U.S. patent application number 11/437011 was filed with the patent office on 2006-09-21 for processes for obtaining (-)-guaiol and the use thereof.
Invention is credited to Victor Paul Eliu, Peter Fankhauser, Gerd Heinemann, William Robert McGilvray.
Application Number | 20060210658 11/437011 |
Document ID | / |
Family ID | 25739023 |
Filed Date | 2006-09-21 |
United States Patent
Application |
20060210658 |
Kind Code |
A1 |
Fankhauser; Peter ; et
al. |
September 21, 2006 |
Processes for obtaining (-)-guaiol and the use thereof
Abstract
A process for obtaining oils of sesquiterpenes and
sesquilactones and (-)-guaiol from the oil of Callitris
intratropica, processes for encapsulation of the oil from Callitris
intratropica, and the various uses of the oil and the encapsulated
oil are described. The oils are suitable for various purposes in
the personal care field, e.g. for the antimicrobial treatment of
skin, mucosa and hair and of textile fibre materials, as an
antimycotic against skin fungi and moulds, as an anti-inflammatory,
as an acaricide against house dust mites and ticks, and for
preserving cosmetic products.
Inventors: |
Fankhauser; Peter;
(Ettingen, CH) ; Heinemann; Gerd; (Schliengen,
DE) ; Eliu; Victor Paul; (Lorrach, DE) ;
McGilvray; William Robert; (Coraki, AU) |
Correspondence
Address: |
CIBA SPECIALTY CHEMICALS CORPORATION;PATENT DEPARTMENT
540 WHITE PLAINS RD
P O BOX 2005
TARRYTOWN
NY
10591-9005
US
|
Family ID: |
25739023 |
Appl. No.: |
11/437011 |
Filed: |
May 18, 2006 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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11061897 |
Feb 18, 2005 |
7071366 |
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11437011 |
May 18, 2006 |
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10181334 |
Jul 17, 2002 |
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PCT/EP01/00414 |
Jan 16, 2001 |
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11061897 |
Feb 18, 2005 |
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Current U.S.
Class: |
424/771 ;
424/770; 568/819 |
Current CPC
Class: |
A61K 31/045 20130101;
A61K 2800/524 20130101; A61K 8/11 20130101; C07C 2602/26 20170501;
B01D 11/0203 20130101; C07B 2200/09 20130101; C07C 29/78 20130101;
C07C 33/16 20130101; A61K 36/14 20130101; C07C 29/78 20130101; A61K
2800/56 20130101; A61K 8/922 20130101; A61K 8/738 20130101; A61Q
19/00 20130101; A61Q 11/00 20130101; A61Q 5/12 20130101; A61Q
17/005 20130101; C07C 29/78 20130101; C07C 2602/30 20170501; A61K
2800/52 20130101; A61K 8/34 20130101; C07C 33/14 20130101; C07C
33/16 20130101; B01D 11/0288 20130101; A61Q 15/00 20130101; C11B
9/025 20130101; A61Q 5/02 20130101 |
Class at
Publication: |
424/771 ;
568/819; 424/770 |
International
Class: |
A61K 36/20 20060101
A61K036/20; A61K 36/13 20060101 A61K036/13; C07C 35/23 20060101
C07C035/23 |
Foreign Application Data
Date |
Code |
Application Number |
Jan 20, 2000 |
EP |
00810046.3 |
Sep 29, 2000 |
CH |
1909/00 |
Claims
1. A process for obtaining (-)-guaiol from the oil of Callitris
intratropica, wherein the oil is held at about from 4 to
-18.degree. C. and the (-)-guaiol which then separates out in the
form of fine needles is isolated from the rest of the oil by
filtration and then washed with cold, nonpolar solvent.
2. A process according to claim 1, wherein a C.sub.5-C.sub.10alkane
is used as solvent.
3. A process according to claim 2, wherein n-hexane or iso-octane
is used as solvent.
4. A process according to claim 1, wherein a mixture of
n-hexane/petroleum ether, ethanol/water, dimethylformamide/water,
methanol/water, ethylene glycol/water, ethylene glycol methyl and
ethyl ester/water, dimethyl sulfoxide/water, tetrahydrofuran/water
or dioxane/water is used as solvent.
