DE1818027A1 - USE OF 2-HYDROXY-3-METHYL- 4-AETHYL-BUTEN- (2) -OLIDE- (4,1) TO CHANGE THE TASTE AND FLAVOR OF TOBACCO - Google Patents

Description

Dlpl.-lng. P. WIRTH Dr. V. SCH M IE D-KOWARZI K Dlpl.-lng. G. DAN N EN B ER G · Dr. P. WEIN HOLD Dr. D. GUDEL

335024 V SIEOFRIEDSTRASSE 8

TELEPHONE: C089) _{8000 MQNCHEN} AQ

Case 700-1 / Div. SK / Me

FIRMENICH S.A, Geneva / Switzerland

Use of 2-hydroxy-3-ethyl-4-ethyl-butene (2) olid- (4 »i) to change the taste and taste Tobacco aromas.

(Removed from P 18 03 867.0)

The present invention relates to the use of 2-hydroxy-3-methyl-4-ethyl-'butene- (2) -olide- (4f 1) the formula

to change the taste and aroma of tobacco.

Compound I is from HeIv. Chim. Acta 21 (1948), 473 and 1P_ (1957), 1983 known.

709846/0001

-f 8-ί8027 3

The abovementioned lactone I is obtained by decarboxylating the acidic precursor II (for preparation see below) by the action of heat. The conversion of the precursor (acid) II in the inventive lactone I can be carried out at temperatures above 5O ⁰ G v / ground. In order to increase the reaction rate, it is expedient to use temperatures of at least 100 ^° C., for example. According to a preferred embodiment, the acid II is converted into the lactone I at temperatures

a g

near the melting point of the Vorlaufera or at / Tempera- · ™ for which is higher than its melting point. The heating time is variable and can be, for example, a few seconds, if the transfer is carried out at high temperatures in a pyrolysis apparatus, or for several hours, e.g. 24 hours when working at lower temperatures. At the higher reaction temperatures should long reaction times are avoided so that the reaction products " don't char.

Yienn the acidic precursor II is incorporated into foods or beverages during the course of their production or before taking a heat treatment, such as boiling, boiling or Baking, are subjected to the conversion of the precursor II into the lactone I easily in the heat treatments for this temperatures used.

/ 0001

The acid II used as the starting product is obtained by heating of 2-ketobutyric acid in the presence of a strong acid, preferably a mineral acid or a mixed mineral-organic acid according to the following reaction scheme:

2 CH ₅ -CH ₂ -CO-COOH * CII)

L.-

The putative formula of II is

H, CCC = O
⁵ II

H _C C _O -CC = O
5 2

f
HOOC Ü

See: Reports 35 (1902), 1625 and J. Food, Sc. 52: 614 (1967)).

Strong acids that can be used are, for example, hydrogen chloride, perchloric acid, phosphoric acid, sulfuric acid, trifluoroacetic acid or p-toluenesulfonic acid. It is advantageous to use dry gaseous hydrogen chloride and to carry out the reaction in benzene at room temperature. However, you can also work at other temperatures, for example at those from 0 to 80 ⁰ C or above, and other common solvents, such as tetrahydrofuran, dioxane, toluene or chloroform, use, - ·

0 984; - / O001

In a suitable dilution, the 2-irydroxy-3-methyl-4-ethyl-buten- (2) -olide- (4.1) To give tobacco a "special, maple-like aroma." The compound mentioned can e.g. in amounts of 50 to 200 parts by weight of lactone per million Add tobacco parts by weight, and so the desired effect achieve.

Lactone I can be used to achieve special aroma effects also mix with other tobacco additives.

709846/00 01

BATH ORIGINAL

In the following reference and in the examples, the Teraperotur eats given in degrees of Celsius.

Attempt ■ ,

Production of 2-hydroxy-3-methyl ~ 4-ethyl-butene - (?.) - olide- (4,1)

a) Manufacture of the precursor II

In a solution of 1387.7 g of ßi-ketobutyric acid in 1338 g Benzene was passed in 135 g of dry hydrogen chloride at 20 ° in the course of 7 hours. The reaction mixture was over Left to its own devices at night at room temperature. The resulting Crystals were suction filtered and the aqueous layer of the filtrate was decanted off. In the remaining ßenzollösung formed in the course of a few hours another amount of crystals that were sucked off again. The total weight of compound II obtained was 1166.5 g, M.p. 152-154 ° (dec.).

b) Preparation of 2-hydroxy-3-methyl-4-ethyl-buten- (2) -olide-U.1) 186 g of the compound obtained according to a) were heated at 160 ° until the development of COp ceased. The reaction product was distilled, 130.7 g of lactone, boiling point 70-71% 0.003 Torr, melting point 21 ° being obtained.

709846/0001

BATH ORIGINAL

example

A pipe tobacco mixture was produced by mixing the tobacco types listed below:

Type of tobacco parts by weight

"Flue cured Virginia", 1st quality,

American origin 20

"India Flue cured Virginia", medium quality Λ

Indian origin 35

"Pakistan Flue cured Virginia", poor quality Pakistani origin 30

"Southern China Flue cured Virginia",

South Chinese origin 5

"Syria Fire cured Latakia", Syrian: Origin 8

"Perique" "2

In 100 kg of the tobacco mixture obtained were sprayed on

2 kg of an I ^ i-igen solution of 2-hydroxy-3 ~ me-öiyl-4-ethyl-butene " en- (2) -olide (4.1) in a mixture of equal volumes of ethanol and Incorporated propylene glycol. The tobacco treated in this way was left to stand until it was sufficiently dry to be tested «The treated tobacco was made by a group of tobacco experts with a tobacco mixture of the same composition

10 984b / ÖO0 1

Ί 818027

which, however, has not been treated with the lactone mentioned above was compared by smoking. All members of the above group agreed that the treated tobacco was one smoke developed more pleasant than the untreated tobacco and that the smoke of the treated tobacco developed a maple-like aroma exhibited.

In the formulation given above, the 2-hydroxy-3-methyl-4-ethyl-buten- (2) -olide (4.1) replaced by the same amount of precursor II. The tobacco mixture obtained in this way showed the same maple-like effect when smoking as the mixtures according to the example.

70984t. / 0001

Claims (1)

P 18 18 027.3 Firmenich S.A. Case 700-1 / Div. P a t.e nt claim The use of the compound of the formula CH ₅ -CH ₂ C CO to change the taste and aroma of tobacco, 7098A6 / O001