DE2120577A1 - Alkyl substituted 3-oxazolines - Google Patents

Description

Alkyl substituted 3-oxazolines

The invention relates to new 2,4,5-alkyl-substituted 3-Oxazolines, which act as aroma (taste and smell) substances suitable. . .

Artificial flavorings are widely used today and are known by the hundreds. A large number of chemical compounds, especially organic compounds, are used as flavorings Compounds in question, including aliphatic and aromatic alcohols, aldehydes, ketones, acids, esters, Phenols and lactones. It is known of certain compounds that they have a specific taste and aroma, which in many cases is more natural Products are the same. For example, 2-T indecalactone,. that as "peach aldehyde" is known as an artificial flavoring agent in the manufacture of products with a peach-like flavor used. With the help of these compounds it is possible to create one using exclusively artificial means. simulate natural taste and aroma. In many cases, the artificial taste

109848/1966

agent compositions are preferred because of their stability, easy accessibility and low cost.

Artificial flavors are widely used in foods ι drinks and, to make it easier to take, also used in medicinal products, e.g. they are used in the coating added by tablets and elixirs.

The new compounds according to the invention have the general formulas

and

,1

in which R, R,

and R ^ alkyl groups of up to 6 carbon atoms and R ^ and R are alkyl groups of 2 to 6 carbon atoms represent"

You can use foods and medicines as flavorings can be added.

The compounds of the present invention are easily obtained by condensation of correspondingly substituted a-ketols and Aldehydes made with ammonia in aqueous solution at room temperature. The alkyl substituents in the positions 4 and 5 of the 3-oxazoline are derived from a-ketol, while the alkyl substituent in the 2-position was derived from the aldehyde 3-oxazolines with alkenyl and aryl substituents in the

1 09848 / 196g

lungs 2, 4 and 5 can be made using the corresponding substituted starting materials can also be produced by this process. The reaction goes smoothly and after stirring the reactants for a few hours at room temperature, the 3-oxazoline is washed with ether extracted. After drying and evaporation of the ether extract, the product can be obtained by fractional distillation, generally under vacuum. If desired, further gas-liquid purification can be carried out Chromatography.

The compounds according to the invention have excellent taste and smell properties o they will therefore advantageously added to foods, confectionery and beverages to impart flavor and aroma. Perfumes and cosmetics, they convey the desired scent notes. aside from that It has been found that the compounds of the invention enhance the taste and aroma of foods.

Bb it was also found that the higher homologues of the compounds according to the invention are significantly more effective as flavorings and aromas than the lower homologues, doh. the 2,4s5 = -trialkyl-3-oxazolines with methyl groups in the 4- and 5-positions are less effective as flavor and aroma enhancers than the higher homologues. The taste and aroma of the higher homologues are more intense than those of the lower members, and the aroma and taste they impart to foods are more pleasant and less desirable five times more intense than that of the already described 2-isopropyl-4s5-dimethyl-3-oxazoline.

The 2,4,5 * i-tetraalkyl - ^ - oxazolines also give food and the like, pleasant taste and aroma properties.

Many of the new compounds according to the invention have an individual taste and aroma. The 2-isopropyl-4,5-diethyl compound has a strong, cocoa-like odor and taste. It can be used to make products with an artificial cocoa flavor. Together with other additives and compounded with soy proteins and dextrose, it makes a chocolate drink that is very similar in appearance, taste and smell to products made with natural chocolate derivatives. Soy proteins are found in soybean oil, flour, and cake. Because of their light weight. Accessibility and low cost, they are recommended as food additives in those areas of the world that are protein deficient. Unfortunately, the taste of raw soy proteins is a bit unpleasant. The use of 2-isopropyl-4,5-diethyl-3-oxazoline to make an acceptable cocoa-tasting protein drink is therefore of great importance. In fact, be priced pleasant tasting drinks with high protein content to a large extent in comparable w different parts of the world to supplement the proteins in food, particularly used in food for children.

