JPS6145976B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention has a fruit-like aroma, is useful in the field of fragrances, and is further useful as a synthetic intermediate; However, in the formula, Y represents =O or (-OR) ₂ ,
Here, the two R are the same or different, C ₁
-represents a group selected from the group consisting of a _C10 alkyl group and a _C3 - _C10 alkenyl group, or the two R together represent a _C2 - _C3 methylene bond. The present invention relates to cis-3 and cis-5-octadienals, their production methods, and further their uses. The present inventors have conducted research on the development of octadienals. As a result, the above formula ()
Cis-3, cis-, which has not been described in the conventional literature, represented by
We succeeded in synthesizing 5-octadienals. Furthermore, it has been discovered that the compound represented by the formula () exhibits an excellent fruit-like aroma and has excellent persistence, and can be used in a wide range of fields as a persistent aroma and flavor imparting or modulating agent. . Therefore, an object of the present invention is to provide cis-3.cis-5-octadienals represented by the above formula (). Another object of the present invention is to provide a method for producing the compound of formula (). Still another object of the present invention is to provide a new type of long-lasting aroma and flavor imparting or modulating agent containing the compound of formula () as an active ingredient. The above objects and many other objects and advantages of the present invention will become more apparent from the following description. The compound of the formula () of the present invention has the following formula (-
1), Cis-3/cis-5-octadienal (boiling point: 72-73°C/15mmHg) represented by and the following formula (-2), However, in the formula, R has the same meaning as described above, and includes an acetal derivative of the compound of formula (-1) represented by: In the above formula (-2), specific examples of R include C ₁ -C ₁₀ alkyl such as methyl, ethyl, propyl, butyl, isobutyl, amyl, isoamyl, hexyl, heptyl, octyl, nonyl, decyl, etc. Groups; for example, 2-propenyl, 2-butenyl, 3-butenyl, 2-pentenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 3-
Octenyl, 5-octenyl, 3,5-octadienyl, 3-nonenyl, 6-nonenyl, 3,6-
Examples include _C3 to _C10 alkenyl groups such as nonadienyl; dimethylene and trimethylene which can be formed by combining two R groups. The two R's may be the same or different. As specific representative examples of such acetal derivatives of formula (-2), the following compounds can be exemplified. (1) Cis-3, cis-5-octadienal dimethyl acetal Boiling point 72-73℃/3mmHg (2) Cis-3,cis-5-octadienal diethyl acetal Boiling point 78-80℃/3mmHg (3) Cis -3, cis-5-octadienal dipropyl acetal Boiling point 85-86℃/3mmHg (4) Cis-3, cis-5-octadienal dibutyl acetal Boiling point 91-93℃/3mmHg (5) Cis-3, Cis-5-octadienal diamyl acetal Boiling point 76-78℃/1mmHg (6) Cis-3-cis-5-octadienal dihexyl acetal Boiling point 87-89℃/1mmHg (7) Cis-3, Cis-5 -Octadienal dioctyl acetal Boiling point 99-101℃/1mmHg (8) Cis-3, cis-5-octadienal didecyl acetal Boiling point 113-115℃/1mmHg (9) Cis-3, cis-5-octadiene Nal ethyl methyl acetal Boiling point 77-78℃/2mmHg (10) Cis-3, cis-5-octadienal ethylpropyl acetal Boiling point 73-74℃/1mm
Hg (11) Cis-3, cis-5-octadienal butyl ethyl acetal Boiling point 79-80℃/1mmHg (12) Cis-3, cis-5-octadienal ethylhexyl acetal Boiling point 89-90℃/1mm
Hg (13) Cis-3, cis-5-octadienal ethyl octyl acetal Boiling point 94-95℃/1mm
Hg (14) Cis-3, cis-5-octadienal propyl butyl acetal Boiling point 82-83℃/1mm
Hg (15) Cis-3, cis-5-octadienal amylpropyl acetal Boiling point 86-87℃/1mm
Hg (16) Cis-3, cis-5-octadienal diallyl acetal Boiling point 84-86℃/2mmHg (17) Cis-3, cis-5-octadienal di-2-butynyl acetal Boiling point 87-89℃ /1
mmHg (18) Cis-3, cis-5-octadienal di-3-hexenyl acetal Boiling point 92-94℃/
1mmHg (19) Cis-3, cis-5-octadienal ethylene acetal Boiling point 75-76℃/2mmHg (20) Cis-3, cis-5-octadienal trimethylene acetal Boiling point 84-85℃/2mm
Hg Among the formula () cis-3 cis-5-octadienals of the present invention, cis-3 cis-3 of the formula (-1)
Cis-5-octadienal is, for example, cis-3/cis-5 of the formula (-2) in the formula ().
