Perfume bases

Details Perfume bases Perfume bases

1992-12-07

1994-04-26

Reamer, James H.

Perfume compositions

Perfume compositions

With preservative, stabilizer, or fixative

512 3, A61K 746

Patent

active

053067061

DESCRIPTION:

BRIEF SUMMARY
Usnic acid, a natural well-known antimicrobial agent, has been demonstrated to be extremely effective against Gram-positive bacteria, fungi, and yeast with Minimum Inhibitory Concentrations as low as 10 ppm for certain species [M. Fontana, G. Proserpio, Riv. Ital. Essenze, Profumi, Piante Off., Aromi, Saponi, Cosmetici, Aerosol (RIPOAM), 1974, 56, 315-336]. The use of free usnic acid in cosmetic formulations is complicated due to its insolubility in all commonly used solvent systems [H. Bergerhausen, Cosmetics and Toiletries 1976, 91, 25-26; Manufacturing Chemist 1989, 22-27]. Soluble derivatives of usnic acid, such as its alkali and ammonium salts, as well as certain esters, have been reported [Handelsgesellschaft Schlosser GmbH, 1975, Ger. Offen. 2354517. Orissa Drebing GmbH, 1975, Ger. Offen. 2351927. Orissa Drebing GmbH, 1975, Ger. Offen. 2351864. Orissa Drebing GmbH, 1976, Ger. Offen. 2432484] The major drawbacks of these derivatives are their insufficient stability properties, such as decolorization, pH-sensitivity, and reduction of antimicrobial activity.
Usnic acid [C.sub.18 H.sub.16 O.sub.7, 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzofurandione] exhibits the following characteristics:
MW 344.32; mp 201.degree.-203.degree. C., [.alpha]sub.D +488.degree. (c 0.4,CHCl.sub.3);mp 204.degree. C.,[.alpha]sub.D +509.4.degree. (c0.697,CHCl.sub.3);
Solubility at 25.degree. C. (g/100 ml): water<0.01, acetone 0.77, ethyl acetate 0.88, ethanol 0.02, chloroform 4.6, pyridine 2.12, benzene 0.94, dioxane 0.99, isopropyl alcohol 0.28, propylene glycol<0.01, dipropylene glycol 0.01, diethyl phthalate 0.45.
Certain perfumery raw materials now have been found to solubilize usnic acid--and leading to stable solutions. This finding allows the direct use of usnic acid, this natural antimicrobial agent isolated from alpine lichen, in numerous types of perfumes, cosmetic and toiletry formulations, without the usually required derivatization to improve its solubility.
The natural and synthetic perfumery raw materials are all characterized by exhibiting an aromatic ring. In the foreground of the interest are such standard perfumery materials as:
benzyl salicylate (1), benzyl benzoate (2), anisic aldehyde (3), isoeugenol methylether (4), cinnamyl acetate (5), and eugenol (6).
These perfumery raw materials exhibiting the desired solubilizing property are thus not only odorants, but also fixatives, blenders and modifiers.
The amount of any of (1) to (6) in the perfume bases is not too critical. Convenient amounts are:
about 20 to about 90% of any of (1) to (6). Mixtures of any one of (1) to (6) are also possible.
The maximum solubility (g/100 ml) of pure usnic acid in the above pure compounds (1) to (6) at 25.degree. C. is:
benzyl salicylate 3.01, benzyl benzoate 1.93, anisic aldehyde 4.06, isoeugenol methylether 2.69, cinnamyl acetate 1.60, eugenol 2.18, anethol 4.30.


EXAMPLES

Three formulae of perfume compositions containing different concentrations of free usnic acid are listed below:


______________________________________ Formula 1. Compound wt. % ______________________________________ Usnic Acid 0.5 1 20.0 2 18.0 6 2.0 Linalool 8.0 Benzyl Acetate 8.0 Hexyl Cinnamic Aldehyde 13.5 Phenyl Ethyl Alcohol 2.0 Hydroxycitronellal 4.0 Ylang Ylang Oil 2.0 Aldehyde C-14 6.0 Aldehyde C-18 6.0 Methyl Anthranilate 4.0 Indolene-50 [8,8-bis-(3H-indol-3-yl)-2,6- 2.0 dimethyl-2-octanal 50% in castor oil] Methyl Salicylate 4.0 100.00 ______________________________________


______________________________________ Formula 2. Compound wt. % ______________________________________ Usnic Acid 1.50 1 70.0 2 7.0 4 0.30 Linalool 1.00 Benzyl Acetate 7.00 Linalyl Acetate 0.70 Hexyl Cinnamic Aldehyde 2.30 Phenyl Ethyl Alcohol 3.00 Hydroxycitronellal 5.70 Geraniol Extra 0.30 Cinnamic Alcohol 0.15 Aldehyde C-14 (10% in DEP) 0.15 Aldehyde C-16 (10% in DEP) 0.15 Aldehyde C-18 (10% in DEP) 0.30 Argeol [hydroxycitronellal-methyl 0.15 anthran

REFERENCES:
M. Fontana et al., Riv. Ital. Essenze, Profumi, Piante Off., Aromi, Saponi, Cosmetici, Aerosol (1974), 56, 315-336.
H. Bergerhausen, Cosmetics and Toiletries, 91 (1976) 25-26.
Manufacturing Chemist, Oct. 1989, 22-27.
Inoue et al, Chem. Abst., vol. 93, #88,256s (1980).

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