Abstract:
Novel thiazolidines, a process for their manufacture, and odorant and/or flavorant compositions containing the novel compounds are disclosed.

Description:
FIELD OF THE INVENTION 
     This invention relates to the fields of odorants and/or fragrances. 
     SUMMARY OF THE INVENTION 
     The present invention relates to thiazolidines as odorant and/or flavoring substances. More particularly, the invention is concerned with odorant and/or flavoring compositions containing thiazolidines and with a method of imparting an odor and/or flavor to products using thiazolidines. The invention is also concerned with certain thiazolidines per se and a process for the manufacture thereof. 
     DESCRIPTION OF THE PREFERRED EMBODIMENTS 
     The odorant and/or flavoring compositions provided by the present invention contain as an essential odor- and/or flavor-imparting ingredient a thiazolidine of the general formula ##EQU1## wherein R 1  represents a hydrogen atom and 
     R 2  represents an aliphatic C 2-10  hydrocarbon group (other than a C 3-6  isoalkyl group), an aliphatic C 1-10  hydrocarbon group substituted by a group X, or a group R 3  ; 
     R 3  represents an araliphatic C 7-10  hydrocarbon group, a 5- or 6- membered monocyclic, carbocyclic or heterocyclic aromatic group, a dioxolane group which may be sutstituted or a group --COOR 4 , 
     X represents an oxo group which may be ketalised or a group --COOR 4 , --SR 5  or --OR 5  ; 
     R 4  represents a C 1-6  alkyl group and R 5  represents a hydrogen atom or a C 1-6  alkyl or C 1-6  acyl group or 
     R 1  and R 2  each independently represents an aliphatic C 1-10  hydrocarbon group, which may be substituted by a group X, or a group R 3  or 
     R 1  and R 2  together represent a --(CH 2 ) 4-7  group. 
     Aliphatic C 2-10  hydrocarbon groups can be straight-chain or branched-chain, unsaturated, preferably mono-olefinically unsaturated, or saturated groups. C 3-6  isoalkyl groups are the isopropyl, isobutyl, isopentyl and isohexyl groups. Examples of araliphatic C 7-10  hydrocarbon groups are the benzyl and phenethyl groups. Examples of 5- or 6-membered monocyclic, carbocyclic or heterocyclic aromatic groups are the phenyl, furyl, pyrrolyl, thienyl, imidazolyl, thiazolyl, pyridyl and pyrazyl groups. An example of a dioxolane group which may be substituted is the 2,2-dimethyl-4-dioxolanyl group. A C 1-6  acyl group is preferably derived from an aliphatic monocarboxylic acid such as formic acid, acetic acid or propionic acid. Examples of ketalised oxo groups are the dimethoxy, diethoxy, methylenedioxy, ethylenedioxy and phenylenedioxy groups. 
     Examples of thiazolidines of formula I in which R 1  represents a hydrogen atom are 2-ethyl-, 2-propyl-, 2-butyl-, 2-secbutyl-, 2-pentyl-, 2-hexyl-, 2-heptyl-, 2-(2-methylthioethyl)-, 2-ethoxycarbonyl-, 2-hydroxymethyl-, 2-phenyl-, 2-benzyl-, 2-(2-furyl)- and 2-(2-pyrrolyl)-thiazolidine. Examples of thiazolidines of formula I in which R 1  and R 2  each independently represent an aliphatic C 1-10  hydrocarbon group, which may be substituted by a group X, or a group R 3  or in which R 1  and R 2  together represent a --(CH 2 ) 4-7  group are 2-methyl-2-(4-methyl-3-penten-1-yl)-, 2-acetyl-2-methyl-, 2-methyl-2-isopropyl-, 2-(1-hydroxyethyl)-2-methyl-, 2-hydroxymethyl-2-methyl-, 2-ethoxycarbonyl-2-methyl-, 2,2-dimethyl-, 2,2-dipropyl-, 2-ethyl-2-methyl-, 2-hexyl-2-methyl-, 2,2-tetramethylene- and 2,2-pentamethylene-thiazolidine. 
