JPS6137722A - Lasting flavoring agent and modifier - Google Patents

Abstract

PURPOSE:A lasting flavoring agent and modifier, containing a novel ozone oxidation product as an active constituent, and useful for fields of cosmetics, foods and drinks, health, sanitary medicines, etc. CONSTITUTION:A lasting flavoring agent and modifier containing an ozone oxidation product of a reactant, expressed by estimated formula III, and obtained by reacting a dihydro-beta-ionylphosphonium halide expressed by formula I (Ph is phenyl; X is halogen) with a compound expressed by formula II in the presence of sodium hydride as an active constituent. Ambrox is known as a key substance to amber aroma, but the above-mentioned ozone oxidation product is much more inexpensive than the synthetic ambrox and can be easily and industrially prepared at a much lower cost and has improved amberlike aroma. The above- mentioned oxidation product is incorporated in various perfume compositions, e.g. woody, floral, green or fruit perfume, and is useful as a flavoring agent and modifier in wide fields.

Description

DETAILED DESCRIPTION OF THE INVENTION This invention relates to a flavor imparting or modulating agent. The present invention also relates to a method for producing the ozone oxidation product, which is used in various cosmetics, quality goods, food and drink products, health and hygiene products, including various synthetic fragrances, natural fragrances, and blended fragrance compositions.・It shows remarkable usefulness as a long-lasting aroma and flavor imparting or modulating agent in a wide range of fields of use such as pharmaceuticals.

More specifically, the present invention relates to a dihydro-β-ionylphosphonium halide represented by the following formula (1) (Ph) where Ph represents a Fe=y group and X represents a halogen atom. and a compound represented by the following formula (2) in the presence of sodium hydride,
Natural ambergris having a typical amber-like aroma is This product is made by drying a foreign substance thought to be a pathological stone formed in the intestine of a Japanese whale, and is an extremely important and expensive animal flavoring substance. The natural ambergris is usually dissolved in alcohol and used in the form of a tincture as a raw material for various perfume preparations. However, in recent years, ambergris has become difficult to obtain due to restrictions on whale hunting.

This ambergris tincture contains various aroma components as a mixture, and the aroma components include, for example, the following compounds and many other compounds.

(Ambroz) (r-4onone)
Among these various aroma components, Ambrox, for example, is known as a key substance for the amber aroma. It is known that these various aromatic acids are produced when amprein, which itself has no gradient and is expressed by the following structural formula and is contained in ampu-grease, decomposes while floating on the ocean. .

Conventionally, various methods for synthesizing Ambrox of the above formula have been proposed. For example, natural Salvia sclarea (Sa
Using (-)-sclareol, an optically active substance present in the essential oil of Lvia 5alarea, as a starting material, it was oxidized with chromic acid to synthesize (+)-noramprenolide.

14.570 (1931)), and then the (+)-noramprenolide is reduced and then ring-closed [Dt-αgoc].

R6pO'rt-11/ 12.276-283 (19
79)).

10) - Ambrox However, the above synthesis method has the disadvantage that the starting material sclareol is an expensive raw material that exists in only a few percent of the essential oil of Salvia scrumum, and also that the raw material supply is limited because sclareol relies on natural products. In addition, there is a lack of stability in
There are also environmental health problems due to the use of toxic romic acid as a reaction reagent, and the use of lithium aluminum hydride in the reduction process, which is highly susceptible to ignition and is not suitable for industrial scale production. -)-Ambrox has many drawbacks and disadvantages, including the fact that it is extremely expensive, which poses a major constraint on its use as a raw material for blended perfume compositions.

As described above, the above-mentioned optically active substance (-)-ambrox is extremely expensive and cannot be widely used as a raw material for various blended fragrance compositions, and natural amber grease is a difficult-to-obtain material. In view of the above, the present inventors have conducted research and development on substances useful as amber uniform flavor substances.

As a result, the above formulas (1) and (
2) The ozone oxidation product of the reaction product formed by reacting a compound in the presence of sodium hydride has an excellent amber-like aroma and excellent persistence, which has not been previously described in the literature. It has been discovered that the present invention is a highly useful and remarkable product as a long-lasting aroma and flavor imparting or modulating agent.