Bas 2-isopropyl-4 »5-diethyl-3-oxazoline can be used as a flavor" streak agent " are used for natural and artificial cocoa and chocolate ingredients. Under a taste --- " Extender "means an ingredient that either enhances a natural taste, i. a flavor enhancer, or a part of the natural flavor while achieving the same flavor effect

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able to replace flavor. It was found that the addition of up to 5 ppm of 2 ~ isopropyl-4,5-diethyl-3-oxazoline to a commercially available cocoa base improves its aroma. In general, it is preferred to use them to achieve flavor effects in foods from about 1 to 100 ppm of the compounds of the invention.

The various other compounds of the invention also have interesting olfactory properties. 2-Isopropyl-4,5-di-n-propyl-3-oxazoline has a banana-like appearance Odor while 2-tert-butyl-4,5,5-trimethyl-3-oxazoline Has a cool, peppermint-like odor. In low concentrations it can be used to manufacture artificial ones Strawberry, banana and butter flavors can be used.

The compounds according to the invention can also be used in various perfumes and cosmetic compositions with the achievement of an unlimited number of fragrance nuances, the nature of which depends on the experience and the instinct of the fragrance composer. In general, about 1 to 200 ppm gives the best results. The compounds according to the invention can also be added to medicaments in order to give them a pleasant taste, in particular tablet coatings and elixirs.

The following examples illustrate the invention.

example 1

11.6 g (0.10 mol) of propionoin and 7.2 g (0.10 mol) of isobutyraldehyde are added to 50 ml of ammonium hydroxide. The Re-. aktionsgeschisch is stirred at room temperature for 6 hours; Then it is extracted several times with diethyl ether. The. Extracts are combined and dried over anhydrous sodium «

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sulfate dried. The residue after filtration and evaporation of the ether v / ill be under reduced pressure through a short column Yigreaux distilled "The at up to 100 ° C / 33 mm fraction passing over is collected to yield 12.4 g (74%) Z-isopropyl ^^ - diethyl-O-oxazoline. The pure material has a pungent cocoa-like odor.

The 3-oxazolines listed in the table were after prepared by the same process from the starting materials given below.

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Raw materials

Aeyloin

aldehyde

Product Kp., ^Υ C

odor

C ₂ H ₅ COCHOHC ₂ H ₅ CH-OOCHOHCoH-

CH ₃ COC (CH ₅ ) OHCH ₅

CH ₃ COC (CH ₃ ) OHCH ₅

CH ₃ COC (CH ₃ ) OHCH

C ₂ H ₅ CHO

JL-C ₅ H ₇ CHO

1-0, H ₇ CHO

! -C ₄ H ₉ CHO 96-1O4 ° / 33 mm according to Grünes

2,4,5-triethyl-3-oxazoline

2-si-butyl-4-, 5-

diet-3-

oxazoline

2-i-propyl-4-, 5-

di-n-propyl-3-

oxazoline 2-i-propyl-4,5,5- 70-75 ° / 3O mm · cool, like menthol;

trTmethyl- <3-

oxazoline 109/15 mm

96 ° / 25 mm

cocoa

cool, like bananas

unroasted cocoa

2-i-butyl-4,5,5-

trimethyl-3-

oxazoline

tert.C _A H _Q CHO 2-tert-butyl-

Λ 4,5,5-trimethyl-3-oxazoline 110-113 ° / 30 mm earthy; Diacetyl

70 ° / 25 mm

cool, like mint

According to the above procedure, the following were also used Connections made.

Acyloin

Starting materials aldehyde

Product.