     A group of novel thiazolidines which are subgeneric to the compounds of formula I referred to earlier, and which also form part of this invention, can be generically formulated thus: ##EQU2## wherein R 6  represents a hydrogen atom or the methyl, ethyl, ethoxycarbonyl, ethoxycarbonylmethyl or acetoxymethyl group and 
     R 7  represents the butyl, secbutyl, pentyl, decyl, 4-methyl-3-pentenyl, dimethoxymethyl, 2-methylthioethyl, 2-furyl, 2-(5-methylfuryl), 2-thienyl, 2-(5-methylthienyl), 2-pyrrolyl, 2-(N-methylpyrrolyl), pyridyl or 4-(2,2-dimethyldioxolanyl) group when R 6  represents a hydrogen atom; or represents the isopropyl, isobutyl, 4-methyl-3-pentenyl, 1-hydroxyethyl, acetyl, propionyl, acetoxymethyl, 2-(1-acetoxyethyl), 3-hydroxypropyl or 2,2-dimethoxyethyl group when R 6  represents the methyl group; or represents the butyl or acetyl group when R 6  represents the ethyl group; or represents the ethoxycarbonyl or 1-ethoxycarbonyl-ethyl group when R 6  represents the ethoxycarbonyl group; or represents the ethoxycarbonylmethyl group when R 6  represents the ethoxycarbonylmethyl group; or represents the acetoxymethyl group when R 6  represents the acetoxymethyl group. 
     The thiazolidines of formula I or formula II can be manufactured according to known procedures; for example, by condensing cysteamine with a keto compound of the formula R 1  --CO--R 2  or R 6  --CO--R 7 . The condensation can be carried out in the presence of, or in the absence of, a solvent. Suitable solvents include water, alcohols such as methanol, ethanol etc, ethers such as diethyl ether, dioxan, tetrahydrofuran etc, hydrocarbons such as benzene, toluene etc, halogenated hydrocarbons such as methylene chloride, chloroform etc, amides such as dimethylformamide etc. Preferred solvents are methanol and ethanol (method A hereinafter) or benzene (method B hereinafter), the condensation proceeding particularly well in the latter case with azeotropic removal of the water which is formed. The molar proportion of cysteamine to keto compound conveniently amounts to 1:1, although one or both condensation components can be employed in excess. Cysteamine can be used as such or in the form of an ammonium salt with an organic or inorganic acid. In the latter case, cysteamine can be liberated in situ by means of a base. It can also be generated in situ from suitable precursors (e.g. from ethyleneimine with hydrogen sulphide). 
     The keto component can be used as such or in protected form (e.g. as the acetal or ketal), in the latter case the condensation conditions being chosen so that the free keto compound is formed in situ. The condensation is conveniently carried out at a temperature between 0°C and 150°C, preferably between room temperature and the boiling temperature of the solvent used. The duration of the condensation amounts to between about 5 minutes and 24 hours depending on the temperature and reactivity of the keto compound used. The condensation is advantageously carried out in an inert gas atmosphere (e.g. nitrogen or argon). 
     The isolation of the condensation product can be carried out according to known methods; for example, by concentrating the solution, taking up the residue in an organic extraction agent, washing and drying the organic phase and distillation or by filtering the concentrated solution through aluminium oxide and subsequent distillation. 
     The thiazolidines of formula I are distinguished by particular fragrance and flavour qualities, different notes in the foreground appearing according to the nature of the substituents in the 2-position. The aroma spectrum of the thiazolidines of formula I can extend from ester like-fruit like, green, mushroom- and vegetable-like (bean, asparagus, onion, radish), through nutty, butter-like, fatty, caramellous to smoky, spicy, meaty or fish-like. 
     The thiazolidines of formula I can accordingly be used for the aromatization of foodstuffs such as soups, vegetables, sauces etc. The pronounced flavour qualities of the thiazolidines enable them to be used in finished products in small concentrations (e.g. in the range of 0.01-10 ppm, preferably 0.1-1 ppm). 
     The thiazolidines of formula I can be mixed with usual carrier materials and/or diluents, if desired with other flavour-imparting ingredients and if necessary with emulsifiers, to form aromatizing agents which confer to foodstuffs, for example, a spicy or a vegetable flavour or which intensify such a flavour. The thiazolidines of formula I can, however, also be added alone to the products to be aromatized. In this case, particular attention must be paid, when carrying out the addition, to providing a homogeneous distribution of the thiazolidine in the product to be aromatized. Where the thiazolidines are used as components for the manufacture of artificial aromas, these aromas can be formulated, for example, as liquids, pastes or powders. The products can, for example, be spray-dried, vacuum-dried or lyophilized. The formulation of such artificial aromas as well as the aromatization of foodstuffs can be carried out in a manner which is known per se [see J. Merory; Food flavourings, composition, manufacture and use; Avi Publ. Co. Inc. Westport (1968)]. 
