JP3170423B2 - Flavor imparting compound comprising 3-alkyl-1,2,4-trithiolanes - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a conventional fragrance compound useful as a flavor compound which has a characteristic vegetable stimulating sensation characteristic of green onions, onions, garlic and the like and a fragrance and flavor characteristic which contributes to the cooked meat sensation when cooking meat. The following formula (Chemical Formula 2 ) not described in the literature of

[0002]

Embedded image

(Wherein R represents an ethyl group / propyl group or an isopropyl group)
The present invention relates to an aroma imparting compound comprising 2,4-trithiolanes.

More specifically, the present invention relates to a compound of the formula (1)
3-ethyl-1,2,4-trithiolane [R is an ethyl group, hereinafter referred to as a compound of the formula (1) -1], 3-propyl-1,2,4-trithiolane [
R is a propyl group, hereinafter referred to as a compound of the formula (Formula 1) -2] and 3-isopropyl-1,2,4-trithiolane
[Where R is an isopropyl group, hereinafter referred to as a compound of the formula (Chem. 1) -3].

[0005]

2. Description of the Related Art The present inventors have paid attention to the fact that compounds having a plurality of sulfur atoms in a 5-membered or 6-membered ring have persistent and unique aroma and flavor characteristics. I went. As a result, 3-alkyl-1,3, which has not been described in the conventional literature and has three sulfur atoms in the 5-membered ring,
It has been found that 2,4-trithiolanes have flavor stimulating sensation characteristic of scallions, onions, garlic and the like, as well as savory flavor characteristics with meaty feeling when cooking meat, and the compound was blended. It has been discovered that the flavor composition has an excellent effect on imparting the flavor of a cooked meat product to foods, livestock feeds and the like.

[0006]

In recent years, the taste of consumers or livestock animals has been diversified, and along with this, foods and livestock feeds having various characteristic aroma and flavor characteristics have been manufactured. In response to these diversifications, the conventional known flavor compounds alone cannot meet the demand for foods and livestock feed flavors having various characteristic flavor characteristics, and a new type of unique and unprecedented. There is a strong demand for the development of blended fragrance materials.

The novel compound of the above formula (1) of the present invention has been found to be extremely useful as a perfume compound having a unique aroma and flavor characteristic which can not solve the above-mentioned required problems and has led to the present invention. completed. That is, the present invention provides the following (Formula 3)

Embedded image (Wherein, R represents an ethyl group, a propyl group, or an isopropyl group), which is a flavor-imparting compound comprising a 3-alkyl-1,2,4-trithiolane. Therefore,
An object of the present invention is to provide a compound of the formula (formula 1) which is useful for imparting a cooked meat cooking aroma and flavor, which is not described in the conventional literature. Another object of the present invention is to provide a compound of the formula (Chemical Formula 1) having a flavory vegetable stimulating sensation characteristic of leek, onion, garlic and the like and an aroma and flavor characteristic contributing to a cooked meat sensation when cooking meat. It is an object of the present invention to provide a novel flavoring composition for a cooked meat product, which is blended as a preparation material.

[0008]

According to the present invention, the compound of the formula (1) is obtained by subjecting an alkyl disulfide to a sulfuryl chloride cleavage and halogenation reaction to form 1-chloroalkylsulfenyl chloride. After that, the product can be easily synthesized by reacting the product with sodium sulfide and methylene chloride in a dimethylformamide solvent. The details will be described below.

The starting materials, alkyl disulfides, are inexpensive and readily available on the market. The reaction temperature and reaction time of the reaction for synthesizing 1-chloroalkylsulfenyl chlorides from the above alkyl disulfides are not particularly limited, and are, for example, about -2.
Conditions of about 1 to 20 hours at a temperature in the range of about 0 ° C to 50 ° C can be employed. The amount of the sulfuryl chloride to be used is, for example, in the range of about 2.0 mol to 10.0 mol per 1 mol of the alkyl disulfide. Specific examples of the thus obtained 1-chloroalkylsulfenyl chlorides include 1-chloropropylsulfenyl chloride, 1-chlorobutylsulfenyl chloride and 1-chloroisobutylsulfenyl chloride. Chloride can be used in the next reaction in either a crude or purified state.

[0010] The synthesis of the fragrant compound comprising 3-alkyl-1,2,4-trithiolanes of the present invention comprises
It can be synthesized by reacting chloroalkylsulfenyl chlorides with sodium sulfide and methylene chloride in dimethylformamide. The reaction temperature and the reaction time in the above reaction are not particularly limited, for example, 0 ° C.
A condition of about 2 to 20 hours at a temperature in the range of about 50 ° C. can be employed. The amount of sodium sulfide used can be, for example, in the range of about 2.0 mol to 10.0 mol with respect to 1 mol of 1-chloroalkylsulfenyl chlorides. For 1 mole of chloroalkylsulfenyl chlorides,
For example, a range of about 2.0 mol to 10.0 mol can be exemplified. Further, the amount of dimethylformamide used is, for example, about 2.0 parts by weight to 10.0 parts by weight based on 1 part by weight of 1-chloroalkylsulfenyl chlorides.

After completion of the reaction, conventional purification means, for example, extraction, washing, drying, distillation and the like, are appropriately employed to obtain 3-alkyl-1,3 of formula (1) in high yield and high purity. 2,4
-Trithiolanes can be synthesized. Formula (Formula 1)
Specific examples of the compound include 3-ethyl-1,2,4-trithiolane [compound of the formula (Chem. 1) -1] and 3-propyl-1,2,4-trithiolane [the compound of the formula (Chem. 1) -2. Compound] and 3-isopropyl-1,2,4-trithiolane
[Compound of the formula (Formula 1) -3].