- An acetal derivative of octadienal can be easily produced in high yield and purity by subjecting it to a deacetalization reaction under acidic conditions. In addition, the acetal derivative of the formula (-2) in the formula () is, for example, the following formula (), However, in the formula, R has the same meaning as described above. By subjecting the acetal derivative of 3,5-octadiyn-1-al represented by the following to a catalytic hydrogenation reaction in the presence of a catalytic hydrogenation catalyst, high yield, Can be easily obtained with high purity. Furthermore, the formula ()
The compound is, for example, the following formula (), However, in the formula, R has the same meaning as above, and a 3-butinal acetal derivative represented by the following formula (), However, in the formula, X represents a halogen atom. It can be easily produced by subjecting 1-halogeno-1-butyne represented by the following formula to a condensation reaction in the presence of amines and cuprous ions. Examples of producing the compound of formula () of the present invention according to the above embodiments will be described in more detail below. The above manufacturing example can be shown diagrammatically as follows. A reaction for producing an acetal derivative of 3,5-octadiyn-1-al of formula () by a condensation reaction between an acetal derivative of 3-butynal of formula () and 1-halogeno-1-butyne of formula () can be easily carried out, for example, by dropping a compound of formula () into a solution of the compound of formula () in water or an appropriate organic solvent in the presence of an appropriate amine and a catalytic amount of cuprous ion. can. The reaction can be carried out at a wide range of temperatures, for example from about -80°C to about 100°C, with a more preferred example being a temperature of about 0°C to about 50°C. The dropping time can be changed as appropriate depending on the reaction temperature, for example, from about 1 to about
A reaction time of about 50 hours can be exemplified. 1-halogen-1-butyne of the above formula () is
For example, Ann.Chim (Paris) [13] 2 852
(1957), Org.Synth V921 (1973), J.Chem.Soc.
1- according to the method described in 1963 2295 etc.
It can be manufactured more easily than butyne. The above halogens of X include chlor, bromine,
I can give an example of iodine. Further, the acetal derivative of 3-butynal of the above formula () is, for example, Ann.
It can be easily produced from propargyl bromide by the method described in Chim [13) 6 1071-1130 (1961). Examples of amines used in the above reaction are:
selected from the group consisting of C ₁ -C ₄ alkyl amines, di(C ₁ -C ₄ alkyl) amines, tri(C ₁ -C ₄ alkyl) amines and C ₁ -C ₆ alkanolamines Preferred examples include amines. Specific examples of such amines include primary amines such as methylamine, ethylamine, propylamine, isopropylamine, butylamine; secondary amines such as dimethylamine, diethylamine, dipropylamine, diisopropylamine, diisobruamine, and dibutylamine; Diamines; tertiary amines such as trimethylamine, triethylamine, triisopropylamine, tripropylamine, and tributylamine; monoethanolamine, diethanolamine, triethanolamine; and the like. These amines can be used alone or in combination of two or more.
There is no particular restriction on the amount of these amines to be used, but for example, about 1 mol to about 1000 times the mol is sufficient, more preferably about 1 mol to about 1000 times the mol of the compound of formula () as the raw material. About 50 moles are often used. The amount of the compound of formula () used in the above condensation reaction can be appropriately selected, and a preferable example is about 1 to about 2 moles of the compound of formula () per 1 mole of the compound of formula (). Further, as the cuprous ion source used in the above condensation reaction, any source that produces cuprous ions within the reaction system can be used. Specific examples include cuprous chloride, cuprous bromide, cuprous iodide, copper cyanide, and cuprous sulfate. These usage amounts are based on the raw material formula () Compound 1
For example, about 0.001 to about 1 mole is sufficient, and more preferably about 0.01 to about 0.05 mole is often employed. Further, in the above condensation reaction, even better results can be obtained by adding a small amount of a reagent having the effect of suppressing the composition of cupric ions, such as hydroxylamine. Further, specific examples of the solvent used in the above condensation reaction include water, alcohol solvents such as methanol and ethanol, ether solvents such as tetrahydrofuran, dioxane, diethyl ether, and diglyme; dimethylformamide, dimethyl sulfoxide, Examples include organic solvents such as amide solvents such as hexamethylene phosphorotriamide; These solvents can be used alone or in combination of two or more. There is no particular restriction on the amount of these solvents to be used, and examples include an amount of about 0 to about 100 times by weight, more preferably about 2 to about 10 times by weight, relative to the compound of formula () as a raw material. be able to. After the completion of the condensation reaction, for example, the reaction product is injected into water, extracted with a suitable solvent, the solvent layer is washed with water, dried, and concentrated.
