegetable-like (celery).

The 2-pyridyl-methyl-disulfide is obtained from dimethyl disulfide and 2-mercapto-pyridine. nD20 = 1.6225. IR (left): gangs etc. at 1580, 1570, 1450, 1420, 1125, 770, 730 cm "-1. Smell and taste: earthy, sulphurous, green, vegetable-like (cauliflower, onions), like wild garlic, cheese.

Dimethyl disulfide and 2-mercapto-thiazole give 2-thiazolyl-methyl disulfide. nD20 = 1.6408. IR (left): gangs etc. at 1485, 1390, 1310, 1060, 1050, 725 cm "1.

Smell and taste: roasted notes, sulphurous, green, cabbage-like, chive-like, meaty (pork).

Dimethyl disulfide and 2-mercapto-pyrimidine give 2-pyrimidinyl-methyl disulfide. nD20 = 1.6620. IR (left): gangs etc. at 1560, 1385, 1200, 1175, 785 cm-1.

Smell and taste: earthy, spicy, vegetable-like (cauliflower, kohlrabi), like cheese.

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The (4,5-dimethyl-2-oxazolyl) methyl disulfide is obtained from dimethyl disulfide and 4,5-dimethyl-2-thiono-4-oxazoline. nD20 = 1.5598. IR (left): gangs etc. at 2950, 1638, 1495, 1435, 1225, 1175, 1102, 950, 745 cnT1.

Smell: spicy, «Maggi». Taste: spicy, chive-like, reminiscent of steamed mushrooms.

b) A solution of 4.18 g (0.022 mol) of triethyloxonium tetrafluoroborate in 12 ml of nitromethane is added dropwise to a solution of 2.86 g (0.022 mol) of diethyl disulfide in 8 ml of nitromethane (filtered through basic aluminum oxide) at reflux temperature. When the addition is complete, the reaction mixture is further stirred at 30-40 ° for 2 hours. A mixture (2 phases) of 2.22 g (0.02 mol) of 2-mercapto-pyridine and 2.58 g (0.02 mol) of diisopropylethylamine in 15 ml of nitromethane is then added dropwise at 30 ° and 2 Hours at about 30-40 °.

Working up is carried out according to Example 3a). 2.29 g (67% based on 2-mercapto-pyridine) of pure 2-pyridyl-ethyl disulfide are obtained. nD20 = 1.6059. IR (left): gangs etc. at 1580, 1570, 1455, 1425, 1125, 775, 730 cm-1.

Odor: sulphurous, onion-like, pungent.

Taste: onion-like, sulphurous, burning.

c) From 3.3 g (0.022 mol) of dipropyl disulfide, 3.26 g (0.022 mol) of trimethyloxonium tetrafluoroborate, 2.22 g (0.02 mol) of 2-mercapto-pyridine and 2.58 g (0.02 mol ) Diisopropylethylamine is obtained according to the method of Example 3b) 2-pyridylpropyl disulfide. Yield: 2.65 g (71.6% based on 2-mercapto-pyridine). nD20 = 1.5916. IR (left): gangs etc. at 1580, 1570, 1450, 1420, 1125, 770, 730 cm "1.

Smell: pungent, sulphurous, green, like chives. Taste: sulphurous, green, like chives.

d) From 3.3 g (0.022 mol) of diisopropyl disulfide, 3.26 g (0.022 mol) of trimethyloxonium tetrafluoroborate, 2.24 g (0.02 mol) of 2-mercapto-pyrimidine and 2.58 g (0.02 mol ) Di-isopropyl-ethylamine is obtained according to the method of Example 3b) 2-pyrimidinyl-isopropyl disulfide. Yield: 2.5 g (67.2% based on 2-mercapto-pyrimidine). nD20 = 1.5858. IR (liq.).): Gangs etc. at 1570, 1560, 1485, 1200, 1175, 1165, 1060, 785, 755 cm "1.

Smell: pungent, sharp, green, like onions.