R '

R '

11-C ₃ H ₇ COCHOH-II-C ₃ H ₇
nC ₆ E ₁ _C OCHOH-nC _g H,
nC ₄ H ₉ COCHOH-nC ₄ H _g
nC ,, Hr ₇ COCHOHC «Η, -

-Dl <L O

C ₂ H ₅ COCHOHC ₂ H ₅ ,

C 2H ₅ COCHOH-IC ₃ H ₇
C ₂ H ₅ COCHOH-IC ₇₅ H
nC, H

"i- ^ 4 ⁿ ₉

C ₂ H ₅
CpHeCOCHOHCpHt

CH ₃ C ₂ H ₅ CHO CHO CHO SC ₃ H ₇ 11-C ₄ H ₉ CHO

^[ 11 11 -C ₅ H ₁₁ CHO

11-C ₆ H ₁₃ CHO

C ₂ H ₅ CHO

11-C ₃ H ₇ CHO

1-C ₃ H ₇ CHO

CH ₃ CHO

CH ₃ CHO

CH ₃

C ₂ H ₅

11-C ₃ H ₇

BC ₄ H ₉

SC ₅ H ₁₁

SC ₆ H ₁₃

C ₂ H ₅

SC ₃ H ₇ .

1-CHr ₇

i- ° 5 ^H 11 CH, SC ₃ H ₇

SC ₃ H ₇ SC ₆ H ₁₃ SC ₆ H ₁₃ SC ₄ H ₉ C ₂ H ₅

SC ₅ H ₁₁ C ₂ H ₅

O ₁ -C ₃ H ₇ AC ₄ H ₉

BC ₄ H ₉

SC ₃ H ₇

SC ₅ H ₁₁

C ₂ H ₅

C ₂ H ₅

C ₂ H ₅

tert. C ₄ H ₉ S "XC ₅ H ₁₁ C ₂ H ₅

i- ^C 6 ^H 13

C ₂ H ₅ C ₂ H ₅ C ₂ H ₅

product

Starting materials acyloin aldehyde R ¹ R ² R ³

C ₂ H ₅ COCOH (C ₂ H ₅ ) ₂
CH ₃ COCOH (CH ₃ ) ₂
C ₂ H ₅ COCOH (CH ₃ ) ₂

C ₂ H ₅ CHO C ₂ H ₅ C ₂ H ₅ C ₂ H ₅₁ C ₂ H ₅ SC ₄ H ₉ CHO SC ₄ H ₉ CH ₃ CH ₃ CH ₃ SC ₅ H ₁₁ CHO nC _s H ₁₁ CH ₃ CH ₃ C ₂ H ₅