According to the research of the present inventors, by reacting the metal compounds of the formulas (1) and (2) in the presence of sodium hydride, it was found that the reactant compound expressed by the following estimated structural formula (, f) Unprein[:JR
It was discovered that (filrn):3450m-') can be formed. The ozone oxidation product obtained by ozone oxidation of the reactant has an excellent amber uniform aroma comparable to the known tincture made by dissolving the natural ambergris in alcohol or the synthetic ambrox,
In addition, ozone oxidation products with excellent persistence [pale yellow oily substance: MS'', 194 (M''), 28B (&'')
, 194 (&”), 266 (&”), refractive index n%01.
5043; presumed to contain multiple types of ozone-oxidized aroma components].

According to the research conducted by the present inventors, the ozone oxidation product, which is much cheaper, easier, and industrially advantageous to produce than the synthetic Ambrox, can be used in various natural fragrances, synthetic fragrances, and mixed fragrance compositions. For example, it can be blended into various fragrance compositions such as water-based, filamentous, green-based, fruit-based, musk-based, citrus-based, etc. to create a round, long-lasting fragrance. It is useful as an excellent long-lasting aroma imparting or flavor modulating agent that provides excellent fragrance compositions, and is a noteworthy fragrance substance in a wide range of application fields such as cosmetics, food and beverages, health, hygiene, and pharmaceuticals. I found out something.

Therefore, the object of the present invention is to provide a long-lasting aroma and flavor imparting or modulating agent which has an excellent amber uniform aroma and contains as an active ingredient an ozone oxidation product which has not been described in any prior literature and has excellent long-lasting properties. is to provide.

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

The reactant norambrene, which can be represented by the deduced structural formula (Aχ) used in the formation of the ozone oxidation product of the present invention, is, for example, the following which can be easily synthesized from dihydro-β-ionone, which is easily synthesized or available and inexpensive. Dihydro-β-ionylphosphonium halide represented by formula +1) and compound 1, 6, 10, 10-tetramethyl-4-hydroxy-5-oxa-triciftetra(7
,4,0''·9.08°6] tridecane in the presence of sodium hydride.

One embodiment of synthesizing the ozone oxidation product of the present invention, including an example of synthesizing the compound (1) above from dihydro-β-ionone, can be illustrated as shown in the reaction process diagram below.

(a) (b)T
s (c) (d) (1) (2) (A) Presumed structure In the above embodiment of the present invention, the ozone oxidation product of the present invention, including the synthesis of the above formula (d) dihydro-β-ionyl halide, The manufacturing mode will be explained according to the above process diagram.

In order to synthesize the above formula (ii) compound, for example, the above formula (b) compound, the formula (c) compound from the above formula (i) dihydro 4-β-ionone, which is easily available or easily synthesized on the market.
It can be easily synthesized through chemical compounds.

The above formula (4) dihydro-β-iononone can be prepared, for example, by adding the above formula (1) dihydro-β-ionone in an organic solvent in the presence of a reducing reagent at a temperature range of about 5 to 50°C and about In a reaction time of about 1 to 5 hours, a human body can be easily synthesized by adding it to the reduction reaction. Examples of the reducing reagent used in the above reaction include lithium aluminum hydride and sodium borohydride.

The amount of these reducing reagents to be used can be selected as appropriate, and may range, for example, from about 0.25 to about 1.5 mol based on the compound of formula (A). Preferred examples of the organic solvent include methanol, ethanol, etc., and the amount of these organic solvents to be used can be selected as appropriate; An example is a range of twice as much. After the reaction is complete,
For example, the reaction product is poured into water, extracted with ether, the organic layer is washed with brine, dried over magnesium sulfate, concentrated, and then distilled under reduced pressure, for example, to easily obtain the compound of formula (b) above. be able to.

The above formula (c) dihydro-β-ionyl tosylate can be easily synthesized, for example, as described above.The above formula (b)
The compound can be easily synthesized by carrying out a contact reaction with tosylchloride in the presence of a base, for example, at a reaction temperature of about 0'' to 40°C for about 1 to 8 hours.

The amount of tosyl silolide used in the above reaction can be selected as appropriate, for example, about 1
The usage amount can range from about 3 moles to about 3 moles. Further, as the base to be present in the above reaction, bases such as pyridine and triethylamine can be preferably exemplified.

Although there are no particular restrictions on the amount of these bases to be used, a preferred range is, for example, about 1 to about 20 times the weight of the compound of formula (b) above.

The reaction product is, for example, poured into water, extracted with ether,
After washing the ether layer with an aqueous copper sulfate solution and further washing with water,
The compound of formula (iii) above can be easily synthesized by drying with magnesium sulfate and purifying, for example, by column chromatography.