Taste: pungent, burning, like onions.

e) From 2.08 g (0.022 mol) of dimethyl disulfide, 4.18 g (0.022 mol) of triethyloxonium tetrafluoroborate, 2.24 g (0.02 mol) of 2-mercapto-pyrimidine and 2.58 g (0.02 mol ) Di-isopropyl-ethylamine is obtained according to the method of Example 3b) 2-pyrimidinyl-methyl-disulfide: Yield 1.8 g (57% with respect to 2-mercapto-pyrimidine). nD20 = 1.62 1 8.IR (liq.): bands etc. at 1560.1385.1200.1175, 785 cm "1.

f) From 2.68 g (0.022 mol) of diethyl disulfide, 3.26 g (0.022 mol) of trimethyloxonium tetrafluoroborate, 2.24 g (0.02 mol) of 2-mercapto-pyrimidine and 2.58 g (0.02 mol ) Di-isopropyl-ethyl-amine is obtained according to the procedure of Example 3b) 2-pyrimidinyl-ethyl-disulfide. Yield: 2.2 g (64% based on 2-mercapto-pyrimidine). nD20 = 1.6025. IR (left): gangs etc. at 1570, 1555, 1385, 1200, 1175, 785, 755 cm "1. Smell: sulfurous, like vegetables (cooked onions). Taste: sulfurous, reminiscent of cooked onions.

Example 4

5.65 g (0.483 mol) of 2-mercapto-thiazole and 10 g (0.483 mol) of N-ethylthiophthalimide are stirred in 60 ml of benzene for 60 hours at room temperature. The reaction product is then filtered through paper and then through 15 g of silica gel. Concentration gives a reddish yellow, still liquid product. A high vacuum distillation over a Vigreux column gives 6.65 g (75%) of a yellowish product with the following data: boiling point 65-66 ° / 0.03 mm Hg; nD20 = 1.6 1 90. It is the 2-thiazolyl-ethyl disulfide, which is present in a purity of 95%. IR (left): bands at 3120, 3000, 1485, 1390, 1260, 1155, 1060, 1040, 755, 725 cm "1.

Smell and taste: sulphurous, roasted, meaty, vegetable-like (leek, onions, cabbage), like potatoes.

Using the same method, 2- (l-methyl-imidazolyl) ethyl disulfide is obtained from l-methyl-2-mer-capto-imidazole and N-ethylthiophthalimide. nD20 = 1.5890. IR (left): bands at 3150, 3000, 1610, 1460, 1415, 1285, 1125, 920, 760,

695 cm-1.

Smell and taste: sulphurous, roasted, vegetable-like (leek, onions), like boiled eggs.

2-Thiazolylbutyl disulfide is obtained from 2-mercapto-thiazole and N-butylthiophthalimide. nD20 = 1.5890. IR (left): bands at 3120, 3000, 1485, 1390, 1310, 1060, 1045, 725 cm "1.

Smell and taste: sulphurous, slightly green, spicy (garlic), sweet, vegetable-like (leek, onions, celery, chives).

The 2- (l-methylimidazolyl) isopropyl disulfide is obtained from l-methyl-2-mercapto-imidazole and N-isopropyl-thiophthalimide. nD20 = 1.5736. IR (left): gangs etc. at 3130, 3000, 1505, 1455, 1285, 1015, 760, 695 cnT1.

Smell and taste: meaty, roasted, spicy, like onions, eggs.

Starting from thenyl mercaptan and N-ethyl thiophthalimide, the ethyl thenyl disulfide is obtained. nD20 = 1.6044. IR (left): gangs etc. at 3000, 1450, 1250, 1035, 850, 700 cm-1. Smell: pungent, spicy, like garlic.

Flavor: spicy, like garlic.

The propyl-thenyl disulfide is obtained from thenyl mercaptan and N-propylthiophthalimide. IR (left): gangs above all. at 2990.1455.1220.1030, 850, 700 cm-1.

Smell: spicy, green (chives).

Taste: slightly spicy, earthy, green.

Starting from l-methyl-2-mercapto-imidazole and N-propylthiophthalimide, the 2- (l-methyl-imidazolyl) propyl disulfide is obtained. nD20 = 1.5756. IR (left): gangs etc. at 3105, 2980, 1500, 1450, 1275, 1115, 1010, 750, 685 cnr1. Smell: sulphurous, green, vegetable-like.

Taste: sulphurous, vegetable-like.

Starting from 2-mercapto-thiazole and N-isopropyl-thiophthalimide, the 2-thiazolyl-isopropyl disulfide is obtained. nD20 = 1.5984. IR (left): gangs etc. at 3010, 1490, 1395, 1160, 1065, 1050.730 cm-1.