1098 4 8- / 196 6

_- Q _

Acyloin 'aldehyde ·. R ¹ 'R ² R ³ R ⁴

11-C ₃ H ₇ COCOH (CH ₃₎ (C ₂ H ₅₎ 11-C ₆ H ₁₃ CHO 11-C ₆ H ₁₃ CH ₃ - C ₂ H ₅ 11-C ₃ H ₇

C ₂ H ₅ COCOH (CH ₃ ) (nC ₆ H ₁₃ ) C ₂ H ₅ CHO C ₂ H ₅ nC ₆ H ₁₃ CH ₃ ^C 2 ^H 5

■ η-σ, -Η.,, COCOH (Ii-O, Hr ₇ ) ο CH _x CHO CH, nC, H ₇ nC, H ₇ n-CJL,

- D \ j -J [C. j j - j \ ~ JI ~~ D \ j

1-C ₄ H ₉ COCOH (CH ₃ ) (C ₂ H ₅ ) 11-C ₃ H ₇ CHO SC ₃ H ₇ C ₂ H ₅ CH ₃ ! -C ₄ H ₉ -

1-C ₅ H _1. , COCOH (CH ₃ ) ₂ 1-C ₃ H ₇ CHO 1-C ₃ H ₇ CH ₃ CH ₃ ! -C ₅ H ₁₁

CH ₃ COCOH (CH ₃ O (SC ₅ H ₁₁ ) CH ₃ CHO CH ₃ SC ₅ H ₁₁ CH ₃ CH ₃

C ₂ H ₅ COCOH (CH ₃₎ (SC ₄ H ₉₎ Jt-C ₄ H ₉ CHO! -C ₄ H ₉ SC ₄ H ₉ CH ₃ C ₂ H ₅

CH ₃ COCOH (CH ₃ ) (SC ₄ H ₉ )! -C ₅ H ₁₁ CHO! -C ₅ H ₁₁ CH ₃ SC ₄ H ₉ CH ₃

CH ₃ COCOH (CH ₃ ) (SC ₆ H ₁₃ ) CH ₃ CHO CH ₃ 'CH ₃ SC ₆ H ₁₃ CH ₃

CH ₃ COCOH (C ₂ H ₅ ) (IC ₅ H ₁₁ ) C ₂ H ₅ CHO C ₂ H ₅ C ₂ H ₅ ! -C ₅ H ₁₁ CH ₃

Example 2 . '"·

The organoleptic properties of typical representative ones according to the invention Connections are listed below. The respective amounts of the specified compounds were in 5 ^ iger dissolved aqueous sucrose solution. Then the smell and the Definitely taste.

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Relatrve (r) intensity and character of the aroma of the examined oxazoline compounds In 5 # sucrose solution ■ '

Concentration of compounds in ppm '

Relative aroma intensity (smell and taste)

2-isopropyl-4,5,5-, trimethyl-3-oxazoline

2-isobutyl-4,5,5-

trimethyl-3-oxazo-

lin

2,4,5-iriethyl-3-oxazoline

2-isopropyl * 4, 5-diethyl-3-.oxazolin

missing threshold weak ■ moderately moderately strong stepping out

very strong

Aroma character (smell and taste)

0.0625

o, 125

; 5 '■ ■;

10

25 · • 50 ■

15 ^; , ■. ■■

ethereal, dry earthy (fungal), etark reminiscent of Jamaica rum essence

earthy (fungal) with the addition of butter and green leaves

below 0.0625 below 0.0625
0.0625. .0.0625

10
25th
50

very strong after very strong sweet green and earth cocoa-like aro- (fungal), strong ma with mild beers reminiscent of a mixture of fresh carrots and greens.

A 1 solution of 2-isopropyl-4,5-dimethyl-3-oxazoline exhibited a very faint cocoa-like odor and taste with a strong unpleasant hote to the green and earth, a 1> solution of 2 ~ isopropyl-4,5-diethyl-3-oxazoline on the other hand had a very strong, sweet, cocoa-like odor and taste with a mild mote of green and earth.

Example 3

Comparison of the intensity and quality of the aroma of 2,4,5-trimethyl-3-oxasoline and 2-methyl-4,5-diethyl-3'-oxazoline.

Cum comparison of the intensity and quality of the aroma; (smell and taste) of 2,4,5-trimethyl-3-oxazo ^ in and 2-methyl-4,5-diethyl-3-oxazolin.in An organoleptic examination was carried out with 5% aqueous sugar solution. Both compounds were tested in the same concentrations according to the following scheme.

13 samples of the 5 fig aqueous sugar solution were prepared. 6 of them contained 1000, 500, 200, 100, 50 or 25 ppm 2,4,5-trimethyl-3-oxazoline and 6 contained 2-methyl-4,5-diethyl-3-oxazoline in the same concentration. One sample served as a control. Me solutions were coded and rated by two experts for the intensity and quality of their aroma. The reviewers were asked to arrange the solutions in the order of their decreasing flavor intensity and to indicate whether they could see any difference in flavor quality. The results of this assessment are summarized below.

