Perfume compositions – Perfume compositions – Ring containing active ingredient
Reexamination Certificate
2000-02-11
2001-10-02
Warden, Jill (Department: 1743)
Perfume compositions
Perfume compositions
Ring containing active ingredient
Reexamination Certificate
active
06297211
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to (6E)- and (6Z)-isomers of 3,6-dimethyloct-6-en- 1-ols and 6-ethyl-3-methyloct-6-en-1-ols and mixtures thereof as well as the use of these mixtures in odorant compositions. The mixtures are free from their corresponding oct-5-ene double bond isomers.
BACKGROUND OF THE INVENTION
Although it has previously not been known that one compound alone can imitate true to nature the complex olfactory impression of lily of the valley, hydroxycitronellal (3,7-dimethyl-7-hydroxyoctan-1-al) comes remarkably close to the odor of lily of the valley. In combination with other lily of the valley odorants such as LYRAL® (4-(4-hydroxy-4-methylpent-1-yl)-cyclohex-3-ene-1-carboxaldelhyde), LILIAL® (3-(4-tert-butylphenyl)-2-methylpropanal) and/or DUPICAL® (4-(octahydro-4,7-methano-5H-inden-5-ylidene)butanal) (G. Frater, J. A. Bajgrowicz, P. Kraft, Fragrance Chemistry, Tetrahedron 1998, 54, 7633-7703) it is, however, possible to come very close to the natural standard. The aldehyde group is common to all of these mentioned odorants with lily of the valley character. This gives rise to an instability of the compounds in oxidizing or strongly alkaline media.
Some lily of the valley odorants without an aldehyde function have been found in the alcohols MAYOL® (4-(1-methylethyl)cyclohexylmethanol), MAJANTOL® (2,2-dimethyl-3-(3-methylphenyl)propanol), FLOROL® (tetrahydro-4-methyl-2-(2-methylpropyl-2H-pyran-4-ol) and MUGETANOL® (U. Harder, E. Oelkers, in: Recent Developments in Flavor and Fragrance Chemistry, published by VCH, Weinheim, 1993, pp. 162-163). Moreover, the carbon analogue to FLOROL® with very similar olfactory properties to FLOROL® has become known from WO 98/47842. However, these alcohols possess neither the naturalness, radiating strength and crispness nor the olfactory strength of the aforementioned aldehydes, and the need for a replacement substance for the lily of the valley aldehydes therefore continues to exist. There is therefore a requirement for additional lily of the valley odorants, especially with a functional group other than the aldehyde function, in order to obviate the previously mentioned disadvantages.
In GB Patent No. 1,167,776 claim is made, inter alia, to supposed compounds of general formulae Ia and Ib.
From the examples given therein it is, however, evident that compounds falling within formulae Ia and Ib were never prepared in pure form. It has now been established that this is also not at all possible on the basis of the route of preparation described. In fact, in the dehydration of the 1,6-diols which are the basis for the compounds Ia and Ib there is obtained a mixture of all three possible isomeric octan-1-ols with respect to the double bond. For example, in the case of compounds Ib there are obtained according to the given process the alcohols (6E)-6-ethyl-3-methyloct-6-en-1-ol (ca. 30%), (6Z)-6-ethyl-3-methyloct-6-en-1-ol (ca. 30%) and 6-ethyl-3-methyloct-5-en-1-ol (ca. 40%). As mentioned in the patent, this mixture of compounds Ib has, in fact, the indicated odor of lily of the valley and rose, but the odor of the rose side notes is unpleasantly musty. Because of this musty rose-like side note, the mixture Ib cannot completely satisfy the requirements of a lily of the valley odorant without an aldehyde function. It has therefore been used in perfumery only sporadically. Today, there is practically no commercial demand for this mixture. The production of the mixture Ib has in the meanwhile been discontinued for this reason.
SUMMARY OF THE INVENTION
It has now surprisingly been found that the undesired must) rose-like side notes of the mixtures Ia and Ib is due to the oct-5-en-1-ols 6-ethyl-3-methyloct-5-en-1-ol and (5E/Z)-3,6-dimethyloct-5-en-1-ol and that in the absence of these compounds there are obtained mixtures which do not have the aforementioned disadvantages. One object of the invention is, therefore, a composition containing a mixture of the following compounds:
wherein R is a methyl or ethyl group. In the present invention, the composition includes all R- and S-enantiomers of the compounds. The class of compositions in the present invention accordingly embraces the compounds II
1a
, II
1b
, II
2a
, and II
2b
and their mixtures (II
1
and II
2
).
Accordingly, one embodiment of the invention is a composition that includes a mixture of compounds having the formula II:
wherein R is methyl or ethyl and which composition is free from the corresponding oct-5-ene double bond isomers. These compositions may be R- and S-enantiomers.
The invention includes a composition containing a mixture of compounds (6E)-3,6-dimethyloct-6-en-1-ol and (6Z)-3,6-dimethyloct-6-en-1-ol (II
1
):
which composition is free from (5E/Z)-3,6-dimethyloct-5-en-1-ol.
The invention also includes a composition containing a mixture of compounds (6E)-6-ethyl-3-methyloct-6-en-1-ol and (6Z)-6-ethyl-3-methyloct-6-en-1-ol (II
2
):
which composition is free from (5E/Z)-ethyl-3-methyloct-5-en-1-ol.
Other embodiments of the invention include odorant compositions containing compositions II, II
1
, and II
2
as defined above.
The invention also provides a process for preparing an odorant composition for use in a perfume or cosmetic composition that includes mixing an effective amount of compositions II, II
1
, or II
2
as defined above with a perfume or cosmetic base.
REFERENCES:
patent: 3959396 (1976-05-01), Ochsner
patent: 338895 (1904-06-01), None
patent: 1562796 (1969-10-01), None
patent: 1167776 (1969-10-01), None
patent: WO 98/47842 (1998-10-01), None
Harder, U., et al.,Recent Developments in Flavor and Fragrance Chemistry, 147-164, (1993).
Frater, G. et al.,Tetrahedron, 54, 7633-7703, (1998).
Frater Georg
Kraft Philip
Muller Urs
Bryan Cave LLP
Cole Monique T.
Givaudan Roure ( International ) SA
Haracz Stephen M.
Hooper Kevin C.
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