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BR-112021007466-B1 - COMPOUND, FRAGRANCE FORMULATION, AND METHOD

BR112021007466B1BR 112021007466 B1BR112021007466 B1BR 112021007466B1BR-112021007466-B1

Abstract

COMPOUND, FRAGRANCE FORMULATION, AND METHOD. The present invention relates to innovative compounds and their use as fragrance materials.

Inventors

  • ANUBHAV P.S. NARULA
  • RICHARD A. WEISS
  • HUGO ROBERT GERMAIN DENUTTE
  • Johan Smets
  • PHILIP JOHN PORTER
  • FREEK ANNIE CAMIEL VRIELYNCK
  • Koen Van Aken
  • BART ANTOON JUDITH RUTTENS

Assignees

  • INTERNATIONAL FLAVORS & FRAGRANCES INC

Dates

Publication Date
20260317
Application Date
20191022
Priority Date
20181024

Claims (6)

  1. 1. Fragrance formulation, characterized in that it comprises an acceptable olfactory quantity of a compound, wherein the compound is a mixture of (E)-1-((1R,6R)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one; (E)-1-((1S,6S)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one; (E)-1-((1R,6S)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one; and (E)-1-((1S,6R)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one, wherein the acceptable olfactory quantity is 0.005 to 50 percent by weight of the fragrance formulation.
  2. 2. Fragrance formulation according to claim 1, characterized in that the acceptable olfactory quantity is from 0.5 to 25 percent by weight of the fragrance formulation.
  3. 3. Fragrance formulation according to claim 1, characterized in that the acceptable olfactory quantity is 1 to 10 percent by weight of the fragrance formulation.
  4. 4. Method, characterized in that it is for enhancing, improving or modifying a fragrance formulation by adding an acceptable olfactory amount of a compound, wherein the compound is a mixture of (E)-1-((1R,6R)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one; (E)-1-((1S,6S)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one; (E)-1-((1R,6S)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one; and (E)-1-((1S,6R)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one, wherein the acceptable olfactory quantity is 0.005 to 50 percent by weight of the fragrance formulation.
  5. 5. Method according to claim 4, characterized in that the acceptable olfactory quantity is from 0.1 to 25 percent by weight of the fragrance formulation.
  6. 6. Method according to claim 4, characterized in that the acceptable olfactory quantity is from 0.5 to 10 percent by weight of the fragrance formulation.

Description

Status of Related Orders [001] This application claims priority to U.S. Provisional Patent Application No. 62/749,711, filed October 24, 2018, the contents of which are incorporated herein by reference in their entirety. Field of Invention [002] The present invention relates to new chemical entities and to the incorporation and use of the new chemical entities as fragrance materials. Background of the Invention [003] There is a continuing need in the fragrance industry to provide new chemicals to give perfumers and others the ability to create new fragrances for perfumes, colognes, and personal care products. Those skilled in the art observe how differences in the chemical structure of the molecule can result in significant differences in the odor, notes, and characteristics of a molecule. These variations and the ongoing need to discover and use new chemicals in the development of new fragrances allow perfumers to apply the new compounds in the creation of new fragrances. Summary of the Invention [004] The present invention provides innovative compounds and their unexpected advantageous use in improving, enhancing or modifying the fragrance of perfumes, colognes, eau de colognes, fabric care products, personal care products and the like. [005] More specifically, the present invention relates to innovative (dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ones(ols) represented by the formula shown below: where R represents H; one of the dashed lines in the ring represents a single carbon-carbon bond, while the other represents a carbon-carbon double bond; and the dashed line in the chain represents either a single carbon-carbon bond or a carbon-carbon double bond, provided that, when the dashed line in the chain represents a carbon-carbon double bond, R is absent. [006] Another embodiment of the present invention relates to a fragrance formulation comprising the innovative compounds provided above. [007] Another embodiment of the present invention relates to a fragrance product comprising the compounds provided above. [008] Another embodiment of the present invention relates to a method for enhancing, improving or modifying a fragrance formulation by adding an acceptable olfactory amount of the innovative compounds provided above. [009] These and other embodiments of the present invention will become apparent from reading the following descriptive report. Detailed Description of the Invention [0010] The (dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one(ol) compounds represented by Formula I of the present invention are illustrated by the following examples.(E)-1-((1R,6R)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one (E)-1-((1S,6S)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one (E)-1-((1R,6S)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one (E)-1-((1S,6R)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-one (E)-1-((1R,6R)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol (E)-1-((1S,6S)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol (E)-1-((1R,6S)-4,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol (E)-1-((1S,6R)-3,6-dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ol [0011] Those skilled in the art will recognize that the compounds of the present invention may have various isomers, such as positional isomers depending on the starting materials available. It is intended in this document that the compounds described herein include isomeric mixtures as well as single isomers that can be separated using techniques known to those skilled in the art. Suitable techniques include chromatography such as high-performance liquid chromatography, called HPLC, and particularly silica gel chromatography, and gas chromatography capture known as GC capture. However, commercial products are mainly offered as isomeric mixtures. The term "a compound" is understood to mean one or more of the (dimethylcyclohex-3-en-1-yl)-2-methylpent-1-en-3-ones(ols) represented by Structures 1 to 8 as described herein. The preparation of the compounds of the present invention is detailed in the Examples. Structures 5 to 8 can be readily prepared from the corresponding structures 1 to 4 by hydrogenation using lithium aluminum hydride (LiAlH4). The materials were purchased from Aldrich Chemical Company unless otherwise indicated. [0012] The compounds of the present invention, for example, have strong and complex fresh notes, crisp, slightly greenish, resinous, coniferous, floral, ionone-like, amber, woody and diffusive. The use of the compounds of the present invention is widely applicable in current perfumery products, including the preparation of perfumes and colognes, the perfuming of personal care products such as soaps, shower gels and hair care products, fabric care products, air fresheners and cosmetic preparations. The present invention can also be used to perfume cleaning agents such as, but not limited to, detergents, dishwashing materials, purification compositions, window cleaners a