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Code of the solutions

Compound concentration in ppm

S P

AKDBJ T EROZ

2,4,5-trimethyl-3-oxazoline

2,4,5-trimethyl-3-oxazoline

2,4,5-trimethyl-3-oxazoline

2,4,5-trimethyl-3-oxazolln

2,4i 5-trimethyl-3 ⁱ -oxazoline

2-Metüyl-4,5-diethyl-3-oxazolin 2-methyl-3,5-diethyl-3-oxazolin _2-methyl-4-f 5Miiäthyl 3-oxazolin 2-methyl ~ 4,5-äiäthyl-3-dxazolin 2-methyl-4,5-diethyl-3-oxazoline, 2-methyl-4,5-diethyl-3-oxazoline

5 $ sugar solution 1,000

. 500

200

100

50

25th

1,000

500

200

100

-5 ¹ O

25th

control

Assessment I: order in which the examiners provided the solutions

in order of decreasing aroma intensity and quality. .

Tester sequence of decreasing aroma intensity aroma quality of the solutions

Bf S, J, P, T, N, E, A, R,

K, ZB, J, Tj E and R have a similar aroma character, which is called pleasantly reminiscent of "green" and / freshly cut beans · S, P, N and A have the same aroma, but the character of the aroma is different differs from B, J, T, E and R. Pure S, 'P, Έ and A were given a "green" flavor with a fungal note.

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Order of examiners from. Aroma quality of the solutions increasing aroiaa intensity

Give 2 B, S, J, 'P ₁ T, If, E, R, B, J »T _v and B.

A, K, Z a sweeter, delicate one

Aroma of "green"} S, P, N and A have against it a coarser aroma

The results of the above flavor comparison show that the Aroma of 2-methyl-4> 5-diethyl-3-oxazoline stronger than that of 2,4,5-trimethyl-3-oxazoline, furthermore; that 2-methyl-4,5-diethyl-3-oxazoline gives a different flavor than 2.4> 5 * - Trimethyl-3-oxazoline. The first mentioned connection mediates a more pleasant, delicate and appealing aroma than 2,4,5-trimethyl-3-oxazoline.

Example 4

Evaluation and comparison of the aroma intensity and quality of 2-isopropyl-4,5-diethyl-3-oxazoline and 2-isopropyl-4,5-dimethyl-3-oxazoline

The flavor intensity and quality of 2-isopropyl-4,5-diethyl-3-oxazoline was compared with that of 2-isopropyl-4,5-dimethyl-3-oxazoline in 5% aqueous sucrose solution. ji's, two sets of test solutions were made. Test series I comprised four samples containing 50, 25, 10 and 1 ppm 2-isopropyl-4,5-diethyl-3-oxazoline. The test suite consisted of four samples which included 50, 25, 10 and 1 ppm 2-isopropyl ~ 4 _? 5-aimethyi-3-oxazoline had been added. The solutions were chilled and rated by two panelists for their smell and taste (aroma) by arranging them in the order of their decreasing aroma intensity. At the same time, the quality of the aroma of the solutions was compared. The results obtained are summarized below.

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Code of Connection concentration 2-isopropyl-4,5-diethyl-3-oxazoline 50 solutions in ppm 2-isopropyl-4,5-diethyl-3-oxazoline 25th Η 2-isopropyl-4,5-diethyl-3-oxazoline 10 26th 2-isopropyl-4,5-diethyl-3-oxazoline 1 33 2-isopropyl-4,5-dimethyl-3-oxazoline 50 7th 2-isopropy1-4,5-dimethyl-3-oxazoline 25th 4th 2-isopropyl-4,5-dimethyl-3-oxazoline 10 13th 2-isopropyl-4,5-dimethyl-3-oxazoN 1 8th 5

Tester order of decreasing aroma intensity

Aroma quality

H, 26, 33 & 4 (comparable), 13, 8, 7, 5

14, 2.6, 4, 33, 13, 7, 8, 5

14, 26, 33 and 7 show a strong sweet cocoa like Aroma with a mild note of "green", while 4, 13, 8 and 5 having a strong fungal aroma of "green" convey a weak cocoa note. '

14, 26, 33 and 7 show a protruding sweet cocoa aroma, while 4, 13, 8 and 5 convey a different, coarser, not so desirable aroma.

