Claims
- 1. A schiff base reaction product produced according to the process of reacting methyl anthranilate having the structure: ##STR74## with ethyl vanillin having the structure: ##STR75##
- 2. A schiff base reaction product having the structure: ##STR76##
BACKGROUND OF THE INVENTION
This is a divisional of application Ser. No. 134,978, filed 12/18/87 now abandoned.
Our invention relates to the novel reaction product which is the schiff base of ethyl vanillin and methyl anthranilate, the compound having the structure: ##STR5## and the organoleptic use thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles and in enhancing or augmenting the effect of deodorancy; as a maskant for malodors emanating from the axillary regions of mammalian species.
Inexpensive chemical compositions of matter which can provide sweet, vanilla bean-like and sassafras aroma profiles with sweet topnotes and which are highly substantive and long-lasting are highly desirable in the art of perfumery. Many of the natural materials which provide such fragrances and contribute desired nuances to perfumery compositions as well as perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions and fabric softener articles are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
Still more desirable are materials which can both provide useful fragrance effects including high substantivity and a long-lasting fragrance and also provide a deodorancy effect whereby malodors can be masked by means of the use of the compound in, for example, the axillary regions of mammalian species including human beings.
Reaction products of carbonyl-containing compounds and amine-containing compounds are well known in the art of flavoring and in the art of of perfumery. Thus, U.S. Pat. No. 4,618,501 issued on Oct. 21, 1986 discloses the flavoring of foodstuffs with alpha,beta-keto-amines and states that an alpha,beta-keto-amine having a nutty corn, cereal aroma may be used for flavoring compositions for foods having the structure: ##STR6## wherein R.sub.1, R.sub.2 and R.sub.3 are selected from the group consisting of a saturated or unsaturated alkyl straight or branched chain hydrocarbons having from 1-3 carbon atoms.
U.S. Pat. No. 3,625,710 issued on Dec. 7, 1971 discloses the use of aldimines as chocolate-like flavors which aldimines are resulting from the reaction product of amines and aldehydes, for example, N-isobutylidenefurfurylamine, N-isopentylidenefurfurylamine, N-isopentylideneisopentylamine.
Schiff bases are also well known in the art of perfumery. Thus, for example, Chemical Abstracts Volume 103, 1985, No. 123134z (Abstract of Japan Kokai No. 60/78951 discloses the use in perfumery of compounds having the structure: ##STR7##
Arctander "Perfume and Flavor Chemicals (Aroma Chemicals)", Volume II, published by the Author in 1969 discloses the organoleptic properties of the schiff base of methyl anthranilate and vanillin having the structure: ##STR8## thusly: ##STR9## Viscous, dark-yellowish liquid, occasionally with an orange-reddish tint, or an olive-green color.
Insoluble in water, soluble in alcohol and oils.
Intensely sweet, balsamic-floral odor of very good tenacity. The odor varies considerably from one sample (supplier) to another, a fact which is often observed in "Schiff's bases". Generally, a mild surplus of the aldehyde component is preferable, except in cases of very pungent aldehydes such as Cuminaldehyde, Cinnamic aldehyde, Methylcinnamic aldehyde, etc.
The title material has very little use in perfumes, and is simply missing from most perfume laboratories. It may be considered as a curiosity, more than a practical perfume material, but it is briefly mentioned in this work because it may often "occur" in a perfume, since the use of Vanillin and Methylanthranilate in the same composition is not a very rare or unusual case. The addition of Vanillin directly into Methylanthranilate may often cause a strong coloring, brown or orange, of the mixture, and it is recommended not to add these materials in sequence, one next to the other.
Among scores of suggested "Schiff's bases", only very few have become standard perfume items, and the title material is not one of them. But it is classified as "interesting", by some perfumers.
Prod.: by condensation of Vanillin with Methylanthranilate in molecular proportions, preferably in a suitable diluent to prevent violent darkening, and to render the final product more pourable, handy for use.
Very slightly soluble in water, moderately soluble in alcohol, soluble in hot alcohol and oils.
The title material is briefly mentioned because it behaves in a rather peculiar manner. Although it has an unquestionable odor of Vanillin-type, rather soft, but quite pleasant and not exactly weak, its aqueous solution or the dry material itself has hardly any taste at all.
This peculiarity has not been explained in literature, but it could well be that the material (molecule), part of which is an aromatic aminoether, has mildly anaesthetic effect upon the human mucous membranes. Many members of this chemical series have anaesthetic effect.
The material was developed many decades ago for pharmaceutical purposes, but was also introduced to the perfume and flavor industry at that time. It has no longer importance to perfumes or flavors, but it is still used in pharmacy.
The compound of our invention having the structure: ##STR11## has unexpected, unobvious and advantageous organoleptic properties including deodorancy properties as opposed to the compounds of the prior art including the compound having the structure: ##STR12##
The book "Flavor & Fragrance Materials-1987" published by Allured Publishing Corporation, P. O. Box 318, Wheaton, Ill. 60189-0318 discloses on page 154 the commercial availability of the following schiff bases:
Nothing in the prior art however discloses the novel reaction products or reaction product mixtures of our invention having unobvious, unexpected and advantageous organoleptic properties.
Indeed, nothing in the prior art is indicative of the novel schiff base reaction products of our invention having deodorizing properties that is, having a deodorant value of 0.50 up to 3.5 as measured by the deodorant value test described in U.S. Pat. No. 4,304,679 incorporated by reference herein or having a Lipoxidase-inhibiting capacity of at least 50% and a Malodour reduction value of from 0.25 up to 3 as measured by the Malodour reduction value test disclosed in U.S. Pat. No. 4,663,068 incorporated by reference herein.
US Referenced Citations (2)
| Number |
Name |
Date |
Kind |
|
4177170 |
Cookson et al. |
Dec 1979 |
|
|
4639330 |
Sprecker et al. |
Jan 1987 |
|
Divisions (1)
|
Number |
Date |
Country |
| Parent |
134978 |
Dec 1987 |
|
Patent Grant
5008437