Furthermore, the dihydro-β-ionyl halide of formula (d) can be obtained by contacting the compound of formula (c), which can be obtained as described above, with sodium halide, for example, in an organic solvent. It can be easily synthesized. The reaction temperature and reaction time can be selected appropriately, and for example, the reaction can be carried out at a reaction temperature of about 5° C. to about 40° C. and a reaction time of about 1 to about 5 hours. Preferred examples of the sodium halide used in the reaction include thorium iodide and sodium bromide. The amount of these sodium halides to be used can be selected as appropriate, but for example, about 1 to
A range of about 5 moles can be mentioned. In addition, examples of organic solvents include acetone, methyl ethyl ketone,
Examples include tetrahydrofuran and benzene. The amount of these organic solvents to be used can be selected appropriately, and the amount used can be, for example, about 1 to about 20 times the weight of the compound of formula (c) above.

After completion of the reaction, for example, the reaction product is poured into water and extracted with ether, the ether layer is washed with a saline solution, dried over magnesium sulfate, concentrated, and purified by column chromatography, for example, to obtain the above formula (d). Compounds can be easily synthesized.

In order to obtain the dihydro-β-ionylphosphonicum halide of the formula (1) of the present invention, for example, the dihydro-β-ionyl halide of the formula (2) obtained as described above can be converted into triphenylphosphine, e.g. About 60° to about 150°C
This can be carried out by contacting the container at a temperature range of about 100 mL and a reaction time ranging from about 5 to about 10 hours, for example. The reaction is preferably carried out under a stream of inert gas such as argon. The amount of triphenylphosphine to be used can be appropriately selected, and may be, for example, about 1 to about 2 times the mole of the compound of formula (2) above. The reaction product is washed with an organic solvent such as ether to easily obtain the phosphonylam salt of the above formula (1).

The noranprene of the putative structural formula (, 4) of the present invention can be obtained by converting the compound of formula (1), which can be synthesized as described above, into a compound of formula (2) which is easily available on the market or which is easily synthesized, for example, by hydrogenation. The formula (231,6,10,10-tetramethyl-4-hydroxy-5-oxa-tricyclo(7,4,0'°9.
02°6] It can be easily synthesized by a catalytic reaction with tridecane, for example, in an organic solvent in the presence of sodium hydride. The above (2) used in this reaction
) compound is, for example, about 0,
It can be carried out in a range of about 5 to about 5 times the mole. In addition, as the amount of sodium hydride used, for example, the above formula (1)
An example is a range of about 1 to about 5 moles relative to the compound. As the organic solvent, for example, dimethyl sulfoxide, ether, benzene, etc. can be preferably used, and there is no particular restriction on the amount of these organic solvents used, but for example, the amount of the organic solvent used is about 1 to about An example is a range of about 50 times the weight. The reaction temperature and reaction time can be selected appropriately, but for example, about 10° to about 1°
The reaction can be carried out at a reaction temperature of about 00° C. for about 10 to 25 hours in a refrigerator. After the reaction is completed, for example, the reaction solution is poured into ice water and extracted with, for example, hexane. The hexane layer is washed with water, dried over magnesium sulfate, concentrated, and the residue is purified by column chromatography, for example, to obtain the structural formula deduced above. (
, 4), the reactant noranprene can be obtained.

In order to obtain the ozone oxidation product of the present invention, which is assumed to contain the above-mentioned multi-component aroma components, has an excellent amber uniform aroma, and has excellent persistence, for example, a reaction can be performed that can be synthesized as described above. The compound noranprene can be obtained, for example, by oxidation with ozone in the presence of an organic solvent. As the organic solvent, for example, an organic solvent such as ethanol can be used, and the amount of these organic solvents can be appropriately selected. Examples of ranges can be given. The reaction is preferably carried out under low temperature conditions, for example in the range of about -50° to about -70°C. The reaction time can be appropriately selected and can be easily set experimentally in advance, if necessary, depending on the ozone oxidation conditions until an ozone oxidation product exhibiting the desired amber uniform aroma is formed. After completion of the reaction, for example, an organic solvent such as dichloromethane is added to the reaction solution to perform extraction, and the dichloromethane layer is washed with, for example, an aqueous sodium thiosulfate solution, and further washed with, for example, an aqueous sodium thiosulfate solution, followed by sulfuric acid.)
The ozone oxidation product of the present invention can be obtained in the form of a pale yellow oil, which is presumed to contain multi-component aroma components with a concentrated amber-like aroma after drying over 300 ml.