     The following Examples illustrate the manner in which the thiazolidines aforesaid can be prepared: 
     METHOD A: 
     EXAMPLE 1 
     37.0 g (0.2 mol) of 6-methyl-hepten-(5)-one-(2) were dissolved in 50 ml of ethanol and treated under an inert gas atmosphere with a solution of 15.43 g (0.2 mol) of cysteamine in 500 ml of ethanol. The mixture was heated for 2 hours under reflux to 100°C. The solution was then concentrated on a rotary evaporator and the residue subjected to a fractional distillation (Widmer column) under a high vacuum. There were obtained 27.38 g (yield 74% of theory) of 2-methyl-2-(4-methyl-3-penten-1-yl)-thiazolidine of boiling point  0 .04 74°-76°C; n D   20  = 1.5150. IR: ν max  = 1445, 1378, 790 cm -   1 . Odour: green, sulphurous; flavour: green, aldehyde-like. 
     EXAMPLE 2 
     4.3 g (0.05 mol) of diacetyl were added under an argon atmosphere to a solution of 3.85 g (0.05 mol) of cysteamine in 40 ml of methanol, whereby a warming of the mixture was observed. Thereafter, the mixture was heated to boiling under an argon atmosphere for 30 minutes. The solvent was removed on a rotary evaporator and the gas-chromatographically uniform crude product was subjected to short-path distillation in a bulb tube. There were thereby obtained 6 g (yield 83% of theory) of gas-chromatographically uniform 2-acetyl-2-methyl-thiazolidine of boiling point  0 .03 65°C; n D   20  = 1.5217. IR: ν max  = 1710, 1430, 1360, 1155, 1075, 855, 790 cm -   1 . Odour: buttery, caramellous note, nutty, reminiscent of biscuit; flavour: diacetyl-like in the direction of caramel-butter, faintly nutty. 
     METHOD B: 
     EXAMPLE 3 
     15.43 g (0.2 mol) of cysteamine and 29.0 g (0.2 mol) of isopropyl methyl ketone were treated with 200 ml of benzene and boiled under an inert gas atmosphere for 14 hours on a water-separator. The solution was concentrated on a rotary evaporator and filtered over 25 g of neutral aluminium oxide (activity I). The aluminium oxide was then flushed with ether. The filtrate was again concentrated and subsequently distilled under a high vacuum through a Widmer column. 22.51 g (yield 77% of theory) of 2-isopropyl-2-methylthiazolidine (n D   20  = 1.5085) passed over in a boiling range of 40°-42°C and at a pressure of 0.009 mm Hg. IR: ν max  = 1440, 1370, 790 cm -   1 . Odour: camphorous, woody; flavour: greenish. 