Acetal derivatives of 5-octadiyn-1-al can be produced with high yield and high purity. If desired, further purification can be carried out by means such as vacuum distillation or column chromatography. Specific examples of 3,5-octadiyn-1-al acetals obtained as described above include:
For example, the following compounds can be exemplified. (1') 3,5-octadiyn-1-al dimethyl acetal Boiling point 83~84℃/3mmHg (2') 3,5-octadiyn-1-al diethyl acetal Boiling point 95~96℃/3mmHg (3') 3. 5-octadiyn-1-al dipropyl acetal Boiling point 102-103℃/3mmHg (4') 3,5-octadiyn-1-aldibutyl acetal Boiling point 108-109℃/3mmHg (5') 3,5-octadiyne-1 -R diamyl acetal boiling point 88~89℃/1mmHg (6') 3,5-octadiyn-1-aldihexyl acetal boiling point 99~100℃/1mmHg (7') 3,5-octadiyn-1-aldioctyl acetal boiling point 103-105℃/1mmHg (8') 3,5-octadiyn-1-aldidecyl acetal Boiling point 125-127℃/1mmHg (9') 3,5-octadiyn-1-almethylethyl acetal Boiling point 85-86℃ /1mmHg (10') 3,5-octadiyn-1-all ethylpropyl acetal Boiling point 87-89℃/1mmHg (11') 3,5-octadiyn-1-allethylbutyl acetal Boiling point 92-93℃/1mmHg (12 ') 3,5-octadiyn-1-arethylhexyl acetal Boiling point 100-102℃/1mm
Hg (13') 3,5-octadiyn-1-arethyl octyl acetal boiling point 105-107℃/1mm
Hg (14') 3,5-octadiyn-1-alpropylbutyl acetal Boiling point 96-97℃/1mmHg (15') 3,5-octadiyn-1-alpropylamyl acetal Boiling point 102-103℃/1mm
Hg (16') 3,5-octadiyn-1-aldiallylacetal Boiling point 92-93℃/1mmHg (17') 3,5-octadiyn-1-aldi-
2'-Butenyl acetal boiling point 103-105℃/1
mmHg (18') 3,5-octadiyne-1-ardi-
3'-hexenyl acetal boiling point 109-111℃/
1mmHg (19') 3,5-octadiyn-1-al ethylene acetal Boiling point 82-83℃/1mmHg (20') 3,5-octadiyn-1-altrimethylene acetal Boiling point 96-97℃/1mmHg Formula of the present invention () In the compound, the above formula (-2)
The acetal derivative of cis-3.cis-5-octadienal can be obtained by converting the acetal derivative of 3,5-octadiyn-1-al of the formula (), which can be obtained as described above, into a catalytic hydrogenation catalyst, for example. It can be easily produced by carrying out a catalytic hydrogenation reaction in the presence of. Examples of the catalytic hydrogenation catalyst include a Lindlar catalyst, a palladium-barium sulfate catalyst, a palladium-calcium carbonate catalyst, a palladium-strontium carbonate catalyst, and a W-1 Raney-nickel catalyst. The amount of catalyst to be used can be selected as appropriate, but for example, about 0.5 to about
About 200% (weight), more preferably about 2 to about 100
% (weight). Although the above catalytic hydrogenation catalyst can be used as it is, it is generally preferable to add a catalyst poison to it. Examples of such catalyst poisons include quinoline, isoquinoline, pyridine, aniline, thiophene, and potassium iodide. The amount of catalyst poison used is, for example, approximately
About 0.5 to 20 times (weight), more preferably about 3 to 20 times (weight)
It is about 7 ml (weight). Although the catalytic hydrogenation reaction can be carried out without a solvent, it is generally preferable to carry out the reaction in a solvent. Examples of such solvents include aliphatic hydrocarbons such as pentane, hexane, cyclohexane, petroleum ether; aromatic hydrocarbons such as benzene, toluene, xylene;
Ethers such as diethyl ether, diisopropyl ether, and tetrahydrofuran, ethyl acetate,
Examples include esters such as propyl acetate and methyl propionate; alcohols such as methanol, ethanol, and propanol. The amount of the solvent to be used can be selected as appropriate, for example, about 0.5 to about 50 times (by weight), preferably about 5 to about 15 times the amount of the compound of formula ().