5. A process according to claim 1, wherein the (-)-guaiol is
isolated from the rest of the oil by filtering under suction.
6. A process according claim 1, wherein, for further purification,
the crude (-)-guaiol is recrystallised from a solvent mixture
selected from n-hexane/-petroleum ether, ethanol/water,
dimethylformamide/water, methanol/water, ethylene glycol/water,
ethylene glycol methyl and ethyl ester/water, dimethyl
sulfoxide/water, tetrahydrofuran/water and dioxane/water.
7. A process according to claim 1, wherein the crude (-)-guaiol is,
after filtration, subjected to vacuum distillation for
purification.
8. A process for obtaining (-)-guaiol, wherein the crude material
of Callitris intratropica, which is contaminated with other
ingredients, is subjected to steam distillation and, for further
purification, is recrystallised from a solvent mixture selected
from n-hexane/petroleum ether, ethanol/water,
dimethylformamide/water, methanol/water, ethylene glycol/water,
ethylene glycol methyl and ethyl ester/water, dimethyl
sulfoxide/water, tetrahydrofuran/water and dioxane/water.
9-15. (canceled)
16. A process for encapsulation of the oil from Callitris
intratropica, or of the (-)-guaiol-depleted oil in accordance with
claim 1 , wherein equimolar amounts of the oil from Callitris
intratropica and an encapsulation material selected from .alpha.-,
.beta.- and .gamma.-cyclodextrins, liposomes, bacteria, fungi,
organic and inorganic porous supports, the latter being selected
from bentonites, modified bentonites and hectorites, are suspended
in water and stirred for from 1 to 4 hours, until a complex of
encapsulation material and oil forms.
17. A process according to claim 16, wherein .alpha.-, .beta.- and
.gamma.-cyclodextrin is used as the encapsulation material.
18. A personal care preparation, containing from 0.01 to 15% by
weight, based on the total weight of the composition, of the oil of
Callitris intratropica cosmetically tolerable adjuvants.
19-24. (canceled)
25. A method for preserving cosmetic products, which comprises
incorporatinq into said cosmetic products an amount of oil of
Callitris intratropica which is effective to preserve them.
Description
[0001] The present invention relates to a process for obtaining
(-)-guaiol from the oil of Callitris intratropica, to processes for
encapsulation of the oil from Callitris intratropica, and to
various uses of the oil or the encapsulated oil.
[0002] Recently there has been a noticeable trend towards the
increasing use of active substances of natural origin in the field
of cosmetics. For example, essential oils, e.g. tea tree oil, are
being used in aromatherapy or in the manufacture of products in the
personal care field.
[0003] From the wood and/or bark of Callitris intratropica
(Australian Blue Cypress), a species native to relatively warm
climatic zones, e.g. Northern Australia, which is mainly cultivated
in plantations, it is possible to obtain an oil consisting of
several fractions, which is called "blue oil" because of its
intrinsic colour. The blue colour of the oil from Callitris
intratropica, as is also the case with other oils (e.g.: camomile
oil, patchouli oil), is caused by (s)-guaiazulene
(1,4-dimethyl-7-isopropylazulene).
[0004] An essential fraction of this oil is (-)-guaiol, a
sesquiterpene alcohol, which corresponds to the formula
##STR1##
[0005] Guaiol has optical isomers; the compound of formula (1)
corresponds to the (-) form.
[0006] The present invention accordingly relates to a process for
obtaining (-)-guaiol corresponding to formula (1) from the oil of
Callitris intratropica, in which process the oil is held at about
from 4 to -18.degree. C. and the (-)-guaiol which then separates
out in the form of fine needles is isolated from the rest of the
oil by filtration and then washed with cold, nonpolar solvent.
[0007] C.sub.3-C.sub.10Alkanes, and especially n-hexane or
iso-octane, are preferably used as the cold, nonpolar solvent.