     EXAMPLE 4 
     In an analogous manner to that described in the previous Examples, the thiazolidines listed in the following Table can be manufactured: 
     
                                           Table__________________________________________________________________________Thiazolidine   B.p./mm Hg                    n.sub.D.sup.20                         Yield                             IR (cm.sup.-.sup.1)                                     Olfactory interpretation__________________________________________________________________________2-(1-Hydroxyethyl)-2-          58°-62°C/0.05                    --   67% 1450, 1370,                                     Odour: burnt,methyl-thiazolidine          M.p. 35°-40°C                             1105, 805                                     caramellous.                                     Flavour: buttery-fatty,                                     faint burnt note.2-Acetyl-2-ethyl-          62°-64°C/0.04                    1.515                         41% 1715, 1435,                                     Odour: burnt, meaty.thiazolidine/2-methyl-2-          1378, 850propionyl-thiazolidine                    Flavour: nutty, meaty.2-Ethyl-2-butyl-          45°-48°C/0.04                    1.5009                         34% 1455, 1378,                                     Odour: pyrazine-like,thiazolidine                      830     milk-like, caramellous.                                     Flavour: weakly minty,                                     (spearmint) weakly nutty.2-Isobutyl-2-methyl-          50°-53°C/0.009                    1.5010                         58% 1465, 1375,                                     Odour: green, flowery,thiazolidine                      770     sweetish.                                     Flavour: greenish,                                     ester-like, fruity.2-Secbutyl-thiazolidine          60°C/0.04                    1.5059                         75% 1460, 1380,                                     Odour: green, fruity,                             1190, 830                                     pyridine-like.                                     Flavour: weakly roasted,                                     somewhat nut-like.2-(2-methylthioethyl)-          85°C/0.04                    1.5645                         69% 1440, 930,                                     Odour: potato-like,thiazolidine                      830     slightly roasted.                                     Flavour: potato-like,                                     slightly fatty.2-Butyl-thiazolidine          60°C/0.08                    1.5031                         63% 1455, 1185,                                     Odour: green-penetrating,                              825, 790                                     bean-like, somewhat                                     sulphurous note.                                     Flavour: greenish,                                     earthy, towards green                                     tomatoes, raw potatoes.2-Pentyl-thiazolidine          60°C/0.08                    1.5002                         83% 1455, 1190,                                     Odour: greenish, spicy-                              855, 810                                     earthy, vegetable-like                                     towards                                     beans, asparagus, tomato).                                     Flavour: strongly green,                                     somewhat fatty, cucumber-                                     like, towards asparagus                                     or tomato.2-(2-Furyl)-thiazolidine          M.p.      --   84% 1450, 1160,                                     Odour: smoky, spicy,          51.5°-58.5°C                             1115, 930,                                     meaty, salami-like.                              840, 815                                     Flavour: mushroom-like,                                     earthy.2-(2-Pyrrolyl)-          M.p. 110°-111°C                    --   72% 1455, 1440                                     Flavour: weakly flowery,thiazolidine                      1190, 1100,                                     somewhat nut-like and                             1030, 915,                                     coffee-like.                              885, 8252-Hydroxymethyl-2-methyl-          M.p. 38°-45°C                    --   55% 1455, 1375,                                     Odour: meaty, bread-thiazolidine                      1075, 805like, hazel-nut like.                                     Flavour: nutty, meaty.2-Ethoxycarbonyl-2-methyl-          93°-96°C/0.04                    1.4985                         67% 1730, 1440,                                     Odour: spicy, greenish-thiazolidine                      1180, 835                                     fruity.                                     Flavour: fruity,                                     caramellous, sweetish,                                     woody.2-Ethoxycarbonyl-          M.p. 27°-29°C                    --   90% 1740, 1450,                                     Odour: fruity, smoky,thiazolidine                      1295, 820                                     pyrazine-like.                                     Flavour: weakly fruity,                                     woody trace, somewhat                                     smoky.2-Hydroxymethyl-          105°C/0.04                    --   37% 1462, 1380,                                     Odour: green, woody,thiazolidine   M.p. 47°-48°C                             1065, 950                                     roasted, spicy.                                     Flavour: greenish,                                     somewhat bitter.2,2-Tetramethylene-          48°-50°C/0.04                    1.5409                         57% 1440, 1325,                                     Odour: greenish, fishy,thiazolidine                      810     meaty.                                     Flavour: roasted,                                     fishy, meaty.2,2-Pentamethylene-          57°-60°C/0.04                    --   76% 1445, 882,                                     Odour: pyrazine-like,thiazolidine   M.p. 29°-31°C                             798     smoky, nutty.                                     Flavour: earthy, nutty,                                     broth-like.2-Methyl-2-propyl-          35°-36°C/0.04                    1.5040                         67% 1460, 1375,                                     Odour: woody, fruity,thiazolidine                      790     nutty-fatty.                                     