Amounts in the range of times (by weight) are most commonly employed. For example, the reaction is carried out by charging the 3,5-octadiyn-1-aldialkyl acetal of the formula (), the solvent, the catalytic hydrogenation catalyst, and the catalyst poison in any order into the catalytic hydrogenation apparatus, injecting hydrogen, and then heating to a predetermined temperature. This can be carried out by allowing the reaction to take place until the stoichiometric amount of hydrogen is absorbed. separating the catalyst from the reaction product liquid;
It is introduced into water and extracted using an appropriate extraction solvent as necessary. The extraction solvent layer is washed, for example, with a dilute mineral acid aqueous solution, washed with water, the solvent is removed, and distilled under reduced pressure, for example, to obtain the target compound, cis-3/cis-5- of formula (-2).
Acetal derivatives of octadienal can be obtained. The hydrogen pressure is usually in the range of about 20 kg/cm ² from atmospheric pressure, preferably about 5 kg/cm ² from atmospheric pressure. The reaction temperature can be appropriately selected depending on the catalyst used, the type and amount of solvent, hydrogen pressure, etc., but is, for example, about -10°C to about 70°C, preferably about 20°C to about 50°C.
A range can be adopted. The reaction time depends on the catalyst used,
It may be changed as appropriate depending on the type and amount of solvent, hydrogen pressure, reaction temperature, etc. In the present invention, among the compounds of formula () that can be formed as described above, cis-3-
Acetals of cis-5-octadienal are
By deacetalizing under acidic conditions, formula (-1) can be easily converted into compounds of formula ().
can be converted to cis-3.cis-5-octadienal. The reaction can be carried out, for example, by subjecting the compound of formula (-2) to acidic conditions in a solvent, for example at a temperature of about -20°C to about 50°C, preferably about 0°C to about Temperature conditions around 35°C can be adopted. The reaction time can be, for example, about 0.5 to about 50 hours. Examples of acids used in the above deacetalization reaction include inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, etc.; p-toluenesulfonic acid, benzenesulfonic acid, methanesulfonic acid, trichloroacetic acid, dichloroacetic acid, monochloroacetic acid, Organic acids such as tri-, di- or mono-fluoroacetic acid, oxalic acid and formic acid; conjugated types such as pyridine hydrochloride; strongly acidic ion exchange resins such as Amberlite IR-120 and the like. These acids can be used alone or in combination. Therefore, the usage amount can be selected as appropriate, but for example, the formula (-
2) About 0.1 to about 5 times the mole of the compound,
More preferably, the amount used is about 0.1 to about 0.5 times the mole. Examples of the above-mentioned solvents include polar solvents such as water, methanol, and ethyl alcohol, as well as hydrocarbon solvents such as benzene, xylene, toluene, and hexane, such as diethyl ether, diisopropyl ether, dimethoxyethane, and tetrahydrofuran. , ether solvents such as dioxane, and the like.
These solvents can be used alone or in combination. The amount used can be selected as appropriate, but for example, it can be used in an amount of about 5 to about 50 times the weight of the compound of formula (-2), more preferably about 3 to about 30 times the weight of the compound. . After carrying out the deacetalization reaction as described above, for example, the reaction product is poured into water and extracted with a suitable solvent such as ether, benzene, toluene, xylene, n-hexane, dichloromethane, etc. The solvent layer is washed with a % sodium carbonate aqueous solution, further washed with water if desired, dried and concentrated to obtain the compound of formula (-1) in high yield and high purity. Furthermore, if desired, it can be further purified by means such as vacuum distillation or column chromatography. In addition, cis-3/cis-5-octadienal of formula (-1) can be acetalized according to known acetalization conditions to form formula (-1), if desired.