[0008] Solvent mixtures may preferably also be used, especially
mixtures of n-hexane/petroleum ether, ethanol/water,
dimethylformamide/water, methanol/water, ethylene glycol/water,
ethylene glycol methyl and ethyl ester/water, dimethyl
sulfoxide/water, tetrahydrofuran/-water and dioxane/water.
[0009] In an especially preferred embodiment, the (-)-guaiol is
isolated from the rest of the oil by filtering under suction.
[0010] For further purification, the crude (-)-guaiol obtained may
be recrystallised from a solvent mixture selected from
n-hexane/petroleum ether, ethanol/water, dimethylformamide/water,
methanol/water, ethylene glycol/water, ethylene glycol methyl and
ethyl ester/water, dimethyl sulfoxide/water, tetrahydrofuran/water
and dioxane/water.
[0011] n-Hexane/petroleum ether or a mixture of ethanol/water is
preferably used for further purification.
[0012] In a further process variant, the crude (-)-guaiol is, after
filtration, subjected to vacuum distillation for purification.
[0013] In another process variant for obtaining (-)-guaiol, the
crude material of Callitris intratropica, which is contaminated
with other ingredients, is subjected to steam distillation and, for
further purification, is recrystallised from a solvent mixture
selected from n-hexane/-petroleum ether, ethanol/water,
dimethylformamide/water, methanol/water, ethylene glycol/water,
ethylene glycol methyl and ethyl ester/water, dimethyl
sulfoxide/water, tetrahydrofuran/water and dioxane/water.
[0014] n-Hexane/petroleum ether or a mixture of ethanol/water is
preferably used for further purification.
[0015] The oil which has been depleted of (-)-guaiol after
filtration can be used for various purposes.
[0016] Oils of sesquiterpenes and sesquilactones can also be
obtained using supercritical solvents. In that process, pieces of
wood with or without bark and/or pieces of bark of Callitris
intratropica, glaucophylla or columellaris are extracted with a
supercritical solvent.
[0017] Suitable supercritical solvents are supercritical media
known from the prior art, which are also used for plant extraction,
for example supercritical ethylene, propane, butane, pentane,
N.sub.2O or CO.sub.2, which basically may be used in an identical
manner in the context of the present invention.
[0018] In a preferred embodiment, the extraction is carried out in
mixtures of CO.sub.2 and cyclic C.sub.1-C.sub.10hydrocarbons or
C.sub.1-C.sub.10-n-alkanes, especially propane, butane and
pentane.
[0019] Preference is also, however, given to lipophilic extraction
with supercritical CO.sub.2 and modifiers, such as short-chain
aliphatic alcohols, for example ethanol or methanol.
[0020] The supercritical solvents are very inert and, because of
their high vapour pressure and their volatility, can be completely
removed, even at low temperatures, without loss of the more
volatile constituents of the extract.
[0021] Extraction processes using supercritical media are generally
known and commercially available.
[0022] Preference is given to the use of bark chips for
extraction.
[0023] Wood chips and bark chips of Callitris intratropica,
glaucophylla or columellaris are extracted at a pressure of from 20
to 2000 bar and at temperatures of from 30 to 80.degree. C. with a
supercritical medium, preferably supercritical CO.sub.2, propane or
butane, and optionally with added amounts of from 0% to 15% of a
short-chain aliphatic alcohol, for example methanol or ethanol,
over a period of from 30 minutes to 5 hours.
[0024] After releasing the pressure, the oil is present in pure
form in a yield of from 1 to 10%, based on the weight of wood
used.
[0025] Compared to steam distillation, the yield of oil is
distinctly higher and the oil has a completely different
composition of individual components.
[0026] It is also possible to obtain (-)-guaiol from the oil
obtained by that process, by allowing the (-)-guaiol to crystallise
out at room temperature or by freezing it out.
[0027] For that purpose, the oil is held at about from 25 to
-18.degree. C. A portion of the (-)-guaiol is separated out in the
form of fine needles. After filtration, the (-)-guaiol-depleted oil
can be used further. The purity of the (-)-guaiol is increased to
>98% by recrystallising from aliphatic (including cyclic)
hydrocarbons or an ethanol/water mixture.