Flavour: onion-like,                                     fruity.2-Methyl-2-pentyl-          74°-75°C/0.04                    1.4979                         60% 1460, 1375,                                     Odour: green, flowery,thiazolidine                      790     sweet.                                     Flavour: flowery, sweet,                                     greenish.2-Hexyl-2-methyl-          79°-81°C/0.04                    1.4955                         60% 1460, 1375,                                     Odour: cocoa-like, fatty,thiazolidine                      800     fruity.                                     Flavour: fatty-waxy,                                     cocoa-like trace.2,2-Dipropyl-thiazolidine          60°-62°C/0.04                    1,4991                         29% 1460, 1380,                                     Odour: pyrazine-like,                             795     ester-like, green, slight                                     caramel note.                                     Flavour: greenish,                                     sulphurous.2-Butyl-2-methyl-          43°-45°C/0.04                    1.5021                         37% 1460, 1375,                                     Odour: ester-like, milk-thiazolidine                       805, 785                                     like, green, slightly burnt                                     Flavour: caramellous,                                     nutty.2-Heptyl-thiazolidine          79°-81°C/0.04                    1.4959                         72% 1460, 1380,                                     Odour: ester-like,                              840, 805                                     green, bean-pod like,                                     ivy, slightly flowery.                                     Flavour: aldehydic-fatty,                                     greenish-flowery.2-Octyl-thiazolidine          98°-99°C/0.04                    1.4938                         71% 1460, 1380,                                     Odour: pyrazine-like,                             810     meaty, roasted.                                     Flavour: strong                                     aldehydic-fatty, metallic.2,2-Diethyl-thiazolidine          37°C/0.01                    1.5086                         75% 1460, 1375,                                     Odour: meaty, fishy,                             835     sardine-like, slightly fatty.                                     Flavour: solvent-like                                     (acetone).2-Benzyl-thiazolidine          80°C/0.06                    --   38% 1605, 1500,                                     Odour: greenish,          M.p.               1460, 1190,                                     flowery, slightly          33.5°-34.5°C                             1120, 805,                                     phenylacetaldehyde-like.                              760, 705                                     Flavour: sweet, flowery                                     such as phenyl-                                     acetaldehyde.2,2-Dimethyl-thiazolidine          80°C/8                    1.5085                         84% 1440, 1360,                                     Odour: meat-, pyridine-                             1115, 1060,                                     like, roasted,                             790     somewhat fatty.                                     Flavour: pyrazine-like,                                     somewhat meaty, slightly                                     roasted, slightly                                     bread-like.2-Propyl-thiazolidine          55°C/0.3                    1.5081                         72% 1460, 1190,                                     Odour: pungent,                              920, 810                                     pyridine-like, harsh                                     radish-like, slightly                                     metallic.                                     Flavour: pungent                                     green, slightly caramellous.                                     note, towards bread.2-Phenyl-thiazolidine          M.p. 109°-110°C                    --   90% 1495, 1450,                                     Odour: weakly greenish-                             1180, 825                                     leafy, earthy.                                     Flavour: weakly greenish.2-Hexyl-thiazolidine          65°C/0.08                    1.4970                         73% 1455, 1190,                                     Odour: green, towards                              930, 820                                     green beans, somewhat                                     fatty note.                                     Flavour: strongly green,                                     towards beans, somewhat                                     fatty.2-Ethyl-thiazolidine          62°-63°C/11                    --   88% 1460, 1195,                                     Odour: pyridine-ammonia                              915, 835,                                     like, strong, slightly                             780     nutty background.                                     Flavour: slightly fruity,                                     after-taste: leeks,                                     mustard-like.2-Ethyl-2-methyl-          50°C/0.07                    1.5080                         59% 1460, 1440,                                     Odour: pungent,thiazolidine                      1375, 1120, pyridine-like, towards                             1090, 805,                                     fish, meat,                             775     camphorous background,                                     woody.                                     Flavour: ammonia-like.2-Ethyl-2-propyl-          69°-70°C/0.01                    1.5027                         63% 3320, 1460,                                     Odour: spicy, slightlythiazolidine                      1375, 1115,                                     milky.                             8252-Ethoxycarbonylmethyl-2-          69°-72°C/0.02                    1.5086                         34% 3340, 1730,                                     Odour: ester-like,methyl-thiazolidine               1610, 1445,                                     sulphurous, green,                             1370, 1175                                     somewhat spicy.2-(2-Ethoxycarbonylethyl)-          101°-104°C/0.03                    1.5038                         54% 3350, 1730,                                     Odour: sulphurous,2-methyl-thiazolidine             1445, 1375,                                     meat-like, sweetish.                             