WO2001085120A1

WO2001085120A1 - 6,10-dimethyl-5,9-undecadien-2-ol

Info

Publication number: WO2001085120A1
Application number: PCT/EP2001/005102
Authority: WO
Inventors: Gerhard Schmaus; Holger Joppe
Original assignee: Dragoco Gerberding & Co. Ag
Priority date: 2000-05-10
Filing date: 2001-05-05
Publication date: 2001-11-15
Also published as: AU6390001A; DE10022616A1

Abstract

The invention relates to the use of 6,10-dimethyl-5,9-undecadien-2-ol as an antimicrobial active agent, especially for inhibiting the growth of the micro-organisms that cause body odour, such as Staphylococcus epidermidis, Corynebacterium xerosis and Brevibacterium epidermidis.

Description

6,10-dimethyl-5,9-undecadiene-2-ol

The present invention relates to the use of 6,10-dimethyl-5,9-undecaden-2-ol as an antimicrobial (bactericidal, bacterostatic) active ingredient for inhibiting the growth of body odor-causing microorganisms, in particular the microorganisms Staphylococcus epidermidis and Corynebakteπum xerosis

In the context of the present text, the term 6, 10-dimethyl-5,9-undecadien-2-ol encompasses each of the following substances or substance mixtures

1 substance mixtures of the cis-trans isomers characterized by the different configuration at C5 according to formula 1 below (CAS 53837- 34-6)

2 the 5 (E) -confused isomer (CAS 7733-91 -7) according to formula 2 known under the common name geranylacetol

3 the 5 (Z) -configured isomer (CAS 6819-38-1) according to formula 3 known under the commercial name nerylacetol

Formula 1: 6,10-dimethyl-5,9-undecadien-2-ol; 5 (E / Z)

Formula 2: 6,10-dimethyl-5,9- Formula 3: 6,10-dimethyl-5,9-undecadien-2-ol; 5 (E) undecadiene-2-oI; 5 (Z)

Human skin is colonized by a large number of different bacteria. Most of these bacteria are not pathogenic and irrelevant for the physiological condition of the skin and for its smell. Others, on the other hand, can have a significant impact on the healthy condition of the skin 1 shown

Table 1 Skin microorganisms relevant to cosmetics

microorganisms:

Staphylococcus epidermidis armpit odor; general body odor

Staphylococcus aureus Atopic eczema wound infection Corynebacterium xerosis Armpit odor Brevibacterium epidermidis Armpit odor; foot odor

Propionibacteπum acnes acne

Eschenchia coli wound infections

Pseudomonas aeruginosa wound infections

Malassezia furfur (syn Pityrosporum oval) dandruff

Candida albicans General Candidiasis

Tπchophyton mentagrophytes skin and nail mycoses

Trichophyton rubrum skin and nail mycoses

Epidermophyton floccosum skin and nail mycoses

Aspergillus niger mold infestation

The bacterial breakdown of the body's own substances contained in sweat, such as unsaturated fatty acids, results in more or less weak-smelling precursors that produce unpleasant-smelling decomposition products that can have a strong influence on physical well-being. In cosmetics, products are used to prevent the development of substances that are responsible for body odor. which either prevent the formation of body sweat (antiperspirants) or substances which inhibit the growth of the bacteria in human skin responsible for odor formation (deodorants) bacterial species such as Staphylococcus epidermidis, Corynebacterium xerosis and Brevibacterium epidermidis, which are highlighted in Table 1, are significant in that Formation of armpit and foot odor or body odor in general involved

In the cosmetic industry, there is a constant need for substances that lower the microorganisms responsible for body odor (including armpit and foot odor) from a dermatological point of view kill harmless concentration or at least inhibit its growth, while being well contracted and stable (especially in the usual cosmetic formulations) and inexpensive to produce (using standard processes and / or starting from

Standard precursors)

The search for suitable (wιrk) substances which all have these properties to a sufficient extent is made more difficult for the person skilled in the art in that there is no clear dependence between the chemical structure of a substance on the one hand and its biological activity against certain germs and its stability on the other hand.

As part of our research to identify new products with the above properties, we have conducted extensive studies on the antimicrobial effects of certain unsaturated, alkyl branched aliphatic alcohols. In the course of this investigation it has now been shown that the 5 (E) and 5 (Z) isomers of 6, 10-dimethyl-5,9-undecadien-2-ol (CAS. -NR 7733-91- 7 or 6819- 38-1) and 5 (E / Z) isomer mixtures of 6, 10-dimethyl-5,9-undecadien-2-ol (CAS No. 53837-34-6) surprisingly have a strong bacteriostatic effect have odor-forming microorganisms in human skin, and can therefore be used as a mild deodorant in addition to or as an alternative to known antimicrobial active ingredients (such as Farnesol) in cosmetic products

The 5 (E / Z) - somerengemιsche are at least more effective than the pure 5 (E) - or 5 (Z) -isomers at least against Corynebacterium xerosis (within the scope of this text substances are also considered to be "pure" which up to 5% by weight of impurities)

Since the 5 (E / Z) isomer mixtures are moreover more economically available than the pure 5 (E) or 5 (Z) isomers, they are particularly preferred. In practice, 5 (E) / 5 (Z) -Mixtures with a molar ratio between 1 9 and 9 1 produce particularly inexpensively and use in cosmetic formulations 6,10-dimethyl-5 9-undecadien-2-ol is well tolerated and its stability (in particular in conventional cosmetic formulations) is surprisingly high

Geranylacetol (CAS 7733-91 -7) is a naturally occurring substance that has been detected in the concrete from the bleeding of Michelia champaca and in the passion fruit (see P Werkhoff et al, Vacuum Headspace Method in Aroma Research, Flavor chemistry of Yellow Passion Fruit, J. Agric. Food Chem 46, p 1076-1093 (1998) and R Kaiser, New Volatile Constituents of the Flower Concrete of Michelia campaca J. Essent. Oil Res 3, p 129-46 (1991))

I Kubo et al, J of Natural Products 57, p 9-17, 1994 describe the antimicrobial activity of the 5 (E) -confugurized 6, 10-dimethyl-5,9-undecadien-2-ol (geranylacetol), limit their statements but the use of this isomer as an anti-acne agent (inhibition of Propionibactenum acnes). Germs responsible for body odor such as Staphylococcus epidermidis or Brevibacterium epidermidis were just as little examined by Kubo et al as the 5 (Z) - configured isomer (Nerylacetol) or a 5 (E / Z) - mixture of isomers

I Kubo et al., J Agric Food Chem, Vol 41, No 12, 1993 describe the antimicrobial activity of the 5 (E) -configured 6, 10-dimethyl-5,9-undecadien-2-ol (geranylacetol) against Streptococcus mutans, a germ responsible for dental caries Germs responsible for body odor such as Staphylococcus epidermidis or Corynebacterium xerosis were again not investigated by Kubo et al, any more than the 5 (Z) - configured isomer (nerylacetol) or a 5 (E / Z) isomer mixture

Our new studies now show that the 5 (E) -confused isomer of 6, 10-dimethyl-5,9-undecadien-2-ol (geranylacetol) of formula 2 surprisingly not only against the anaerobic germ Propionibactenum acnes and Streptococcus mutans but also against germs causing body odor such as Staphylococcus epidermidis Corynebacterium xerosis or Brevibacterium epidermidis has a strong antimicrobial effect and causes a complete inhibition of these germs in concentrations of approximately 100 ppm in the agar dilution process Similar activity was also obtained for the 5 (Z) -confused isomer (nerylacetol) of the formula 3

The 5 (E / Z) isomer mixture according to formula 1 was surprisingly even more effective than Corynebacterium xerosis than any of the isomers

there is a syπergistic interaction of the isomers contained in the mixture

The use concentration of 6,10-dimethyl-5,9-undecaden-2-ol in the cosmetic end product is preferably between 0.0069 and 20% by weight, preferably between 0.05 and 0.5% by weight.

In a preferred process for the treatment of body odor, a cosmetic formulation which comprises 6,10-dimethyl-5,9-undecadien-2-ol (and optionally further deodorants) as an antimicrobial agent against in particular the above-mentioned microorganisms causing body odor such an amount applied topically to the body that the growth of the microorganism or microorganisms is inhibited

6,10-Dimethyl-5,9-undecadien-2-ol of the formulas 1, 2 or 3 can also impart a bacterostatic effect to finished products perfumed as a component of perfume compositions since the proportion of perfume in the finished cosmetic product is usually only about 1% , a perfume which contains the substance as an antimicrobial active ingredient should consist of about 5-50% by weight of 6 10-dimethyl-5,9-undecaαιen-2-ol since the substances of the formulas 1, 2 and 3 are only relatively weak Possess a smell, they can be safely used in such a high concentration as a component of perfume compositions

The invention is explained in more detail below with the aid of examples

1 syntheses of 6 10-dimethyl-5 9-undecadien-2-ol of the formulas 1 -3 Example 1 Synthesis of 6 10-dimethyl-5 9-undecadien-2-ol (E / Z isomer mixture formula 1)

776 g (4 mol) of an E / Z isomer mixture of 6 10- dimethyl-5 9-undecadion-2-one (syn geranylacetone / nerylacetone ratio EZ = 40 60 GC purity sum of the isomers> 96% ) together with 77 6 mg of sodium acetate and 700 g of methanol were then introduced into this solution with cooling, a mixture of 120 g of water, 0.23 g of sodium hydroxide and 46 g of sodium pumoranate (1.21 mol)

The metering end was stirred for a further 15 minutes and the degree of conversion was checked by TLC and GC. After the starting material had been converted quantitatively, 60 g of 50% sodium hydroxide solution and 166 g of water were added and the mixture was stirred under reflux for 2.5 hours a further 200 g of water were added and methanol was distilled off at atmospheric pressure to an internal temperature of 100 ° C. After cooling, the residue was taken up in 250 g of toluene and the aqueous phase was separated off. The organic phase was then washed twice with 10% sodium carbonate solution 5% saline solution, the toluene was distilled off. The crude yield was approx. 850 g (content of 6, 10-dimethyl-5,9-undecadien-2-ol approx. 90% sum of the E / Z-isomeric quantitative GC determination). The crude fraction was then passed through a 0 5 full-body column (Sulzer packing ) fractionally distilled yield of end product 750g (purity> 96%, E / Z isomer ratio 55 43, determination of the E / Z isomer ratio by means of GC / MS, mass spectrometric identification of the E and Z isomers see Examples 2 and 3)

Spectroscopic data ¹³ C (CDCl ₃ , 75.5 MHz) 5 (ppm) see Examples 2 and 3 Synthesis of the pure isomers starting from pure 6, 10-dimethyl-5 (E) 9-undecadien-2-one or 6.10 -Dιmethyl-5 (Z), 9-undecadιen-2-one (geranyl or nerylacetone)

Example 2 Synthesis of 6 10-dimethyl-5 (E) 9-undecadien-2-ol (Geranylacetol Formula 2)

Synthesis instructions see example 1, pure 5 (E) -isomer of 6, 10-dimethyl-5 9-undecadien-2-one was used as the starting material, (syn geranylacetone GC purity> 98%) Performed analogously to Example 1 Yield of 6 10-dimethyl-5 (E) 9-undecadien-2-ol (geranylacetol) 740 g, GC purity 97 6%

Spectroscopic data ¹³ C (CDCI ₃ , 75 5 MHz) δ (ppm) = 16 0 (q) 17 7 (q) 23 4 (q) 24 4 (t), 25 7 (q), 26 7 (t), 39 2 (d), 39 8 (d), 67 6 (d), 124 1 (d) 124 3 (d) 131, 3 (s) 135 4 (s) MS m / z (%) = 196 (0 , 1M ⁺ ), 153 (42) 135 (30), 123 (15), 109 (80), 95 (20), 81 (32) 69 (100), 67 (83), 55 (31), 41 (77)

Example 3 Synthesis of 6, 10-dimethyl-5 (Z), 9-undecadien-2-ol (Nerylacetol, Formula 3)

Synthesis instructions see example 1, pure 6, 10-dimethyl-5,9-undecadion-2-one, (5 (Z) -isomer), (syn nerylacetone GC purity> 98%) was used as starting material. The synthesis was carried out in analogy to Example 1 carried out yield of 6,10-dimethyl-5 (Z), 9-undecadien-2-ol (nerylacetol) 770 g, GC purity 95.5%

Spectroscopic data ³ C (CDCI ₃ , 75 5 MHz) δ (ppm) = 17 7 (q), 23 4 (2q), 24 3 (t), 25 7 (q), 26 6 (t), 32 0 ( t), 39 5 (t), 67 8 (d), 124 3 (d), 124 9 (d), 131 5 (s), 135 6 (s), MS m / z (%) = 196 (0 , 6, M ⁺ ), 153 (29), 135 (20), 123 (10), 109 (50), 95 (20), 81 (25), 69 (100), 67 (56), 55 (23 ), 41 (63)

2 studies on the antimicrobial effect of 6,10-dimethyl-5,9-undecadien-2-ol

The finding that 6, 10-dimethyl-5,9-undecaden-2-ol is particularly suitable for combating germs which are responsible for body odors goes back to a series of studies in which, in addition to the germs which are particularly relevant in the given context, Staphylococcus epidermidis, Corynebacterium xerosis and Brevibacterium epidermidis also a large number of other test germs were examined. In the following, not only the results for the inhibition of Staphylococcus epidermidis Corynebacterium xerosis and Brevibacterium epidermidis are given, but also the results of the further tests. The activity of 6 5-9-Dιm -undecadιen-2-ol compared to some of the other test germs is also astonishingly high. So 6 10- dimethyl-5 9-undecadιen-2-ol has a strong antimicrobial effect also against Staphylococcus aureus Malassezia furfur, Trichophyton rubrum and Tnchophyton mentagrophytes

2 1 General test conditions

The antimicrobial effect of the substances synthesized according to Examples 1-3 (formulas 1, 2, 3) was demonstrated using the agar dilution method based on DIN 58 940 / ICS and DIN 58 944 / ICS. Petri dishes with a diameter of 5 5 cm were also included 8.7 ml of freshly prepared Mueller-Hinton agar (Merck, type 1 05437 or Wilkins-Chalgren agar boil, Oxoid, type CM 643, supplemented with 10 g agar / liter) kept at 50 ° C , to which the various concentrations of the diluted sample were added in 3 3% by volume = 0.3 ml. For the test germ Malassezia furfurwurόe Mueller-Hinton agar was used, which contained 3% TweenδO (Merck, Art 8 22 187)

2.6 ml of the 3.3% samples were diluted with ethanol (96%, Merck, Art 1 00971). Continuous 2 1 dilution with ethanol (96%) resulted in the further test concentrations of the respective dilution series, which are given in Geometric rows were created

A further dilution with the test agar (0.3 ml sample or corresponding dilutions + 8.7 ml agar) resulted in 30-fold lower final concentrations (this corresponds to an initial concentration of 1 100 ppm each). The concentrations given below refer to the pure substance and are converted into ppm. 2 agar plates were poured per test concentration and nutrient medium

The following controls were carried out with 2 agar plates each K1 9.0 ml Mueller-Hinton agar (unvaccinated)

K2 8 7 ml Mueller-Hinton agar + 0 3 ml ethanol (96%) (uninoculated)

K3 8.7 ml Mueller-Hinton agar + 0 3 ml ethanol (96%) (inoculated)

K4 9 0 ml Mueller-Hinton agar (inoculated)

K5 9.0 ml Mueller-Hinton agar + 3% TweenδO (unvaccinated)

K6 9.0 ml Mueller-Hinton agar + 3% TweenδO + 0 3 ml ethanol (96%) (uninoculated)

K7 9.0 ml Mueller-Hinton agar + 3% TweenδO + 0 3 ml ethanol (96%) (inoculated)

K8 9.0 ml Mueller-Hinton agar + 3% TweenδO (inoculated)

K9 9.0 ml Wilkins-Chalgren agar (unvaccinated)

K10 9.0 ml Wilkins-Chalgren agar + 0.3 ml ethanol (96%) (uninoculated)

K1 1 9.0 ml Wilkins-Chalgren agar + 0.3 ml ethanol (96%) (inoculated)

K12 9.0 ml Wilkins-Chalgren agar (inoculated)

After solidification and drying (approx. 1 h at 37 ° C), the test plates were inoculated punctually with 1 μl each of the test germ suspensions listed in the examples below. To check purity and identity, the aerobically growing bacteria (Brevibacterium epidermidis, Corynebactium xerosis, Staphylococcus aureus Staphylococcus epidermidis) on Columbia blood agar (BioMeπeux, Art 43049) skin and mold fungi {Epidermophyton floccosum, Trichophyton rubrum, Tπchophyton mentagrophytes) on Sabouraud agar (BioMeπeux Art 43555) %, Lecithin 0.3%, histidine 0.1% Merck, type 1 13363) grown Propionibactenum acnes was cultivated on Schaedler agar (BioMeneux, type 43273). Further information on the test germs can be found in Table 2

Table 2 Test germs (strain names) and bacterial counts

Test germ strain reference KBEVml

Brevibacterium epidermidis ATCC 35514 2 1 x 10 ⁷

Corynebacterium xerosis ATCC 771 1 2.2 x 10 ⁷

Propionibactenum acnes ATCC 1 1829 2 8 x 10 ⁸

Staphylococcus aureus ATCC 6538 2.5 x 10 ⁷

Staphylococcus epidermidis ATCC12228 2.8 x 10 ⁷

Malassezia furfur DSM 6171 3.0 x 10 ⁷

Epidermophyton floccosum CBS 55384 2.2 x 10 ⁷

Trichophyton mentagrophytes CBS 26379 2.5 x 10 ⁷

Trichophyton rubrum DSM 4167 2.1 x 10 ⁷

KBE ^* = colony forming units

The test germ suspensions of the test germs for Brevibacterium epidermidis, Corynebacterium xerosis, Staphylococcus aureus and Staphylococcus epidermidis were prepared by incubation of Mueller-Hinton broth (Merck, type 1 10293) at 36 ° C, which was the case with a few single colonies of the respective test germs To achieve a clear turbidity, so much sterile nutrient broth was added to the suspensions that their turbidity corresponded to the McFarland standard 0.5 (approx. 10 ⁸ CFU / ml)

To prepare the remaining test germ suspensions (Propionibactenum acnes Malassezia furfur Epidermophyton floccosum, Trichophyton rubrum and Trichophyton mentagrophytes, the test strains were cultured on the above-mentioned solid nutrient media, harvested using a sterile swab and the suspension was diluted in so much Mueller-Hinton broth conformed to the McFarland standard 0 5

All test germ suspensions with the exception of Propionibactenum acnes were again diluted with sterile broth 1 10 and their germ count was determined using the surface method using a spiralometer (results see Table 2) The inoculated plates were incubated under the conditions given in Table 3 and then evaluated. The lowest active ingredient concentration, at which macroscopically no growth is present, was regarded as MIC (minimal inhibitory concentration). Minimal, barely visible growth or a few small individual colonies were assessed as inhibition

Table 3 Inoculation and Incubation

Test germ strain-Bez growth nutrient medium incubation conditions

Brevibacterium epidermidis ATCC 35514 Aerob Mueller-Hinton-18h at 36 ° C agar

Corynebacterium xerosis ATCC 771 1 aerobic Mueller-Hinton 18h at 36 ° C agar

Propionibactenum acnes ATCC 11829 anaerobic Wilkins- 72h at 36 ° C Chalgren agar

Staphylococcus aureus ATCC 6538 aerobic Mueller-Hinton-18h at 36 ° C agar

Staphylococcus ATCC 12228 aerobic Mueller-Hinton-18h at 36 ° C epidermidis agar

Malassezia furfur DSM 6171 aerobic Mueller-Hinton- 72h at 30 ° C agar + 3% Tween 80

Epidermophyton floccosum CBS 55384 aerobic Mueller-Hinton- 72h at 30 ° C agar

Trichophyton CBS 26379 aerobic Mueller-Hinton- 72h at 30 ° C mentagrophytes agar

Trichophyton rubrum DS 4176 aerobic Mueller-Hinton- 72h at 30 ° C agar 2 2 MIC values for 6 10-dimethyl-5 9-undecadien-2-ol of the formulas 1 2 and 3

The MIC values of the substances or substance mixtures with the formulas 1 2 or 3 were determined in accordance with the general test conditions described under 2 1

Example 4 MIC values for 6 10-dimethyl-5 9-undecadien-2-ol 5 (E / Z) Formula 1

Suspensions of Corynebacterium xerosis Staphylococcus epidermidis (ATCC 12228) and other test germs were inoculated and incubated according to the conditions described in Section 2 1 (General Test Conditions). The results are shown in Table 4. A significant inhibition of growth even at a very low concentration of 5 (E / Z) -Isomeregemιschs (EZ ratio 40-60 weight percent) was compared to the bacteria responsible for body odor Staphylococcus epidermidis (MIC value 69 ppm = 69 μg / ml) and Corynebacterium xerosis (MIC value 69 ppm = 69 μg / ml) observed

The MIC value is also particularly low compared to Staphylococcus aureus (MIC value 69 ppm = 69 μg / ml)

Test microbial suspensions of Epidermophyton floccosum (CBS 55384) Trichophyton mentagrophytes (CBS 26379) Trichophyton rubrum (DSM 4167) and Malassezia furfur (DSM 6171) were also inoculated and incubated according to the conditions described in Section 2 1 (General Test Conditions). The results are also incubated Table 4 shown With these germs - with the exception of Malassezia furfur (DSM 6171) and Propionibactenum acnes (ATCC 7711) - an inhibition of growth was observed at concentrations below 100 ppm = 100μg / ml Table 4 MIC values for 6, 10-dimethyl-5 9-undecadien-2-ol (5 (E / Z) -isomer mixture according to formula 1)

Example 5 MIC values for 6 10-dimethyl-5 9-undecadien-2-ol (pure 5 (E) isomer according to formula 2 geranylacetol)

Suspensions of Corynebacterium xerosis (ATCC 10231) Staphylococcus epidermidis (ATCC 12228) and other test germs were inoculated and incubated according to the conditions described in Section 2 1 (General Test Conditions). The results are shown in Table 5. A significant inhibition of growth even at very low levels Concentration could be observed with Staphylococcus epidermidis (MIC value 69 ppm = 69 μg / ml) and Corynebacterium xerosis (MIC value of 138 ppm = 138 μg / ml) for the 5 (E) isomer

The MIC value compared to Corynebacterium xerosis is somewhat worse in comparison with the MIC value of the 5 (E / Z) isomer mixture

The MIC value is also particularly low compared to Staphylococcus aureus (MNK value 69 ppm = 69 μg / ml),

Test germ suspensions of Epidermophyton floccosum (CBS

55384), Trichophyton mentagrophytes (CBS 26379) Trichophyton rubrum (DSM 4167) and Malassezia furfur (DSM 6171) inoculated and incubated according to the conditions described in Section 2 2 1 (General Test Conditions). The results are also shown in Table 5 for these germs With the exception of Malassezia furfur (DSM 6171), growth inhibition was observed at concentrations below 100 ppm = 100 μg / ml

Table 5 MIC values for 6,10-dimethyl-5,9-undecaden-2-oi, (pure 5 (E) -isomer of formula 2, geranylacetol)

Example 6 MIC values for 6 10-dimethyl-5 9-undecadien-2-ol (pure 5 (Z) -isomer according to formula 3 nerylacetol)

Suspensions of Corynebacterium xerosis (ATCC 10231) Staphylococcus epidermidis (ATCC 12228) and other test germs were inoculated and incubated according to the conditions described in Section 2 1 (General Test Conditions). The results are shown in Table 6. Dιmethyl-5 (Z), 9-undecadιen-2-ol in comparison with geranylacetol and the 5 (E / Z) - isomer mixture mostly only at somewhat higher concentrations MIC values Staphylococcus epidermidis (MIC value 138 ppm = 138 μg / ml), Corynebacterium xerosis (MIC value of 138 ppm = 133 μg / ml) Staphylococcus aureus (MIC value 138 ppm = 138 μg / ml)

In addition, test germ suspensions of Epidermophyton floccosum (CBS 55384), Trichophyton mentagrophytes (CBS 26379), Trichophyton rubrum (DSM 4167) and Malassezia furfur (OSM 6171) were inoculated and incubated according to the conditions described in Section 2 2 1 (General Test Conditions) Results are also shown in Table 6. In comparison with Examples 4 and 5, an inhibition of growth could only be observed with these germs at a slightly higher concentration

Table 6 MIC values for 6, 10-dimethyl-5,9-undecadien-2-ol (pure 5 (Z) -isomer according to formula 3, nerylacetol)

Example 7 MIC values for 6 10-dimethyl-5,9-undecaden-2-ol isomers of the formulas 1 (5E / Z isomer mixture) 2 (5E isomer) and 3 (5Z isomer) compared to Brevibacterium epidermidis strain name ATCC 35514)

Suspensions of Brevibacterium epidermidis (ATCC 35514) were inoculated and incubated according to the conditions described in Section 2 1 (General Test Conditions). However, the initial concentrations of the various 6 10-dimethyl-5 9-undecadien-2-ol isomers were in this case around the Factor 3 3 increased (highest concentration 3600 ppm) The results are shown in Table 7. A complete inhibition of growth was possible for the 6, 10-dimethyl-5 9-undecadien-2-ol isomers of the formulas 1 and 2 at 1 12 ppm The 5 (Z) -isomer of formula 3 was somewhat weaker effective MIC value 225 ppm Table 7 MIC values for 6 10-dimethyl-5,9-undecaden-2-ol isomers of the formulas 1 (5E / Z isomer mixture), 2 (5E isomer) and 3 (5Z isomer) against Brevibacterium epidermidis strain name ATCC 35514)

Examples 4-7 describe 6, 10-dimethyl-5,9-undecadien-2-ol of the formulas 1 (5E / Z isomer mixture), 2 (5 (E) isomer, purity> 95%) and 3rd (5 (Z) -isomer, purity> 95%) as antimicrobial substances

In a direct comparison of the pure isomers, the (5E) -configured 6 10-dimethyl-5,9-undecadien-2-ol proves to be slightly more active

Compared to Corynebacterium xerosis, however, the 5 (E / Z) isomer mixture is surprisingly more active than the pure 5 (E) isomer

All of the substances mentioned (formulas 1 2 and 3) can be used as an antimicrobial active ingredient, but the particular economic viability of the production process was generally allowed to speak for the 5 (E / Z) isomer mixture

A preferred application of 6 10-dimethyl-5 9-undecaden-2-ol is the inhibition of the bacteria responsible for the formation of body odor (including armpit and foot odor) (in particular Staphylococcus, Corynebacterium and Brevibactenum arias) In addition, 6 10-dimethyl-5,9-undecadion-2-ol can be used to inhibit mycosis-causing skin and nail fungi (dermatomycoses, nail mycoses, trichophyton and epidermophyton species) and to inhibit microorganisms responsible for dandruff formation {Malassezia furfur, or Syn Pityrospor orbiculares) can be used

Antimicrobial 6 10-dimethyl-5,9-undecaden-2-ol of the formulas 1 (5E / Z isomer mixture), 2 (5 (E) isomer) and / or 3 (5 (Z) isomer) containing Mixtures of active ingredients, insofar as they are used against germs causing body odor, are generally administered topically in the form of solutions, creams, lotions, gels, sprays

For other purposes, oral (tablets, capsules, powder, drops), intravenous, intraocular, intrapeπtoneal or intramuscular application or application in the form of an impregnated dressing is useful in some cases

The concentration of the active ingredients 6,10-dimethyl-5,9-undecaden-2-ol of the formulas 1 (5E / Z isomer mixture), 2 (5 (E) isomer) and / or 3 (5 (Z) -Isomer) in the applied formulations is in the range from 0.0069% to 20% and preferably in the range from 0.05% to 0.5% by weight. The antimicrobial complex of active ingredients can be used prophylactically or if necessary (especially if there is an acute bad smell) Come into play

The concentration of the amount of active ingredient to be applied daily, for example, varies and depends on the physiological state of the test subject and individual-specific parameters such as age or body weight

6,10-dimethyl-5,9-undecaden-2-ol of the formulas 1 (5E / Z isomer mixture), 2 (5 (E) isomer) and / or 3 (5 (Z) isomer) both alone and in combination with other antimicrobial substances

Claims

claims

Use of 6 10-dimethyl-5 9-undecadien-2-ol as an antimicrobial active ingredient for inhibiting the growth of body odor-causing microorganisms

Use of 6,10-dimethyl-5 9-undecaden-2-ol as an antimicrobial agent against body odor-causing germs of the genus Staphylococcus, Corynebacterium and / or Brevibacterium

Use of 6,10-dimethyl-5,9-undecaden-2-ol as an antimicrobial agent against Staphylococcus epidermidis and / or Corynebacterium xerosis and / or Brevibacterium epidermidis

Use of 6,10-dimethyl-5,9-undecaden-2-ol for the production of a pharmaceutical or cosmetic formulation with an antimicrobial effect against microorganisms causing body odor

Use according to one of claims 1-3, characterized in that the 6,10-dimethyl-5,9-undecadien-2-ol is a 5 (E / Z) isomer mixture with a molar 5 (E): 5 (Z) -Verhaltnιs between 1 9 and 9 1 is

Cosmetic formulation comprising an antimicrobial anti-body odor microorganism of the genus Staphylococcus Corynebacterium or Brevibacterium effective amount of 6, 10-dimethyl-5,9-undecaden-2-ol

Process for combating body odor, wherein a cosmetic formulation which comprises at least one antimicrobial agent effective against one or more body odor microorganisms is applied topically to the body in an amount which inhibits the growth of the microorganism (s), characterized in that the formulation is antimicrobial effective agent against body odor causing microorganisms 6 10-Dιmethyl-5,9-undecadιen-2-ol comprises Fragrance composition comprising a fragrance 5-50% by weight 6, 10-dimethyl-5,9-undecadien-2-ol and one or more customary additives

Use of 6,10-dimethyl-5,9-undecaden-2-ol as an antimicrobial agent against skin and nail fungi causing mycoses and / or microorganisms causing dandruff