Fragrances with rose scent

Patent metadata

Field	Value
Publication number	US-11634659-B2
Application number	US-201817261444-A
Country	US
Kind code	B2
Filing date	Jul 23, 2018
Priority date	Jul 23, 2018
Publication date	Apr 25, 2023
Grant date	Apr 25, 2023

Abstract

The present invention primarily concerns the use of compounds of the following formula (I)wherein X represents an oxygen atom, a —CHO, an —OH, or a —CH2OH group, a single bond or a double bond is present at the respective location of one of the dotted lines, at least one double bond is present when X is an OH group, and the 3-isopentyl or 3-isopent-2-enyl residue is connected to the ring in the ortho, meta, or para position to the X group, as perfuming and/or flavouring agents.The invention further relates to fragrance and flavour compositions containing one or more of these compounds, perfumed or flavoured articles comprising one or more of these compounds and corresponding processes for imparting, modifying and/or enhancing certain odour notes.

First claim

The invention claimed is:

1. A method comprising using a compound of formula (Ib),

where
X represents an —OH group,
at the respective location of one of the dotted lines there is a single bond or a double bond, and wherein at least one double bond is present
as a fragrance and/or flavour substance.

2. The method according to claim 1 , wherein the fragrance is a rose note fragrance.

3. The method according to claim 1 , comprising using the compound of formula (I) for imparting, modifying and/or enhancing one, two or more olfactory notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, sweet, earthy, greasy, metallic and balsamic.

4. A fragrance and/or flavour composition, the fragrance and/or flavour composition comprising at least one compound of formula (Ib),

where
X represents an —OH group,
at the respective location of one of the dotted lines there is a single bond or a double bond, wherein at least one double bond is present.

5. A fragrance and/or flavour mixture, the fragrance and/or flavour mixture comprising at least one fragrance and/or flavour composition according to claim 4 , and
further comprising one or more additional fragrances and/or flavouring substances, wherein the additional or one, more or all fragrances and/or flavouring substances are selected from the group consisting of: extracts from natural raw materials, essential oils, creams, absolutes, resins, resinoids, balms, tinctures and/or single fragrance substances; and mixtures thereof.

6. A fragrance and/or flavour composition, the fragrance and/or flavour composition comprising:
(a) at least one of one or more compounds of the formula (Ib),

where
X represents an —OH group,
at the respective location of one of the dotted lines there is a single bond or a double bond, wherein at least one double bond is present, and
(b) one or more other fragrance and/or flavour substances.

7. A fragrance and/or flavour composition according to claim 6 ,
wherein the one or more further fragrance and/or flavour substance(s) is/are selected from the group consisting of: ethyl 2-cyclopent-2-en-1-yl acetate, 1-cyclohexylethyl (E)-but-2-enoate, (2-cyclopentylcyclopentyl) (E)-but-2-enoate, allyl hexanoate, 1,3-dimethylbutyl (E)-but-2-enoate, 1,3-dimethylbut-3-enyl 2-methyl propanoate, and (E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one.

8. A perfumed or flavoured article, the perfumed or flavoured article comprising
(a) at least one of one or more compounds of the formula (Ib),

where
X represents an —OH group,
at the respective location of one of the dotted lines there is a single bond or a double bond, wherein at least one double bond is present,
(b) one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance and/or flavour substances; and
(c) one or more further additives, excipients and/or active substances.

9. A perfumed or flavoured article according to claim 8 , wherein the perfumed or flavoured article is selected from the group consisting of:
perfume extracts, eau de parfums, eau de toilettes, aftershave lotions, eau de colognes, pre-shave products, splash colognes, perfumed refreshing tissues, acid, alkaline or neutral detergents, textile fresheners, ironing aids, liquid detergents, powder detergents, laundry pre-treatment products, fabric softeners, laundry soaps, washing tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, personal care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair care products, deodorants, antiperspirants, decorative cosmetic products, candles, lamp oils, incense sticks, insecticides, repellents and fuels.

10. A perfumed or flavoured article according to claim 8 , wherein the total amount of compounds of formula (I), and/or 2-(3-methylbutyl)cyclohexan-1-ol, and/or 2-(3-methylbutyl)cyclohexan-1-one, and/or 3-(3-methylbutyl)cyclohexan-1-ol, and/or 3-(3-methylbutyl)cyclohexan-1-one, and/or 4-(3-methylbutyl)cyclohexan-1-one is in the range from 0.00001 to 10 wt. % based on the total mass of the article.

11. The method of claim 1 , wherein the compound of formula (Ib) is selected from

12. The fragrance and/or flavour composition of claim 4 , wherein the compound of formula (Ib) is selected from

13. The fragrance and/or flavour composition of claim 6 , wherein the compound of formula (Ib) is selected from

14. The perfumed or flavoured article of claim 8 , wherein the compound of formula (Ib) is selected from

15. The fragrance and/or flavor composition according to claim 6 , further comprising one or more compounds selected from the group consisting of 2-(3-methylbutyl)cyclohexan-1-ol, 2-(3-methylbutyl)cyclohexan-1-one, 3-(3-methylbutyl)cyclohexan-1-ol, 3-(3-methylbutyl)cyclohexan-1-one, 4-(3-methylbutyl)cyclohexan-1-ol, and 4-(3-methylbutyl)cyclohexan-1-one.

16. The perfumed or flavored article of claim 8 , further comprising one or more compounds selected from the group consisting of 2-(3-methylbutyl)cyclohexan-1-ol, 2-(3-methylbutyl)cyclohexan-1-one, 3-(3-methylbutyl)cyclohexan-1-ol, 3-(3-methylbutyl)cyclohexan-1-one, 4-(3-methylbutyl)cyclohexan-1-ol, and 4-(3-methylbutyl)cyclohexan-1-one.

Assignees

• Symrise Ag

Inventors

• Hoelscher Bernd
• Chandrasekaran Vijayanand

Classifications

• C07C47/32

  with a six-membered ring · CPC title

• C07C47/42

  with a six-membered ring · CPC title

• C07C47/45

  having unsaturation outside the rings · CPC title

• C07C49/603

  of a six-membered ring, e.g. quinone methides · CPC title

• C07C49/647

  having unsaturation outside the ring · CPC title