1180, 8002-Methyl-2-nonyl-          108°-112°C/0.03                    1.4895                         57% 3320, 1465,                                     Odour: slightly fish andthiazolidine                      1375, 1135,                                     amine-like, tunny-like.                              790, 7302-Dimethoxymethyl-          52°-55°C/0.01                    1.5027                         49% 3340, 1440,                                     Odour: meat-like,thiazolidine                      1375, 1105,                                     slightly roasted.                             10902-Decyl-thiazolidine          115°-125°C/0.03                    --   14% 3300, 1465,                                     Odour: woody earthy,          M.p. 25°-30°C                              805, 715                                     quinoline-like.2-Acetoxymethyl-2-methyl-          70°-72°C/0.02                    1.5070                         58% 3350, 1740,                                     Odour: roasted,thiazolidine                      1450, 1380,                                     spicy, peanut-like.                             1235, 10352-(1-Acetoxyethyl)-2-          66°-70°C/0.02                    1.5004                         40% 3350, 1740,                                     Odour: sulphurous,methyl-thiazolidine               1445, 1370,                                     slightly burnt, kohlrabi.                                     1240, 10552,2-Bis(acetoxymethyl)-          122°--123°C/0.03                    1.5149                         50% 3350, 1740,                                     Odour: spicy, roasted,thiazolidine                      1440, 1375,                                     pyrazine-like,                             1235, 1015                                     bread-like.                                     Flavour: bread-like,                                     somewhat burnt.2,2-Bis(ethoxycarbonyl)-          115°-117°C/0.04                    --   45% 3340, 1735,                                     Odour: sweet, fruity,thiazolidine   M.p. 31°-33°C                             1450, 1370,                                     somewhat burnt.                             10252-(3-Hydroxypropyl)-2-          109°-111°C/0.02                    1.5290                         56% 3300, 1450,                                     Odour: roasted,methyl-thiazolidine          M.p. 23°C   1380, 1210,                                     burnt, sulphurous.                             10702-(2,2-Dimethoxyethyl)-2-          68°-71°C/0.02                    1.4978                         40% 3360, 1445,                                     Odour: spicy, meat-methyl-thiazolidine               1375, 1125,                                     like, fatty, salami.                             1050, 7902-Ethoxycarbonyl-2-(1-          105°-110°C/0.05                    1.4902                         29% 3360, 1735,                                     Odour: roasted,ethoxycarbonyl-ethyl)-            1465, 1370,                                     peanut-like, bread-like.thiazolidine                      1250, 1190                                     Flavour: bread-like.2-[2-(5-Methylthienyl)]-          M.p. 66°-67°C                         31% 1445, 839,                                     Odour: spicy, green,thiazolidine                      805     slightly phenolic, celery-                                     like.2-[2-(5-Methylfuryl)]-          M.p. 46°-48°C                         38% 1456, 1178,                                     Odour: mushroom-like,thiazolidine                      1160, 1023,                                     slightly roast.                             8382-(2-Pyridyl)-thiazolidine          123°-124°C/0.3                         54% 1476, 1457,                                     Odour: woody, cedarwood-                             1436, 1186,                                     like, somewhat smoky,                             1002, 833,                                     meaty, sausage-like.                             7902,2-Bis(ethoxycarbonyl-          126°-134°C/0.06                    1.4911                         36% 3350, 1735                                     Odour: fatty, slightlymethyl)-thiazolidine              1470, 1370,                                     greenish, salami-like,                             1180, 1030                                     meaty.                                     Flavour: slightly                                     greenish, mushroom-like,                                     meaty.2-(4-Methyl-3-pentenyl)-          58°-62°C/0.01                    1.5209                         47% 3300, 1670,                                     Odour: green, amine-thiazolidine                      1450, 1380,                                     like, vegetable-like,                             830     slightly flowery.2-[4-(2,2-Dimethyl-          84°-87°C/0.02                    1.5128                         75% 3340, 1475,                                     Odour: sardine-like,dioxolanyl)]-thiazolidine         1375, 1210,                                     slightly roasted.                             1070, 850                                     Flavour: nutty-earthy,                                     towards peanuts.2-(2-Thienyl)-thiazolidine          106°-107°C/0.35                         47% 1450, 1235,                                     Odour: spicy, slightly          M.p. 44°-46°C                             1195, 1180,                                     sulphurous, smoky.                              929, 857,                                     Flavour: smoky, phenolic.                             8332-[2-(N-methyl-pyrrolyl)]-          105°-106°C/0.2                         50% 1495, 1448,                                     Odour: slightly metallic,thiazolidine                      1300, 1193,                                     fatty.                              848, 790__________________________________________________________________________ 
    
     The following Examples illustrate typical odorant and/or flavouring compositions provided by the invention: 
     EXAMPLE A 
     
         Composition (Smoke Aroma)              A          B            Parts by Weight______________________________________Methylisoeugenol   0.5        0.5Pyruvic acid       3.0        3.0Heliotropin        3.0        3.0Furfurol           5.0        5.0Eugenol            5.0        5.0Vanillin           9.0        9.0Guaiacol           20.0       10.02,2-Pentamethylene-thiazolidine              --         10.0Alcohol            954.5      954.5              1000.0     1000.0______________________________________ 
    
     The partial replacement of guaiacol in aroma composition A by 2,2-pentamethylene-thiazolidine gives a more typical smoky note. 
