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Novel resorcinol derivatives for skin

a technology of resorcinol and derivatives, which is applied in the field of substituting cycloalkyl methyl resorcinol derivatives, can solve the problems of low efficacy or undesirable side effects of substances identified so far, difficult formulation and/or irritation of skin

Inactive Publication Date: 2006-09-21
UNILEVER HOME & PERSONAL CARE USA DIV OF CONOPCO IN C
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"The present invention provides new compounds that have skin lightening activity. These compounds can be used in cosmetic compositions and methods for skin lightening. The invention also includes a process for synthesizing these compounds. The technical effect of this invention is to provide new and effective compounds for skin lightening that can be used in cosmetic products."

Problems solved by technology

However, the substances identified thus far tend to have either low efficacy or undesirable side effects, such as, for example, toxicity or skin irritation.
Some of these compounds can be difficult to formulate and / or irritating to the skin.

Method used

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  • Novel resorcinol derivatives for skin
  • Novel resorcinol derivatives for skin
  • Novel resorcinol derivatives for skin

Examples

Experimental program
Comparison scheme
Effect test

examples 1-7

[0065] A set of compositions within the scope of the present invention were prepared and listed in the Table below. The compositions are in weight per cent.

TABLE 2Ingredient Trade and CTFA NamePhase1234567Stearic acidA14.914.912.917.914.014.014.0Sodium cetearyl sulfateA1.01.01.51.5111Myrj 59A2.01.522222Span 60A2.01.522222Propyl parabenA0.100.100.100.100.100.100.10BHTA0.10.10.10.10.10.10.1DimethiconeA0.500.750.750.750.75WaterBBAL*BALBALBALBALBALBALEDTAB0.040.040.040.040.040.040.04Pemulen TR 2B0.100.050.050.050.05Methyl parabenB0.150.150.150.150.150.150.15Parsol MCX (organic sunscreen)C0.751.25110.750.750.75Parsol 1789 (organic sunscreen)C0.400.40.40.40.40.4Micronized Titanium oxideC0.20.20.2Propylene glycolD888TranscutolD4444-cyclopentyl methyl resorcinolD0.052.02.03.54-cyclohexyl methyl resorcinolD2.54-cyclothiane methyl resorcinolD3.514-cycloamido methyl resorcinolD5.0

*BAL = balanced to 100%

[0066] The compositions of Examples 1-7 in the Table above were prepared in the following...

example 8

[0067] This Example demonstrate an inventive process for producing 4-cyclohexyl methyl resorcinol (CHMR).

aReagents and conditions: (a) cyclohexylcarbonyl chloride, ZnCl2, dichloromethane, 64 h at R.T. (room temperature of about 20-25° C.); (b) acetic anhydride, triethylamine, tetrahydrofuran, 4 h at R.T.; (c) hydrogen, 5% Pd / C, acetic acid, 16 h at 30° C., 16 h at 50° C.; (d) 3M HCl:methanol (16:84), 4 h at R.T.

[0068]aReagents and conditions: (a) cyclohexylcarbonyl chloride, ZnCl2, dichloromethane, 64 h at R.T.; (b) acetic anhydride, triethylamine, tetrahydrofuran, 4 h at R.T.; (c) hydrogen, 5% Pd / C, acetic acid, 16 h at 30° C., 16 h at 50° C.; (d) 3M HCl:methanol (16:84), 4 h at R.T.

Specific Procedure: 4-cyclohexyl methyl resorcinol (CHMR or B2)

[0069] Cyclohexylcarbonyl chloride (1.54 ml, 11.3 mmol) was added to a suspension of zinc chloride (4.20 g, 31.4 mmol) in dichloromethane (10 ml) at room temperature, followed by resorcinol A (1.38 g, 12.5 mmol) and the solution stirre...

example 9

[0085] This example demonstrates the skin lightening activity of 4-cycloalkyl methyl resorcinol.

Mushroom Tyrosinase Assay

[0086] Mushroom tyrosinase inhibition is indicative of reduction in melanin synthesis, thereby showing skin lightening effect.

Reagents:

Assay buffer: phosphate (100 mM, pH 7.0)

Mushroom tyrosinase stock solution (Sigma-Aldrich, Batch # 023K7024): 0.2 mg / ml in assay buffer

L-DOPA stock solution: 1.05 mM in assay buffer

Test compound stock solutions: 10 mM in DMSO

Assay Conditions:

Mushroom tyrosinase: 0.1 mg / ml in assay buffer

L-DOPA: 0.5 mM in assay buffer

Test compounds: various concentrations, 2.5% final [DMSO]

Temperature: room temperature

Procedure:

Test compounds (5 uL of stock solutions) are added into wells of a 96-well plate, followed by L-DOPA (L-3,4-Dihydroxyphenylalanine; 95 uL of stock solution).

[0087] The reaction is started by adding mushroom tyrosinase (100 uL of stock solution) into each well and the absorbance is monitored at 490 nm...

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Abstract

New 4-substituted resorcinol derivatives of general formula I and / or B and process for synthesizing same, cosmetic compositions and methods of using same, particularly for skin lightening: Wherein X1 and / or X2 represents hydrogen (H), linear or branched, saturated or unsaturated C1-C12 alkyl, alkenyl, or acyl groups. Preferably, X1 and / or X2 represents hydrogen (H); linear or branched, saturated or unsaturated C1-C12 alkyl or acyl groups; R1 represents hydrogen (H), linear or branched, cyclic or acyclic, saturated or unsaturated C1-C12 alkyl, alkenyl, cycloalkyl, or cycloalkenyl group. Preferably, R1 represents hydrogen (H) or a C1 alkyl group (i.e, methyl group). More preferably, R1 represents hydrogen; n represents 0, 1. When n=0, the ring is a cyclopentyl with or without one heteroatom from O, N or S and / or with or without one double bond. When n=1, the ring is a cyclohexyl with or without one heteroatom from O, N or S and / or with or without one double bond; and m represents an integer between 1 and 6.

Description

FIELD OF THE INVENTION [0001] The invention relates to 4-substituted cyclo-alkyl methyl resorcinol derivatives, cosmetic compositions containing same, and cosmetic methods of using and making same. More specifically, the present invention relates to 4-substituted cyclo-alkyl methyl resorcinol derivatives as skin lightening actives, cosmetic compositions and methods of using same for skin lightening. BACKGROUND OF THE INVENTION [0002] Many people are concerned with the degree of pigmentation of their skin. For example, people with age spots or freckles may wish such pigmented spots to be less pronounced. Others may wish to reduce the skin darkening caused by exposure to sunlight or to lighten their natural skin color. To meet this need, many attempts have been made to develop products that reduce the pigment production in the melanocytes. However, the substances identified thus far tend to have either low efficacy or undesirable side effects, such as, for example, toxicity or skin ir...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K8/34C07C39/12
CPCC07C39/17C07C69/017C07C2101/14C07C2601/14C07C43/164
Inventor HARICHIAN, BIJANROSA, JOSE GUILLERMO
Owner UNILEVER HOME & PERSONAL CARE USA DIV OF CONOPCO IN C