[0028] Solutions of from 30 to 2000 mg/litre in ethanol are
prepared from the untreated oil from Callitris intratropica and
from the (-)-guaiol-depleted oil.
[0029] The colourless to slightly yellow oil so obtained exhibits a
distinctly greater antimicrobial action than the oil obtained by
steam distillation.
[0030] The oil obtained from Callitris intratropica by the
processes according to the invention may advantageously be
encapsulated. Suitable encapsulation materials are especially
.alpha.-, .beta.- and .gamma.-cyclodextrins, liposomes, bacteria,
fungi, organic and inorganic porous supports, the latter being
selected from bentonites, modified bentonites and hectorites. The
invention also relates to the process for encapsulation of the oil
from Callitris intratropica, in which process equimolar amounts of
the oil from Callitris intratropica and one of the previously
mentioned encapsulation materials are suspended in water and
stirred for from 1 to 4 hours until a complex of encapsulation
material and oil forms.
[0031] If a fungus is used as encapsulation material, typical
examples are yeasts, for example Saccharomyces cerevisiae (brewer's
yeast and baker's yeast), Kluyveromyces fragilis (dairy yeast) and
Candida utilis, and also filamentous fungi, for example Aspergillus
niger.
[0032] The encapsulation material preferably has a cell diameter
of, for example, about 5 .mu.m. Bacteria can have a smaller cell
size of about from 1 to 2 .mu.m and can be cultured to produce a
larger cell diameter.
[0033] The oil of Callitris intratropica obtained in accordance
with the invention exhibits pronounced antimicrobial action,
especially against pathogenic gram-positive and gram-negative
bacteria and also against bacteria of skin flora, for example
Corynebacterium xerosis (bacteria that cause body odour), and also
as an antimycotic against yeasts and moulds. It is therefore
especially suitable in the disinfection, deodorising and general
antimicrobial treatment of the skin and mucosa and of integumentary
appendages (hair), more especially in the disinfection of the hands
and wounds.
[0034] It is therefore suitable as an antimicrobial active
ingredient in personal care preparations, for example shampoos,
bath additives, hair-care products, liquid and solid soaps (based
on synthetic surfactants and salts of saturated and/or unsaturated
fatty acids), lotions and creams, deodorants, other aqueous or
alcoholic solutions, e.g. cleansing solutions for the skin, moist
cleansing cloths, oils or powders.
[0035] The invention accordingly relates also to a personal care
preparation containing from 0.01 to 15% by weight, based on the
total weight of the composition, of the oil of Callitris
intratropica, or of the encapsulated oil prepared in accordance
with the invention, or of the oil obtained using supercritical
solvents or of the (-)-guaiol-depleted oil, and cosmetically
tolerable adjuvants.
[0036] Depending on the form of the personal care preparation, it
comprises--besides the oil of Callitris intratropica or the
encapsulated oil prepared in accordance with the invention--further
constituents, e.g. sequestering agents, colorants, perfume oils,
thickening or solidifying (consistency-regulating) agents,
emollients, UV absorbers, skin protection agents, antioxidants,
additives that improve the mechanical properties, for example
dicarboxylic acids and/or aluminium, zinc, calcium and magnesium
salts of C.sub.14-C.sub.22fatty acids and, optionally, additional
preservatives and antimicrobial active ingredients.
[0037] The personal care preparation according to the invention may
be formulated as a water-in-oil or oil-in-water emulsion, as an
alcoholic or alcohol-containing formulation, as a vesicular
dispersion of an ionic or non-ionic amphiphilic lipid, as a gel, a
solid stick or as an aerosol formulation.
[0038] A water-in-oil or oil-in-water emulsion containing the oil
of Callitris intratropica preferably contains, as cosmetically
tolerable adjuvants, from 5 to 50% of an oily phase, from 5 to 20%
of an emulsifier and from 30 to 90% water.
[0039] The oily phase may contain any oil suitable for cosmetic
formulations, e.g. one or more hydrocarbon oils, a wax, a natural
oil, a silicone oil, a fatty acid ester or a fatty alcohol.