     EXAMPLE B 
     
         Composition (Licorice Aroma)              A          B            Parts by Weight______________________________________Dimethylresorcin (10% alcohol)              2.0        2.0Isobutylquinoline (10% alcohol)              5.0        5.0Mousse de Chene (10% alcohol)              10.0       10.0Corylone           30.0       30.0Methylionone       60.0       60.0Maltol             10.0       10.0Anethol synth.     160.0      100.02,2-Dimethylthiazolidine              --         60.0Alcohol            723.0      723.0              1000.0     1000.0______________________________________ 
    
     The partial replacement of Anethol synth. in aroma composition A by 2,2-dimethylthiazolidine gives a slightly greenish, nut-like note which is strongly reminiscent of licorice. 
     EXAMPLE C 
     
         Composition (Hazelnut Aroma)              A      B      C              Parts by weight__________________________________________________________________________Maltol             2.0    2.0    2.0Acetylmethylcarbinol              2.0    2.0    2.0Acetophenone       3.0    3.0    3.0Acetanisole        3.0    3.0    3.0Furfurylmercaptan  5.0    5.0    5.0Cinnamic acid amyl ester(10% in alcohol)   5.0    5.0    5.0Vanillin           10.0   10.0   10.0Diacetyl (10% in alcohol)              10.0   10.0   10.0Aldehyde C 18      10.0   10.0   10.0Phenylacetic acid amyl ester(10% in alcohol)   10.0   10.0   10.0Phenylacetaldehyde 10.0   10.0   10.0Corylone           15.0   15.0   15.0Benzaldehyde       100.0  100.0  100.0Dimethylresorcinol 350.0  300.0  270.02-Acetyl-2-ethyl-thiazolidine/2-methyl-2-propionyl-thiazolidinemixture            --     50.0   --2-Ethoxycarbonyl-2-methyl-              --     --     80.0thiazolidineAlcohol            465.0  465.0  465.0              1000.0 1000.0 1000.0__________________________________________________________________________ 
    
     The partial replacement of dimethylresorcinol in aroma composition A by a 2-acetyl-2-ethyl-thiazolidine/2-methyl-2-propionyl-thiazolidine mixture or by 2-ethoxycarbonyl-2-methyl-thiazolidine gives a nut-like note which is strongly reminiscent of hazelnut. 
     EXAMPLE D 
     
         Composition (Bean Aroma)             A      B      C             Parts by Weight__________________________________________________________________________Methylchavicol (1% in alcohol)             0.5    0.5    0.5Garlic (1% in alcohol)             2.0    2.0    2.0Thymol (1% in alcohol)             0.5    0.5    0.5Isobutyric acid piperonyl ester(1% in alcohol)   3.0    3.0    3.0Nona-2,6-dienal (1% in alcohol)             5.0    5.0    5.0Acetic acid linalyl ester (1% in             5.0    5.0    5.0alcohol)3-Hexenyl-acetylacetate             10.0   10.0   10.02-(2-Methylthioethyl)-thiazolidine      --     1.0    --2-Pentylthiazolidine             --     --     0.5Alcohol           974.0  973.0  973.5             1000.0 1000.0 1000.0__________________________________________________________________________ 
    
     The addition of 2-(2-methylthioethyl)-thiazolidine and/or 2-pentylthiazolidine to aroma composition A gives an intense vegetable-like note which is reminiscent of beans.