DE10022616A1 - Inhibiting growth of microrganisms causing body odor, skin or nail mycosis or dandruff, using 6,10-dimethyl-5,9-undecadien-2-ol as potent, well tolerated antimicrobial agent - Google Patents

Abstract

Use of 6,10-dimethyl-5,9-undecadien-2-ol (I) as an antimicrobial agent for inhibiting the growth of microorganisms causing body odor or combating skin or nail fungi causing mycoses and/or microorganisms causing dandruff, is new. Independent claims are included for the following: (i) (I)-containing cosmetic formulations for inhibiting the growth of microorganisms causing body odor; (ii) a method for controlling body odor, involving topical application of a (I)-containing formulation; and (iii) a perfume composition, containing a perfume, (I) and one or more conventional additives.

Description

The present invention relates to the use of 6,10-dimethyl-5,9- undecadien-2-ol as an antimicrobial (bactericidal, bacteriostatic) active ingredient for Inhibition of the growth of odor-causing microorganisms, in particular the microorganisms Sfaphylococcus epidermidis and Corynebacterium xerosis.

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

• 1. Substance mixtures due to the different configuration on the C5 marked cis-trans isomers according to formula 1 below (CAS: 53837-34-6).
• 2. the 5 (E) -configured isomer known under the common name geranylacetol (CAS: 7733-91-7) according to formula 2.
• 3. the 5 (Z) -configured isomer (CAS: 6819-38-1) according to formula 3, known under the common name nerylacetol.
  

The human skin is colonized by a large number of different bacteria. the most of these bacteria are not pathogenic and are physiological the skin and irrelevant to its smell. Others, however, can do the healthy Significantly influence the condition of the skin. Some, the human skin flora strong Influencing microorganisms are shown in Table 1.

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 Propionibacterium acnes acne Escherichia coli Wound infections Pseudomonas aeruginosa Wound infections Malassezia furfur (syn.Pityrosporum ovale) Flaking Candida albicans General candidiasis Trichophyton mentagrophytes Skin and nail mycoses Trichophyton rubrum Skin and nail mycoses Epidermophyton floccosum Skin and nail mycoses Aspergillus niger Mold growth

Due to the bacterial breakdown of the body's own substances contained in sweat, such as B. Unsaturated fatty acids arise from more or less weakly smelling Precursors unpleasant smelling decomposition products that affect the physical Can have a major impact on well-being. To prevent the emergence of the for Substances responsible for body odor are used in cosmetics Products that either prevent the build-up of body sweat (Antiperspirants) or substances that stimulate the growth of the odor inhibit responsible bacteria in human skin (deodorants).

Bacterial species such as Staphylococcus epidermidis, Corynebacterium xerosis and Brevibacterium epidermidis, which are highlighted in Table 1, are relevant involved in the formation of armpit and foot odor, or body odor in general.

There is a constant need in the cosmetic industry for substances that

• - especially those for body odor (including armpit and foot odor) responsible microorganisms already in lower, from dermatological Kill the view of harmless concentration or at least their growth inhibit it
• - well tolerated and
• - stable (especially in the usual cosmetic formulations) as well
• - Can be produced inexpensively (using standard processes and / or based on standard precursors).

The search for suitable (active) substances that have all of these properties in Have sufficient measure, is made difficult for the skilled person that none clear dependence between the chemical structure of a substance on the one hand and their biological activity towards certain germs and their stability on the other hand exists.

As part of our research to identify new products with the We have carried out intensive studies on the above properties antimicrobial effects of certain unsaturated, alkyl-branched aliphatic Alcohols carried out. In the course of this investigation it has now been shown that the already known literature 5 (E) - and 5 (Z) -isomers of 6,10-dimethyl-5,9- undecadien-2-ol (CAS No. 7733-91-7 or 6819-38-1) and 5 (E / Z) - Mixtures of isomers of 6,10-dimethyl-5,9-undecadien-2-ol (CAS no .: 53837-34-6) Surprisingly, a strong bacteriostatic effect opposite odor-causing microorganisms of the human skin, and thus in Supplement to or as an alternative to known antimicrobial agents (such as Farnesol) can be used in cosmetic products as mild deodorants.

The 5 (E / Z) isomer mixtures are at least against Corynebacterium xerosis even more effective than the pure 5 (E) - or 5 (Z) -isomers (as "pure" are im In the context of this text, substances are also understood that contain up to 5% by weight Contain impurities).

Since the 5 (E / Z) isomer mixtures are also available more economically than the pure 5 (E) - or 5 (Z) -isomers, they are particularly preferred. In practice In particular, 5 (E) / 5 (Z) mixtures with a molar ratio can be used Manufacture between 1: 9 and 9: 1 particularly inexpensive and in cosmetic Use formulations.

6,10-Dimethyl-5,9-undecadien-2-ol is well tolerated and its stability (especially in customary cosmetic formulations) is surprisingly high.

Geranylacetol (CAS: 7733-91-7) is a naturally occurring substance that is under among other things in the concrete from the flowers of Michelia champaca and in the Passion fruit has been detected (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 Michella 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 Effectiveness of the 5 (E) -configured 6,10-dimethyl-5,9-undecadien-2-ol (Geranylacetol), but restrict their explanations to the use of this Isomers as an anti-acne agent (inhibition of Propionibacterium acnes). For Germs responsible for body odor such as Staphylococcus epidermidis or Corynebacterium xerosis have been reported by Kubo et al. just as little studied as that 5 (Z) -configured isomer (nerylacetol) or a 5 (E / Z) -isomer mixture.

I. Kubo et al. J. Agric. Food Chem., Vol. 41, No. 12, 1993 describe the antimicrobial effect of 5 (E) -configured 6,10-dimethyl-5,9-undecadien-2-ol (Geranylacetol) against Streptococcus mutans, one responsible for dental caries Germ. Germs responsible for body odor such as Staphylococcus epidermidis or Corynebacterium xerosis have been reported by Kubo et al. again, just as little investigated like the 5 (Z) configured isomer (nerylacetol) or a 5 (E / Z) isomer mixture.

Our new investigations now show that the 5 (E) -configured isomer of 6,10-dimethyl-5,9-undecadien-2-ol (geranylacetol) of formula 2 Surprisingly, not only against the anaerobic germ Propionibacterium acnes and Strepfococcus mutans but also against germs that cause body odor like Staphylococcus aureus or Corynebacterium xerosis, strongly antimicrobial is effective and in the agar dilution process already in concentrations of approx. 100 ppm causes complete inhibition of these germs.

Similar effectiveness was also found for the 5 (Z) -configured isomer (nerylacetol) of formula 3 obtained.

The 5 (E / Z) isomer mixture according to formula 1 was surprisingly opposite Corynebacterium xerosis even more potent than either isomer; apparently there is a synergistic interaction of the im Isomers contained in the mixture.

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

In a preferred method of controlling body odor, a cosmetic formulation that acts as an antimicrobial agent against in particular the above-mentioned microorganisms causing body odor 6,10-dimethyl-5,9-undecadien-2-ol (and possibly other deodorants) includes, applied topically to the body in such an amount 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 be used as Part of fragrance compositions perfumed finished products a give bacteriostatic effect. As the percentage of perfume in the cosmetic Finished product is usually only around 1%, should a perfume, which the substance contains as an antimicrobial agent, about 5-50% by weight of 6,10-dimethyl-5,9- undecadien-2-ol exist. Since the substances of formulas 1, 2 and 3 only have one Have a relatively faint odor, they can be safe in such high levels Concentration can be used as a component of perfume oil 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 formulas 1-3 example 1 Synthesis of 6,10-dimethyl-5,9-undecadien-2-ol (E / Z- Mixture of isomers; formula 1

776 g (4 mol) of an E / Z isomer mixture of 6,10-dimethyl-5,9-undecadien-2-one (syn .: geranylacetone / nerylacetone; ratio E: Z = 40:60; GC purity: sum of the isomers <96%) presented together with 77.6 mg of sodium acetate and 700 g of methanol. A mixture of 120 g of water, 0.23 g of caustic soda and 46 g of sodium borate (1.21 mol) was then metered into this solution with cooling. After the end of the metering, stirring was continued for about 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% strength sodium hydroxide solution and 166 g of water were added and the mixture was stirred under reflux for 2.5 h. The reaction mixture was then admixed with a further 200 g of water and methanol was distilled off at atmospheric pressure up to an internal temperature of 100.degree. 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. After washing neutral with 5% sodium chloride 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 isomers: quantitative GC determination). The crude fraction was then fractionally distilled on a 0.5 m packed column (Sulzer packing). Yield of end product: 750 g (purity <96%; E / Z isomer ratio: 55: 43; determination of the E / Z isomer ratio by means of GC / MS; identification of the E and Z isomers by mass spectrometry: see Examples 2 and 3)
Spectroscopic data: ¹³ C (CDCl ₃ ; 75.5 MHz): δ (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-dimethyl-5 (Z), 9-undecadien-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 served as starting material; (Syn .: geranylacetone; GC purity: <98%). The synthesis was carried out in analogy 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 (CDCl 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 (0.1, M ⁺

), 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-undecadien-2-one, (5 (Z) isomer) served as starting material; (Syn .: nerylacetone; GC purity: <98%). The synthesis was carried out in analogy to Example 1. Yield of 6,10-dim / ethyl-5 (Z), 9-undecadien-2-ol (nerylacetol): 770 g; GC purity: 95.5%
Spectroscopic data: ¹³

C (CDCl 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 knowledge that 6,10-dimethyl-5,9-undecadien-2-ol is particularly suitable for Is suitable for combating germs that are responsible for body odors, goes back to a series of studies in which, in addition to those given in Connection particularly relevant germs Staphylococcus epidermidis and Corynebacterium xerosis also examined a large number of other test germs became. The following are not just the results for the inhibition of Staphylococcus epidermidis and Corynebacterium xerosis indicated, but also the results of further tests. The activity of 6,10-dimethyl-5,9-undecadiene-2- ol compared to some of the other test germs is also astonishingly high. So 6,10-dimethyl-5,9-undecadien-2-ol has a strong antimicrobial effect too against Staphylococcus aureus, Malassezia furfur, Trichophyton nibrum and Trichophyton mentagrophytes.

2.1. General test conditions

Evidence of the antimicrobial effect of the examples 1-3 synthesized substances (formulas 1, 2,3) took place with the help of the Agar dilution method based on DIN 58 940 / ICS and DIN 58 944 / ICS. It were Petri dishes of 5.5 cm diameter with 8.7 ml freshly made and with 50 ° C liquid Mueller-Hinton agar (Merck, Art. 1.05437 or Wilkins Chalgren agar boillon, Oxoid, Art. Cm 643, supplemented with 10 g agar / liter) loaded, which the different concentrations of the diluted sample in 3.3% by volume = 0.3 ml were added. For the test germ Malassezia furfur was Mueller-Hinton agar was used which contained 3% Tween80 (Merck, Art. 8.22 187).

2.6 ml of the 3.3% samples were treated with ethanol (96%; Merck, Art. 1.00971) diluted. Continuous 2: 1 dilution with ethanol (96%) made the further test concentrations of the respective dilution series, which are in the form geometric rows were created.

By further dilution with the test agar (0.3 ml sample or equivalent Dilutions + 8.7 ml agar) were each 30-fold lower final concentrations reached (this corresponds to an initial concentration of 1100 ppm in each case). The in The following specified concentrations relate to the pure substance and are converted to ppm. For each test concentration and nutrient medium, 2 Poured agar plates.

The following controls were carried out with 2 agar plates each:
K1: 9.0 ml Mueller Hinton Agar: (uninoculated)
K2: 8.7 ml Mueller-Hinton agar + 0.3 ml ethanol (96%): (not inoculated)
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% Tween80: (not inoculated)
K6: 9.0 ml Mueller-Hinton agar + 3% Tween80 + 0.3 ml ethanol (96%): (not inoculated)
K7: 9.0 ml Mueller-Hinton agar + 3% Tween80 + 0.3 ml ethanol (96%): (inoculated)
K8: 9.0 ml Mueller-Hinton agar + 3% Tween80: (inoculated)
K9: 9.0 ml Wilkins Chalgren Agar: (uninoculated)
K10: 9.0 ml Wilkins Chalgren agar + 0.3 ml ethanol (96%): (not inoculated)
K11: 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 punctiform with 1 µl each of the examples listed below Test germ suspensions inoculated. To check purity and identity were made the aerobically growing bacteria (Corynebacterium xerosis, Staphylococcus aureus; Staphylococcus epidermidis) on Columbia Blood Agar (BioMerieux, Art. 43049). Skin- and molds (Epidermophyton floccosum; Trichophyton rubrum; Trichophyton mentagrophytes) cultivated on Sabouraud agar (BioMerieux, Art. 43555). Malassezia furfur was grown on Sabourad agar with disinhibitors (Tween80: 1%, lecithin: 0.3%; Histidine: 0.1%; Merck, Art. 1.18368). Propionibacterium acnes was on Schaedler agar (BioMerieux, Art. 43273) cultivated. Further information on the Test germs can be found in Table 2.

Table 2

Test germs (strain names) and germ count

The test germ suspensions of the test germs for Corynebacterium xerosis, Staphylococcus aureus and Staphylococcus epidermidis were prepared by incubating Mueller-Hinton broth (Merck, item 1.10293) at 36 ° C, which had been inoculated with a few individual colonies of the respective test germs. After the suspension had become distinctly cloudy, so much sterile nutrient broth was added that its turbidity corresponded to the McFarland Standard 0.5 (approx. 10 ⁸ CFU / ml).

For the preparation of the remaining test germ suspensions (Propionibacterium acnes, Malassezia furfur, Epidermophyton floccosum, Trichophyton rubrum and Trichophyton mentagrophytes were the test strains on the above, cultured solid culture media, harvested using a sterile swab and in so much Mueller-Hinton broth added or diluted that the cloudiness of the Suspensions conformed to the McFarland Standard 0.5.

All test germ suspensions, with the exception of Propionibacterium acnes, were again diluted 1:10 with sterile broth and its bacterial count im Surface method determined using a spiralometer (results: see Table 2).

The inoculated plates were processed under the conditions given in Table 3 incubated and then evaluated. As MIC (minimum inhibitory concentration) the lowest material concentration was considered, at which macroscopically none Growth is present. Minimal, barely visible growth or a few small ones Single colonies were scored as inhibition.

Table 3

Inoculation and incubation

2.2. MIC values for 6,10-dimethyl-5.9-undecadien-2-ol of the formulas 1, 2 and 3

According to the under 2.1. general test conditions described were the MIC values of the substances or substance mixtures with the formulas 1, 2 and 3 certainly.

Example 4 MIC values for 6,10-dimethyl-5,9-undecadien-2-ol; 5 (E / ZI: Formula 1

Suspensions of Corynebacterium xerosis (ATCC 10231), Staphylococcus epidermidis (ATCC 6538) and other test germs were determined according to the procedures in Section 2.1. (General test conditions) inoculated and incubated. The results are shown in Table 4. A marked inhibition of the Growth even at a very low concentration of the 5 (E / Z) isomer mixture (E: Z ratio approx. 40: 60 percent by weight) was compared to that for body odor responsible germs Staphylococcus epidermidis (MIC value: 69 ppm = 69 µg / ml) and Corynebacterium xerosis (MIC value of 69 ppm = 69 µg / ml) were observed.

The MIC value for Staphylococcus aureus is also particularly low (MIC value: 69 ppm = 69 µg / ml).

Test suspensions of Epidermophyton floccosum (CBS 55384), Trichophyton mentagrophytes (CBS 26379), Trichophyton rubrum (DSM 4167), and Malassezia furfur (DSM 6171) according to the procedures in section 2.2.1. (General Test conditions) are inoculated and incubated. the Results are also shown in Table 4. Even with these germs - with the exception of Malassezia furfur (DSM 6171) and Propionibacterium acnes (ATCC 7711) - an inhibition of growth at concentrations still below of 100 ppm = 100 µg / ml can be observed.

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 6538) and other test germs were determined according to the procedures in Section 2.1. (General test conditions) inoculated and incubated. The results are shown in Table 5. A marked inhibition of the Sfaphylococcus could grow even at very low concentrations epidermidis (MIC value: 69 ppm = 69 µg / ml) and Corynebacterium xerosis (MIC- Value of 138 ppm = 138 μg / ml) can be observed for the 5 (E) isomer.

The MIC value against Corynebacterium xerosis is compared with the MIC value Value of the 5 (E / Z) isomer mixture somewhat worse.

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

Test germ suspensions of Epidermophyton floccosum were also used (CBS 55384), Trichophyton mentagrophyfes (CBS 26379), Trichophyton rubrum (DSM 4167), and Malassezia furtur (DSM 6171) according to the in section 2.2.1. (General test conditions) are inoculated and incubated. The results are also shown in Table 5. Even with these germs could - with the exception of Malassezia furfur (DSM 6171) - an inhibition of the Growth observed at concentrations below 100 ppm = 100 µg / ml will.

Table 5

MIC values for 6,10-dimethyl-5,9-undecadien-2-ol; (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; Nerve acetol)

Suspensions of Corynebacterium xerosis (ATCC 10231), Staphylococcus epidermidis (ATCC 6538) and other test germs were prepared according to the methods described in Section 2.1. (General test conditions) are inoculated and incubated. The results are shown in Table 6. Compared with geranylacetol and the mixture of 5 (E / Z) isomers, 6,10-dimethyl-5 (Z), 9-undecadien-2-ol could generally only be inhibited completely at slightly higher concentrations.
MIC values: Staphylococcus epidermidis (MIC value: 138 ppm = 138 µg / ml), Corynebacterium xerosis (MIC value of 138 ppm = 138 µg / ml), Staphylococcus aureus (MIC value: 138 ppm = 138 µg / ml ).

Test germ suspensions of Epidermophyton floccosum were also used (CBS 55384), Trichophyton mentagrophytes (CBS 26379), Trichophyton rubrum (DSM 4167), and Malassezia furfur (DSM 6171) according to the procedures in section 2.2.1. (General test conditions) are inoculated and incubated. The results are also shown in Table 6. Even with these germs was only able to inhibit growth in comparison to Examples 4 and 5 can be observed 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)

Examples 4-6 describe 6,10-dimethyl-5,9-undecadien-2-ol of the formula 1 (5E / Z isomer mixture), 2 (5 (E) isomer; purity <95%) and 3 (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 as slightly more active.

In comparison to Corynebacterium xerosis, however, surprisingly the 5 (E / Z) - Isomer mixture even more active than the pure 5 (E) isomer.

All substances mentioned can be used as an antimicrobial agent (Formulas 1, 2 and 3) find the particular economic efficiency of the Manufacturing process should, however, as a rule, be used for the 5 (EIZ) isomer mixture speak.

A preferred area of application of 6,10-dimethyl-5,9-undecadien-2-ol is Inhibition of the formation of body odor (including armpit and foot odor) responsible bacteria (especially Staphylococcus and Corynebacterium Species).

In addition, 6,10-dimethyl-5,9-undecadien-2-ol can be used to inhibit mycoses causative skin and nail fungi (dermatomycosis, nail mycosis; Trichophyton and Epidermophyton species) and to inhibit dandruff responsible microorganisms (Malassezia furfur, Syn .; Pityrosporum ovale or P. orbiculare) can be used.

Antimicrobial, 6,10-dimethyl-5,9-undecadien-2-ol of the formula 1 (5E / Z-isomer Mixture), 2 (5 (E) -isomer) and / or 3 (5 (Z) -isomer) containing Mixtures of active ingredients are used to the extent that they are used against germs that cause body odor be used, usually topically in the form of solutions, creams, lotions, Gels, sprays applied.

For other purposes, oral (tablets, capsules, powder, Drops), intravenous, intraocular, intraperitoneal or intramuscular application or an application in the form of an impregnated bandage makes sense.

The concentration of the active ingredients 6,10-dimethyl-5,9-undecadien-2-ol of the formula 1 (SE / Z isomer mixture), 2 (5 (E) isomer) and / or 3 (5 (Z) isomer) in the applied formulations is in the range of 0.0069% -20% and preferably in Range from 0.05% -0.5% by weight. The antimicrobial active ingredient complex can here prophylactically or if necessary (especially with acute body odor) for Use.

The concentration of z. B. is the amount of active ingredient to be applied daily varies and depends on the physiological condition of the subject as well individual-specific parameters such as age or body weight.

6,10-dimethyl-5,9-undecadien-2-ol of the formula 1 (SE / Z isomer mixture), 2 (5 (E) -isomer) and / or 3 (5 (Z) -isomer) can either alone or in combination be used with other antimicrobial substances.

Claims (9)

1. Use of 6,10-dimethyl-5,9-undecadien-2-ol as an antimicrobial Active ingredient to inhibit the growth of body odor Microorganisms. 2. Use of 6,10-dimethyl-5,9-undecadien-2-ol as an antimicrobial Active ingredient against germs of the genus that cause body odor Staphylococcus, Corynebacterium and / or Brevibacterium. 3. Use of 6,10-dimethyl-5,9-undecadien-2-ol as an antimicrobial Active ingredient against Staphylococcus epidermidis and / or Corynebacterium xerosis and / or Brevibacterium epidermidis. 4. Use of 6,10-dimethyl-5,9-undecadien-2-ol for the production of a pharmaceutical or cosmetic formulation with antimicrobial Action against microorganisms that cause body odor. 5. Use according to any one of claims 1-3, characterized in that the 6,10-dimethyl-5,9-undecadien-2-ol a 5 (E / Z) -isomer mixture with a 5 (E): 5 (Z) molar ratio is between 1: 9 and 9: 1. 6. Cosmetic formulation comprising an antimicrobial against Body odor causing microorganisms of the genus Staphylococcus, Corynebacterium or Brevibacterium effective amount of 6,10-dimethyl-5,9- undecadien-2-ol. 7. Method of combating body odor, wherein
a cosmetic formulation which comprises at least one antimicrobial agent which is effective against one or more microorganisms which cause body odor,
is applied topically to the body in an amount that inhibits the growth of the microorganism (s),
characterized in that the formulation comprises 6,10-dimethyl-5,9-undecadien-2-ol as an antimicrobial agent against microorganisms which cause body odor. 8. Fragrance composition comprising a fragrance, 5-50 wt .-% 6,10-dimethyl 5,9-undecadien-2-ol and one or more customary additives. 9. Use of 6,10-dimethyl-5,9-undecadien-2-ol as an antimicrobial Active ingredient against mycosis-causing skin and nail fungi and / or Microorganisms that cause dandruff.