Based on the above results, the flavor intensity of 2-isopropyl-4f5-diethyl-3-oxazoline became about five times stronger rated as the flavor of 2-isopropyl-4,5-dimethyl-3-oxazolino The above results also show that 2-isopropyl-4,5-diethyl-3-oxazoline gives an aroma that was consistently recognized as strongly sweet, cocoa-like, while the aroma of 2-isopropyl-4,5-dimethyl-3-oxazoline as coarser in character with a strong fungal smell of "green" and less intense cocoa grinder flavor.

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Example 5

Chocolate flavored compositions were made from the following ingredients;

ν "Chocolate flavoring ingredients

Vanillin

Vanitrope, 1 ^α / Ό in propylene glycol maltol, 4 $ in propylene glycol 2-isopropyl-4,5-diethyl-3-oxazoline propylene glycol

Ooca extract (Anthoine Ghiris)

100.0 100.0

The organoleptic evaluation of the above compositions was made by panelists who examined the aroma and the Flavors of the two compositions in milk drinks compared. A number of milk samples were obtained with sufficient Amount of composition A produced so that the samples contained t * -5Q ppm 2-isopropyl-4,5-diethyl-3-oxazoline. Another set of milk samples was run with equivalent results 'the composition B made «

Aromazus amme ri Aromas together sentence A, g setting Β »g 3.0 3.0 3.0 3.0 10.0 10.0 in 0.5 - 73.5 74.0 10.0 10.0

In each case it would be shown that the milk samples produced with the formulation 1, which contained the 2-isopr * opyi-4,5 "* ^b diethyl-3-oxazoline, compared to the milk samples with the olejc ^ Zueöffiii * 3tiset5ung B Samples of milk produced which do not contain this compound have a much stronger aroma and taste, and the products made with composition A had a more natural aroma and taste than those made with composition B.

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Example 6

A number of samples were prepared by 2 up to 100 ppm of 2-isopropyl-4,5-diethyl-3-oxazoline added to bakery products and chocolate-flavored confectionery (either with natural cocoa powder or cocoa extract or with natural chocolate products and the usual synthetic ones Flavorings). In all cases, a comparable set of control samples was used without 2-isopropyl-4,5-diethyl-5-oxazoline manufactured.

It has been found that the addition of the compound according to the invention has the effect of enhancing the aroma. The usage this connection gives a more real and. stronger chocolate flavor.

Example 7

2-Isobutyl-4> 5j5-trimethyl-5-oxazoline was as follows, indicated for the production of artificial strawberry and banana nar oma used.

Artificial banana flavor.

Components Aromas together
sfctation C, g Aromas together
setting D, $ Ethyl alcohol, 95 #, U.S, .P. 10,480 15.480 * Vanillin 0.570 0.370 ■ orange oil, California U, .S.P. 0.066 0.066 Myrtle oil, bourbon '"* ■ 0.555 0.355 Propylene glycol 26,421 26,421 Amyl acetate 5,000 5,000- '" Amyl valerate 5.350 3.350 acetaldehyde 1,000 1,000 2-isobutyl-4-, 5} 5-trimethyl-3-
oxazoline - - 5,000 _m . "'■ ..

50,000 50,000

109 84 8/1966

Artificial strawberry flavor

Components Aromas together
setting B, g Aromas together
setting: F, g Heliotropin 0.20 0.20 ß-methyl naphthyl ketone 0.60 0.60 Nerolin 0.04 0.04 Diacetyl " 0.80 0.80 Methyl heptine carbonate, $ 5 in
Ethyl alcohol 0.20 0.20 Dirnethyl anthranite 0.20 0.20 Geranyl isobutyrate 0.12 0.12 Orange Oil, California CP. 1.44 1.44 Ethylmethylphenylglyci.dat 10.40 10.40 Jasmine abs. $ 10 in ethyl alcohol 0.12 0.12 Rose Moroc abs. 0.04 0.04 Vanillin .1.00 1.00 Ethyl maltol 3.00 3.00 Ethyl butyrate 2.00 2-isobutyl-4,5,5-trimethyl-3-
oxazoline 2.54 Ethyl alcohol, 95 # Ü.S.P. ■ 27.30 31.84

