JPS6313963B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides substantially pure 2-acetyl-1,
The present invention relates to a fragrance composition prepared by adding an olfactory effective amount of 3,3,4,4-pentamethyl-cyclopentene. The invention was originally published by M. Kolobielski in Ann. de Chim.
10, 271-314 (1955), which is a known compound and which uses substantially pure 2-acetyl-1,3,3,4,4-pentamethyl-cyclopentene. It also relates to a method for improving the smell of. The prior art makes no mention of its odor properties or of any use for the fragrance composition. Regarding the present invention, “2-acetyl-1,3,3,
4,4-Pentamethylcyclopentene" can be synthesized synthetically (e.g. by reductive dipolymerization in the presence of metallic magnesium and acetic acid, then
Generate 1 as described by Kolobielski,
3,3,4,4-pentamethyl-2-acetyl-
It should relate to compounds obtained (from mesityl oxide by dehydration of cyclopentanol) and contained in substantially pure form after isolation (for example by distillation) from the reaction mixture. The material can be further purified (eg, by distillation). The term "substantially pure" refers to isolated (and/or
(or purification, respectively) refers to a synthetically produced material, i.e., having a purity of greater than about 90%. 2-Acetyl-1,3,3,4,4-pentamethylcyclopentene has an odor that can be described as mild, spice-like, pepper-like, camphoric and musty. Any of these notes can be used to great advantage in a wide variety of fragrance compositions. It has been found that by carefully mixing this compound with other ingredients, distinct notes can be enhanced. Another important property of the present compounds is their ability to blend with other ingredients, providing "roundness" and "lift" to the final fragrance composition. The words "round" and "lift" are technical terms used by perfumers. "Roundness"
refers to that quality of a perfume composition that provides a pleasant blended odor without any individual chemically "standing out" odors from the total bouquet of the perfume composition. The word "lift" refers to the initial impact when first perceived by the sense of smell.
and odor intensity refers to its quality of the final fragrance composition. Obviously any perfume must provide a smooth, blended overall bouquet and have a distinct initial impact on the consumer if it is to be commercially acceptable. The pleiotropy of 2-acetyl-1,3,3,4,4-pentamethylcyclopentene can be explained in a variety of ways. In the case of florals, it provides a "roundness" and "lift" to the final fragrance composition that is more reminiscent of natural floral fragrances. Each floral has its own unique character, and through careful formulation perfumers can exploit the distinct characteristic notes of 2-acetyl-1,3,3,4,4-pentamethylcyclopentene. can. For carnation-type fragrances, if a spice-like note is desired, 2-acetyl-1,
The addition of 3,3,4,4-pentamethylcyclopentene enhances and contributes to the spice-like, floral quality of the final fragrance. white flower iris (orris)
or 2-acetyl-1,3, if the violet-type flower is more important.
