WO2008065527A2

WO2008065527A2 - Gallic acid esters of fragrant alcohols

Info

Publication number: WO2008065527A2
Application number: PCT/IB2007/003804
Authority: WO
Inventors: Carlo Ghisalberti
Original assignee: Carlo Ghisalberti
Priority date: 2006-11-27
Filing date: 2007-12-06
Publication date: 2008-06-05
Also published as: WO2008065527A3

Abstract

Gallates formed by condensation of gallic acid with a hydroxyl-containing fragrance for the use in a composition suitable for disinfecting and seboregulating purposes.

Description

GALLIC ACID ESTERS AND COMPOSITIONS COMPRISING THEREOF

FIELD OF THE INVENTION

The present invention relates to gallic acid esters and their use in disinfecting and/or seboregulating applications. BACKGROUND OF THE INVENTION

The gallic acid esters, also known as "gallates", are antioxidant compounds widely used in the food, cosmetics and drug industries, e.g. as oulined in reference 1.

1) Pucci B, et all. HeIv. Chim. Acta 2003, 86(2), 247-265. Synthetic Gallic Acid Derivatives as Models for a Comprehensive Study of Antioxidant Activity. On the other side, the increasing prevalence of bacteria and other microbes that are resistance to existing antimicrobial agents necessitates the identification of new classes of antimicrobials. Accordingly there is a need both in industry and in the home for safe and effective antimicrobial compositions which can be used as antimicrobials in or on a wide variety of substances and surfaces to reduce or eliminate microorganisms and which can be used to therapeutically or prophylactically treat animals, plants or inanimate objects.

Recent studies has pointed out that gallates may provide a powerful antimicrobial/ biocidal activity, e.g. disclosed in references 2-10.

2) Kubo I, et all. Bioorg Med Chem Lett. 2001; 12;l l(3):347-50. Antifungal activity of octyl gallate: structural criteria and mode of action.

3) Kubo I, et all. Bioorg Med Chem Lett. 2002; 21;12(2):113-6. Anti-MRSA activity of alkyl gallates.

4) Liao S, et all. Biochem Pharmacol. 2002; 15;63(6):1165-76. Structure-activity relationships for in hiuman 5alpha-reductases by polyphenols. 5) Fujita K & Kubo I. J Appl Microb, 2002; 92(6), 1035. Plasma membrane injury induced by nonyl gallate in Saccharomyces cerevisiae

6) Kubo I₃ et all. J Agric Food Chem. 2002; 3;50(14):3992-8. Molecular design of antifungal agents.

7) Fujita K & Kubo I. Int J Food Microbiol. 2002; 15;79(3):193-201. Antifungal activity of octyl gallate.

8) Kubo I, et all. Bioorg Med Chem. 2003; 20;l l(4):573-80. Non-antibiotic antibacterial activity of dodecyl gallate.

9) Higuti T, et all. Bioorg Med Chem. 2003; 15;l l(19):4255-62. Molecular design of multifunctional antibacterial agents against methicillin resistant Staphylococcus aureus (MRSA). 10) Higuti T, et all. Antimic Agents Chemother. 2005; 49(2):549-55. Alkyl Gallates, Intensifiers of β -Lactam Susceptibility in Methicillin-Resistant Staphylococcus aureus.

However, gallates are also sensitizing agents, as illustrated in references 11-12.

11) Hausen BM & Beyer W. Contact Dermatitis. 1992; 26(4):253-8. The sensitizing capacity of the antioxidants propyl, octyl, and dodecyl gallate and some related gallic acid esters.

12) D. Mufioz D, et all. Alergol Immunol Clin 2002; 17: 173-177. Contact dermatitis due to gallates

Gallates behave as powerful antigens in animal models. The most frequent clinical presentation in humans is cheilitis, although eczema in other locations and even generalised dermatitis are also possible. Widely different concentrations and vehicles have been used for the epicutaneous tests in the cases reported. As for the therapeutic management of gallate-induced contact dermatitis, the preventive measures may be restricted to the use of cosmetics and the manipulation of certain foodstuffs. Noteworthy, the references also point out many shortcomings which the present invention may overcome. SUMMARY

The present invention generally relates to a treatment gallic acid ester of gallic acid with "fragrance alcohols", and composition and method comprising thereof. The gallates formed by condensation of gallic acid with a hydroxyl-containing fragrance are suitably used in composition for disinfecting and seboregulating purposes.

It is therefore an object of this invention to provide compounds of formula (I) that are useful as agents for the treatment of super-infected skin and seal along with a sebaceous over-production.

Another aspect of the invention is therefore a composition that is effective in treating or preventing an infection and regulating sebaceous glands.

These and other embodiments of the present invention will become apparent in conjunction with the figures, description and claims that follow. DETAILED DESCRIPTION OF THE INVENTION According to the invention, there is provided gallic acid esters made of gallic acid and a "fragrance alcohol", for the use in manufacturing a medicament compositions having both disinfecting and seboregulating activities.

Suitable gallic acid esters of "fragrance alcohol" as used herein are e.g. the compounds formed by condensation of gallic acid or a derivative thereof with OH- containing substances selected among those listed in the Inventory of fragrance ingredients (perfume and aromatic materials issued by EC - Enterprise and Industry

Directorate General - Cosmetics 24/02/06 Section 1 (CD 2006/257/EC, 09.02.2006).

More specifically, the gallic acid esters which are the active ingredients of the present invention are compound of formula (I):

wherein: A is selected among:

A' = residue of an unsaturated and/or branched C6-C12 hydroxyalkyl; A" = terpene alcohol residue selected among a non-sensitazing, non-harmful aliphatic or alicyclic terpene alcohol;

A° = C6-C12 phenol residue of formula (II):

wherein:

R₁ and R₂, each independently, are H, COOH, COOR₃, R₃, 0-CO-R₃, CO-R₃, OR₃, or CHO₅ and R₃ is H or a lower alkyl group; or two vicinal R₁ and R₂, together with the two C atom to which are bonded, may form a 5-to-6-membered aromatic or non-aromatic ring; A°° = C7-C13-aryl-hydroxyalkyl residue of formula (II):

wherein:

X is a linear or branched, saturated or unsaturated Cl-C6-alkylen; with R₄ and R₅, each independently, are H, R₃, OR₃; or two vicinal R₁ and R₂, together with the two C atom to which are bonded, may form a 5-to-6-membered non-aromatic ring;

R₃ is H or a lower alkyl group; and esters, salts and solvates thereof.

