IMPROVEMENTS TO EXTRACTION METHODS, EXTRACTION SYSTEMS, COMPOUNDS AND FORMULATIONS
20240009592 ยท 2024-01-11
Assignee
Inventors
Cpc classification
International classification
Abstract
Described are methods of extracting target compounds from vanilla, including compounds having beneficial anti-aging properties. The method includes the steps of performing a first extraction step on a feedstock to produce a first extract fraction and a marc; and a subsequent second extraction step on the marc to produce a second extract fraction. Also disclosed are formulations containing compounds containing active compounds obtained using the methods, and ingredients containing the actives compounds for use in various applications.
Claims
1-93. (canceled)
94. An extraction method comprising: (a) performing a first extraction step on a feedstock to produce a first extract fraction and a marc; and (b) subsequent to step (a) performing a second extraction step on the marc to produce a second extract fraction.
95. The method of claim 94, wherein the feedstock is vanilla beans.
96. The method of claim 94, wherein the feedstock is a raw material.
97. The method of claim 94, wherein the first extraction step does not substantially or completely extract target compounds to be extracted at the second extraction step.
98. The method of claim 94, wherein the marc is substantially or completely spent of compounds that contribute to the flavour and aroma of vanilla.
99. The method of claim 94, wherein the second extraction step comprises extracting a lipid soluble fraction from the marc.
100. The method of claim 99, wherein the lipid soluble fraction comprises at least one active compound that has a beneficial effect on skin aging.
101. The method of claim 94, wherein the second extraction step involves a super critical CO.sub.2 (SCCO.sub.2) extraction process.
102. The method of claim 94, further comprising a third extraction step.
103. The method of claim 102, wherein the third extraction step involves a process to remove at least one compound or substance from the second marc.
104. The method of claim 103, wherein the third extraction step comprises an SCCO.sub.2 extraction process performed at different conditions to a SCCO.sub.2 performed at the second extraction step.
105. An extraction method, including a step of extracting a target compound from a feedstock, wherein the feedstock is the fruit of a plant in the orchid family of the genus Vanilla, and further wherein the method utilizes an SCCO.sub.2 extraction process.
106. The method of claim 105, wherein the method further includes a first extraction step which occurs before the SCCO.sub.2 process wherein the first extraction step includes a food grade solvent extraction process and wherein the food grade solvent contains substantially 35% by weight ethanol.
107. The method of claim 105, wherein the method further includes a first extraction step which occurs before the SCCO.sub.2 extraction process and wherein the first extraction step produces a marc wherein the marc is substantially or completely spent of compounds that contribute to the flavour and aroma of vanilla.
108. The method of claim 107, wherein the SCCO.sub.2 extraction process comprises extracting a lipid soluble fraction from the marc.
109. The method of claim 108, wherein the lipid soluble fraction comprises at least one active compound.
110. The method of claim 109, wherein the at least one active compound has a beneficial effect on skin aging.
111. The method of claim 105, wherein the SCCO.sub.2 extraction process produces a second marc and wherein the method further comprises an extraction process to remove at least one compound or substance from the second marc.
112. The method of claim 111, wherein the extraction process to remove at least one compound or substance from the second marc comprises an SCCO.sub.2 process performed at different conditions to the SCCO.sub.2 extraction process to produce the first marc.
113. A formulation comprising at least one active compound extracted by the method of claim 94.
Description
5. BRIEF DESCRIPTION OF THE DRAWINGS
[0074] One or more embodiments of the invention will be described below by way of example only, and without intending to be limiting, with reference to the following drawings, in which:
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6. DETAILED DESCRIPTION OF THE PRESENT TECHNOLOGY
[0087] 6.1 Overview of a Method according to the Present Technology
[0088] Referring first to
[0089] The method 100 involves a pre-treatment step 102, a first extraction step 104, and a second extraction step 106.
[0090] In addition, the method includes a preparation step 104A, a post extraction step 108 and a fractionation step 110.
[0091] The method 100 is configured to selectively extract one or more compounds from a feedstock, which in 30 the preferred form comprises vanilla beans (not shown in the Figures). The vanilla beans can be the fruit of any known variety of vanilla, e.g. vanilla planafolia. Further aspects of the method 100 should become clearer from the following discussion.
6.1.1 Pre-Treatment Step
[0092] During the pre-treatment step, raw (green) vanilla beans are subjected to one or more processes to assist with increasing the efficiency of the first extraction step 104 which is to follow. Suitable techniques for the pre-treatment step include at least one of grinding, maceration and sizing.
