Perfume compositions – Perfume compositions – Oxygen containing active ingredient
Patent
1996-06-14
1998-04-14
Reamer, James H.
Perfume compositions
Perfume compositions
Oxygen containing active ingredient
508596, 426650, A61K 746
Patent
active
057391009
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to a cis-3-hexenal-cis-3-hexenyl acetal compound, a process for producing the same, a fragrance- or flavor-imparting or fragrance- or flavor-retaining agent containing the same, and a perfume composition containing the same.
BACKGROUND ART
Fragrance- or flavor-imparting agents and fragrance- or flavor-retaining agents are widely used in the fields including beverages and comestibles, cosmetics, sanitary and hygienic goods, detergents, bath refreshing additives, and medicines and agricultural chemicals. Fragrance- or flavor-imparting agents are used for imparting fragrance or flavor. Fragrance- or flavor-retaining agents are used for enhancing or modifying, or retaining pleasant odor of a perfume or sweet taste of a flavoring agent. Fragrance-imparting agents and flavor-imparting agents are referred to as "fragrance/flavor-imparting agents", and fragrance-retaining agents and flavor-retaining agents are referred to as "fragrance/flavor-imparting agents" in this specification.
Fragrance/flavor-imparting agents include numerous kinds of fragrance-imparting agents and flavor-imparting agents. As examples of fragrance/flavor-retaining agents, there can be mentioned solvents such as benzyl benzoate, dialkyl phthalates, Hercolyn, limonene dimer, alkylene glycols, polyalkylene glycols, alkyl citrates and dialkyl adipates; perfumes such as myrrh, Peru balsam, Tolu balsam, musks, civet, vanillin, hydroxycitronellal, olibanum, vetivert, benzyl isoeugenol, ambrette, benzoin, labdanum, clary sage, cinnamic alcohol, orris, styrax, costus, coumarin, methyl naphthyl ketone, cinnamyl cinnamate, ethyl cinnamate, 2-ethoxynaphthalene, naphthol ether, ambergris, rose phenone, oak moss, dimethyl hydroquinone, elemi, mastic indole, patchouli basil, musk ketone and diphenyl methane; and zeolite, starch, talc, plastics, clays and cellulose. A suitable fragrance/flavor-retaining agent is chosen from these fragrance/flavor-retaining agents depending upon the particular use thereof.
In recent years, green note fragrance/flavor-imparting agents including cis-3-hexenyl alcohol (leaf alcohol) are widely used, and analogues thereof such as esters are now being developed. As an example of such analogues, synthesis of cis-3-hexenal-di-cis-3-hexenyl acetal has been reported in S. Arctander, "Perfume and Flavor Chemicals", Steffen, Arctander's Publications, Las Vegas, Nev. 1969. In this publication, it is reported that this compound has a low purity and its nature is extremely unstable, and thus, the compound would be of no practical use as a fragrance/flavor-imparting agent.
The present inventors have conducted researches into compounds of the type described in the above publication, and found that, when the compounds are highly purified, the compounds exhibit pleasant and strong fragrance and flavor, and are stable to a sufficient extent for the use as a fragrance/flavor-imparting agent.
DISCLOSURE OF INVENTION
An object of the present invention is to provide a novel cis-3-hexenal-cis-3-hexenyl acetal compound having favorable characteristics as a fragrance/flavor-imparting agent and/or a fragrance/flavor-retaining agent.
Another object of the present invention is to provide a process for industrially advantageously producing the novel cis-3-hexenal-cis-3-hexenyl acetal compound.
Still another object of the present invention is to provide a fragrance/flavor-imparting or fragrance/flavor-retaining agent comprising as an active ingredient a cis-3-hexenal-cis-3-hexenyl acetal compound.
In one aspect of the present invention, there is provided a cis-3-hexenal-cis-3-hexenyl acetal compound represented by the following formula (1): ##STR3## wherein R represents an alkyl group having 1 to 20 carbon atoms, which may have a substituent.
In another aspect of the present invention, there is provided a process for preparing a cis-3-hexenal-cis-3-hexenyl acetal compound represented by the following formula (3): ##STR4## wherein R.sup.3 represents a hydrocarbon group which may have a substituent, which compr
REFERENCES:
patent: 3751486 (1973-08-01), Schleppnik et al.
patent: 4209644 (1980-06-01), Ichikawa et al.
Takei et al, Chem. Abst; vol. 29, #8229-30 (1935).
"Perfume and Flavor Chemicals", S. Arctander, Steffen, Arctander's Publications, Las Vegas, NV 1969; abstract.
Hirakawa Shin-ichi
Horino Hiroshi
Nippon Zeon Co. Ltd.
Reamer James H.
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