Smell: sulphurous, weak roasted notes.

Taste: sulphurous, weak roasted notes, burning.

Starting from l-methyl-2-mercaptomethyl-pyrrole and N-ethylthiophthalimide, the (l-methyl-2-pyrro-lyl) methylethyl disulfide is obtained. nD20 = 1.5816. IR (left): gangs etc. at 3140, 3000, 1495, 1310, 1250, 1090, 720 cnr1. Smell: sweet, green, sulphurous (onion-like).

Taste: sulphurous (onion-like), sweet.

Starting from 4,5-dimethyl-2-thiono-4-oxazoline and N-ethylthiophthalimide, the (4,5-dimethyl-2-oxazo-lyl) ethyl disulfide is obtained. nD20 = 1.5467. IR (left): gangs etc. at 3020, 2970, 1640, 1450, 1175, 1105, 950, 745 cm-1.

Smell and taste: spicy, «Maggi», mushroom-like.

Starting from 4-ethyl-2-thiono-4-oxazoline and N-ethylthiophthalimide, the (4-ethyl-2-oxazolyl) ethyl disulfide is obtained. nD20 = 1.5549. IR (left): gangs etc. at 3000, 2970, 1590, 1485, 1250, 1135, 1080, 950, 760 cnr1.

Smell: spicy (lovage), slightly sulphurous, cheese-like. Taste: «Maggi», onion-like, reminiscent of full-ripe soft cheese.

Starting from 4,5-dimethyl-2-thiono-4-oxazoline and N-propylthiophthalimide, the (4,5-dimethyl-2-oxazo-ly) propyl disulfide is obtained. nD20 = 1.5321. IR (left): gangs etc. at

5

10th

15

20th

25th

30th

35

40

45

50

55

60

65

2980, 1635, 1450, 1225, 1173, 1100, 945, 740 cm-1.

Smell and taste: slightly sulphurous, like chives and ramsons.

Example 5

A mixture of 8.26 g (0.052 mol) of 2- (4-methyl-5-thiazolyl) ethyl mercaptan and 33.07 g (0.208 mol) of dimethyl disulfide is mixed with 50 mg of sodium hydride (50% dispersion in oil ) added and heated to reflux temperature for 4 hours. The reaction mixture is allowed to cool, filtered through 10 g of aluminum oxide (activity level I, neutral), washing with ether, and concentrated in vacuo. The crude product obtained (9.5 g) is distilled through a Hempel column under high vacuum, 6.45 g of [2- (4-Me-thyI-5-thiazolyl) ethyl] methyl disulfide being obtained. Boiling point 104-110 ° / 0.02 mm Hg; nD20 = 1.5944; Purity 99%. IR (left): gangs etc. at 3100, 2960, 1545, 1415, 1220, 955, 1005, 840, 795 cnr1.

Odor: sulphurous, spicy (mustard).

Taste: sulphurous, spicy, biting.

Example 6

a) 8 g (0.058 mol) of phenättiyl mercaptan are added to a suspension of 12 g (0.058 mol) of N-ethylthiophthalimide in 70 ml of benzene with vigorous stirring. After a few minutes, a homogeneous solution forms, from which phthalimide slowly begins to precipitate. After stirring for 48 hours at room temperature, the mixture is filtered through a paper filter, the filtrate is concentrated in vacuo and the crude 2-phenylethyl-ethyl disulfide (12 8 g) obtained is distilled through a Vigreux column. 10.5 g of pure product (91% of th.) Are obtained which have a purity of 99% (gas chromatographic determination). Boiling point 87-88 mm Hg / 0.04 mm Hg; nD20 = 1.5742. IR ~ (Bq.): Gangs etc. at 3020, 1610, 1505, 1460, 1260, 710 cm-1.

Smell: sulphurous, spicy, sweet.

Taste: spicy, sweet, somewhat sulphurous.

b) Starting from 5 g (0.033 mol) of 3-phenylpropylmer-captan and 6.65 g (0.033 mol) of N-ethylthiophthalimide analogously to Example 6a), after distillation, 4.85 g of 3-phenylpropyl-ethyl disulfide (purity 98 %) receive. Boiling point 90-91 ° / 0.04 mm Hg; nD20 = 1.563 9.IR (liq.): bands etc. at 3080, 2980, 1950, 1605, 1700, 1455, 1250, 845, 805 cnr1. Smell: sulphurous, green, vegetable-like.

