JPS58140032A - 2,6-dimethyl-2,7-octadiene-1,6-diol and utilization thereof - Google Patents

Abstract

NEW MATERIAL:2,6-Dimethyl-2,7-octadiene-1,6-diol expressed by formula 1. USE:A lasting perfume and flavor imparting and modifying agent, useful in wide fields of cosmetics, health, hygiene and medicines, etc., and having improved green, fruity, herbal aromas and flavors and lasting property. PROCESS:Linalyl acetate of formula 4 is oxidized in the presence of an oxidizing agent preferably in the presence of an organic solvent to give 2,6-dimethyl-6- acetoxy-2,7-octadienal of formula 3, which is then hydrogenated with a reducing reagent preferably in the presence of an organic solvent to afford 2, 6-dimethyl- 6-acetoxy-2,7-octadienol of formula 2. The resultant 2,6-dimethyl-6-acetoxy-2,7- octadienol of formula 2 is then hydrolyzed with an alkali to give the compound of formula 1 easily in high purity and yield.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides 2,6-dimethyl-snow, τ
-OctaVene-1,@-diol, its production method, and further relates to its use.

Furthermore: l1ll'L
．． Regarding 6-diol. Furthermore, the present invention provides the above formula (1)
2,6-dimethyl=sufuoctaVene-
Containing 1,6-diol as an active ingredient t4I
The present invention also relates to a persistent aroma and flavor imparting or modulating agent as mold, and also relates to a method for producing the compound of formula (1) above.

The present inventors have been conducting research on terpene compounds. As a result, it was found that λ6-ymethyl-2,7-octaVene-1,6-Vol represented by the formula (11) is a compound that has not been previously described in the literature, and that the scissors compound can be easily synthesized in good yield. It can be synthesized, and furthermore, the compound of Isah formula (1) has an excellent green, fruity, and barpal-like aroma and flavor,
In addition, we have discovered a unique compound that has excellent persistence and is extremely excellent as a long-lasting aroma and taste imparting agent. Furthermore, the Compound (1) is useful as an excellent aroma and flavor imparting or modulating agent in a wide range of fields, including food and beverages (including luxury goods), cosmetics, health, hygiene, and pharmaceuticals. We have discovered a very useful compound in the field as an excellent long-lasting aroma and flavor imparting or flavor modulating agent.

Therefore, the object of the present invention is to solve the above formula (1) which has not been described in the literature.
The present invention provides a compound and a method for producing the same.

Another object of the present invention is to provide a long-lasting aroma and flavor imparting or modulating agent containing the compound of formula (1) as an active ingredient.

The above objects as well as many other objects and advantages of the present invention will become more apparent from the following description.

The compound of formula (1) of the present invention can be obtained, for example, by oxidizing linalyl acetate represented by the following formula (4) with an oxidizing agent in the presence or absence of an organic solvent. 2,6-N methyl-6-acetoxy-3,
7- Form octagenal, then weiwu (2)
The compound tn is subjected to a hydrogenation reaction with a reducing reagent in the presence or absence of a solvent to form 2,6 represented by the following formula (2).
-Dimethyl-6-acetoxy-89-octadienol is formed, and the compound of formula (2) is further hydrolyzed with an alkali, whereby it can be easily produced with high purity and high yield.

The above reaction example can be expressed as shown below in a reaction diagram.

(2) (3) (1) The oxidation reaction of the compound of formula (4) can be easily carried out by bringing the compound of formula (4) into contact with an oxidizing agent, preferably in the presence of an organic solvent. It can be carried out.

Examples of the oxidizing agent to be used include two-chain ichselene, ditalomic acid, and chromic acid. ! !
! The fecal dose of the oxidizing agent can be selected as appropriate, but examples include a fecal dose of about α5 to about 5 equivalents, more preferably about 0.8 to about zO equivalent, relative to the compound of formula (4). can do.

Examples of organic solvents include dioxane, acetic acid, ether, V-chloromethane, benzene, and hexane. The amount of such a solvent can be selected as appropriate, but for example, for the compound of formula (2), the amount is about αS to about 20% by weight O1! Examples can include dosages.