The addition of 3,4,4-pentamethylcyclopentene contributes to the daytime note, which increases the "roundness" and provides an aroma closer to the natural smell. A notable feature of 2-acetyl-1,3,3,4,4-pentamethylcyclopentene is its miscibility,
namely, the ability to combine a large number of individual odor characteristics to provide an integrated blend. The ability to blend and provide "roundness" and "lift" to the final fragrance composition is noted as above. This ability is also dramatically illustrated by Lavandein type Fragrance. In this case 2-acetyl-1,3,3,4,4-pentamethylcyclopentene, which itself has no grass notes, is mixed with the grass notes of its fragrance;
Provides a final integration effect. Blending properties are also useful in colognes. Many colognes have a sreen, citrus, amber, or
Has a mellow and herbal note. The addition of 2-acetyl-1,3,3,4,4-pentamethylcyclopentene blends the individual notes and provides "roundness" and "lift" to the final composition. 2-acetyl-1,3,3,4,4- of the present invention
Compounds with structures closely related to pentamethylcyclopentene () do not have the desirable olfactory properties possessed by (). For example, 2-acetyl-3,3,5-trimethylcyclopentene ()
has an undesirable irritant note,
Described by perfumers as having a leafy-grassy odor. 2-Acetyl-1,4,4-trimethylcyclopentene (2) is described by perfumers as having a fuzzy, plastic-like, metallic, earthy odor with more pronounced undesirable pungent notes than that of (2). It was done. [Formula] [Formula] [Formula] () has the ability to combine with the odor characteristics of a fragrance composition to provide a complete blend or "rounded"aroma; substitutions for () or () have the opposite effect. It had The characteristic odors of () and () were notable for being immiscible and causing harm rather than benefit to the aromatic mixture. Of course, perfume technology is subjective. The amount used will ultimately depend on the ingenuity and personal preference of the perfumer as well as the range of such use. The amount used will also depend on the type of fragrance. It is then well within the skill in the art to add the compound in various amounts to determine a preferred range. Often 2-acetyl-1,3,3,4,
4-pentamethylcyclopentyne is 0.01% to 30
%, preferably in the practical range of 0.3% to 25%. This will of course vary depending on the type of fragrance formulation. 30% or more, 80 or 90
Even % concentrations can be successfully used for special effects. The compounds can be used to produce fragrance bases for the production of perfumes and lotions by adding customary alcoholic and aqueous diluents. About 15-20% by weight of the base is used in perfumes and about 3-5% in lotions. Similarly, the base composition can be used to scent soaps, cleaning products, cosmetics, etc.
In these cases, base concentrations of about 0.5 to about 2% by weight may be used. DESCRIPTION OF PREFERRED EMBODIMENTS The following examples are provided solely for the purpose of illustrating preferred embodiments of the invention. It should not be construed as a limitation. Unless otherwise indicated, perfume ingredients are given in 1/1000 parts by weight. If the material used is better known by its common, trademark, or trade name, such name should be used in conjunction with the chemical name shown in brackets. Example 2-acetyl-1,3, into a floral composition
The use of 3,4,4-pentamethylcyclopentene is illustrated by its use in the following carnation base. [Table]
[Table] * Givaudan trademark for citronella oil and acetone concentrate products.
The above carnation composition contains 2-acetyl-
The addition of 1,3,3,4,4-pentamethylcyclo-pentene greatly enhances the spice character of the carnation, creating a more balanced note and adding a 'roundness' and a great 'lift' to the overall composition.
Grant. 2-acetyl-1,3,3,4,4
Without the addition of -pentamethyl-cyclopentene, the formulation is flat, incomplete and lacks final fragrance quality. Example The following example shows 2-acetyl-1,3,3, which incorporates notes of herbal compositions such as lavandein synthesis.
Explain the ability of 4,4-pentamethylcyclopentene. Labandein synthetic component Linalool 100 Isobornyl acetate 100 Labandein strengthener ^* 20 Linalyl acetate 300 Labandurol 50 Devander 33/42 ^** 150 Coumarin 50 2-acetyl-1,3,3,4,4-pentamethylcyclopentene () 230 1000 *Lavandein toughener is a mixture consisting of 5.0 parts methyl amyl ketone, 20.0 parts methyl hexyl ketone, 10.0 parts methyl nonyl ketone and 0.5 parts butyl acetate. **Liquid fragrance base consisting primarily of linalool and linalool acetate for use in finished perfumes, colognes, cosmetics and soaps. A composition that does not contain 2-acetyl-1,3,3,4,4-pentamethylcyclopentene is incomplete;
It is essentially a mixture of individual odors. Alkyl ketone notes are individually noticeable. Approximately 20-25% 2-acetyl-1,3,3,4,
The addition of 4-pentamethylcyclopentene blends these individual notes into a unity. The herbal notes are blended and the final fragrance is "rounded" and full, showing the natural herbal qualities of the natural oil. Example 2-acetyl-1,3,3, to colon base
The use of 4,4-pentamethylcyclopentene is illustrated in the following formulation. Colon base ingredients Acetate PA (allyl phenoxy acetate) 10 Amblate (acetoxy-2-see-butyl-1-ethynylcyclohexane) 50 Benzyl acetate extra 40 Herboral ^* 30 Lemon oil California 230 Distilled lime 100 Linalool 50 Tonalyl acetate 150 Dipropylene glycol 120 Petitgrain oil (South America) 30 Phenylethyl alcohol 50 Sandera ^** 30 Terpineol Extra 30 2-Acetyl-1,3,3,4,4-pentamethylcyclopentene () 80 1000 *Mainly acetylated Givaudan trademark for a product that is citronellal. **Givaudan trademark for polycyclic alcohols with strong odor. The above colon base without 2-acetyl-1,3,3,4,4-pentamethylcyclopentene is incomplete. Contains ingredients that contribute to grassy, sweet-fruity, amber, dewy, and grassy notes.