Preferred mono- or poly-ols are ethanol, isopropanol, propylene
glycol, hexylene glycol, glycerol and sorbitol.
[0040] The oil used in accordance with the invention may be
contained in a variety of cosmetic preparations. Especially the
following preparations, for example, come into consideration:
[0041] skin-care preparations, e.g. skin-washing and cleansing
preparations in the form of tablet-form or liquid soaps, soapless
detergents or washing pastes;
[0042] bath preparations, e.g. liquid (foam baths, milks, shower
preparations) or solid bath preparations, e.g. bath cubes and bath
salts;
[0043] skin-care preparations, e.g. skin emulsions, multi-emulsions
or skin oils; cosmetic personal care preparations, e.g. facial
make-up in the form of day creams or powder creams, face powder
(loose and pressed), rouge or cream make-up, eye-care preparations,
e.g. eyeshadow preparations, mascara, eyeliner, eye creams or
eye-fix creams; lip-care preparations, e.g. lipsticks, lip gloss,
lip contour pencils, nail-care preparations, such as nail varnish,
nail varnish removers, nail hardeners or cuticle removers;
[0044] intimate hygiene preparations, e.g. intimate washing lotions
or intimate sprays;
[0045] foot-care preparations, e.g. foot baths, foot powders, foot
creams or foot balsams, special deodorants and antiperspirants or
callus-removing preparations;
[0046] light-protective preparations, such as sun milks, lotions,
creams and oils, sun blocks or tropicals, pre-tanning preparations
or after-sun preparations;
[0047] skin-tanning preparations, e.g. self-tanning creams;
[0048] depigmenting preparations, e.g. preparations for bleaching
the skin or skin-lightening preparations;
[0049] insect-repellents, e.g. insect-repellent oils, lotions,
sprays or sticks;
[0050] deodorants, such as deodorant sprays, pump-action sprays,
deodorant gels, sticks or roll-ons;
[0051] antiperspirants, e.g. antiperspirant sticks, creams or
roll-ons;
[0052] preparations for cleansing and caring for blemished skin,
e.g. soapless detergents (solid or liquid), peeling or scrub
preparations or peeling masks;
[0053] hair-removal preparations in chemical form (depilation),
e.g. hair-removing powders, liquid hair-removing preparations,
cream- or paste-form hair-removing preparations, hair-removing
preparations in gel form or aerosol foams;
[0054] shaving preparations, e.g. shaving soap, foaming shaving
creams, non-foaming shaving creams, foams and gels, preshave
preparations for dry shaving, aftershaves or aftershave
lotions;
[0055] fragrance preparations, e.g. fragrances (eau de Cologne, eau
de toilette, eau de parfum, parfum de toilette, perfume), perfume
oils or cream perfumes;
[0056] dental-care, denture-care and mouth-care preparations, e.g.
toothpastes, gel tooth-pastes, tooth powders, mouthwash
concentrates, anti-plaque mouthwashes, denture cleaners or denture
fixatives;
[0057] cosmetic hair-treatment preparations, e.g. hair-washing
preparations in the form of shampoos and conditioners, hair-care
preparations, e.g. pretreatment preparations, hair tonics, styling
creams, styling gels, pomades, hair rinses, treatment packs,
intensive hair treatments, hair-structuring preparations, e.g.
hair-waving preparations for permanent waves (hot wave, mild wave,
cold wave), hair-straightening preparations, liquid hair-setting
preparations, foams, hairsprays, bleaching preparations, e.g.
hydrogen peroxide solutions, lightening shampoos, bleaching creams,
bleaching powders, bleaching pastes or oils, temporary,
semi-permanent or permanent hair colorants, preparations containing
self-oxidising dyes, or natural hair colorants, such as henna or
camomile.
[0058] An antimicrobial soap has, for example, the following
composition:
[0059] 0.01 to 5% by weight of the compound of the oil from
Callitris intratropica,
[0060] 0.3 to 1% by weight titanium dioxide,
[0061] 1 to 10% by weight stearic acid and
[0062] ad 100% soap base, e.g. the sodium salts of tallow fatty
acid and coconut fatty acid or glycerol.