For example, the ozone oxidation product having an amber uniform aroma of the present invention, which can be obtained as described above, has an excellent amber uniform aroma comparable to that of a tincture of natural ambergris dissolved in alcohol or the synthetic ambrox described above. It has been found that it has an aroma with excellent persistence and is useful as a persistent aroma and flavor imparting or modulating agent. The ozone oxidation product of the present invention, which has an amber-like aroma, has excellent sustainability, softness, and roundness as an aroma, flavor imparting, or modulating ingredient for various cosmetics, foods and beverages, health/hygiene/medicines, etc. Has aroma and flavor.

More specifically, by blending an ozone oxidation product having an amber-like aroma with, for example, one or more synthetic single fragrances, a variety of new and new persistent aroma and flavor imparting/distortion modulators can be prepared. Furthermore, when it is blended with synthetic essential oils such as bergamot oil, lemon oil, geranium oil, mandarin oil, and lavender oil, it is possible to prepare a new, long-lasting aroma and flavor imparting or modulating agent that has the mild and elegant properties inherent in natural essential oils. Furthermore, for example,
To prepare a novel long-lasting aroma flavor imparting or modulating agent containing orange oil, lime oil, lemon oil, grapefruit oil, oakmoss oil, citronella oil, loofah oil, cinnamon oil, patchouli oil, thyme oil, black I can do it.

Furthermore, blended fragrances made by blending two or more types of natural fragrances and synthetic single fragrances, such as rose, jasmine, lilac, osmanthus, carnation, and muguet, and combinations thereof. Fragrance compositions such as modern 70-ral pouquets or oriental bouquets with fji-n notes, spicy notes, taraldehyde notes, strawberries, lemons, oranges, crepes, roots, apples, etc. When incorporated into a flavor composition such as pineapple or other flavor compositions, a novel aroma and flavor imparting or modulating agent with a mild, rich, natural flavor and enhanced sustainability can be obtained.

The amount of the ozone oxidation product of the present invention varies depending on its purpose and the aroma/flavor imparting or modulating agent, but for example, it is in the range of about 0.001 to about 50% by weight of the total. I can do it.

Thus, according to the present invention, it is possible to provide a persistent aroma/flavor imparting or improved reinforcing agent containing the ozone oxidation product of the present invention as an active ingredient, and by using a nucleating agent, the ozone oxidation product of the present invention can be used as an aroma/flavor imparting or improving reinforcing agent. Foods and drinks containing the ozone oxidation product of the present invention as an aroma component, cosmetics containing the ozone oxidation product of the present invention as an aroma component, and cosmetics containing the ozone oxidation product of the present invention as an aroma component. We can provide distinctive health, hygiene, pharmaceutical products, etc.

For example, beverages such as fruit juice drinks, fruit alcoholic beverages, milk drinks, and carbonated drinks; frozen desserts such as ice cream, sherbet, and popsicles; Japanese and Western sweets, jams, chewing gums, breads, and coffee. Appropriate amount to impart unique aroma and flavor to luxury goods such as , cocoa, tea, and tea; soups such as Japanese soups and Western soups; flavor seasonings, various instant beverages and foods, and various snack foods. It is possible to provide food and drinks containing the following. Also, for example, ζ-Chands, hair creams, pomades, and other hair cosmetic bases; Oshiroi, lipstick,
Cosmetics can be provided by blending other cosmetic detergents or cosmetic detergent bases in an appropriate amount that imparts the unique fragrance. Furthermore, laundry detergents, disinfectant detergents, deodorizing detergents, and various other health and hygiene detergents: toothpaste,
Various health and hygiene materials such as tissues and toilet vapors: Flavoring and flavoring agents to make it easier to take medicines, etc. Appropriate amount combination or flavoring agent that can impart unique flavor to health, hygiene and medicines. Applied health, hygiene,
We can provide pharmaceutical products.

EXAMPLES Below, several embodiments of production and usage examples of the ozone oxidation product of the present invention will be explained in more detail with reference to Examples.

Reference example 1 Synthesis of dihydro-β-ionono (b) 95% ethanol 75-1 Sodium borohydride s#
(o, 21 mol) in dihydro β-ionone 691i (
A mixed solution of 0,355 mo/L/) and 95% ethanol is added dropwise at a temperature of 15° to 17° C. over a period of 1 i. After stirring at the same temperature for 2 hours, the reaction mixture was poured into water and extracted with ether. The ether layer was washed with brine, dried over magnesium sulfate, concentrated, and distilled under reduced pressure to reduce the boiling point to 1.
Compound 6 of formula (b) having a temperature of 06” to 108°C/3mHg
I got 6I. (Yield E5%) IR (film): 3400, 1380, 1360 cm
−”, NMR(aD (Ill'l'a) "δ
1.00 (6H.