The compound of the formula (I) -1 included in the compound of the formula (I) of the present invention is used for cooking meat having a fresh flavored vegetable stimulating feeling characteristic of raw onions and garlic. The compound of formula (1) -2 has a flavor and vegetable stimulating sensation characteristic of leek, onion and the like, and the flavor and flavor characteristics of vegetables and meat soup, and the compound of formula (1) -3 The compound has a flavor and flavor characteristic of vegetable and meat saute, which are characteristic of flavor and flavor of green onions and onions, and can be used by being added to various flavor compositions. The amount of the compound of the formula (Chemical Formula 1) varies depending on the purpose or the type of the fragrance composition, but for example, generally, about 0.0001 to about 3.0 wt. % Range can be exemplified.

Thus, according to the present invention, by adding the compound of the formula (Formula 1) as an active ingredient, it is possible to impart the flavor characteristics of cooked meat accompanied by the stimulating feeling of flavored vegetables .
It can provide novel perfume composition given, foods, characterized in that the utilizing the composition a compound of the formula (Formula 1) containing as an aroma flavor components, fragrance flavor ingredient, a compound of the formula (Formula 1) And feed for livestock, etc., characterized by containing

[0014] For example, cooked meats and processed vegetables such as curries, stews and hamburgers; soups such as Japanese soups, Western soups, and soups for ramen; and various snack foods. It is possible to provide foods to which an appropriate amount capable of imparting an appropriate flavor is added.
Further, feeds can be provided in which an appropriate amount capable of imparting a unique aroma is added to feeds for various pets and livestock.

Hereinafter, embodiments of the present invention will be described more specifically with reference to examples.

[0016]

EXAMPLES Example 1: Synthesis of 1-chloropropylsulphenyl chloride. In a 300 ml reaction flask, 96 g (0.64 mol) of propyl disulfide is charged and cooled to -10 ° C. Thereto, 216 g (1.60 mol) of sulfuryl chloride is added dropwise at -10 ° C to 0 ° C over 3 hours. The reaction solution is gradually brought to room temperature, and the reaction is further stirred for 15 hours. After the reaction,
After distilling off excess sulfuryl chloride under reduced pressure of about 100 mmHg, 160 g of 1-chloropropylsulfenyl chloride was purified by distillation under reduced pressure (yield 86).
%)Obtained. Boiling point: 60-65 ° C / 30 mmHg.

Example 2: Synthesis of 1-chlorobutylsulphenyl chloride. Using 89 g (0.50 mol) of butyl disulfide,
It was synthesized in the same manner as in Example 1 to obtain 140 g (88% yield) of 1-chlorobutylsulfenyl chloride. Boiling point: 68-75 ° C / 30 mmHg.

Example 3: Synthesis of 1-chloroisobutylsulphenyl chloride. Synthesized in the same manner as in Example 1 using 89 g (0.50 mol) of isobutyl disulfide, 135 g of 1-chloroisobutylsulfenyl chloride (85% yield)
Obtained. Boiling point: 66-71 ° C / 30 mmHg.

Example 4: Synthesis of 3-ethyl-1,2,4-trithiolane [compound of formula (I) -1]. 350 g (1.46 mol) of sodium sulfide / 9-hydrate, 650 g of methylene chloride and 500 g of dimethylformamide are charged into a 2 liter reaction flask, and 1-chloropropylsulfenyl chloride 106 is stirred at room temperature.
g (0.73 mol) is added over 30 minutes, and the mixture is further reacted at room temperature for 10 hours.

After completion of the reaction, the reaction product was added to 500 g of water and separated, and the aqueous layer was extracted with hexane (500 ml × 2 times).
And combined with the previous oil layer and washed with saline (300 ml x
3 times), dried over anhydrous magnesium sulfate, and then the solvent was recovered and purified by distillation to obtain 81 g (yield 73%) of a compound of the formula (Formula 1) -1. Boiling point: 80-82 ° C / 1 mmHg.

Example 5 Synthesis of 3-propyl-1,2,4-trithiolane [compound of formula (1) -2] 79.5 g of 1-chlorobutylsulfenyl chloride
(0.5 mol) was synthesized in the same manner as in Example 4,
62 g of the compound of the formula (Chem. 1) -2 of the present invention (yield 75
%)Obtained. Boiling point: 88-91 ° C / 1 mmHg.

Example 6: 3-isopropyl-1,2,4
-Synthesis of trithiolane [compound of formula (I) -3]. 79.5 g of 1-chloroisobutylsulfenyl chloride
(0.50 mol) and synthesized in the same manner as in Example 4 to obtain 64 g of the compound of the formula (Chemical Formula 1) -3 (yield 77).
%)Obtained. Boiling point: 87-89 ° C / 1 mmHg.

[0023]

According to the present invention, the 3-alkyl-1,2,4 Torichioran compound represented by the novel formula (Formula 1)
The present invention can provide an aroma and flavor imparting compound . The formula compound has a characteristic flavor of vegetable onion, onion, garlic, and the like, and has a flavor and flavor characteristic of contributing to a cooked meaty feeling when meat is cooked, and is used in foods, livestock feeds and the like. It is useful as a composition material of the composition.

Continuation of the front page (56) References Journal of Agricultural and Food Chemistry, (1992) Vol. 40, No. 10, p. 1906-1910 (58) Fields investigated (Int. Cl. ⁷ , DB name) C07D 341/00 A23L 1/22-1/24 C11B 9/00 CA (STN) REGISTRY (STN)

Claims (1)

(57) [Claims] [Claim 1] The following formula (Formula 1) (Wherein, R represents an ethyl group, a propyl group or an isopropyl group), a flavor-imparting compound comprising a 3-alkyl-1,2,4-trithiolane represented by the formula: