AU7507598A - Methods of producing essential oils from species of the genus callitris - Google Patents
Methods of producing essential oils from species of the genus callitris Download PDFInfo
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- AU7507598A AU7507598A AU75075/98A AU7507598A AU7507598A AU 7507598 A AU7507598 A AU 7507598A AU 75075/98 A AU75075/98 A AU 75075/98A AU 7507598 A AU7507598 A AU 7507598A AU 7507598 A AU7507598 A AU 7507598A
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- Australia
- Prior art keywords
- oil
- wood
- bark
- distillation
- callitris
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- 238000000034 method Methods 0.000 title claims description 44
- 241000722891 Callitris Species 0.000 title claims description 24
- 241000894007 species Species 0.000 title claims description 23
- 239000000341 volatile oil Substances 0.000 title description 6
- 239000002023 wood Substances 0.000 claims description 60
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 claims description 52
- 241001397836 Callitris glauca Species 0.000 claims description 35
- TWVJWDMOZJXUID-SDDRHHMPSA-N Guaiol Chemical compound C1([C@H](CC[C@H](C2)C(C)(C)O)C)=C2[C@@H](C)CC1 TWVJWDMOZJXUID-SDDRHHMPSA-N 0.000 claims description 28
- 238000004821 distillation Methods 0.000 claims description 28
- TWVJWDMOZJXUID-QJPTWQEYSA-N guaiol Natural products OC(C)(C)[C@H]1CC=2[C@H](C)CCC=2[C@@H](C)CC1 TWVJWDMOZJXUID-QJPTWQEYSA-N 0.000 claims description 28
- 229960002350 guaiazulen Drugs 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000001256 steam distillation Methods 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 4
- 238000004508 fractional distillation Methods 0.000 claims description 3
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 239000003921 oil Substances 0.000 description 93
- 238000000926 separation method Methods 0.000 description 6
- 238000010561 standard procedure Methods 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000036962 time dependent Effects 0.000 description 3
- 241000036317 Callitris verrucosa Species 0.000 description 2
- 238000000222 aromatherapy Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WXQGPFZDVCRBME-QEJZJMRPSA-N (-)-thujopsene Chemical compound C([C@@]1(C)CC=C2C)CCC(C)(C)[C@]11[C@H]2C1 WXQGPFZDVCRBME-QEJZJMRPSA-N 0.000 description 1
- 241000566113 Branta sandvicensis Species 0.000 description 1
- 241000767832 Engraulis australis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 230000002009 allergenic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 150000001545 azulenes Chemical class 0.000 description 1
- CCDWGDHTPAJHOA-UHFFFAOYSA-N benzylsilicon Chemical compound [Si]CC1=CC=CC=C1 CCDWGDHTPAJHOA-UHFFFAOYSA-N 0.000 description 1
- 150000004334 bicyclic sesquiterpene derivatives Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000003621 hammer milling Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WXQGPFZDVCRBME-UHFFFAOYSA-N thujopsene Natural products CC1=CCC2(C)CCCC(C)(C)C22C1C2 WXQGPFZDVCRBME-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003171 wood protecting agent Substances 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Medicines Containing Plant Substances (AREA)
- Cosmetics (AREA)
Description
AUSTRALIA
Patents Act 1990 COMPLETE
SPECIFICATION
STANDARD PATENT Applicants: VINCENT JOSEPH COLLINS AND MARYANN
COLLINS
Invention Title: METHODS OF PRODUCING ESSENTIAL OILS FROM SPECIES
OF
THE GENUS CALLITRIS The following statement is a full description off this invention, including the best method of performing it knoT.rn to
US:
2 The invention relates to methods for producing an essential oil. The oils produced by the methods have been found to contain compounds of commercial worth, and the invention also relates to methods of producing those compounds. The oils and the compounds produced by the methods are also encompassed by the invention.
Background of the Invention Essential oils such as that of tee tree are known in the art and preparations containing them find use in perfumery and medicinal applications. Such oils are particularly useful in aroma therapy due to their desirable aromas and in the manufacture of cosmetic or body care products. Essential oils may also have anti-microbial properties as well as wood preservative uses.
In recent years, there has been a trend away from synthetic products toward naturally derived substances.
This has resulted in growth in the demand for essential oils as well as the demand for variety in such oils.
Summary of the Invention 20 In one aspect, the present invention provides a method of producing an oil comprising the step of obtaining the oil from a mixture of the bark and wood of one or more species of the genus Callitris.
The bark and wood used in the method may be obtained from the trunk and/or branches of a single species or a plurality of different species of the genus Cailitris.