50.00 50.00

The above flavor compositions have been used to make a variety of gelatin desserts. Sufficient Flavor Compositions C and E were used so that the dessert samples contained 2-100 ppm 2-isobutyl-4 _} 5> 5-trimethyl-3-oxazoline. The control samples contained the flavor compositions D and P.

Aroma and taste of the 2-isobutyl-4,5 * 5-trimethyl-3-oxazoline containing the composition were much stronger than the control samples (composite

103848 / 196S

composition D and 3?). From the testers the aroma, the of the compositions mediated with the tea compound became as natural and the taste as pleasant and fuller denotes the aroma and taste of the control samples,

Similar results were obtained by considering the rest Compounds of Example 1 instead of 2-isobutyl-4 »5,5-trimethyl-3-oxazoline used.

Example 8

Between 2 and 4% by weight of 2-isobutyl-4,5,5-trimethyl-3-oxazoline were mixed with the following composition and sufficient propylene glycol added to make the total weight to bring the composition to 100 parts.

- butter flavor
Components parts by weight

Butyric acid .4,4

Ethyl butyrate 3.2

Amyl butyrate 4.3

Diacetyl 1.1

Benzyl alcohol 5.0

Phenoxyethyl isobutyrate 4.3

2-isobutyl-4,5,5-trimethyl-3-oxazoline 2-4

Propylene glycol to make up to 100

It has been found that butter flavor compositions, which contained 2-isobutyl-4,5,5-trimethyl-3-oxazolih, im Compared to control samples which did not have these compounds, the aroma and taste improved significantly. Indeed, the latter samples have been going strong negative ratings.

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Similar results were obtained when the remaining compounds of Example 1 were used as additives.

Example 9 '

If you add 2-50 ppm of 2-isopropyl-4,5-diethyl-3-oxazoline Traditional peanut flavored products (which are either natural Peanut flavoring or containing both natural and artificial flavorings), products will be more delicate Preserve aroma.

Similar results are obtained with the remaining compounds of Example 1 achieved.

Example 10

A cocoa-flavored elixir for pharmaceutical use was made prepared as indicated below;

2-IsGpropyl-4,5-diethyl-3-oxazoline sucrose liquid glucose glycerin Sodium Chloride Vanillin Sodium Benzoate

Purified water, sufficient to make up to 1000 ml

The sucrose and. the ^ -Isopropyl - ^, 5-diethyl-3-oxazoline 'are mixed * A solution of liquid glucose, glycerin, sodium chloride, vanillin is slowly added to this mixture and sodium benzoate in 325 ml of hot purified water given. The entire mixture is boiled for 2 minutes. ■ Then it is allowed to cool to room temperature. One adds Add enough purified water to make up to 1000 ml.

5 G 650 G 200 G 50 ml 1 G 0 , 2 g 1 G

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- 20 -

Similar elixirs are obtained with the other compounds of example 1.

109848/198

Claims (2)

Claims Alkyl-substituted 3-oxazolines of the general formula 3 r ² \ ^ ** and HR H in which R, R, R and R ^ * AXkyl ^{groups with up to 6 carbon atoms and R 3} and R are alkyl groups with 2 to 6 carbon atoms. 2. 2 ^ Iaopropyl-4 ,, 5-diethyl-3-oxazoline. 3 * 2 »4i.5 4 «BIe use of the compounds according to claim 1 to as aromas and flavors in food and medicine average » for Pfizer, Inc. lew York, Ef · Y., ¥. S t, A. Lawyer 10984a / T9β6