Sandalwood-type fragrance compounds

Patent metadata

Field	Value
Publication number	US-12410113-B2
Application number	US-202017614238-A
Country	US
Kind code	B2
Filing date	Jun 12, 2020
Priority date	Jun 13, 2019
Publication date	Sep 9, 2025
Grant date	Sep 9, 2025

Abstract

The present invention relates to novel fragrance compounds derived from campholenic aldehyde according to general Formula (II) or from the cyclopropanated campholenic aldehyde according to general Formula (III), or to compositions comprising one or more such fragrance compounds. The invention also relates to methods for preparing these compounds and to particular intermediates which are used in the preparation processes according to the present invention. It also pertains to a method for producing, enhancing or modifying a sandalwood odor in a formulation. The invention also relates to the use of such compounds or fragrance compositions comprising one or more compounds according to the invention as an odorant or for improving the fixation of a fragrance compound or a composition comprising a fragrance compound or for preparing perfumed products. Finally, the invention relates to corresponding perfumed products.

First claim

The invention claimed is:

1. A compound of general Formula (I):

wherein
R 1 represents H, an alkyl or an alkenyl group,
R 2 represents an alkyl or an alkenyl group, and
R 3 represents H or an alkyl group;
wherein at the position of the dotted lines there is optionally a C═C double bond or a cyclopropane ring; and
wherein the butyl chain C1 to C4 is either saturated or is unsaturated and contains one double bond in position C2/C3 or C3/C4;
wherein the compound comprises either
at least one cyclopropane substituent attached to the butyl chain in position C2 or C4; or
at least one alkenyl group attached to the butyl chain in position C2 or C4, wherein if the alkenyl group is attached to the butyl chain in position C4, the butyl chain comprises a C═C double bond in position C2/C3 or a further alkenyl group in position C2;

or at least one stereoisomer of the compound of general Formula (I); or
a compound of general Formula (VI):

wherein
R 1 represents H, an alkyl or an alkenyl group,
R 2 represents H or an alkyl, and
R 3 represents H or an alkyl group;
wherein at the position of the dotted lines there is optionally a C═C double bond or a cyclopropane ring; and
wherein the butyl chain C1 to C4 is either saturated or is unsaturated and contains one double bond in position C2/C3 or C3/C4;
wherein the compound comprises either
at least one cyclopropane substituent attached to the butyl chain in position C2 or C4; or
at least one alkenyl group attached to the butyl chain in position C2 or C4, wherein if the alkenyl group is attached to the butyl chain in position C4, the butyl chain comprises a C═C double bond in position C2/C3 or wherein if the alkenyl group is attached to the butyl chain in position C2, the butyl chain comprises a C═C double bond in position C3/C4; or
an alkyl group attached to the butyl chain in position C2 and C4, wherein the butyl chain comprises a C═C double bond in position C2/C3;

or at least one stereoisomer of the compound of general Formula IV.

2. The compound according to claim 1 , wherein the alkyl group is a methyl, ethyl, propyl or butyl group and the alkenyl group is an ethenyl, propenyl or butenyl group.

3. The compound according to claim 1 , wherein the compound is present in the form of:
(a) a pure optically active enantiomer;
(b) a racemic mixture of the enantiomers; or
(c) an optically active mixture of various enantiomers.

4. The compound according to claim 1 , wherein the compound of general Formula (I) is selected from the group of the following compounds:

Compound

No.
Structure

A

A1

B

B1

C

D

E

F

G

I

J

K

L

Assignees

• Symrise Ag

Inventors

• Chandrasekaran Vijayanand
• Hoelscher Bernd
• Kiermasch Eva

Classifications

• C11B9/0019

  carbocylic acids; Salts or esters thereof · CPC title

• C07C67/343

  by increase in the number of carbon atoms · CPC title

• C07C45/62

  by hydrogenation of carbon-to-carbon double or triple bonds · CPC title

• C07C45/41

  by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof · CPC title

• C07C17/16

  of hydroxyl groups · CPC title