Taste: vegetable-like, sulphurous, green.

c) Starting from 5 g (0.028 mol) of 5-phenylpentyl-mercap-tan and 5.62 g (0.028 mol) of N-ethylthiophthalimide analogously to Example 6a), after filtration through silica gel (washing with hexane) and Kugelrohr distillation, 2.98 g 5 -Phenyl-pentyl-ethyl disulfide (purity: 99%) obtained. Boiling point: 150-180 ° (oven temperature) / 0.02 mm Hg; nD20 = 1.5512. IR (left): gangs etc. at 2930, 1950, 1600, 1590, 1445, 1250, 1025, 840, 795 cm-1.

Smell: sulphurous, green, floral.

Taste: floral, green.

d) Starting from 5.6 g (0.048 mol) of 2-furylethyl-mercap-tan and 9.1 g (0.048 mol) of N-ethylthiophthalimide, analogously to Example 6a) and after chromatography on 100 g of silica gel (elution with toluene) 2, 38 g of ethyl 2- (2-furyl) ethyl disulfide (purity: 96%) were obtained. nD20 = 1.54 5 0.IR (liq.): bands etc. at 3000, 1600, 1505, 1150, 1010, 735 cm- '.

Odor: sulphurous, pungent, of onions.

Taste: sulphurous, green, slightly flowery.

Example 7

A broth can be made as follows:

623 568

A. 20.0 g each of a mixture A or B

A B

Parts by weight

2-pyrimidinyl-methyl disulfide

-

0.5

Diallyl disulfide

60

60

Allyl mercaptan

0.5

0.5

Mustard oil synth.

2.5

2.5

Dimethyl disulfide

0.5

-

2,4-decadienal (10% in ethyl alcohol)

1

1

Caprinaldehyde

0.1

0.1

Maltol

2.5

2.5

Butyric acid (10% in ethyl alcohol)

0.2

0.2

Benzyl alcohol

132.7

132.7

200.0

200.0

are mixed with 1000 g of onion oil. At a dosage of 20 g / 1001 broth, the smell and taste of the broth prepared with composition A are bland; the broth prepared with composition B has an excellent onion taste.

B. 20.0 g of a mixture A or B

A B

Parts by weight

2- (l-methylimidazolyl) ethyl disulfide

-

20th

Diallyl disulfide

60

40

Allyl mercaptan

0.5

0.5

Mustard oil synth.

2.5

2.5

Dimethyl disulfide

0.5

0.5

2,4-decadienal (10% in ethyl alcohol)

1.0

1.0

Caprinaldehyde

0.1

0.1

Maltol

2.5

2.5

Butyric acid (10% in ethyl alcohol)

0.2

0.2

Benzyl alcohol

132.7

132.7

200.0

200.0

mixed with 1000 g of onion oil.

At a dosage of 20 g / 1001 broth, the broth flavored with composition A, a conventional aroma composition, has a metallic aftertaste in addition to the unsatisfactory onion note. By partially replacing the diallyl disulfide with 2- (l-methylimidazolyl) ethyl disulfide (composition B), the flavored broth gains a pleasant, sweet note reminiscent of cooked onions.

C. 20.0 g each of a mixture A or B

A B

Parts by weight

2-pyridyl-ethyl disulfide

0.5

Diallyl disulfide

60

60

Mustard oil synth.

2.5

2.5

Dimethyl disulfide

0.5

-

Methylthiopropionic acid methyl ester

0.5

0.5

Leaf alcohol

2.0

2.0

Diacetyl (10% in ethanol)

0.2

0.2

Maltol

2.0

2.0

Benzyl alcohol

132.3

132.3

2000.0

200.0

are mixed with 1000 g of onion oil.

7

5

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15

20th

25th

30th

35

40

45

50

55

60

65

623 568

8th

At a dosage of 20 g / 1001 broth, the smell and taste of the broth prepared with composition A are bland.

The broth prepared with composition B has an excellent onion taste; a slightly biting, burning note reminiscent of fresh onions is perceived.

D. 20.0 g each of a mixture A or B

A B

Parts by weight

2-pyrimidinyl-ethyl disulfide

-

0.5

Diallyl disulfide

60

60

Mustard oil synth.

