Use of specific compounds for modifying odors

Patent metadata

Field	Value
Publication number	US-9340751-B2
Application number	US-201313886134-A
Country	US
Kind code	B2
Filing date	May 2, 2013
Priority date	May 10, 2012
Publication date	May 17, 2016
Grant date	May 17, 2016

Abstract

The use of certain compounds for masking or decreasing the or one or a plurality of unpleasant olfactory impressions of one or a plurality of substances with an unpleasant odor and/or for enhancing the or one or a plurality of pleasant olfactory impressions of one or a plurality of substances with a pleasant odor and new fragrance mixtures and perfumed products containing such compounds.

First claim

What is claimed is:

1. A method
(a) for masking or decreasing one or a plurality of unpleasant olfactory impressions of one or a plurality of substances with an unpleasant odor having one or a plurality of the unpleasant olfactory impressions selected from fatty, technical and metallic, and/or
(b) for enhancing or improving the natural freshness and/or radiance one or a plurality of substances with a pleasant odor and/or for enhancing the flowery scent of one or a plurality of substances with a pleasant odor,
comprising the step of:
mixing said substance(s) with an unpleasant odor having one or a plurality of the unpleasant olfactory impressions selected from fatty, technical and metallic, and/or the substance(s) with a pleasant odor with (i) an individual compound of formula (I) or (ii) a mixture comprising or consisting of two or a plurality of compounds of formula (I)

wherein for the compound of formula (I) or for each compound of formula (I)
none, one or two of the four jagged lines denotes or denote a double bond and the other jagged lines in each case denote a single bond and
X is selected from the —O—CH 2 — and —O—CH 2 ;

wherein said substance(s) with an unpleasant odor and said substance(s) with apleasant odor are not a compound of formula (I), and
the ratio of the total mass of the substances with a pleasant and/or unpleasant odor not corresponding to formula (I) to the total mass of compound(s) of formula (I) is greater than or equal to 99:1.

2. The method according to claim 1 , wherein
(i) the compound of formula (I) or (ii) one or a plurality of compounds of formula (I) is or are selected from the group consisting of cyclohexadec-8-en-1-one (Aurelione, CAS No. 88642-03-9, 3100-36-5; Globanone, CAS No. 3100-36-5), cyclohexadecanone (Isomuscone, CAS No. 2550-52-9), oxacyclohexadecen-2-one (Globalide, CAS No. 34902-57-3, 111879-80-2), cyclopentadecanolide (Macrolide, CAS No. 106-02-5) and (9Z-17-Oxacycloheptadec-9-en-1-one (Ambrettolide, CAS No. 28645-51-4).

3. The method according to claim 1 , wherein one or a plurality of the substances(s) with a pleasant and/or unpleasant odor not corresponding to formula (I) is or are selected from the group consisting of fragrances with a molecular weight in the range 150 g/mol through 285 g/mol.

4. The method according to claim 1 , wherein one or a plurality of the substance(s) with a pleasant and/or unpleasant odor not corresponding to formula (I) is or are selected from the group consisting of methyl dihydrojasmonate, benzyl salicylate, cis-3-hexenyl salicylate, isoamyl salicylate, hexyl salicylate, 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-napbthalenylmethyl ketone, linalyl acetate, ethyllinalyl acetate, cedryl methyl ether, cedryl methyl ketone, cedryl acetate, (4aR,5R,7aS,9R) -octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methano azuleno (5,6-d)-1,3-dioxol), 1′,1′,5′,5′-tetra methylhexahydro-spiro[1.3-dioxolan-2.8′(5′H)-2H-2.4a]methanonaphthalene, cyclododecyl methyl ether, (ethoxymethoxy)cyclododecane, decahydro-beta-naphthyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5(-6)-indenyl acetate, allyl-3-cyclohexyl propionate, allylcyclohexyloxy acetate, benzyl benzoate, benzyl cinnamate, 15-hydroxy-Pentadocanonsaurelacton, 3-methyl-cyclopentadecenone, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl cyclopenta[g]-2-benzopyrane, 2-[1-(3,3-dimethylcyclohexyl)ethoxy]-2-methyl-, 1-propanoate, 1,4-dioxacycloheptadecan-5,17-dione, 3-methyl-cyclopentadecanone, 3a,6,6,9a-tetramethyl dodecahydronaphtho[2,1-b]furan alpha-irone, beta-irone, alpha-n-methylionone, beta-n-methylionone, alpha -isomethylionone, beta-isomethylionone and allyl ionone, 2-methyl-3-(4-tert-butylphenyl)propanal, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexencarboxaldehyde, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal, 1-methyl-4-(4-methyl-3-penten-1-yl)-3-cyclohexencarboxaldehyde, 3-(3-isopropyl-phenyl)-butyraldehyde, (E)-2,6,10-trimethyl-undeca-5,9-dienal, benzo[1,3]dioxole-5-carbaldehyde, 2,2-dimethyl-3-phenyl -propan-1-ol, 2,2-dimethyl-3-m-tolyl-propan-1-ol, 1-(4-isopropyl-cyclohexyl)-ethanol, (4-isopropyl-cyclohexyl)-methanol, 2-phenyl-ethanol, 2-isobutyl-4-methyl-tetrahydro-pyran-4-ol, 3,7-dimethyl-octa-1,6-dien-3-ol, (Z)-3,7-dimethyl-octa-2,6-dien-1ol, (E)-3,7-dimethyl-octa-2,6-dien-1-ol, 3,7-dimethyl-oct-6-en-1-ol, 2,6-dimethyl-oct-7-en-2-ol, 3,7-dimethyl-octan-1-ol, 2-methyl-6-methylenoct-7-en-2-ol and (E/Z)-3,7-dimethyl-nona-1,6-dien-3-ol.