4.1 (IH, m).

Reference Example 2 Dihydro-β-ionyl tosylate.

Synthesis of (c) Dihydro-β-ionono (c) 5119 (0,2
Add 57.9 (0.3 mol) of tosyl chloride to 300 ml of dry pyridine at 0°C, stir for 1 hour at the same temperature, and stir for 5 hours at room temperature (20°C). The reactant was poured into water and extracted with ether. The ether layer was washed with an aqueous copper sulfate solution and further washed with water. The ether layer was dried over magnesium sulfate, concentrated, and purified by column chromatography (540!, ethyl acetate/hexane="/,) to give the formula (Ha ) Compound 511 (yield 56%) was obtained.

Reference example 3 Dihydro-β-ionyl iodide (1)
Synthesis of dihydro-β-ionyl tosylate (c) 45, . 9(
Sodium iodide 6111 (0.45 mol) was added to 500 d of acetone and stirred at room temperature (20°C) for 24 hours. The reaction product was poured into water, extracted with ether, and the ether layer was washed with brine, dried and concentrated with magnesium chloride, and purified with column chromatography (SO, hexane/ethyl acetate = 20/1) to obtain the formula (1) Chemicals 3
9 g (yield 99%) was obtained. JR (ftlrn):
1380cut-", 1360m-', NMR (CD
CI, ): δ0.99 (6H, a), 1.58 (3H
, 8), 1.2-2-3 (10H), 1.92 (3H
, d, J=8Hz), 3.9-4.5 (IH, regret).

Example 1 Synthesis of dihydro-β-ionylphosphonium iodide (2) Under an argon atmosphere, dihydro-β-ionyl phosphonium iodide 3
5.9 (0,114 mol) totriphenylphosphine 5
5# (0.21, mol) was reacted at 120°C for 8 hours.

After cooling! After washing with ether, 57 g (yield: 88%) of the compound of formula (2) was obtained.

NMR (CDC1,): δ0.90 (6H;s),
0, 9-22 (16N), &2-&6 (IH), 7.3-8.2 (18H).

Example 2 Synthesis of noranprene formula (A) 62% sodium hydride Z9I in 100 m of dry dimethyl sulfoxide! (0.07 mol), 50''~70
If heated to ℃ and stirred for 2 hours, no gas will be generated. Next, a mixed solution of 34.9 (0.06 moA/) of dihydro-β-ionylphospho A iodide (2) and 100 mg of dry dimethyl sulfoxide was heated at 15°C.
Add to the mixture and stir for 30 minutes at the same temperature. Then 1.6,1
0.10-tetramethyl-4-hydroxy-5-oxa-tricyclo(7,4,0"°9.02°'))
! J tecan (3) and dimethyl sulfoxide 100fnt
Add the mixed solution and stir at room temperature (20°C) for 24 hours.

The reaction solution was poured into ice water and extracted with hexane. The hexane layer is washed with water, dried over magnesium sulfate, and concentrated.

The residue was purified by column chromatography (St., nifl/hentane/cyclohexane = 4/1/2) to obtain formula (4) 6.2.9 (yield 50%).

IR, (film); 3450cIIL-''Example 3 Synthesis of ozone oxidation product with amber-like aroma 4.51! (0,0108 mol) of noranprene, unreacted at 65°C in 600 g of ethanol. Relax.

Dichloromethane is added to the reaction solution for extraction. The dichloromethane layer was washed with an aqueous sodium thiosulfate solution, further washed with an aqueous sodium bicarbonate solution, dried over magnesium sulfate, and concentrated to obtain a pale yellow oily substance 4.2.9 with an amber-like aroma. This product contained multiple aromatic components (like GLC).

Refractive index n〒1.5043, M, 5: xs4 (M”), 2
6g (M+), 194 (Af”), 288 (J/+).

Example 4 The following components (parts by weight) were mixed as an orchid type perfume composition.

Cyclopentadecanolide 5 Coumarin 1 Heliotropin
3 ylang ylang oil
8 Methyl ionone
10 neroli oil
3 hydroxycitronellal 5
Linaloo/L/
Physobutyl salicylate 11 5-cyclohexadecenone 2 Amyl salicylate 14 Oakmoss absolute 3 Vanillin 7 Phenylacetaldehyde 2 Phenylethyl alcohol 20 Benzyl acetate
6 By adding 9 g of an ozone oxidation product having an amber-like aroma to 91 g of the above composition, a novel blended fragrance composition with excellent persistence and a fresh and natural orchid type was obtained. It was done.