2.5

2.5

Dimethyl disulfide

0.5

-

Methylthiopropionic acid methyl ester

0.5

0.5

Leaf alcohol

2.0

2.0

Diacetyl (10% in ethanol)

0.2

0.2

Maltol

2.0

2.0

Benzyl alcohol

132.3

132.3

200.0

200.0

are mixed with 1000 g of onion oil.

At a dosage of 20 g / 1001 broth, the smell and taste of the broth prepared with composition A are bland.

When dimethyl disulfide is replaced by 2-pyrimidinyl-ethyl disulfide, the onion taste of the broth is advantageously changed with the same dosage of composition B, in which a slightly bitter-biting note reminiscent of fresh onions now appears.

Example 8

A brown meat sauce can be obtained as follows: 125.0 g of a mixture consisting of

Parts by weight

Table salt

8.00

Monosodium glutamate

2.67

sugar

4.00

HVP, type 4 BE (hydrolized vegetable

proteins)

6.40

Onion powder

1.84

Caramel powder

1.12

Tomato powder

5.33

VEE cream (artificial cream based on

vegetable oils, spray dried)

26.67

Laurel, soluble

0.04

Pepper white, soluble

0.08

Thyme, soluble

0.04

Marjoram, soluble

0.04

Nutmeg, soluble

0.04

Modified waxy mize com starch (corn starch)

18.67

White flour

25.06

100.00

are stirred into 1 liter of cold water and boiled with constant stirring. After a cooking time of 3 minutes, the

The taste of this brown meat sauce is initially bland and not typical. After adding 2 ppm of 2-thiazolyl-methyl-disulfide, an excellent meat aroma with a distinct roasted onion-like, meaty note is found.

Example 9

An onion cream soup can be obtained as follows:

A. 140.0 g of a mixture consisting of

Parts by weight

margarine

28.70

wheat flour

18.61

Dried onions

12.52

Skimmed milk powder

12.52

Potato starch

12.52

Onion powder

3.75

Table salt

8.75

Monosodium glutaminate

1.25

HVP (hydrolized vegetable proteins)

1.25

Pepper white, ground

0.13

100.00

pour in 1 liter of cold water, boil and take off the fire as soon as the onion pieces are done.

The taste of this onion soup is bland, not pronounced, the aroma hardly comes into its own. By adding 2 ppm [1- (2-thiazolyl-2-methylpropyl)] methyl disulfide, the onion aroma present is advantageously enhanced. The soup also gets a pleasant vegetable-like, spicy note that is reminiscent of celery.

B. 140.0 g of a mixture consisting of

Parts by weight

Margarine 28.70

Wheat flour 18.61

Dried onions 12.52

Skimmed milk powder 12.52

Potato starch 12.52

Onion powder 3.75

Cooking Salt 8.75

Monosodium glutaminate 1.25

HVP (hydrolized vegetable proteins) 1.25

Pepper white, ground 0.13

100.00

pour in 1 liter of cold water, boil and take off the fire as soon as the onion pieces are done.

The taste of this onion soup is bland, not very pronounced, the aroma is only weak. The addition of 0.5 ppm of 2-thiazolyl-ethyl-disulfide enhances the onion aroma in an extremely advantageous manner, as a pronounced, pleasant note of roasted onions and a weak note of bouillon appear.

s

10th

15

20th

25th

30th

35

40

45

50

55

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65

9

623 568

Example 10

A clear meat soup can be obtained as follows: 20.0 g of a mixture consisting of

Parts by weight

Cooking salt 50.00

Monosodium glutaminate 20.04

Caramel powder 0.20

Nutmeg, soluble 0.06

Carnations, soluble 0.06

Coriander, soluble 0.08

Pepper white, soluble 0.06

HVP, type 3 HI (hydrolized vegetable proteins) 8.90 HVP, type RF-B (hydrolized vegetable proteins) 2.60

Vegetable fat, mp. 40 ° C 17.00

Fried onion powder 1.00

100.00

are added to 1 liter of hot water.