5. The method according to claim 1 , wherein
the quantity of compounds(s) of formula (I) used for decreasing or masking and/or for enhancing is not sufficient to impart a musk odor.

6. A fragrance mixture comprising
(A) (i) an individual compound of formula (I) or
(ii) a mixture comprising or consisting of two or a plurality of compounds of formula (I)

wherein for the compound of formula (I) or for each compound of formula (I)
none, one or two of the four jagged lines denotes or denote a double bond and the other jagged lines in each case denote a single bond and
X is selected from the —O—, and —O—CH 2 —; and
(B) one, two, three, four, five, six or a plurality of (further) fragrances, wherein the (further) fragrance(s) is or are not a compound of formula (I) and
one, two, three, four, five, six or a plurality of or all of the (further) fragrances has or have a molecular weight in the range 150 g/mol through 285 g/mol, characterized in that the ratio of the total mass of fragrances not corresponding to formula (I) to the total mass of compound(s) of formula (I) is greater than or equal to 99:1,

wherein the quantity of compound(s) of formula (I) in the fragrance mixture is sufficient,
(a) to mask or decrease one or a plurality of unpleasant olfactory impressions of one or a plurality of fragrances according to ingredient (B),
wherein one or a plurality of the unpleasant olfactory impressions is or are selected from fatty, technical and metallic, and/or
(b) to enhance or improve the natural freshness and/or radiance of one or a plurality of fragrances according to ingredient (B) and/or to enhance the flowery scent of one or a plurality of fragrances according to ingredient (B).

7. The fragrance mixture as claimed in claim 6 , wherein (i) the compound of formula (I) or (ii) one or a plurality of compounds of formula (I) is or are selected from the group consisting of cyclohexadec-8-en-1-one (Aurelione, CAS No. 88642-03-9, 3100-36-5; Globanone, CAS No. 3100-36-5), cyclohexadecanone (Isomuseone, CAS No. 2550-52-9), oxacyclohexadecen-2-one (Cilobalide, CAS No. 34902-57-3, 111879-80-2), cyclopentadecanolide (Macrolide, CAS No. 106-02-5) and (9Z)-17-Oxacycloheptadec-9-en-1-one (Am-brettolide, CAS No. 28645-51-4).

8. The fragrance mixture according to claim 6 , wherein the fragrance or a plurality of fragrances according to ingredient (B) is or are selected from the group consisting of methyl dihydrojasmonate, benzyl salicylate, cis-3-hexenyl salicylate, isoamyl salicylate, hexyl salicylate, 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenylmethyl ketone, linalyl acetate, ethyl linalyl acetate, cedryl methyl ether, cedryl methyl ketone, cedryl acetate, (4aR,5R,7aS,9R)-oetahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methano azuleno 5,6-d)-1′,1′,1′,5′,5′-tetra methyl-hexahydro-spiro[1.3-dioxolan-2.8′(5′H)-2H-2.4a]methanonaphthalene, cyclododecyl methyl ether, (ethoxymethoxy)cyclododecane, decahydro-beta-naphthyl acetate, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5(-6)-indenyl acetate, allyl-3-cyclohexyl propionate, allylcyclohexyloxy acetate, benzyl be

Assignees

• Symrise Ag

Inventors

• Hölscher Bernd
• Chmelnyk Annabel

Classifications

• A61K8/35

  Ketones, e.g. benzophenone · CPC title

• A61Q5/02

  Preparations for cleaning the hair · CPC title

• C11D3/50

  Perfumes · CPC title

• A61K8/4973

  with oxygen as the only hetero atom · CPC title

• A61Q13/00

  Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00) · CPC title