In addition, 9 g of (-)-Ambrox was added to 91 g of the above composition in place of the ozone oxidation product having a uniform aroma of Ambrox to prepare a blended fragrance composition. Compare the color with a blended fragrance composition with added. As a result, 6 out of 10 expert panelists said that the perfume composition containing the product of the present invention was superior in terms of sustainability and fresh, natural appearance.

Example 5 The following components (parts by weight) were mixed as a bouquet type perfume composition.

Phenylethyl alcohol-A/18 Linari acetate 3 Bergamot oil 4 Geranium oil
5 Benzyl acetate
6 heliotropin
8 Geraniol
11 Lavender oil 2
By adding β-ionone, 10 amyl salicylate, 45 turbinyl acetate, 1 & 5 cedar oil, 10 citronellone/I15 and 12.5 I of oxidation product, a new bouquet perfume composition which is natural and has excellent persistence is obtained. It was done.

In addition, (-)-Ambrox 2.9 was added to the above composition 989 as a substitute for the ozone oxidation product having a uniform aroma of Ambrox to prepare a blended fragrance composition, and an expert panelist - 10 said that it was useful for people, A comparison was made with a blended fragrance composition containing the product of the present invention. As a result, 6 out of 10 expert panelists added this invention,
The prepared fragrance composition was said to be excellent in terms of aroma and persistence.

Example 6 The following components (parts by weight) were mixed as a gardenia type mixed fragrance composition.

Benzyl acetate 10 Hydroxycitronellal 15 Coumarin
1. Diasmine Apunryuto 3. Orange Flower Absolute 2. Phenyl Methyl Carbinyl Acetate
3 Heliotropine 10 Bergamotu oil 10 Linaloo/I/10 Amyl cinnamic aldehyde 4 Ylang ylang oil 7 Galaxolide
3α-ionone
10 true resinoid
2 Phenylacetaldehyde
1.5 isoeugenyl acetate
&5 Cipet 10% Alcohol/L/1 Octyl Aldehyde 10% Alcohol # 0.5 Decyl Aldehyde 10% Alcohol 0.5 Cyclohexyl Butyrate 3100.0 Ozone oxidation product with amber uniform aroma in the above composition 94.9 By adding 611, a new gardenia perfume composition which is natural and has excellent persistence was obtained.

In addition, 6 g of (-)-Ambrox was added to the above composition 94.9 as a substitute for the ozone oxidation product having a uniform aroma of Ambrox to prepare a blended fragrance composition. A comparison was made with a blended fragrance composition containing the invention product. As a result, 7 out of 10 expert panelists agreed that the blended fragrance composition to which the present invention was added was superior to the above-mentioned comparative blended fragrance composition in terms of durability.

Example 7 The following components (parts by weight) were mixed to prepare a 0's type perfume composition.

Phenylethyl alcohol 20 Geraniol 5 Coumarin
2 Heliotropin
l citronellol
10 nerol
3hydrogishicitronella-y
2 Methyl phenyl carbinyl acetate 0.5 Geranium oil 1 Linalool 3 Benzyl acetate 3.5 Benzyl alcohol 20-Zphenone 10 Synol
280-z oil
1β-ionone
5 Benzyl salicylate
4 cyclopentadecanolide
3 Guaiyaud oil 5
By adding 10 g of the product of the present invention to 90.9 g of the above composition, a novel rose blended fragrance composition with very long-lasting properties was obtained.

Also, add 10 parts of natural ambergris tincture to 90 g of the above composition as a substitute for the product of the present invention! A blended fragrance composition was prepared by adding the product of the present invention, and compared with a blended fragrance composition containing the product of the present invention by 10 expert panelists. As a result, 6 out of 10 expert panelists agreed that the blended fragrance composition containing the product of the present invention was superior to the above-mentioned comparative blended fragrance composition in terms of durability.

Patent applicant: Hasegawa Perfume Co., Ltd. 1 other person

Claims (1)

[Claims] 1. Dihydro-β represented by the following formula (1) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (1) In the formula, Ph represents a phenyl group and X represents a halogen atom. -Ionylphosphonium halide and the compound represented by the following formula (2) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(2) in the presence of sodium hydride,
A persistent aroma and flavor imparting or modulating agent characterized by containing as an active ingredient an ozone oxidation product of the reactant formed by the reaction.