It can also be converted to the compound 2). It has been discovered that the cis-3.cis-5-octadienals of formula () of the present invention are extremely useful as fruity, persistent aroma flavor imparting or modulating agents. That is, the compound of formula () has excellent persistence and unique aroma or flavor. Thus, according to the present invention, cis-
A persistent aroma and flavor imparting or modulating agent characterized by containing 3.cis-5-octadienals as an active ingredient can be provided. Furthermore, this agent can be used to produce food and drink products that contain the compound of formula () as an aroma component; soaps, detergents, and cosmetics that contain the compound of formula () as an aroma component. It is possible to provide health care, sanitary, pharmaceutical products, etc., which are characterized by containing a compound of formula () as an aromatic flavor component. For example, drinks such as juices, fruit alcoholic beverages, milk drinks, lactic acid bacteria drinks, lactic acid drinks; frozen desserts such as ice creams and ice candy;
Its unique aroma and flavor can be applied to a variety of edible foods, including Japanese and Western sweets; jams, breads, chewing gum, coffee, cocoa, black tea, tea, and other edible foods, as well as various instant beverages and foods. It is possible to provide food and drink containing the appropriate amount. For example, cosmetics containing shampoos, hair rinses, hair creams, pomades, and other hair cosmetic bases; cosmetic soaps and other makeup/facial cleansing bases in an appropriate amount to impart the unique fragrance. Can be provided. Furthermore, cleaning detergents, disinfectant detergents, deodorizing detergents, and various other health and sanitary detergents; toothpaste,
It is possible to provide health, hygiene, and pharmaceutical products that are blended or applied in an appropriate amount to impart the unique aroma and flavor to various health and hygiene materials and pharmaceuticals, such as toilet paper and toilet paper. Reference Example 1 Production of Γ1-bromo-1-butyne In a solution of 120 g of caustic soda in 400 ml of water, at 0 to 5°C.
Add bromine and stir at the same temperature for 30 minutes. next,
32.5 g of 1-butyne was injected at -10 to -5°C, and the mixture was further stirred at 0 to 5°C for 4 hours. After washing the oil layer with salt water, drying with magnesium sulfate, 1-bromo-1
- Obtain 70 g of butyne (yield 88%). Reference Example 2 Production of Γ1,1-diethoxy-3-butyne A catalytic amount of iodine and mercuric chloride was added to a mixture of 27.0 g of aluminum foil and 500 ml of dry THF, and a solution of 179 g of propadyl bromide in 200 ml of dry THF was refluxed for 1 hour. and further stirred at room temperature for 30 minutes. Next, a solution of 185 g of ethyl orthoformate in 200 ml of dry THF was added dropwise at -20 to -30°C for 1 hour.
Further, the mixture was stirred at the same temperature for 1 hour. The reactant was poured into 11 liters of saturated ammonium chloride water and extracted with ether. The ether layer is washed with brine, dried over magnesium sulfate, and concentrated. By distilling the obtained residue, pure 1,1-diethoxy-3-butyne
162 g (melting point: 50-52°C/12 mmHg) are obtained with a yield of 91%. Example 1 Production of Γ3,5-octadiyn-1-ar diethylacetal Cuprous iodide 1.0g, hydroxyamine chloride 1.5g
37 g of 1,1-diethoxy-3-butyne was added to a mixture of 150 ml of 33% ethylamine aqueous solution, and 1-bromo-
A solution of 35 g of 1-butyne in 50 ml of n-hexane was added dropwise, and the mixture was further stirred at room temperature for 2 hours. The reaction product was extracted with ether, and the ether layer was washed with brine, dried over magnesium sulfate, and concentrated. By distilling the obtained residue, pure 3,5-octadiyne-
1-R diethyl acetal 43g (yield 86%)
is obtained. Melting point: 95-96℃/3mmHg NMR (CCl ₄ ): δ1.16 (3H, t, J = 7Hz),
1.17 (6H, t, J = 7Hz), 2.25 (2H, q, J
= 7Hz), 2.47 (2H, d, J = 7Hz), 3.54
(4H, q, J=7Hz), 4.55 (1H, t, J=7
Hz). Example 2 Production of acetals of Γ3.5-octadiyn-1-al It can be produced in the same manner as in Example 1 from 1-bromo-1-butyne and 3-butinal acetals.

[Table] Example 3 Production of Γ cis-3, cis-5-octadienal diethylacetal 29.1 g of 3,5-octadiyn-1-al diethylacetal, 2.9 g of Lindlar catalyst, 2.9 g of quinoline, and methanol in an autoclave.