Individual notes are noticeable. The addition of 2-acetyl-1,3,3,4,4-pentamethylcyclopentene to the colon base blends the composition to provide a unified bouquet. Although the sweet orange notes are enhanced, there is a "roundness",
blended into the overall composition. EXAMPLE The use of 2-acetyl-1,3,3,4,4-pentamethylcyclopentene in a Wednesday floral-type composition is illustrated with the following white-flowered iris base. White flower iris base component α-ionone 225 Raldeine γ-pure
225 Anisic aldehyde 30 Terpineol 200 Heliotropin 30 Ethyl vanillin 10 Musk ketone 10 Coumarin 10 Dipropylene glycol 95 White flower iris absolute resin 20 Concrete white flower iris absolute 30 Vetiver 25 Cedryl acetate crystals 20 Carrot seed oil 10 % (in DEP) 10 Ionone 10 2-acetyl-1,3,3,4,4-pentamethylcyclopentene () 50 2-acetyl 1, in the above white flower iris base
3,3,4,4-Pentamethylcyclopentene enhances the white iris character and imparts more "roundness" and "lift" to the final composition. EXAMPLE The use of 2-acetyl-1,3,3,4,4-pentamethylcyclopentene in fuguet compositions is described below. Fugue Ingredients Amyl salicylate 130 Anisic aldehyde 50 Benzoin siam soluble resin 30 Benzyl acetate extra 100 Bergamot 65GD ^* 350 Coumarin 20 Dipropylene glycol 103 Estragol (p-allylanisole) 5 Phorurusia (p-isopropylcyclohexanol) 10 Geranium Bourbon 30 Heliotropin Crystals 50 Citral 2 Mask Ambrette 30 Nerol Prime 10 Phenylethyl Alcohol 30 Wood Burnt 50% (in Dipropylene Glycol) 4 Thymol 10% (in Dipropylene Glycol) 1 Vanillin USP 5 2-Acetyl- 1,3,3,4,4-Pentamethylcyclopentene () 40 1000 *Liquid fragrance used in finished perfumes, colognes, cosmetics and soaps. 2-acetyl-1,3, in the above Fugue base
3,4,4-Pentamethyl-cyclopentene adds body, lift and strength. Gives a more natural quality to the overall composition.

Claims (1)

[Claims] 1. Substantially pure 2-acetyl-1,3,3,
1. A fragrance composition comprising at least one olfactory component to which is added an olfactory effective amount of 4,4-pentamethylcyclopentene. 2 added substantially pure 2-acetyl-1,
The olfactory effective amount of 3,3,4,4-penta-methylcyclopentene is from 0.01 to 0.01 on a fragrance basis.
30%. 3 Added substantially pure 2-acetyl-1,
The olfactory effective amount of 3,3,4,4-pentamethyl-cyclopentene is from 0.3 to 0.3 on a fragrance basis.
25% of the composition of claim 2.