Species of the genus Callitis include Callitris intratropica, Callitris collumnellaris, Callitris preissii and Callitris verrucosa.
Usually, the species of the genus Callitris will be Callitris intratropica. Callitris intratropica is a species of Cypress pine commonly grown in plantations located in warmer climates such as that of the Northern Territory, Australia.
It has been found that by using the bark and wood of i Callitris intratropica the oil obtained is coloured blue. A 3 blue oil is not obtained when oil is obtained from the bark or the wood of Callitris intratropica alone.
In a second aspect, the present invention provides a method of producing a blue oil comprising the step of obtaining the oil from a mixture of the bark and wood of Callitris intratropica.
It has also been found that a blue coloured oil is produced when oil is obtained from a mixture of the bark of Callitris intratropica and the wood of other species of the genus Callitris.
In a third aspect. the present invention provides a method of producing a blue oil comprising the step of obtaining the oil from a mixture of the bark of Call itris intratropica and the wood, or bark and wood, of one or more species of the genus Callitris.
The blue colour of the oil enhances the suitability of the oil for various applications, such as the use of the oil in aroma therapy, or in the manufacture of cosmetics and body care products.
The oil will typically be obtained from the bark and "wood by distillation and usually by a hydro-distillation or steam distillation method. Preferably, cohobation will be used during the distillation.
In one embodiment, the oil is obtained from the bark and wood by hydro-distillation or steam distillation, and the miscible components of the oil present in the water collected during the distillation process (the condensate water) are extracted from the condensate water. Typically, the miscible components of the oil are extracted from the condensate water by solvent extraction using a suitable organic solvent.
Guaiol is found in oil obtained from the wood of species of the genus Callitris. The oil obtained from the wood, or the bark and wood, of Callitris intratropica has a particularly high guaiol content. Guaiol finds use in perfumery compositions for its fixative properties. Guaiol I(~MIIICIICI~T~~ XI ~YI- IIIIIIIY 11- 4 is a precursor of guaiazulene and it is believed the blue colour in the oil produced in accordance with the second or third aspects of the present invention is due to the presence of guaiazulene or a derivative thereof in the oil.
Guaiol and guaiazulene are both azulene compounds and more particularly bicyclic sesquiterpenes (Freiser, L.G. and M., Organic Chemistry, 3rd Ed., pp 915-948, Reinhold Pub. N.Y.
1956.).
The fact that a blue coloured oil is not produced when oil is obtained from the bark or from the wood of Callitris intratropica alone, or when oil is obtained from the wood of other species of the genus Callitris alone, but is produced when oil is obtained from a mixture including the bark of Callitris intratropica and the wood of one or more species of the genus Callitris, indicates that the bark of Callitris intratropica provides a catalytic component which catalyses the conversion of guaiol to guaiazulene or alternatively, contributes in another way to the conversion such as by altering pH so that the conversion occurs during the oil extraction process.
The rate of formation of the blue colour in the oil has been found to be time-dependent. As will be appreciated, the rate of obtaining the oil from the bark and wood will depend on a number of variables such as whether the bark and wood have been coarsely or finely chipped, whether the bark and wood have been subjected to hammer milling prior to obtaining the oil or whether the bark and wood are tightly or loosely packed during the process of obtaining the oil. Knowing that the development of the colour of the oil is time dependent, the skilled addressee will be readily able to determine the appropriate rate of obtaining the oil from the bark and wood to obtain and maximise the intensity of the colour. Generally, the rate of obtaining the oil from the bark and wood will be comparatively slow.
It has also been found that a blue coloured oil is produced when oil obtained from the bark of Callitris intratropica is mixed with oil obtained from the wood of Callitris intratropica or oil obtained from the wood, or the bark and wood, of other species of the genus Callitris, and the mixture subjected to conditions effective to produce a blue coloured oil.
In fourth aspect, the present invention provides a method of producing a blue oil comprising the steps of mixing oil obtained from the bark of Callitris intratropica with oil obtained from the wood of Callitris intratropica, and subjecting the mixture to conditions effective to produce a blue oil.
In a fifth aspect, the present invention provides a method of producing a blue oil comprising the steps of mixing oil obtained from the bark of Callitris intratropica with oil obtained from the wood, or the bark and wood, of other species of the genus Callitris, and subjecting the mixture to conditions effective to produce a blue oil.
The oil obtained from the bark of Callitris intratropica will typically be obtained by distillation and usually by a hydro-distillation or steam distillation method. The oil obtained from the wood of Callitris intratropica, or the wood, or bark and wood, of one or more other species of the genus Callitris will typically be obtained by distillation and usually by a hydrodistillation or steam distillation method. Preferably, cohobation will be used during the distillation.