Charge 290 ml, and after purifying the room with hydrogen, stir at room temperature and under a hydrogen pressure of 2 Kg/cm ² until the theoretical amount of hydrogen is absorbed. The catalyst is removed from the reaction and concentrated. By distilling the obtained residue under reduced pressure, 24.7 g of pure cis-3, cis-5-octadienal diethyl acetal is obtained with a yield of 83%. Melting point: 78-80℃/3mmHg IR (liquid film): 1650, 1600, 720cm ^-1 . NMR (CCl ₄ ); δ1.00 (3H, t, J=7Hz),
1.14 (6H, t, J=7Hz), 1.8~2.7 (4H),
3.2-3.8 (4H, m), 4.42 (1H, t, J=7
Hz), 5.1-6.5 (4H, m). Example 4 Production of Γ cis-3, cis-5-octadienal dimethyl acetal In a 500 ml flask, 3,5-octadiyne-
3.3 g of 1-al methyl acetal, 3.3 g of Lindlar catalyst and 50 ml of n-hexane are charged, and after nitrogen substitution, a theoretical amount of hydrogen is absorbed at room temperature and pressure.
The catalyst is removed from the reaction and concentrated. By distilling the obtained residue under reduced pressure, pure cis-3,
Cis-5-octadienal dimethyl acetal
3.1 g are obtained with a yield of 91%. Melting point: 72-73°C/3mmHg IR (liquid film): 1650, 1600, 720cm ^-1 . NMR (CCl ₄ ); δ1.01 (3H, t, J=7Hz), 1.8
~2.6 (4H), 3.43 (6H, s), 4.44 (1H, t,
J=7Hz), 5.1-6.5 (4H, m). Example 5 Production of acetals of Γcis-3, cis-5-octadienal It can be produced from acetals of 3,5-octadiyn-1-al in the same manner as in Example 4.

[Table] Example 6 Production of Γ cis-3, cis-5-octadienal (a) 19.8 g of cis-3, cis-5-octadienal diethyl acetal was added to a 5% aqueous oxalic acid solution.
Add to 200ml and stir at room temperature for 20 hours. The reaction product is extracted with ether, and the ether layer is washed with saturated sodium chloride solution, brine, dried over magnesium sulfate, and then concentrated. By distilling the obtained residue under reduced pressure, 9.7 g of pure cis-3, cis-5-octadienal is obtained with a yield of 78%. Melting point: 72-73°C/15mmHg IR (liquid film): 1720, 1650, 1600, 720cm ^-1 . NMR ( _CCl4 ); 0.99 (3H, t, J=7Hz),
2.20 (2H, bt, J=7Hz), 3.23 (2H, bt,
J=7Hz), 5.2-6.5 (4H, m), 9.60 (1H,
t, J=2Hz). (b) Add 17.0 g of cis-3, cis-5-octadienal dimethyl acetal to 100 ml of 5% hydrochloric acid water and stir at room temperature for 5 hours. After post-treatment, pure cis-3, cis-
8.3 g of 5-octadienal are obtained with a yield of 67%. Usage examples 1 Ethyl acetate 50 Ethyl butyrate 150 Ethyl acetylacetate 90 Ethylcinnamate 20 Linalool 10 Amyl butyrate 30 Amyl acetate 40 Ethyl propionate 40 Ionone 10 Benzyl acetate 30 Linalyl acetate 20 Ethyl isovalerate 40 Vanillin 10 Maltol 20% PG 400 Cis-3-hexenol 40 Isobutyric acid 20 total 1000 By adding 20 g of cis-3-cis-5-octadienal to the above composition, an apple aroma and flavor with a fresh light grassy aroma is obtained. A new composition with excellent long-lasting properties was obtained. Similar results were obtained by using cis-3.cis-5-octadienal diethylacetal in place of cis-3.cis-5-octadienal. Usage Example 2 Composition for Soap A Narcissus-like fragrance composition was produced by mixing the following components (parts by weight). Bergamot oil 20 Ylang-ylang oil 5 Linalool 25 Benzyl acetate 5 Benzyl alcohol 22 Terpineol 10 Paracresyl acetate 1 Cinnamic alcohol 4 Eugenol 3 Heliotropin 3 Absolute diasmine 2 total 100 98g of the above composition was added with cis-3 and cis A fragrance composition having excellent persistence was prepared by mixing 2 g of -5-octadienal.

Claims (1)

[Claims] 1. The following formula (1), However, in the formula, Y represents =O or (-OR) ₂ ,
Here, the two R's are the same or different, and C ₁ ~
represents a group selected from the group consisting of a C ₁₀ alkyl group and a C ₃ to _{C 10} alkenyl group, or the two R together represent a C ₂ to _{C 3} methylene bond; -3.cis-5-octadienals.