Derivatives of benzyl benzoate

Abstract

A compound of the general formula (I) ##STR00001## A cosmetic composition including such a compound and its use as a deodorant.

Claims

1. A compound of the general formula (I) ##STR00008## wherein: x is an integer equal to 1, 2, 3, 4 or 5; y is an integer equal to 0, 1, 2, 3, 4 or 5; each substituent R.sup.1 is chosen independently from a phenoxy group, optionally substituted with one or several substituent(s) chosen independently from a hydroxyl group, a C.sub.1-C.sub.6-alkyl group, a C.sub.1-C.sub.6-hydroxyalkyl group, a C.sub.1-C.sub.6-alkoxy group or a C.sub.1-C.sub.6-alkylcarbonyloxy group; or a benzoyloxy group, substituted with one or several substituent(s) chosen independently from a hydroxyl group, a C.sub.1-C.sub.6-alkyl group, a C.sub.1-C.sub.6-hydroxyalkyl group, a C.sub.1-C.sub.6-alkoxy group or a C.sub.1-C.sub.6-alkylcarbonyloxy group; and each substituent R.sup.2 is chosen independently from a phenoxy group, a phenylC.sub.1-C.sub.6-alkoxy group or a phenylC.sub.1-C.sub.6-alkylcarbonyloxy group, each of these groups optionally substituted with one or several substituents chosen independently from a hydroxyl group, a C.sub.1-C.sub.6-alkyl group, a C.sub.1-C.sub.6-hydroxyalkyl group, a C.sub.1-C.sub.6-alkoxy group or a C.sub.1-C.sub.6-alkylcarbonyloxy group.

2. The compound according to claim 1, wherein x is equal to 1, 2 or 3.

3. The compound according to claim 1, wherein y is equal to 0, 1 or 2.

4. The compound according to claim 1, wherein each substituent R.sup.1 is chosen independently from a phenoxy optionally substituted with one or several hydroxyl groups; or benzoyloxy group, substituted with one or several hydroxyl groups.

5. The compound according to claim 1, wherein each substituent R.sup.2 is chosen independently from a phenoxy or benzoyloxy group, each of these groups optionally substituted with one or several substituents chosen independently from a hydroxyl group, a C.sub.1-C.sub.6-alkyl group, a C.sub.1-C.sub.6-hydroxyalkyl group, a C.sub.1-C.sub.6-alkoxy group or a C.sub.1-C.sub.6-alkylcarbonyloxy group.

6. A compound of the general formula (I-a) ##STR00009## wherein R.sup.1 and R.sup.2 are as defined in claim 1.

7. A compound of the general formula (I-b) ##STR00010## wherein R.sup.1 is as defined in claim 1.

8. A method for preparing a compound according to claim 1 according to the following reaction scheme: ##STR00011##

9. A cosmetic composition comprising a compound according to claim 1.

10. A deodorant comprising a composition according to claim 9.

Description

(1) The present invention is illustrated in a non-limiting manner by the following examples.

EXAMPLE 1

Compounds According To The Invention

(2) TABLE-US-00001 Compound M.P. ( C.) 112-120

EXAMPLE 2

Preparation Of The Benzyl[4-(4-Phenoxy)Benzoyloxy]Benzoate (Compound 1)

2-1 Preparation of the 4-phenoxybenzoyle chloride

(3) 10.7 g (50 mmol) of 4-phenoxybenzoic acid (CAS #2215-77-2; Aldrich 246182) are suspended in 75 ml of thionyl chloride (CAS #7719-09-7).

(4) Heating is carried out progressively under magnetic stirring. The complete solubilization is obtained when the 60 C. temperature is reached. The set is maintained under gentle reflux for 45 minutes, then, evaporated to dryness in a Rotavapor.

(5) The obtained yellow oil is the 4-phenoxy benzoyle chloride.

2.2 Preparation of the benzyl[4-(4-phenoxy)benzoyloxy]benzoate

(6) In a 250 ml round-bottom flask, we place 11.4 g (50 mmol) of benzyl 4-hydroxybenzoate (CAS #94-18-8; Aldrich 300709), 55 ml of acetone (CAS #67-64-1) and 6.9 g (50 mmol) of anhydrous potassium carbonate (CAS #584-08-7).

(7) The set is put under magnetic stirring and we rapidly add all the 4-phenoxybenzoyle chloride obtained at step 2.1 which has been dissolved beforehand in 100 ml of acetone.

(8) After 2h15, stirring is made impossible by the formation of white-colored block.

(9) The block is finely divided then diluted by additional 100 ml of acetone. The mixture has been poured into an excess of water. The solution is acidified by concentrated hydrochloric acid (CAS #7647-01-0) and extracted by 2200 ml of dichloromethane.

(10) The combined organic phases are evaporated to dryness resulting in 26 g of a white solid.

(11) A filtration on 30 parts of silica (Kieselgel 60A, 70-230 mesh, Fluka) followed by an elution with dichloromethane then combination of the pure fractions (1) and concentration until the beginning of crystallization, dilution with pentane, spinning and washing with pentane, provides 15.85 g of white crystals (74.8% yield).

EXAMPLE 3

Deodorant Activity And Durability

(12) Protocol

(13) The test is carried out in vitro.

(14) The compound 1 and the benzyl-4-benzoyloxybenzoate (reference compound described in the international patent application WO 91/07165) are both 10% diluted in benzylbenzoate, and incorporated in a specific culture medium at the moment of distribution in 50 ml vials.

(15) The composition of the vials is characterized as follows: Vial No. 1 Brain Heart Infusion (medium)+0.5% Tween 40 Compound 1 or benzyl-4-benzoyloxybenzoate0.25% Enzyme (Lipozyme CALB, Novozymes)2% Bacteria (Corynaebacterium xerosis)about 106 CFU/ml Vial No. 2 Brain Heart Infusion (medium)+0.5% Tween 40 Compound 1 or benzyl-4-benzoyloxybenzoate0.25% Bacteria (Corynaebacterium xerosis)about 106 CFU/ml Vial No. 3 Brain Heart Infusion (medium)+0.5% Tween 40 Compound 1 or benzyl-4-benzoyloxybenzoate0.25% Enzyme (Lipozyme CALB, Novozymes)2%

(16) Afterwards, the vials are incubated under stirring at 37 C. for 48 hours.

(17) After 24 hours, a collection is performed, and 100 l of a dilution to 1/1000th are spread out on gelose. Counting of the number of CFU (Colony Forming Units) is performed.

(18) Results

(19) It is the comparison of the ratios between the amount of CFU/ml at a time t for the product+enzyme and the product alone which allows assessing the inhibiting activity of the product.

(20) The obtained results are reported in the Table hereinbelow.

(21) TABLE-US-00002 Number of CFU/ml Number of CFU/ml No. of the vial/Compound at t + 24 h at t + 48 h Vial 1/Compound 1 10.sup.7 36000.sup. Vial 1/benzyl-4- 2.7 10.sup.6 10.sup.8 benzoyloxybenzoate Vial 2/Compound 1 10.sup.8 3.2 10.sup.6 Vial 2/benzyl-4- 10.sup.8 10.sup.9 benzoyloxybenzoate Vial 3/Compound 1 .sup.0 .sup.0 Vial 3/benzyl-4- .sup.0 .sup.0 benzoyloxybenzoate

(22) The obtained results clearly highlight: a comparable deodorant activity of the compound and of the benzyl-4-benzoyloxybenzoate after 24 hours, a deodorant activity of the compound 1 which is significantly higher relative to the benzyl-4-benzoyloxybenzoate after 48 hours.