In order to produce a blue oil the mixture of the oil obtained from the bark of Callitris intratropica and the oil obtained from the wood of Callitris intratropica, or the wood, or bark and wood, of one or more other species of the genus Callitris, must be heated. Typically, the mixture is heated to about 90°C to 100°c, and the temperature of the mixture is maintained at about 90°C to 100°C for a sufficient period of time for the oil to 6 develop a blue colour. The rate of formation of the blue colour has been found to be time dependent.
In a further aspect, the present invention provides an oil produced by the above defined methods.
Once the oil has been produced in accordance with the above defined methods, it is possible to analyse the oil by standard techniques, identify the various components in the oil by standard techniques, and isolate some or all of those components by standard techniques.
If desired, guaiol may be isolated from the oil.
If desired, guaiazulene may be isolated from the oil produced in accordance with the second, third, fourth or fifth aspects of the present invention. Guaiazulene is known to be an anti-inflammatory and an antiulcerative (The Merck Index, 1 2 L" Edition, Merck Research Laboratories,
NJ,
1996, page 776). It has also been suggested that guaiazulene may have antipyretic, anti-allergenic and antibacterial properties.
In a further aspect, the present invention provides a method of producing guaiol or guaiazulene comprising the steps of: obtaining oil from a mixture of the bark and wood of Callitris intratropica; and isolating the guaiol or guaiazulene from the oil.
In a further aspect, the present invention provides, a method of producing guaiol or guaiazulene comprising the steps of: obtaining oil from a mixture of the bark of Callitris intratropica and the wood of one or more species of the genus Callitris; and isolating the guaiol or guaiazulene from the oil.
The oil will typically be obtained from the bark and wood by distillation and usually by a hydro-distillation or steam distillation method- Preferably, cohobation will be used during the distillation.
The guaiol or guaiazulene may be isolated from the oil using standard techniques. Typically, the guaiol or guaiazulene is isolated from the oil by the fractional distillation of the oil.
In a further aspect, the present invention provides a method of producing guaiol or guaiazulene comprising the steps of: producing a blue oil in accordance with the fourth or fifth aspect of the present invention; and isolating the guaiol or guaiazulene from the oil.
S" The guaiol or guaiazulene may be isolated from the oil using standard techniques. Typically, the guaiol or guaiazulene is isolated from the oil by the fractional S 15 distillation of the oil.
Brief Description of the Drawings The invention will hereinafter be described with reference to preferred, non-limiting embodiments with reference to the accompanying drawings wherein: 20 Figure 1 is a schematic view of apparatus suitable for use in obtaining oil from a mixture of bark and wood of species of the genus Callitris; Figure 2 is a gas chromatogram for oil obtained from the bark and wood of Callitris intratropica; and Figure 3 shows the infra-red spectra for guaiol obtained from oil obtained from the bark and wood of Callitris intratropica.
Detailed Description of Preferred Embodiments of the Invention Apparatus used to obtain the oil in a pilot study by steam distillation is shown in Figure 1. The apparatus comprises a 30 kW Lucas LB146 boiler 5 having a maximum pressure capacity of 700 kPa and an 18 mm outlet pipe connected to a manifold 15 comprising a 20 cm length of 2 cm diameter galvanised pipe. A pressure gauge 20 is located at one end of the manifold and a reducing valve -8set to 60 kPa is located between outlet pipe 10 and manifold 15. As indicated in the figure, c harge housing is connected to manifold 15 by 3 mn of 12 mm lagged copper piping 35. More particularly, end 40 of lagged piping is secured to coil 45 located between the base 50 and charge chamber 55 of the charge housing 30. Coil 45 is formed from 1 cm diameter copper tubing and is capped with a plurality of evenly spaced holes 60 for passage of steam from boiler 5 into charge chamber 55 in use. The charae housing 30 is further provided with an outlet 65 for the release of waste fluid.
The apparatus also comp~rises a condenser vessel consisting of a 2 cm diameter galvanised coil 75 having a plurality of turns located in a condenser tank 80 with a water inlet 85 and water outlet 90. Galvanised coil 75 is in communication with a top region 95 of charge chamber through a 0. 5 mn length of 15 mm diameter copper tubing while an opposite end 100 of coil 75 empties into separation vessel 105- SeparatiLon vessel 105 consists of a tank 110 with a funnel 115 for collecting condensate and having an outlet 120 located in a lower region of the tank. The separation vesl105 is also provided with a baffle plate 125 for isolating extracted oil from outlet tube 130 for passage of excess water from the separation vessel 105 in use. To avoid escape of extracted oil from tank 110, the entrance 135 of the outlet tube 130 is located below the water level of the tank 110 as shown.