[0063] A shampoo has, for example, the following composition:
[0064] 0.01 to 5% by weight of the oil from Callitris
intratropica,
[0065] 12.0% by weight sodium laureth-2-sulfate,
[0066] 4.0% by weight cocamidopropyl betaine,
[0067] 3.0% by weight NaCI and water ad 100%.
[0068] A deodorant has, for example, the following composition:
[0069] 0.01 to 5% by weight of the oil from Callitris
intratropica,
[0070] 60% by weight ethanol,
[0071] 0.3% by weight perfume oil and
[0072] water ad 100%.
[0073] Example of an O/W emulsion:
[0074] 0.01-5% by weight of the oil from Callitris
intratropica,
[0075] 12% by weight glyceryl stearate,
[0076] 6% by weight paraffin oil,
[0077] 6% by weight caprylic/capric triglyceride,
[0078] 4% by weight glycerol,
[0079] 0.2% by weight disodium EDTA,
[0080] 1.0% by weight citric acid (20%) and
[0081] 65.8-70.8% by weight water.
[0082] Example of an O/W emulsion:
[0083] 0.01-5% by weight of the oil from Callitris
intratropica,
[0084] 3.5% by weight PEG-30 dipolyhydroxystearate,
[0085] 10.0% by weight paraffin oil,
[0086] 4% by weight caprylic/capric triglyceride,
[0087] 4% by weight dicaprylic ether,
[0088] 0.2% by weight disodium EDTA,
[0089] 3.4% by weight glycerol and
[0090] 69.9-74.9% by weight water.
[0091] The oil of Callitris intratropica, or the encapsulated oil
prepared in accordance with the invention, or the oil obtained in
accordance with the invention, or the (-)-guaiol-depleted oil, is,
moreover, used as an anti-inflammatory and also as an acaricide
against house dust mites and ticks.
[0092] The oil of Callitris intratropica, or the encapsulated oil
prepared in accordance with the invention, or the oil obtained in
accordance with the invention, or the (-)-guaiol-depleted oil, is
also suitable for the antimicrobial treatment of textile fibre
materials, the latter being undyed or dyed or printed fibre
materials, for example of silk, wool, polyamide, polyester,
polypropylene or polyurethanes, and especially of all kinds of
cellulosic fibre materials. Such fibre materials include, for
example, natural cellulose fibres, such as cotton, linen, jute and
hemp, and also cellulose and regenerated cellulose. Preferred
suitable textile fibre materials are of cotton.
[0093] The oil of Callitris intratropica, or the encapsulated oil
prepared in accordance with the invention, or the oil obtained in
accordance with the invention, or the (-)-guaiol-depleted oil, is
also suitable for preserving cosmetic products, for example
shampoos, bath additives, hair-care preparations, liquid and solid
soaps (based on synthetic surfactants and salts of saturated and/or
unsaturated fatty acids), lotions and creams, deodorants, other
aqueous or alcoholic solutions, e.g. cleansing solutions for the
skin, moist cleansing cloths, oils or powders and household
products, e.g. in washing and cleaning formulations, e.g. in liquid
and powder washing compositions or fabric softeners.
[0094] The following Examples illustrate, but do not limit, the
invention.
EXAMPLES
Example 1
Preparation of Oil Encapsulated With Cyclodextrin, From Callitris
intratropica (ABC)
[0095] 340 g (30 mmol) of cyclodextrin having a molecular mass of
1134 are suspended in 1 litre of water. 66 g of ABC are added to
the suspension and the mixture is stirred for from 4 to 8 hours at
room temperature.
[0096] Filtration is then carried out through a suction filter and
the filter cake is washed with ethanol, dioxane or some other
water-miscible solvent in which the oil is readily soluble. The
washing procedure is not imperative if free non-encapsulated ABC
may remain behind on the product.
[0097] The wet filter cake is then dried at about 20 mbar and
100.degree. C. in a drying cabinet or using a paddle dryer.