The reaction temperature and reaction time depend on the type of oxidation catalyst used.
Therefore, you can choose to sleep as appropriate, but for example, d about 00 to about 100
It can be carried out at temperatures on the order of °C and reaction times of from about 1 to about 30 hours at S degrees. After the reaction is completed, the oxidation catalyst is removed, the solvent used is distilled off, and the desired compound of formula (2) can be easily synthesized in high yield by employing purification means such as distillation.

The hydrogenation reaction of the compound of formula (2) above can be easily carried out by bringing the compound of formula (4) into contact with a reducing reagent, preferably in the presence of an organic solvent.

The reducing reagent used is cr! For example, reducing agents such as sodium hydride, lithium hydride, and O may be used. The amount of these reducing agents to be used can be selected as appropriate, but for example, it can be approximately determined based on the amount of the (adult) compound.

Examples of single solvents include ethanol, methanol, ethyl ether, benzene, dichloromethane,
Examples include M-soluble compounds such as ethyl acetate. The amount of these organic solvents can be selected as appropriate, and for example, the amount used can be about 1 to about 10 times the weight of the compound of formula (3).

The reaction temperature and reaction time vary depending on the type of reducing agent used, but for example, the reaction can be carried out in a temperature range of about 0.11 to about SG°C and a reaction time of about Q, 1S to about 24 hours. After completion, the Fit source agent and solvent are removed, and the compound of formula (2) can be easily synthesized in high yield by purifying, for example, by distillation means.

The compound of the above formula (1) of the present invention can be synthesized by hydrolyzing the compound of formula (14) obtained as above with an alkali.

Specific examples of the alkali to be used include alkalis such as sodium hydroxide, potassium hydroxide, and sodium carbonate. There is no particular restriction on the amount used, but for example, about 1
Usage amounts of ~5 molar seeds can be mentioned. usually,
It is preferable to use the alkali in the form of an aqueous solution. In this case, the concentration can be selected as appropriate. 6. After the reaction is completed, the product is extracted with a solvent and purified by, for example, distillation means to synthesize the compound of formula (1) in high yield. The compound of formula (1) of the present invention has green, fruity, and herbal-like aromas, and has excellent persistence, so it is useful as a persistent aroma and flavor imparting or modulating agent.

Owing to its unique aroma and flavor and excellent persistence, the long-lasting aroma and flavor imparting/modulating agent is widely used in foods and beverages (including luxury goods), soaps, detergents, cosmetics, health/hygiene/pharmaceuticals, and other areas. It can demonstrate excellent effects in the field of use.

Therefore, by using the persistent aroma and flavor imparting or flavor modulating agent of the present invention, 2.6-1/methyl-2,7-octadiene-1
, 6-N-ol as an aroma component 1. Soaps and detergents containing the compound of the formula (1) as an aroma component 1. We can provide cosmetics, health care, hygiene, medicines, etc.

For example, juices, fruit alcoholic beverages, milk drinks and lactic acid soda drinks, 1) Beverages such as citric acid drinks, 1) Frozen desserts such as ice creams and popsicles, 1) Japanese and Western confectioneries, etc.
Yum FLAS breads: chewing, go (-), cocoa, black tea, tea, etc. 110 foods and beverages each including 1IIIll! and 6 types of instant beverages and instant foods #1, etc., with its Yueta aroma and flavor. For example, it can be used in shampoos, hair rinses, hair creams, pomades, other hair cosmetic bases, cosmetic soaps, and other makeup/facial cleansing bases. Nine cosmetics can be provided by blending the right amount of ants to give a unique fragrance.

In addition, laundry detergents, disinfectant detergents, deodorant cleaning products, and various health and hygiene detergents, toothpaste, tissues,
Health e-hygiene Φ medicines can be provided for the combination or application of soy sauce health and hygiene materials such as toilet paper, pharmaceuticals & IIIK, and appropriate amounts that can impart their unique aroma and flavor.

Some examples of embodiments of the present invention will be shown below in Examples.