To extract the oil, a 95.5 1 charge of 1 to 2 cm Cal1itrjs intratropica bark and wood chip is located in charge chamber 55. Steam at a pressure of 50 to 60 kPa from the boiler 5 is then passed through the charge after release from holes 60 of coil 45. The resulting vapours are collected in galvanised coil 75 where they are caused to condense after cooling as a result of the passage of water through the condenser vessel 70. The rate of water lll~--II -CVI-CI~~-II-XI~- L I C*ll-~ly flow is controlled such that the temperature of the condensate is maintained between 85 to 90 0 C. As shown in Figure 1, the extracted oil separates from water contained in the condensate in separation vessel 105 where it forms a pool 140 for collection.
The intensity of the blue colour of the oil increases significantly after about 3 to 4 hours. The distillation will generally be carried over a period of about 8 hours and more usually about 10 hours or more.
To obtain maximum oil yield, miscible components in the water present in separation tank 110 can be extracted with the use of a suitable organic solvent. The miscible component of the oil present in the water may also be subjected to cohobation by returning the water from the separation tank 110 to boiler 5 for repassage through charge housing 30. When hydro-distillation is used to obtain the oil, the condensate water may be returned directly to the vessel or chamber containing the bark and wood chips.
The Callitris intratropica oil produced was subjected to analysis by gas chromatography and infra-red spectroscopy. For gas chromatography, a 50 m x 0.22 mm internal diameter column coated with a 0.25 um thick film of 5% phenylmethylsilicone (BP5, S.G.E Australia). To prepare the test sample, 2 mg of the oil was dissolved in 1 ml of n-hexane and a 0.5 il aliquot introduced to the column via an on-column injector (OCI-3, S.G.E. Australia).
The gas chromatography operating conditions are set out in Table 1.
0 Table 1 Operating Conditions for Gas Chromatography Condition Variable Initial temp: 40 3
C
initial time: 0 min Final Temp: 290 0
C
Temo. program: 4 0 C min Final time: 10 min Carrier gas (hydrogen) flow: 40 cm sec- (approx) Chromatograms were acquired between 10 and 50 minutes using the default set of functional group intervals at a sampling rate of 4 scans per scanset and a resolution of 8 cm The speed of the ZnSe slide used was maintained at a nominal setting of 2. The gas chromatogram obtained for the oil is shown in Figure 2. The peak believed to contain guaiol has a retention time of 32.353 minutes in the column used. The intra-red trace corresponding to that peak is shown in Figure 3.
Analysis by mass spectrometry has revealed that the Callitris intratropica oil produced contains a substantial number of components other than guaiol and guaiazulene.
Some of the components are listed in Table 2.
11 Table 2 Components of -Cajjitr;S intLratropica oil detected by MLass Spec trome try 3 -Car nene Carayphynep IX-Terinene Thuj opsene para-CLymene 2 Although the present invention has been described hereinbefore with reference to several eri.bodLrnents, numerous variations and modifications are Possible without 12 departing from the scope of the invention which is defined in the following claims.
Claims (17)
1. A method of producing an oil comprising the step of obtaining the oil from a mixture of the bark and wood of one or more species of the genus Callitris.
2. A method of producing a blue oil comprising the step of obtaining the oil from a mixture of the bark and wood of Callitris intratropica.
3. A method of producing a blue oil comprising the step of obtaining the oil from a mixture of the bark of Callitris intratropica and the wood, or bark and wood, of one or more species of the genus Callitris.
4. A method according to any one of claims 1 to 3 wherein the oil is obtained from the bark and wood by distillation. A method according to claim 4 wherein the distillation is hydro-distillation or steam distillation.
6. A method according to claim 4 or 5, wherein miscible components of the oil present in water condensed during the distillation are extracted from the water by solvent extraction.
7. A method of producing a blue oil comprising the step of mixing oil obtained from the bark of Callitris intratropica with oil obtained from the wood of Callitris intratropica, and subjecting the mixture to conditions effective to produce a blue oil.
8. A method of obtaining a blue oil comprising the step of mixing oil obtained from the bark of Callitris intratropica with oil obtained from the wood, or the bark and wood, of one or more other species of the genus Callitris, and subjecting the mixture to conditions effective to produce a blue oil.