The taste of this clear meat soup is initially unsatisfactory (meat and onion taste weak).

a) By adding 3-5 ppm of 2- (2-pyrazinylethyl) methyl disulfide, meat and onion flavors are enhanced in an extremely advantageous manner.

b) By adding 3-5 ppm of 2-pyridyl-propyl-disul-fid, the meat taste is enhanced in an advantageous manner, and a spicy green note now appears, which is reminiscent of chives and harmonises well with the meat taste.

Example 10A

A clear broth can be composed as follows:

20.0 g of a mixture consisting of:

Parts by weight

salt

45.0

Sodium glutamate

20.0

sugar

2.4

Hydrolyzed vegetable protein

(e.g. HVP type 4 BE and type 245)

14.0

Celery powder

1.6

Onion powder

1.6

Garlic powder

0.6

Turmeric powder

0.3

Pepper powder, white

0.1

Potato starch

4.4

Vegetable fat (mp 40 ° C)

10.0

100.0

are poured into 1 liter of hot water.

The taste of this soup is bland, weak and not convincing.

By adding 3-5 ppm (4,5-dimethyl-2-oxa-zolyl) ethyl disulfide, the existing, weak meat taste is significantly enhanced, along with a pleasant, spicy note reminiscent of roasted onions, which is associated with the existing meat taste harmonized perfectly.

Example 11

A broth can be obtained as follows:

18.0 g of a mixture consisting of:

Parts by weight

Cooking salt 45

Monosodium glutaminate 20

Sugar 2.4

HVP, type 4 BE (hydrolyzed vegetable proteins) 5.6

HVP, Type 245 (hydrolyzed vegetable proteins) 8.4

Celery powder 1.6

Onion powder 2.2

Pepper, white 0.4

Potato starch 4.4

Hardened vegetable oil 10

100.0

are poured into 1 liter of hot water.

The taste of this broth is bland and not pronounced. The addition of 2 ppm of 2- (l-methylimidazolyl) isopropyl disulfide advantageously enhances the meat taste. In addition to the pronounced meat note, the meat broth thus obtained also has a pleasant vegetable-like note.

Example 12

An exotic fruit aroma can have the composition A or B:

A B

Parts by weight

2-thiazolylbutyl disulfide

-

1.5

Propyl mercaptan (10% in ethyl alcohol)

2.5

1.0

Leaf alcohol (10% in ethyl alcohol)

1

1

a-pinene

5

5

Isobutyric acid linearyl ester

5

5

Amyl acetate

7

7

Propionic acid geranyl esters

10th

10th

Aldehyde C 16

12

12

Aldehyde C18 (10% in ethyl alcohol)

3rd

3rd

Maltol (2% in ethyl alcohol)

4th

4th

Aldehyde C 14

25th

25th

Garlic oil (0.5% in ethyl alcohol)

250

250

Propylene glycol

670.5

670.5

1000.0

1000.0

The partial replacement of propyl mercaptan with 2-thiazo-lyl-butyl disulfide (composition B) results in a much more typical, fruity, sweet note that is strongly reminiscent of the durian fruit.

Example 13 A

A vegetable flavor can have the composition A or B:

A B

Parts by weight

2-pyridylmethyl disulfide

-

5

Methylchavicol (1% in ethyl alcohol)

0.5

0.5

garlic oil

2.0

2.0

Thymol (1% in ethyl alcohol)

0.5

0.5

Isobutyric acid piperonylester

(1% in ethyl alcohol)

3rd

3rd

Nona-2,6-dienal (1% in ethyl alcohol)

5

5

Ethyl acetate (1% in ethyl alcohol)

5

5

3-hexenyl acetylacetate

10th

10th

Ethanol

974

969

1000.0

1000.0

5

10th

15

20th

25th

30th

35

40

45

50

55

60

65

623 568

10th

The presence of 2-pyridyl-methyl-disulfide in composition B above enhances the vegetable-like note, which is now strongly reminiscent of fresh, green beans.

Example 13B

A vegetable flavor can have the composition A or B:

A B

Parts by weight

2- (1-methyl-2-imidazolyl) propyl

disulfide (10% in ethanol)

10.0

Garlic oil (l% o in ethanol)

2.0

2.0

Thymol (1% in ethanol)

0.5

0.5

Isobutyric acid piperonylester

(1% in ethanol)

3.0

3.0

Ethyl acetate (1% in ethanol)

5.0

5.0

3-hexenyl acetylacetate

8.0

8.0

Methional

2.0

2.0

Ethanol

979.5

969.5

1000.0

1000.0

The smell of conventional composition A is inferior to the smell of composition B.

Only the addition of 2- (l-methyl-2-imidazolyl) propyl disulfide gives a distinctly enhanced, vegetable-like, green note that is reminiscent of fresh green beans.

Example 14

An onion aroma can have the composition A or B:

A B

Parts by weight

2-pyrimidinyl-ethyl disulfide

Onion oil

Onion powder

Maltodextrin (in powder form)

2.0 400.0 598.0

The comparison of the conventional thread aroma A with the new composition B shows that the presence of 2-phenyl-ethyl-ethyl disulfide (composition B) results in a noticeable improvement in taste. The impression of cooked onions is only present in composition B.

Example 16

An onion aroma can have the composition A or B:

10th

15

25th

4.0 2.0 400.0 594.0

1000.0 1000.0

The flavor and taste of an onion powder produced with composition A appear bland in comparison to an onion powder produced with composition B.

The addition of 2-pyrimidinyl-ethyl disulfide greatly improves the smell and taste of the onion powder. A clear, very pleasant new note comes to the fore, strongly reminiscent of cooked onions.

Example 15

An onion aroma can have the composition A or B:

A B

Parts by weight

(l-methyl-2-pyrrolyl) methyl ethyl disulfide (10% in ethanol)

Onion oil ethanol

20 980

1000

5

20 975

1000

20th

The smell of conventional composition A is inferior to that of composition B.

The addition of (l-methyl-2-pyrrolyl) methyl ethyl disulfide greatly improves the smell. The note reminiscent of cooked onions only appears clearly in case B.

Example 17

A soy flavor can have composition A or B:

A B

Parts by weight

35

3-phenylpropyl ethyl disulfide

-

5

2,4-decadienal (10% in ethanol)

0.8

0.8

2-hexenal

10th

10th

Capronaldehyde

20th

20th

Dimethyl sulfide

20th

15

Methional

40

40

Piperidine

60

60

Ethanol

849.2

849.2

1000.0

1000.0

45

A comparison of A and B shows that the conventional composition A has a strong odor and taste decrease. By partially replacing the dimethyl sulfide with 3-50 phenylpropyl-ethyl disulfide, the note reminiscent of Soya comes to the fore much more.

Example 18

Senfaromas (A and B)

55

A B

Parts by weight

A

B

[2- (4-methyl-5-thiazolyl) ethyl] -

Parts by weight

60 methyl disulfide

-

1

Methylchavicol

2nd

2nd

2-phenylethyl-ethyl disulfide

Eugenol

3rd

3rd

(0.1% in ethanol)

0.5

Mace oil

5

5

Onion oil

1-0

1.0

Thymol (10% in ethanol)

30th

30th

Ethanol

10.0

10.0

65 synthetic mustard oil

60

60

Migliol (neutral oil)

989.0

988.5

Ethanol

900

899

1000.0

1000.0

1000

1000

11

623 568

The smell and taste of the mustard composition A are not very pronounced.

By adding [2- (4-methyl-5-thiazolyl) ethyl] methyl disulfide (composition B), on the one hand, the spicy character is advantageously enhanced. There is also a biting note, which is desirable for mustard.

Example 19

A horseradish aroma can have the composition A or B:

A B

Parts by weight

2-thi azolyl isopropyl disulfide

-

1.0

acetic acid

0.6

0.6

Clove oil

1.0

1.0

Mace oil

1.4

1.4

1-acetoxy-2-butyl-ethane

7.0

7.0

Mustard oil synth.

30.0

30.0

Ethanol

960.0

959.0

1000.0

1000.0

A comparison of composition B with conventional composition A immediately shows that the latter drops sharply.

The addition of 2-thiazolyl-isopropyl-disulfide significantly improves the smell and taste by making the biting-burning note reminiscent of horseradish much more prominent.

Example 20

A garlic flavor can have the composition A or B:

A B

Parts by weight

Ethyl-thenyl-disulfide (0.1% in ethanol)

0.5

garlic oil

1.0

1.0

alcohol

10th

10th

Tween 80 (polyoxyethylene sorbitan monooleate)

30th

30th

Propylene glycol

30th

30th

Sorbitol

35

35

water

894

893.5

1000.0

1000.0

The smell and taste of the conventional composition A drop sharply compared to B.

The addition of ethyl-thenyl-disulfide significantly improves the garlic character, since only in case B does the characteristic sulfurous-spicy note come to the fore.

Example 21 Mushroom Soup (Bag Soup)

A mixture consisting of:

Parts by weight

Skimmed milk powder 35

Margarine 25

White flour 26

Table salt 5.5

dried mushroom pieces 4,5

Parts by weight of natural mushroom aroma

2.5

Sodium glutaminate

1.6

Onion powder

0.8

sugar

0.4

Pepper aroma, soluble

0.4

Clove aroma, soluble

0.3

100.0

is dissolved in water in the usual way and boiled.

The taste of this soup is not typical enough in relation to the mushroom aroma.

By adding 3-5 ppm propyl-thenyl-disulfide, the existing mushroom aroma is activated. The soup looks stronger and fresher. The impression of using fresh mushrooms is created.

Example 22

A honey flavor can have the composition A or B:

A B

Parts by weight

5-phenylpentyl ethyl disulfide

-

2nd

Methyl acetophenone

0.5

0.5

Geranium oil

0.3

0.3

Ethyl vanillin

6

6

Phenylacetic acid

12

12th

Ethyl pelargonate

30th

30th

Amyl acetate

200

200

Ethyl acetate

100

100

V aleric acid amyl ester

250

250

Ethanol

401.2

399.2

1000.0

1000.0

A comparison of A and B shows that the conventional composition A falls sharply.

By adding 5-phenylpentyl-ethyl-disulfide, an olfactory improvement occurs. The ester note is now muffled; a faint floral note comes to the fore, which is strongly reminiscent of blossom honey.

Example 23

A fragrance composition (floral note) can have the composition A or B:

A B

Parts by weight

Ethyl 2- (2-furyl) ethyl disulfide

_

5

Methylheptenone

5

5

Linalool

5

5

Acetic acid in alkyl ester

10th

10th

Citronellol

30th

30th

Geraniol

40

40

Ethanol

910

905

1000

1000

A comparison of A with B immediately shows that the conventional composition A drops sharply.

The addition of ethyl 2- (2-furyl) ethyl disulfide increases the floral-green note of the composition; it is intensely reminiscent of Géranium.

5

10th

15

20th

25th

30th

35

40

45

50

55

60

65

Claims (3)

623 568 2 PATENT CLAIMS 1. Process for the preparation of compounds of the formula RHY ^ -S-S-R, (I) wherein Ra is optionally substituted phenyl, furyl or a nitrogen and / or sulfur and optionally additionally contains oxygen as ring members, optionally substituted monocyclic radical, R2 is lower alkyl or lower alkenyl and Y is optionally mono- or di-substituted methylene and n = 0 Is -5, or 2-5 if Ra is phenyl or furyl, with the exception of 2-thienyl-ethyl disulfide, 2-pyridylmethyl disulfide, 4-chlorophenyl-methyl disulfide and 3-nitrophenyl-isopropyl disulfide, characterized in that that you have a compound of the formula A — S — N — NH — COOR (II) COOR or A-S-SCN (III) or S II A-S-S-COCH3 (IV) or A-S-S-A (V) or A-S-N ^ X (VI) or a — s-sCL z © (vn) R with a mercaptan of the formula A-SH (VIII) implements where in one reactant A represents a radical Ri (Y) n and in the other reactant A represents a radical R2, Y and n are as defined above, but n should only be 1-4 in the case of formulas II, III and V, R represents lower alkyl, X is the diacyl radical of an aliphatic or aromatic dicarboxylic acid and Ze represents an anion. 2. Fragrance and / or flavor composition, characterized in that it is a compound of the formula as an active component Ri— (Y) “S — S — R2 (I) contains wherein Rx optionally substituted phenyl, furyl or a nitrogen and / or sulfur and optionally additionally containing oxygen as ring members, optionally substituted monocyclic radical, R2 lower alkyl or lower alkenyl and Y optionally mono- or di-substituted methylene and n = 0 -5, or 2-5 if Ra is phenyl or furyl, with the exception of 2-thienyl-ethyl-disulfide, 2-pyridylmethyl-disulfide, 4-chlorophenyl-methyl-disulfide and 3-nitrophenyl isopropyl disulfide.