Example 1 A fragrance composition for shampoo was produced by mixing each component (parts by weight).

Linalool 5 Absolute V Yasmin 2β-Phenylethyl Alcohol 150V Nor
15 absolute raw gel hydroxycitronellol 30 indyl 10%-'l penzoate solution
! Staylux oil
3 hexyl 7 nna? ivy aldehyde
IIs Cyclamenaldehyde 4
Nan-rutsudo oil 5 Phenylacetaldehyde toe g Above composition 9
11fK! ,6-Nmethy'-2m? By adding 2 ft of -octadiene-1,6-diol, a new composition with fresh lily of the valley-like properties and excellent persistence was obtained.

Example 8 Composition for Soap A Narcisse-like fragrance composition was produced by heating the following components (parts by weight).

Pel t-% oil 8. Ylang Ylang oil 5 Linalool
! i-Pen V Ru Acetate
zbenzyl alcohol
$3 Terpineol
1 Paracle V Ru Acetate 1 Cinnag Alcohol 2 Oil Norl 4 Heliotro 2
4 needles 100 The above composition 1199 was mixed with 1 ft of 2.61' methyl-2,7-octarenine-1,18-diol to produce a fragrance composition.

This product and a composition to which 2.6-V methyl-2,7-octadiene-1,6-diol is not added are added to an unscented soap paste in a ratio of 1 part by weight, and then molded into soap. Manufactured.

m, @-1) Methyl-2,7-octazine-6-s
Compared to soaps with the addition of /all and no soap, a skin control composition with natural Narcissus-like characteristics and excellent long-lasting properties was obtained.

Example 3 /#The following components (by weight) were mixed as aroma and flavor components for Inaguru.

ethyl acetate) 300 ethyl butyrate 25G inanluacetate 100 isoanluparerate ss isobutyric acid VO invaleric acid me allylka/roe) 38 ethylcagroate sO ethyl caprylate 15 ethyl caprate! O-in-a Densil Alfur 11 Citral
Easy Narol
S Maltol
Needle 1000 Add 2.6-1'methyl-λ2octadiene-1,11-1/ol Sft to the above composition tooot
Therefore, an extremely excellent new composition having excellent persistence as a Δinaggle aroma and flavor component was obtained.

! , τ-octaV enal) Production of selenium dioxide 111f%V oxane@00f and water 1of
+! 11 liquid (65 to 1% linalyl acetate in 1 hour) was added dropwise to 198 PVt, reacted at the same temperature for 2 hours, stirred, recovered dioxone, and the remaining liquid was distilled under reduced pressure.
7~1! t” / !g # j Obtain 991 compound (3) as a fraction. Yield 47-0 Production example * 2. @
-V methyl-6-acedokicou 2.7-octane enol (button creationsO ethanol aqueous solution @OfK sodium ahi 2
FLO4ttfliM*2.6-dimethyl-6-acetoxy2.7-octagenal (3)! iF was added at about 10 minutes at room temperature and reacted for 8 hours.

Next, 110f of water was added, and the mixture was extracted repeatedly with 100aJ of ether each time, and after recovering the ether, it was distilled under reduced pressure to obtain 148-b hardware (2). Yield it.

IUI example&t, @-ylfk-2. '(-yt?f
it/en-1,8-1/ol (1) O production 1091
*Some aqueous solution%0tvcN, @-yfi Chiru 6-
Ding Setoxie! , τ-octaV enol (2) 1aSf
t and reacted at room temperature for 5 hours. After neutralizing with dilute sulfuric acid, extracting twice with ether and distilling under reduced pressure after ether wAtlL.
L142~145℃/ Goose #11 as g1 minute
Compound (1) of t was obtained. Yield: -0 but 1 person

Claims (1)

[Scope of Claims] (1) The meaning represented by the following formula (1): -dimethyl-, fuoctaVen-x,syol. i The following formula (1) is represented by fl ＠-dimethyl-! Contain 1-octadiene-1.6-N as an active ingredient
- Persistent aroma and flavor imparting or modulating agent with % compensation.