[0098] When preparing smaller amounts, freeze-drying is suitable if
moisture contents of less than 5% water are to be obtained.
Example 2
Antimicrobial Action Test
[0099] In the microbial test, the extract or fractions of the
extract from the wood and/or bark of the Australian Blue Cypress
(Callitris intratropica) exhibits a pronounced inhibitory action on
various fungi of the skin, yeasts and, especially, bacteria. The
MIC values (minimum inhibitory concentration) are in a range from
125 to 600 ppm with respect to gram-positive bacteria, e.g.
Staphylococcus aureus, Staphylococcus epidermidis or
Corynebacterium xerosis; markedly .ltoreq.125 ppm in some cases,
with respect to moulds, e.g. A. niger, Pidermophyton floccosum and
Trichophyton mentagrophytes; and 2000 ppm with respect to yeasts,
e.g. Candida albicans.
[0100] Examples (Table 1): (MIC--minimum inhibitory concentration)
TABLE-US-00001 TABLE 1 MIC of 10% oil in MIC of pure Test organism
MIC of pure oil cyclodextrin cyclodextrin Porphyromonas 500 ppm 250
ppm >10000 ppm gingivalis Selenomonas artemidis 750 ppm 500 ppm
>10000 ppm Staphylococcus aureus 250 ppm 10000 ppm >10000 ppm
Staphylococcus mutans 125 ppm 2000 ppm >10000 ppm Staphylococcus
125 ppm 2000 ppm >10000 ppm sobrinus Malassezia furfur 10000 ppm
2000 ppm >10000 ppm Epidermophyton 125 ppm 750 ppm >10000 ppm
floccosum Microsporum canis 60 ppm 500 ppm >10000 ppm
Microsporum gypseum 60 ppm 750 ppm >10000 ppm Trichophyton 60
ppm 750 ppm >10000 ppm mentagrophytes Trichophyton rubrum 30 ppm
750 ppm >10000 ppm Trichophyton 60 ppm 500 ppm >10000 ppm
schoenleinii
Formulation Examples for oils from Callitris intratropica (ABC)
Example 3
Clear Aqueous Solution
[0101] Composition:
[0102] 0.01 to 1% ABC,
[0103] 0.5% benzyl alcohol,
[0104] 1.5 to 3.5% polysorbate 20 or some other non-ionic
surfactant,
[0105] 0.1% of a chelate-former, e.g. sodium EDTA,
[0106] 0 to 5.0% butylene glycol, in distilled water.
Example 4
Shampoo
[0107] 0.01 to 1% ABC,
[0108] 0 to 0.5% benzyl alcohol,
[0109] 8 to 12% sodium lauryl ether sulfate,
[0110] 0 to 0.1% disodium EDTA,
[0111] 2 to 4% of a betaine (e.g. coco betaine),
[0112] 3% coconut diethanolamide,
[0113] 0 to 0.1% Polyquaternium-10,
[0114] 0 to 0.5% sodium chloride, organic acid (e.g. citric acid
10%) for adjustment to a pH of from 6.0 to 7.0.
Example 5
Hair Conditioner
[0115] 0.01 to 1% ABC,
[0116] 0 to 0.5% benzyl alcohol,
[0117] 2.5 to 3.5% stearyl alcohol,
[0118] 0.05% PEG-7 glyceryl fatty acid (e.g. Cetiol HE),
[0119] hydrolysed wheat protein (e.g. Hydrotriticum),
[0120] 0.1 to 0.2% citric acid (10%),
[0121] 0.1% Panthenol and
[0122] 1% cetyl trimethyl ammonium chloride (50%) or some other
cationic surfactant, made up
[0123] to 100% with distilled water.
[0124] For preparation of further formulations (Examples 6 to 9),
an active ingredient concentrate having the following composition
is used as starting material:
[0125] 1 to 80% ABC, or mixtures of ABC with other active
ingredients, e.g. tea tree oil (TTO),
[0126] 5 to 80% of a phenyl-substituted alcohol, e.g. benzyl
alcohol,
[0127] 0 to 80% of a surfactant (anionic, cationic or amphoteric,
but preferably non-ionic, for example polyethylene oxide ester or
carboxylic acid ester),
[0128] 0 to 80% of a dispersion aid.