The term "lower alkyl" refers to an alkyl- group of 1 to 5 carbon atoms, and may be a straight chain, branched, or cycloalkyl groups. Examplary compounds of formula (I) with A = A' include: usaturated C6-C12 such as 2-Hexen-l-yl gallate, 3-Hexen-l-yl gallate, 4-Hexen-l- yl gallate, cis-4-Hexen-l-yl gallate, cis-2-Hexen-l-yl gallate, cis-3-Hexen-l-yl gallate, trans-2-Hexen-l-yl gallate, 2,4-Hexadien-l-yl gallate, 2-Hepten-l-yl gallate,

3-Hepten-l-yl gallate, 2,4-Heptadien-l-yl gallate, cis-3-Octen-l-yl gallate, cis-5- Octen-1-yl gallate, trans-2-Octen-l-yl gallate, 3,5-Octadien-l-yl gallate, cis-2-

Nonen-1-yl gallate, trans-2-Nonen-l-yl gallate, cis-6-Nonen-l-yl gallate, cis-3-

Nonen-1-yl gallate, 2,6-Nonadien-l-yl gallate, 2,4-Nonadien-l-yl gallate, 3,6-

Nonadien-1-yl gallate, trans-2,cis-6-Nonadien-l-yl gallate, trans,cis-3,6-Nonadien-l- yl gallate2,4-Decadien-l-yl gallate, trans-2-Decen-l-yl gallate, 2-Undecen-l-yl gallate, 9-Decen-l-yl gallate, 10-Undecen-l-yl gallate; branched C6-C12 such as Hexan-2-yl gallate, Hexan-3-yl gallate, 2-Methylpropan- 2-yl gallate, 3-Methylpentan-l-yl gallate, Heptan-2-yl gallate, Heptan-3-yl gallate, 2- Methylhexan-3-yl gallate, Octan-2-yl gallate, Octan-3-yl gallate, 2,6- Dimethylheptan-4-yl gallate, 2-Ethylhexan-l-yl gallate, Nonan-2-yl gallate, Nonan- 3-yl gallate, 2-Methyloctan-l-yl gallate, 3,5,5-Trimethylhexan-l-yl gallate, Decan-3- yl gallate, 3,6-Dimethyloctan-3-yl gallate, Undecan-2-yl gallate, Dodecan-2-yl gallate; unsaturated and branched C6-C12 such as l-Hexen-3-yl gallate, l-Hepten-3-yl gallate, 2-Octen-4-yl gallate6-Methylhept-5-en-2-yl gallate, l-Nonen-3-yl gallate, 1- Decen-3-yl gallate, l-Octen-3-yl gallate, 3-Octen-2-yl gallate, l,5-Octadien-3-yl gallate, 2,6-Dimethylhept-6-en-l-yl gallate, (-)-3,7-Dimethyl-6-octen-l-yl gallate2,6- Dimethyloct-7-en-2-yl gallate, 2,6-Dimethylocta-l,5,7-trien-3-yl gallate, 3,7- Dimethylocta-l,5,7-tπen-3-yl gallate, and l,5-Undecadien-3-yl gallate.

Preferred compounds of formula (I) with A = A' are: trans-2-Octen-l-yl gallate, cis-3-Octen-l-yl gallate, cis-2-Nonen-l-yl gallate, trans-2-Nonen-l-yl gallate, cis-6- Nonen-1-yl gallate, cis-3-Nonen-l-yl gallate, trans-2-Decen-l-yl gallate, cis-4- Decen-1-yl gallate, 2-Undecen-l-yl gallate, and 10-Undecenyl gallate. Examplary compounds of formula (I) with A = A" include: linear terpene alcohols such as R-(+)-β-Citronellyl gallate, cis-Neryl gallate, Dehydrolinalooyl gallate, 1,2-Dihydrylinlooyl gallate, Tetrahydrolinalooyl gallate, Tetrahydrogeranyl gallate; Phytyl gallate, Isophytyl gallate, cis-Nerolidyl gallate, trans-Nerolidyl gallate, Myrcenyl gallate, Dihydomyercenyl gallate, Tetrahydromyercenyl gallate, and Lavandulyl gallate; heaxanoic terpene alcohols such as 1-Menthyl gallate, d,l-Menthyl gallate, p-Mentha-l,8-dien-7-yl gallate, Mentha-l,8(10)-dien-9-yl gallate, p-Menthan-8-yl gallate, p-Menthan-2-yl (Carvomenthyl) gallate, d-Neomenthyl gallate, Isopulegyl gallate, Piperityl gallate, Homomenthyl gallate, Carveoyl gallate, Dihydrocarveoyl gallate, neo- Dihydrocarveoyl gallate, Isodihydrocarveoyl gallate, Pine hexanyl gallate, α- Terpineyl gallate, β-Terpineyl gallate, 1-Terpineyl gallate, 4-Terpineyl (Carvomenthenyl) gallate, and (±)-α-Bisabolyl gallate; bicyclic terpene alcohols such as Isobornyl gallate, α-Fenchyl gallate, 2- Ethylfenchyl gallate, t,t-Farnesyl gallate, cis-2-Pananyl gallate, 4-Thujanyl gallate, cis-Pinocarveyl gallate, cis-Myrtanyl gallate, trans-Myrtanyl gallate, Myrtenyl gallate, Verbenyl (Pin-2-en-4-yl) gallate, Vetiveryl gallate, 9-Cedrenyl gallate, 2- Cedren-15-yl gallate, Cedryl gallate, and Caryophyllyl gallate (tricylo); other terpens alcohols such as α-Ionyl gallate, β-Ionyl gallate, β-Dihydroionyl gallate, Nopyl gallate, Cedanyl (arbanyl) gallate, α-Camphyl gallate, beta-Santalyl gallate, and α-Santalyl gallate. Preferred compounds of formula (I) with A = A" are: cis-Nerolidyl gallate, trans- Nerolidyl gallate, Myrcenyl gallate, Tetrahydromyercenyl gallate; R-(+)-β- Citronellyl gallate, Neryl gallate, Phytyl gallate, Lavandulyl gallate, t,t-Farnesyl gallate, 1-Menthyl gallate, d-Neomenthyl gallate, Isopulegyl gallate, Carveoyl gallate, Isobornyl gallate, α-Fenchyl gallate, 4-Terpineyl gallate, α-Ionyl gallate, (±)-α- Bisabolyl gallate, and Cedanyl gallate:

Examplary compounds of formula (I) with A = A° include: 4-Syringyl gallate, 4- Hydroxybenzyl gallate, 2-(4-Hydroxyphenyl)ethan-l-yl gallate, Eugenyl gallate, Isoeugenyl gallate, Gauacyl gallate, Thymyl gallate, 2-Methoxy-4-methylphenyl gallate, 4-Ethylguaiacyl gallate, 2-Methoxy-4-vmylphenyl gallate, 2,5- Dimethylphenyl gallate, 3,5-Dimethylphenyl gallate, 3-Ethylphenyl gallate, 4- Ethylphenyl gallate, o-Cresyl gallate, m-Cresyl gallate, p-Cresyl gallate, Carvacryl gallate, Syringyl gallate, 4-Ethoxyphenyl gallate, Phenyl gallate, Salicyl gallate, Methyl salicyl gallate, 2,6-Hylenyl gallate, o-Cumenyl gallate, 2- (Ethoxymethyl)phenyl gallate, 2-Propylphenyl gallate, 3,4-Xylenyl gallate, 2- Methoxy-4-propylphenyl gallate, 4-Propylphenyl gallate, 4-Methoxyeugenyl gallate, 4-Ethylsyringyl gallate, 4-Methylsyringyl gallate, Fragaryl gallate, 4- Propenylsyringyl gallate, 4-Propylsyringyl gallate, 4-Vinylphenyl gallate, 4-tert- Butylphenyl gallate, Hydroxyanisol gallate, 2,3-Xylenyl gallate, 2,4-Xylenyl gallate, Phloryl gallate, 3-Isopropylphenyl gallate, 4-Isopropylphenyl gallate, 6-tert-Butyl-m- cresyl gallate, 5-Methylguaiacyl gallate, 2,3,6-Trimethylphenyl gallate, 2-Methoxy- 6-(2-propeny)phenyl gallate, Vanillyl gallate, and Ethyl vanillyl gallate.

Preferred compounds of formula (I) with A = A⁰ are: Hydroxyanisol gallate, Salicyl gallate, Metyl salicyl gallate, Guaiacyl gallate, Vanillyl gallate, Vanillylic gallate, o- Cresyl gallate, p-Cresyl gallate, p-Cresotyl gallate, 2-Naphthyl gallate, Tymol gallate, Carvacryl gallate, 4-tert-Butylphenyl gallate, Phenyl gallate, and Syringil gallate. Examplary compounds of formula (I) with A = A°° include: Benzyl gallate, 2- Phenylethan-1-yl gallate, 3-Phenylpropan-l-yl gallate, 1-Phenylpropan-l-yl gallate, l-Phenylpentan-2-yl gallate, 2-Methyl-l-phenylpropan-2-yl gallate, 4-Phenylbutan- 2-yl gallate, 3 -Methyl- l-ρhenylpentan-3-yl gallate, 4-Phenylbutan-l-yl gallate, Cuminyl gallate, p-Cymen-8-yl gallate, 5-Phenylpentan-l-yl gallate, 1-Phenylethan- 1-yl gallate, 4-Methyl-l-phenylpentan-2-yl gallate, Hydratropyl gallate, 2-Methyl-4- phenylbutan-2-yl gallate, p-Anisyl gallate, 3-(4-Methoxyphenyl)propan-l-yl gallate, 2-Phenylpropan-2-yl gallate, and Piperonyl gallate.

Preferred compounds of formula (I) with A = A°° are: 2-Phenylethan-l-yl gallate, 1-Phenylpropan-l-yl gallate, 4-Phenylbutan-l-yl gallate, Cuminyl gallate, p-Cymen- 8-yl gallate, p-Anisyl gallate, and Piperonyl gallate.

The compounds of formula (I) can be used in the present invention either singly or as mixtures of different compounds of formula (I).

The compound of formula (I) may be otained with common esterification technics from gallic acid and the corresponding alcohol or phenol, e.g. by refluxing in standard condition (Vogel's Textbook of Organic Chemistry, 4th Ed., rev. by Furniss et all., Longman Inc., NY, 1978), or by refluxing in dioxane in the presence of p- toluenesulfonic acid and zeolite (Chen, & Wu, HuaxueShiji, 1997, 19, 382); or by using condensationg agents such as DCC (e.g. Bioorg Med Chem. 2003, 11(19), pag. 4260) or by enzymatic catalysis with lipases or tannases (e.g. EP0137601).

The compound of formulae (I) is optionally in the form of an ester with a carboxylic acid comprising an alkyl group containing from 1 to 6 carbon atoms.

Esters may be formed with one or more or all of the OH groups in the compound of formula (I). Suitable carboxylic acids include acetic acid, propionic acid and butyric acid; of these, acetic acid is preferred, eg. mono- or di-acetates.

The compounds may be used in the form of a acceptable salt. Thus salts may be formed between the anion produced by the loss of the OH proton and a base-derived cation. Examples of suitable bases are the alkali metal hydroxides, e.g. NaOH, quaternary ammonium hydroxides and amines such as mono-ethanolamine, dimethylamine, "tris" (tris means 2-amino-2-hydroxymethyl propane 1,3-diol), morpholine, or piperdine. The compositions of the invention will comprise a compounds of formula (I) in an amount of from 0.01% to 20% w/w, such as from 0.1% to 10% w/w, preferably from 0.6% to 5% w/w, more preferably from 0.8% to 3% w/w, e.g., from 1.5% to 2.5% w/w. Amounts w/w are based on the total weight of the composition. Thus, the compounds of formula (I) are effective anti-acne in that combine an antibacterial actvity against Propionibacterium species, for example P. acnes, with a lower subum production, as weel as an endowed low if any sensitizing effect compared to the classic C3-C12 linear ester of gallic acid. There can be advantages when the compounds of formula (I) are used as anti-acne/ anti-sebborheic ingredients together with further anti-acne agents. This is particularly the case when the further disinfecting and/or anti-acne agent, e.g. selected from desquamators, keratolytics, comedolytics and exfoliants. In these situations, there is an advantage from the combination of at least two therapeutic ingredients with distinct, but complementary, modes of action. An advantage is also gained from the delivery of a compound of formula (I) in increasing the skin and scalp with enhanced penetration with the presence of desquamating, keratolytic, comedolytic or exfoliating acting agents. A further advantage is gained due to the combined antibacterial effect against the organisms implicated in acne vulgaris, typically Propionibacterium species, especially P. acnes and seboregulatory activity of the compound of formula (I).

Product types suitable for the compositions of the invention include: skin products such as creams, lotions, ointments, sunscreens, anti-aging formulations, sunless tanners; colour cosmetics, including foundations and moisturisers; perfumes; hair treatments including shampoos, conditioners, mousses and gels; personal wash products including soap bars and shower gels; and shaving preparations. The products may take any shape or form. They may be liquids (preferably emulsions), gels, sticks, aerosols, mousses, skin patches, wiping articles, pads, pastes or powders.

Nonliving material such as but not limited to soil, porous and non-porous surfaces, etc., may be usefully treated with the instant compounds and compositions comprising the compounds to remove, retard or reduce the growth or, infectivity of parasites, bacteria, algae, fungi, viruses or prions including dormant and/or resistant forms such as spores and cysts, and disinfect the surface. The disinfectant compositions ma be applied for example in a spray, foam or dip.

The compositions that are useful in the present invention comprise a safe and effective amount of the topically-acceptable carrier or diluent which can have a variety of different forms. By "safe and effective" is meant an amount sufficient to act as a suitable vehicle for the required components and any other optional components, but not so much as to cause any side effects or skin reactions. The topically-acceptable carrier should be non-irritant. "Topically-acceptable" therefore means that the carrier is suitable for topical application to the skin without causing any untoward safety or toxicity concerns. In other words, these carriers are suitable for use on mammalian skin.

The topically-acceptable diluents or carriers, in total, typically constitute from about 0.1% to about 99.8% w/w of the compositions of the present invention, preferably from about 80% to about 99%, most preferably from about 85% to about 95% w/w.

One suitable diluent or carrier for use in the compositions of the invention comprises water together with one or more components selected from aliphatic alcohols containing two to four, more preferably two or three, carbon atoms.

Another optional component of the compositions useful in the instant invention is at least a surfactant, a humectant, a gel-forming material, an emollient, a variety of acids, bases, and buffers can be utilized to adjust the pH of the compositions.

In addition to the required components of the compositions useful in the present invention, a variety of optional components can also be incorporated. Preferred optional components include antioxidants (e.g., BHT), fragrances, clays (e.g., bentonite), silicones, and pigments. These optional materials may be used singly, or two or more of each type of materials may be used.

The invention is particularly useful for treating acne vulgaris with both reduction of the Propionibacterium species, especially P. acnes, and of sebum over-production from the sebaceous glands. The present invention is illustrated by the following examples that should not be considered limiting. EXAMPLES

General method of preparation

The compound can be prepared from a a solution of gallic acid (2.0 niM) and the corresponding alcohol (2.0 to 4.0 niM) in THF (6 niL) cooled at O⁰C is added with ΛyV'-dicyclohexylcarbodiimide (DCC) (4.2 mM) in THF (6 mL). After the solution is stirred for 6 to 20 h, the solvent is vacuum removed. The residue is extracted with several small portions of ethyl acetate and filtered. The filtrate is washed successively with diluted aqueous citric acid solution, saturated aq. NHCO₃ solution, and water, then dried over Na₂SO₄, filtered, and vacuum evaporated. The crude product can be purified by chromatography means, e.g. in SiO₂ by eluting with CHCl₃ZMeOH, with a gradient from 98:2 to 1 : 1. Structural Examples A' 1-A' 11

A'l - frαrø-2-Octen-l-ol gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.23 (s, 2H, ArH), 5.59 (m, IH, OCH₂CH=), 5.44 (m, IH, OCH₂CH-CHj, 4.79 (d, 2Η, OCH₂), 2.06 (m, 2Η, CH=CH-CH₂), 1.29 (m, 6Η, other CH₂), 0.87 (t, 3H₅ CH₅)

A'2 - crø-3-Octen-l-ol gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH)₃ 7.22 (s, 2Η, ArH), 5.43 (m, 2Η, CH=CH), 4.15 (t, 2H, OCH₂), 2.10 (m, 2Η, CH=CH-CH₂CH₂O),

2.02 (m, 2H, CH=CH-CH₂), 1.40 (m, 4Η, other CH₂), 0.96 (t, 3H₅ CH₅)

A'3 - cfo-5-Octen-l-ol gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH), 7.18 (s, 2H, ArH), 5.25 (m, 2Η, CH=CH), 4.2 (t, 2H, OCH₂), 2.03 (m, 2Η, CH=CH-CH₂CH₂), 1.97 (m, 2H, CH=CH-CH₂CH₃), 1.67 (m, 4H, other CH₂), 0.87 (t, 3H, CH₅) A' 4 - ris-2-Nonen-l-ol gallate: ¹NMR δ: 8.96 (s broad, 3Η, OH), 7.23 (s, 2Η, ArH),

6.03 (m, 1Η, CH=CHCH₂O), 5.51 (m, IH, CH=CHCH₂O), 4.95 (d, 2H, OCH₂), 1.98 (m, 2Η, CH=CH-CH₂), 1.36 (m, 8Η, other CH₂), 0.88 (t, 3H, CH₅) A'5 - arø»-2-Nonen-l-ol gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.23 (s, 2Η, ArH), 5.63 (m, IH, CH=CHCH₂O), 5.46 (m, IH, CH=CHCH₂O), 4.79 (d, 2H₅ OCH₂), 2.04 (m, 2Η, CH=CH-CH₂), 1.36 (m, 6Η, other CH₂), 1.26 (m, 2H₅ CH=CH- CH₂CH₂), 0.88 (t, 3Η, CH₅)

A'6 - cfe-6-Nonen-l-ol gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH), 7.18 (s, 2Η, ArH)₅ 5.25 (m, 2Η, CH=CH), 4.21 (t, 2H, OCH₂), 1.98 (m, 4Η, CH₂CH=CH-CH₂), 1.61 (qth, 2Η, OCH₂CH₂),1.48 (qth, 2Η, OCH₂CH₂CH₂), 1.33 (qth, 2Η, OCH₂CH₂CH₂CH₂), 0.87 (t, 3Η, CH₅)

A'7 - cfe-3-Nonen-l-ol gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.22 (s, 2Η, ArH), 5.33 (m, 2Η, CH=CH), 4.15 (t, 2Η, OCH₂), 2.13 (m, 2Η, OCH₂CH₂), 2.02 (m, 2H₅ CH₂CH=CH), 1.27 (m, 6H₅ other CH₂), 0.85 (t, 3H, CH₅)

A' 8 - frfltw.s-2-Decen-l-ol gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.23 (s, 2Η, ArH), 5.63 (m, 2Η, OCH₂CH=CH)₅ 5.43 (m, 2H, OCH₂CH=CH)₅ 4.78 (d, 2Η, OCH₂), 2.04 (m, 2Η, CH=CH-CH₂), 1.30 (m, 10H₅ other CH₂), 0.88 (t, 3H, CH₅) A'9 - cw-4-Decen-l-ol gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.18 (s, 2Η, ArH)₃ 5.36 (m, 2Η, OCH₂CH₂CH₂CH=CH)₅ 5.28 (m, 2Η, OCH₂CH₂CH₂CH=CH)₅

3.80 (t, 2H₅ OCH₂), 2.07 (m, 2H₅ OCH₂CH₂CH₂), 1.99 (CH₂CH=CH), 1.66 (qth, 2H₅ OCH₂CH₂CH₂), 1.26 (m, 8H, other CH₂), 0.87 (t, 3H, CH₃)

A' 10 - 2-Undecen-l-ol gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH)₅ 7.23 (s, 2Η, ArH)₅ 5.64 (m, 2Η, OCH₂CH=CH), 5.44 (m, 2H₅ OCH₂CH=CH)₅ 4.79 (t, 2H₅ OCH₂), 2.06 (m, 2Η, CH=CHCH₂), 1.26 (m, 12H₅ other CH₂), 0.88 (t, 3H, CH₅)

A' 11 - 10-Undecenyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.18 (s, 2Η, ArH),

5.81 (m, IH₅ CH₂=CH)₅ 4.97 (m, 2H₅ CH₂=CH)₅ 4.21 (t₅ 2H₅ OCH₂), 2.04 (m, 2H₅ CH₂=CHCH₂), 1.64 (qth, 2Η, OCH₂CH₂), 1.44 (qth, 2Η, OCH₂CH₂CH₂), 1.27 (m, 10H₅ other CH₂). Structural Examples A"l-A"15 A"l - cis-Nerolidyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH), 7.05 (s, 2H, AxH), 5.90 (dd, IH, CH=CH₂), 5.25 (dd, IH, CH=CH₂), 5.12 (m, IH₅ CH=C(CH₃)CH₂), 5.05 (dd, IH, CH=CH₂), 4.61 (m, 1Η, CH=C(CΗ₃)₂), 2.20 (m, 2H, OCCH₂CH₂), 1.90 (m, 6 other CH₂), 1.63 (2xd, 6Η, CH₃), 1.60 (d, 3Η, CH₃), 1.43 (s, 3Η, OCCH₃) A"2 - trans-Nerolidyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.05 (s, 2H, ArH), 5.90 (dd, 1Η, CH=CH₂), 5.25 (dd, IH, CH=CH₂), 5.13 (m, 1Η, CH=C(CH₃)CH₂), 5.07 (m, IH, CH=C(CH₃)₂), 5.06 (dd, IH, CH=CH₂), 2.20 (m, 2Η, OCCH₂CH₂), 2.00 (m, 4Η, ^C(CH₃)CH₂CH₂C=), 1.89 (t, 2Η, OCCH₂CH₂), 1.67 (s, 3H, t-CH₃), 1.60 (s, 3Η, CiS-CH₃), 1.56 (s, 3Η, CH=C(CH₃)CH₂), 1.43 (s, 3H, OCCH₃) A"3 - Myrcenyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 6.92 (s, 2H, ArH), 6.36 (dd, 1Η, CH=CH₂), 5.22 (dd, IH, CH=CH₂), 5.04 (dd, IH₅ CH=CH₂), 4.86 (d, 1Η, C=CH₂), 4.83 (dd, 1Η, C=CH₂), 2.14 (t, 2Η, CH₂-C=CH₂), 1.41 (q, 2H₅ OC(CH₃)₂CH₂CH₂))₅ 1.36 (s, 6H₅ OC(CH₃)₂), 1.22 (m, 2Η, CH₂CH(CH₃)CH=CH₂) A"4 - Tetrahvdromvercenyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.02 (s, 2H, ArH)₅ 1.59 (m, 1Η, CHCH₃), 1.57 (t, 2H, C(CH₃)₂CH₂), 1.36 (qth, 2Η, CH₂CH₂), 1.36 (qth, 2H₅ CH₂CH₃),1.36 (s, 6H, O(CH₃)₂), 1.06 (dd, 2Η, CH₂CH₂CH₂), 0.87 (d, 3Η, CH₃), 0.84 (d, 3Η, CH₃)

A"5 - R-(+)-beta-Citronellyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.18 (s, 2H₅ ArH), 5.09 (t, 1Η, CH=CH₂), 4.38 (t, 2H₅ OCH₂), 2.00 (q, 2H₅ CH₂CH=CH₂), 1.70 (s, 3H, =CCH₃), 1.62 (s, 3Η, =CCH₃), 1.55 (m, 5Η, CH₂CH(CH₃)CH₂), 0.91 (d, 3Η, CH-CH₃)

A"6 - Neryl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH), 7.23 (s, 2H, ArH), 5.58 (t, IH₅ CH=C CH₃), 5.09 (t, IH, CH=CH(CH₃)₂), 4.70 (d, 2H, OCH₂), 2.10 (m, 4Η,

CH₂CH₂), i.74 (s, 3Η, CH₃), l.ss (s+s₅ 6Η, CH₃) A"7 - Phvtyl gallate: 1H-NMR δ: 8.96 (s broad, 3Η, OH), 7.23 (s, 2H, ArH), 5.31 (t, IH, CH=CCH₃), 4.70 (d, 2H₅ OCH₂), 2.00 (t, 2Η, CH₂ allylic), 1.71 (s, 3Η, C=CCH₃), 1.52 (m, IH₅ CH(CH₃)₂), 1.23 (m, 20 other H)₅ 0.87 (3xd, 9H₅ CH₃ ) A"8 - Lavandulyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH)₅ 7.23 (s, 2H₅ ArH)₅ 5.16 (d₅ IH₅ C(CH₃)=CH₂)₅ 5.11 (t, IH₅ CH=C(CH₃)₂), 4.81 (d₅ IH₅ C(CH₃)=CH₂)₅ 4.23 (d, 2H₅ OCH₂), 3.09 (m₅ OCH₂CH)₅ 2.48 (m, OCH₂ CHCH₂), 1.74 (s₅ 3H₅ CH₃), 1.66 (s, IH₅ CH₃), 1.60 (s, IH₅ CH₃)

A"9 - tt-Farnesyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH), 7.23 (s, 2H₅ ArH)₅ 5.27 (m, IH₅ 1° CH=), 5.15 (m, 1Η, 3° CH=), 5.08 (m, IH₅ 2° CH=), 4.70 (d₅ 2Η, OCH₂), 1.99 (m, 8H₅ CH₂), 1.63 (m₅ 12Η, CH₃) A"l l - 1-Menthyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH), 6.97 (s, 2H₅ ArH)₅ 4.68 (m, IH₅ OCH)₅ 2.00 (m₅ IH₅ CHC(CΗ₃)₂), 1.87 (dd, IH CH₂), 1.67 (m₅ 1Η, CH), 1.40 (m, 2Η, CH₂), 0.99 (m₅ 2H₅ CH₂), 0.89 (dd₅ 6Η, CHC(CH₃)₂)₅ 0,85 (d₅ IH₅ CH)₅ 0,76 (d, 3Η, CH₃) A"12 - d-Neomenthyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH), 6.97 (s, 2H₅ ArH)₅ 4.60 (m, IH₅ OCH)₅ 2.44 (sept, 1Η, CHC(CΗ₃)₂), 1.75 (m, IH₅ CHCH₃), 1.47 (m₅ IH₅ CH(CH₃)₂)₅ 1.43 (m₅ 6H other CH₂), 0.96 (d₅ 3H, CH₃), 0,86 (d, 3H₅ CH₃), 0,78 (d₅ 3H₅ CH₃)

A"13 - Isopulegyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH)₅ 6.97 (s₅ 2H₅ ArH), 5.59 (m, 1Η, =CH ring), 5.18 (m₅ IH₅ OCH), 4.97 (d, IH₅ C=CH₂), 4.72 (d, 1Η, C=CH₂), 2.41 (m, 1Η, CH ring), 2.24 (m, 2Η, OCHCH₂), 2.23 (m, 1Η, CH₂ ring), 2.00 (m, IH₅ CH₂ ring), 1.76 (s, 3Η, CH₃ ring), 1.74 (s, 3Η, CH₃) A"14 - Carveoyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 6.97 (s, 2H₅ ArH)₅ 5.59 (m, IH₅ =CHring), 5.18 (m, 1Η, OCH)₅ 4.97 (d, IH₅ C=CH₂), 4.72 (d, IH₅ C=CH₂), 2.41 (m_s 1Η, CH ring), 2.24 (m, 2Η, OCHCH₂), 2.23 (m, 1Η, CH₂ ring), 2.00 (m₅ 1Η, CH₂ ring), 1.76 (s, 3H₅ CH₃ ring), 1.74 (s₅ 3Η, CH₃) A"15 - Isobomyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH)₅ 6.94 (s, 2H, AxH), 5.07 (dd, IH, OCH), 1.70 (m, 7H other H), 0.94 (s, 3H, OCCH₃), 0.84 (s, 3H, CH₃), 0.83 (s, 3Η, CH₃)

A"16 - alpha-Fenchyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH)₅ 6.95 (s, 2H, ArH), 4.58 (s, IH₅ OCH)₅ 2.06 (m, IH₅ C(CH₃)₂CH)₅ 1.88 (m, 2H₅ CH₂<), 1.52 (m₅

4H₅ OC(CH₃)CH₂CH₂), 1.05 (s, 3Η, OCCH₃), 1.00 (s, 3Η, CH₃), 0.95 (s, 3H₅ CH₃)

A"16 - 4-Terpineyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 6.97 (s, 2H₅ ArH), 5.59 (m, 1Η, =CH ring), 5.18 (m, IH₅ OCH), 4.97 (d, IH₅ C=CH₂), 4.72 (d, 1Η, C=CH₂), 2.41 (m, IH₅ CH ring), 2.24 (m, 2H₅ OCHCH₂), 2.23 (m, 1Η, CH₂ ring), 2.00 (m, IH₅ CH₂ ring), 1.76 (s₅ 3Η, CH₃ ring), 1.74 (s, 3Η, CH₃)

A"17 - alpha-Ionyl gallate: ¹H-NMR δ: 8.96 (s broad, 3Η, OH)₅ 7.23 (s, 2H₅ ArH)₅ 5.90 (d, IH₅ OCH₂CH=CH)₅ 5.61 (td, 1Η, OCH₂CH=CH)₅ 5.42 (m₅ 3H₅ =CH and =CH₂ cyclo), 4.97 (dd, 2Η, OCH₂CH=CH), 2.24 (d, IH, CH cyclo), 1.54 (s, 3H₅ CH₃), 1.54 (t₅ 2Η, CH₂C(CH₃)₂), 0.91 (s, 3H, CH₃), 0.78 (s, 3Η, CH₃) A" 18 - (±Va-Bisabolyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.03 (s, 2H₅ ArH), 5.43 (m, 1Η, =CH ring), 5.35 (m, IH₅ =CH chain), 1.96 (m, 6Η, CH₂), 1.76 (m, 4Η other CH₂), 1.72 (q, 1Η, CH ring), 1.67 (s, 3Η, CH₃), 1.64 (s, 3Η, CH₃), 1.58 (s, 3Η, CH₃), 1.31 (s₅ 3H₅ OCCH₃) A"19 - Cedanyl gallate: ¹H NMR δ: 8.96 (s broad, 3H₅ OH)₅ 7.10 (s, 2H₅ ArH)₅ 4.28 (t, 2Η, COOCH₂), 3.84 (t.₅ 2H₅ COOCH₂CH₂), 3.49 (t, 1Η, OCH)₅ 1.63 (m, 7Η other 7H), 0.94 (s, 3H, CH₃), 0,84 (s, 3H₅ CH₃), 0,81 (s, 3Η, CH₃) Structural Examples A⁰I-A⁰17

A°l - Ηvdroxyanisol gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH)₅ 7.23 (s₅ 2H₅ ArH o-Gall), 7.20 (d₅ 2H₅ ArH)₅ 7.09 (d, 2H₅ ArH), 3.74 (s, 3Η, CH₃) A°2 - Salicyl gallate: ¹H-NMR δ: 8.58 (s broad, 4H, OH)₅ 8.14 (d, IH, H₆), 7.71 (t, IH, ArH), 7.61 (s, 2Η, ArHo-GaIl)₅ 7.39 (t, IH, ArH)₅ 7.29 (d, 1Η, ArH) A°3 - Metylsalicyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 8.10 (d, IH, ArH), 7.68 (t, 1Η, ArH), 7.27 (s, 2Η, ArH o-Gall), 7.29 (d, IH₅ ArH)₅ 7.21 (t, 1Η, ArH)₅ 3.87 (s, 3Η, CH₃) A°4 - Guaiacyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH)₅ 7.32 (d, IH, ArH)₅ 7.13 (t, IH₅ ArH)₅ 7.20 (s, 2H₅ ArHo-GaIl)₅ 7.05 (t₅ IH₅ ArH), 7.01 (d, 1Η, ArH)₅ 3.79 (s, 3H, CH₃)

A⁰S - Vanillyl gallate: ¹H-NMR δ: 9.97 (s, IH, CHO), 8.96 (s broad, 3H, OH), 7.65 (s, IH₅ ArH), 7.64 (d, 1Η, ArH), 7.41 (d, IH₅ ArH)₅ 7.20 (s, 2Η, ArHo-GaIl)₅ 3.91 (s₅ 3Η, CH₃)

A°6 - Vanillylic gallate: ¹H-NMR δ: 9.14 (s broad, 4H, OH)₅ 7.79 (s, IH, ArH), 7.76 (d, IH₅ ArH), 7.30 (d, IH₅ ArH)₅ 7.20 (s, 2H₅ ArHo-GaIl)₅ 3.87 (s₅ 3H₅ CH₃) A°7 - o-Cresyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH)₅ 7.21 (s₅ 2H₅ ArH o- GaIl), 7.03 (m, 2Η, ArH), 7.18 (m, 2Η, ArH)₅ 2.33 (s, 3H₅ CH₃) A°8 - p-Cresyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH)₅ 7.23 (s, 2H₅ ArH o- GaIl)₅ 7.13 (dd, 4Η, ArH), 2.30 (s, 3Η, CH₃)

A°9 - p-Cresotyl gallate: ¹H-NMR δ: 8.58 (s broad, 4H₅ OH), 7.77 (d, IH, ArH), 7.60 (d, IH₅ ArH),7.59 (s, 2H₅ ArHo-GaIl)₅ 7.06 (t₅ IH₅ ArH)₅ 2.34 (s₅ 3H₅ CH₃) A⁰IO - 2-Naphthyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH)₅ 8.02 (d, IH₅ NaphH), 7.67 (d₅ IH₅ NaphH), 7.57 (t, 1Η, NapriH), 7.57 (s, IH₅ NaphH), 7.46 (d, IH₅ NaphH), 7.44 (d, IH₅ NaphH), 7.24 (t, IH₅ NaphH), 7.23 (s, 2Η, ArHo-GaIl) A⁰I l - Thymol gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.22 (s, IH, ArH), 7.21 (s, 2Η, ArHo-GaIl), 7.19 (s, 1Η, ArH), 7.03 (d, 1Η, ArH), 2.75 (sept., 1Η, CH), 2.16 (s, 3H, CH₃), 1.07(d, 6H, CH(CH₃)₂) A⁰12 - Carvacryl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.22 (s, IH₅ ArH)₅ 7.21 (s, 2H, ArHo-GaIl)₅ 7.18 (s, IH, AiH), 7.15 (d, IH, ArH)₅ 2.82 (sept., IH₅ CH),

2.29 (S₅ 3H₅ CH₃), 1.41(d, 6H₅ CH(CH₃)₂)

A°13 - 4-t-Butyl-phenyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH)₅ 7.25 (d, 2H,

ArH)₅ 7.23 (s, 2H₅ ArHo-GaIl)₅ 7.15 (d₅ 2Η, ArH)₅ 1.27 (s, 9Η, CiCH^) A°14 - Phenyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.33 (t, 2H, ArH), 7.23

(s, 2H₅ ArHo-GaIl)₅ 7.21 (t₅ 1Η, ArH)₅ 7.15 (d, 2Η, ArH)

A⁰15 - Syringyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH)₅ 7.16 (s, 2H₅ ArH o-

GaIl), 7.13 (t, IH₅ ArH)₅ 6.73 (d₅ 2Η, ArH), 3.09 (s, 6Η, OCH₃)

Structural Examples A°°1-A^OO7 A⁰⁰I - 2-Phenylethan-l-yl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.36 (t, IH,

ArH), 7.26 (t, 1Η, ArH), 7.19 (s, 2Η, ArH), 7.17 (d, 2Η, ArH), 4.27 (t, 2Η, OCH₂ ),

2.96 (s, 3Η, OCH₂CH₂)

A°°2 - 1-Phenylpropan-l-yl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH)₅ 7.38 (d,

2H, ArH), 7.29 (t, 1Η, ArH), 7.21 (t, 1Η, ArH), 6.94 (s, 2H₅ ArH), 5.80 (t, IH₅ OCH ), 1.94 (m, 1Η, OCHCH₂), 1.79 (dd, 1Η, OCHCH₂), 1.01 (d, 3Η, CH₃)

A°°3 - 4-Phenylbutan-l-yl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.41 (t, 2H,

ArH)₅ 7.28 (d, 2Η, ArH), 7.26 (t, 1Η, ArH)₅ 7.08 (s_; 2Η, ArH), 6.60 (d, 1Η, =CH),

6.00 (dd, 1Η, CH=), 5.34 (m, IH₅ OCH), 1.37 (d, 3Η, CH₃)

A^OO4 - Cuminyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.40 (d, 2H, ArH)₅ 7.26 (d, 2Η, ArH)₅ 7.23 (s, 2H₅ ArH), 5.13 (s, 2Η, OCH₂), 2.90 (s, IH₅ ArCH), 1.25 (d,

6H₅ CH₃)

A°°5 - p-Cvmen-8-yl gallate: ¹H-NMR δ: 8.96 (s broad, 3H, OH), 7.02 (d, 2H, ArH),