9. A method according to claim 7 wherein the oil obtained from the wood of Callitris intracropica is obtained from the wood by distillation. 14 A method according to claim 8 wherein the oil obtained from the wood, or the bark and wood, of one or more species of the genus Callitris is obtained from the wood, or the bark and wood, by distillation.
11. A method according to any one of claims 7 to wherein the oil obtained from the bark of Callitris intratropica is obtained from the bark by distillation.
12. A method according to any one of claims 9 to 11 wherein the distillation is hydro-distillation or steam distillation.
13. Oil produced by a method according to any one of claims 1 to 12.
14. A method of producing guaiol or guaiazulene comprising the steps of: S 15 obtaining oil from a mixture of the bark and wood of Callitris incratropica; and isolating the guaiol or guaiazulene from the oil. A method of producing guaiol or guaiazulene comprising the steps of: 20 obtaining oil from a mixture of the bark of Callitris intratropica and the wood of one or more species of the genus Callitris; and isolating the guaiol or guaiazulene from the oil.
16. A method according to claim 14 or 15 wherein the oil is obtained from the bark and wood by distillation.
17. A method according to claim 16 wherein the distillation is hydro-distillation or steam distillation.
18. A method according to any one of claims 14 to 17, wherein the guaiol or guaiazulene is isolated from the obtained oil by fractional distillation.
19. A method of producing guaiol or guaiazulene comprising the steps of: producing a blue oil in accordance with the method of any one of claims 7 to 12; and isolating the guaiol or guaiazulene from the oil. rerm-i~ A method according to claim 19 wherein the guaiol or guaiazulene is isolated from the oil by the fractional distillation of the oil.
21. A method of producing a blue oil comprising the step of obtaining the oil by distillation from a mixture of the bark and wood of Callitris intratropica, substantially as herein described with reference to Figure 1. Dated this 8th day of July 1998 VINCENT JOSEPH COLLINS AND MARYANN COLLINS By their Patent Attorneys GRIFFITH HACK i. ftH
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU75075/98A AU742711B2 (en) | 1997-07-08 | 1998-07-08 | Methods of producing essential oils from species of the genus callitris |
| AU22609/00A AU723540C (en) | 1997-07-08 | 2000-03-24 | Extraction of essential oil from cypress pine |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPO7783A AUPO778397A0 (en) | 1997-07-08 | 1997-07-08 | Distillation of essential oil from callitris intratropica |
| AUPO7783 | 1997-07-08 | ||
| AU75075/98A AU742711B2 (en) | 1997-07-08 | 1998-07-08 | Methods of producing essential oils from species of the genus callitris |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU22609/00A Division AU723540C (en) | 1997-07-08 | 2000-03-24 | Extraction of essential oil from cypress pine |
| AU33005/02A Division AU3300502A (en) | 1997-07-08 | 2002-04-10 | Extraction of essential oil from cypress pine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7507598A true AU7507598A (en) | 1999-01-21 |
| AU742711B2 AU742711B2 (en) | 2002-01-10 |
Family
ID=25637810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU75075/98A Expired AU742711B2 (en) | 1997-07-08 | 1998-07-08 | Methods of producing essential oils from species of the genus callitris |
Country Status (1)
| Country | Link |
|---|---|
| AU (1) | AU742711B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000004871A1 (en) * | 1998-07-22 | 2000-02-03 | Bretts Pty. Limited | Fragrance composition |
| AU752938B2 (en) * | 1998-07-22 | 2002-10-03 | Bretts Pty Limited | Fragrance composition |
| WO2001053441A3 (en) * | 2000-01-20 | 2002-11-21 | Ciba Sc Holding Ag | Processes for obtaining (-)-guaiol and the use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB708251A (en) * | 1948-11-15 | 1954-05-05 | Hugo Oskar Janistyn | Improvements in azulene-containing preparations compatible to the skin and mucous membrane |
-
1998
- 1998-07-08 AU AU75075/98A patent/AU742711B2/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000004871A1 (en) * | 1998-07-22 | 2000-02-03 | Bretts Pty. Limited | Fragrance composition |
| AU752938B2 (en) * | 1998-07-22 | 2002-10-03 | Bretts Pty Limited | Fragrance composition |
| WO2001053441A3 (en) * | 2000-01-20 | 2002-11-21 | Ciba Sc Holding Ag | Processes for obtaining (-)-guaiol and the use thereof |
| US7071366B2 (en) | 2000-01-20 | 2006-07-04 | Ciba Specialty Chemicals Corporation | Processes for obtaining (-)-guaiol and the use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| AU742711B2 (en) | 2002-01-10 |
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