[0129] An active ingredient content of from 5 to 50%, an alcohol
content of from 30 to 50%, a surfactant content of from 30 to 50%
and a dispersion aid content of from 20 to 50% are ideal.
Example 6
Example of a Typical Cream
[0130] 2% ABC,
[0131] 2 to 3% glycerol,
[0132] 5% groundnut oil,
[0133] 10% of a colloidal dispersion of cetyl stearyl alcohol
together with non-ionic emulsifiers based on saturated fatty acid
polyglycol ethers (e.g. Emulgate 1000 NI), in water.
Example 7
Example of a Typical Lotion
[0134] 2% ABC,
[0135] 15% glycerol monostearate A-S,
[0136] 3% Emulgin B1,
[0137] 5% glycerol,
[0138] 2% cetyl alcohol, in water.
Example 8
Example of a Typical Gel
[0139] 2% ABC,
[0140] 5% glycerol,
[0141] 3% Sepigel 305, in water.
Example 9
Example of a Typical Conditioner
[0142] 2% ABC,
[0143] 2% cetyl alcohol,
[0144] 3% cetostearyl alcohol,
[0145] 3% Vantoc CC (cetyl trimethyl ammonium chloride),
[0146] 5% lauryidiimoniumhydroxypropyl hydrolysed collagen and
[0147] 0.5% Dipanthenol.
Exemplary Embodiments:
Example 10
[0148] The trunk of Callitris intratropica comminuted into wood
chips and bark chips is comminuted using a suitable mill,
preferably a hammer mill or an impact bar mill. Material that has
already previously undergone steam distillation (SD) may also be
used. 2 kg of the material are subjected to extraction with
supercritical CO.sub.2 at .ltoreq.400 bar (preferably 250 bar) and
at from 20 to 60.degree. C. (preferably 45.degree. C.). The
duration of the extraction is, depending on pressure and
temperature, from 1 to 8 hours, ideally 4 hours.
[0149] The main components found were (in GC area %):
TABLE-US-00002 Component pure oil* from SD pure oil from SE pure
oil from SFE (-)-guaiol 12-14% 14-16% 12-15% .alpha.-, .beta.-,
13-15% 6-8% 6-8% .gamma.-eudesmols bulnesol 11-13% 4-6% 4-6%
.beta.-, .gamma.-costol <1% 3-5% 3-5% dihydro- 8-10% 28-32%
28-32% columellarins callitrisin 1-2% 8-10% 8-10% columellarin
<1% 7-9% 7-9%
[0150] Examples: (MIC=minimum inhibitory concentration)
TABLE-US-00003 MIC pure oil pure oil pure oil Test organism from SD
from SE from SFE Aspergillus niger 31 ppm 60 ppm 60 ppm Candida
albicans >10000 ppm 125 ppm 125 ppm Candida tropicalis >10000
ppm 125 ppm 125 ppm Selenomonas artemidis 750 ppm 60 ppm 60 ppm
Staphylococcus aureus 250 ppm 60 ppm 60 ppm Staphylococcus mutans
125 ppm 60 ppm 60 ppm Staphylococcus sobrinus 125 ppm 30 ppm 30 ppm
Malassezia furfur 10000 ppm 60 ppm 60 ppm Epidermophyton floccosum
125 ppm 60 ppm 60 ppm Microsporum canis 60 ppm 60 ppm 60 ppm
Microsporum gypseum 60 ppm 60 ppm 60 ppm Propionibacterium acnes 62
ppm 30 ppm 30 ppm Trichophyton 60 ppm 60 ppm 60 ppm mentagrophytes
Trichophyton rubrum 30 ppm 60 ppm 60 ppm Trichophyton schoenleinii
60 ppm 60 ppm 60 ppm *) after isolating the guaiol that has
crystallised out SD = steam distillation; SE = solvent extraction;
SFE = supercritical fluid extraction
* * * * *