6.92 (s, 2Η, ArH)₅ 6.82 (d, 2Η, ArH)₅ 5.66 (m, 1Η, OCH), 3.13 (dd, 1Η, OCHCH₂),

2.74 (dd, 1Η, OCHCH₂) 2.25 (s, 3Η, CH₃), 1.19 (d, 3H, CH₃) A°°6 - p-Anisyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH), 7.23 (s, 2H₅ ArH), 7.34 (d, 2H, AxH), 6.96 (d, 2H, AiH), 5.13 (s, 2H, OCH₂), 3.77 (s, 6H, OCH₃) A°°7 - Piperonyl gallate: ¹H-NMR δ: 8.96 (s broad, 3H₅ OH), 7.23 (s, 2H, ArH), 7.18 (s, 1Η, ArH), 7.13 (d, 1Η, ArH), 6.99 (d, 1Η, ArH), 5.97 (d, 1Η, OCH₂), 5.81 (d, 1Η, OCH₂O), 5.26 (s, 2Η, OCH₂). Composition Example 1 - Anhidrous spry

Ingredient (g)

Gallic ester of formula (I) 0.5

Tocoferyl acetate 0.15

GIy colic acid 4.0 Ethanol 95% 40

Salicylic acid 0.5

Perfume, additives, preservatives qb

Aqua qb a lOO

Composition Example 2 - Ηydroalcoholic gel #1 Ingredient (g)

Gallic ester of formula (I) 0.2

Ethanol 80% 70

Ricinoleic-EO (40 moles) 0.5

Tocopheryl acetate 0,1 Carbopol™ Ultrez 10NF 0.6

Pemulen™ TR-2 NF 0.3

NaOΗ sol. (10N) 0.5

Perfume, additives, preservatives qb

Water qb to 100 g Composition Example 3 - Ηydroalcoholic gel #2

Ingredient (g)

Gallic ester of formula (I) 2.0 Propylene glycol 5.0 Dehydrated castor oil 20-OE 0.4 Buthyl ether 20-OE 3.6 Xantham gum 1.0 Perfume, additives, preservatives qb Ethanol 70% qb to 100 g

Composition Example 4 - Cream Ingredient (g)

Gallic ester of formula (I) 1.0 Whale wax 0.5 Cethanol 2.0 Petrolatum 5.0 Squalane 10 Polyoxyethylene (10 moles) monostearate 2.0 Sorbitan monooleate 1.0 Glycerine 10 Perfume, additives, preservatives qb Water qb to 100 g Biological Example - Combined antimicrobial and seboregulating effect

To assess the antimicrobial activity of compound of formula (I) in pathogenic bacteria and fungi, test substances or vehicle are added to test wells containing the selected microorganisms (1x10⁴ to 5x10⁵ CFU/ml) in cultures grown under controlled conditions. The final inoculum concentration is determined by reference to a standard optical density curve and adjusted as required. After 1 to 4 days, culture growth is examined and scored positive (+) for inhibition of growth or turbidity, or negative (-) for no effect. An initial test cone, of 3.2 mg/ml in acqueous DMSO and further dilutions to establish the minimal inhibitory concentration (MIC).

Table 1 shows the MIC (microg/ml) as average figure obtained on 3 bacterial strain, namely Streptococcus mutans, Staphylococcus aureus, and P. acnes; on 3 fungal strain namely Pityrosporum ovale; C. albicans, and Aspegillus niger.

The seboregulatory activity of compound of formula (I) by the application of a topical composition can be assessed by facial sebum reduction with Sebumeter^® (SM815; C-K Electronics, Cologne, D) according to Youn et all., Br J Dermatol. 2005, 153(5), 919-924, with a score between 3 (high) to 1 (modest). TABLE 1

Claims

CLAIMS 1. Composition comprising at least one compound of formula (I):

OH _(I) wherein A is selected among:

A' = residue of an unsaturated and/or branched C6-C12 hydroxyalkyl; A" = terpene alcohol residue selected among a non-sensitazing aliphatic or alicyclic terpene alcohol; A° = C6-C 12 phenol residue of formula (II) :

wherein:

R₁ and R₂, each independently, are H, COOH, COOR₃, R₃, 0-CO-R₃, CO-R₃, OR₃, or CHO, and R₃ is H or a lower alkyl group; or two vicinal R₁ and R₂, together with the two C atom to which are bonded, may form a 5-to-6~membered aromatic or non-aromatic ring;

A°° = C7-C13-aryl-hydroxyalkyl residue of formula (II):

wherein:

X is a linear or branched, saturated or unsaturated Cl-C6-alkylen; with R₄ and R₅, each independently, are H, R₃, OR₃; or two vicinal R₁ and R₂, together with the two C atom to which are bonded, may form a 5-to-6-membered non-aromatic ring; R₃ is H or a lower alkyl group; and esters, salts and solvates thereof.

2. Composition according to claim 1 for the use in disinfecting human skin and scalp from bacterial, viral, protozoan, algal or fungal growth while also inhibiting the 5α-reductase enzyme.

3. Composition according to claim 1 or 2 wherein said compound has formula (Y):

with A = A' = residue of an unsaturated and/or branched C6-C12 hydroxyalkyl.

4. Composition according to claim 1 or 2 wherein said compound has formula (F):

with A = A" = terpene alcohol residue selected among a non-sensitazing aliphatic or alicyclic terpene alcohol.

5. Composition according to claim 1 or 2 wherein said compound has formula (I°):

with A = A° = C6-C 12 phenol residue of formula (II) :

wherein:

R₁ and R₂, each independently, are H, COOH, COOR₃, R₃, 0-CO-R₃, CO-R₃, OR₃, or CHO, and R₃ is H or a lower alkyl group; or two vicinal Ri and R₂, together with the two C atom to which are bonded, may form a 5-to-6-membered aromatic or non-aromatic ring.

6. Composition according to claim 1 or 2 wherein said compound has formula (I°°):

with A = A°° = C7-C13-aryl-hydroxyalkyl residue of formula (II):

wherein:

X is a linear or branched, saturated or unsaturated Cl-C6-alkylen; with R₄ and R₅, each independently, are H, R₃, OR₃; or two vicinal R₁ and R₂, together with the two C atom to which are bonded, may form a 5-to-6-membered non-aromatic ring; and

R₃ is H or a lower alkyl group.

7. Composition according to one or more claims from 2 to 6 for the use in topical and cosmetic applications.

8. Composition according to claim 7 for the use in acneic and/or seborrheic skin.

9. Composition according to claim 7 for the use in seborrheic and/or balding scalp.

10. Composition according to any one of the preceeding claims also comprising cosmetically acceptable ingredients and diluents.