[0093] The raw (green) vanilla beans may have been cured by techniques as should be known to one skilled I the art before the pre-treatment step. Alternatively,
6.1.2 First Extraction Step
[0094] The first extraction step 104 is used to produce a first extract fraction comprising one or more compounds having a desired taste or flavour profile. For instance, the target compounds comprise a mixture containing vanillin and optionally one or more other compounds.
[0095] Any suitable process may be used for the first extraction step 104. However, in the preferred embodiment, the first extraction process is a solvent extraction as should be known to one skilled in the art.
[0096] Suitable solvents include ethanol, a mixture of water and ethanol methanol, acetonitrile, acetone, chloroform and hexane, or any other solvent in which vanillin is soluble. However, in the preferred form, the solvent is ethanol e.g. at least 35% w/w or other food or cosmetic grade solvent e.g. glycerine.
[0097] To perform the first extraction step 104, the solvent and the vanilla beans are mixed together for a pre-determined period of time.
[0098] In addition, other techniques may used to improve extraction of the target compounds from the vanilla beans, as should be known to one skilled in the art. For instance, the first extraction step may be an assisted solvent extraction process using techniques such as heating agitation/stirring, or ultrasonication.
[0099] After the pre-determined period of time, the solvent is separated from the vanilla beans e.g. by filtration or decanting. Separation of the solvent and vanilla beans produces a marc (not illustrated in the Figures), being the vanilla beans which are at least partially, substantially or completely spent of the target compound e.g. vanillin and one or more compounds that contribute to the flavour and aroma of vanilla.
[0100] The first extraction step 104 produces a first extraction fraction, which comprises a vanilla extract e.g. vanillin (and optionally one or more other compounds), in the solvent.
6.1.3 Preparation Step
[0101] The method 100 optionally includes a preparation step 104A. In the preparation step 104A, the marc (not illustrated in the Figures) produced by the first extraction step 104 is prepared before being used in the second extraction step 106.
[0102] The preparation step 104A may involve one or more of the following processes: [0103] 1. microbe reduction; [0104] 2. drying; [0105] 3. separation e.g. to remove vanilla seeds from the vanilla beans; [0106] 4. size reduction e.g. a grinding process such as coarse mill.
[0107] The methods and components used to complete the process(es) of the preparation step 104A are as should be known to one skilled in the art. Further aspects of the preparation step 104A should become clearer from the following description.
[0108] 6.1.4 Second Extraction Step
[0109] The method 100 includes a second extraction step 106. The second extraction step comprises a process to extract compounds from the marc produced by the first extraction step 104. The second extraction step 106 produces a second extract fraction which contains one or more target compounds e.g. a mixture of lipid soluble compounds. The second extract fraction therefore comprises the lipid soluble fraction.
[0110] The second extraction step 106 may comprise any known method or system for extracting target components. However, in the preferred form, the second extraction step 106 comprises super critical CO.sub.2 (SCCO.sub.2) extraction and reference will be made herein as such.
[0111] The conditions and duration of the second extraction step 106 can be varied to achieve a desired composition for the second extract fraction. For instance, the time, pressure, flow rate, temperature and feed ratio may all be varied.
[0112] In some forms, the second extraction step 106 may be performed in multiple steps e.g. it also involves a third extraction step 11013, and a fourth extraction step 110C. The third extraction step 11013 and the fourth extraction step 110C differ to each other in the parameters under which the extraction occurs. For instance, at least one of the time, pressure, flow rate, temperature and feed ratio may all be varied to achieve a desired extract profile.
6.1.5 Post Extraction Step
[0113] The post extraction step 108 can be performed on the second marc produced by the second extraction step 106.
[0114] For instance, the post extraction step 106 can be used to convert the second marc into a commercial product. In these embodiments, the post extraction may produce a powder suitable for use as an ingredient in food or cosmetics. The second extraction step may involve at least one of washing, drying, grinding, and sizing.
6.1.6 Fractionation Step
[0115] The method 100 optionally includes a fractionation step 110 which can be used to separate the second extract fraction into mixtures of compounds or substantially purified compounds. For instance, the fractionation step 110 may comprise gas chromatography to produce two or more distinct fractions of active compounds.
6.2 Extraction Examples
[0116] Further features of the method 100 should become clearer from the following discussion of examples of the technology which are provided in non-limiting terms and do not narrow the scope of the technology.
6.2.1 Lab Scale Extraction 1
[0117] A marc was prepared by performing a first extraction step 104 as described above. The marc was subsequently processed by preparation step 104A, to produce a dried, ground marc powder.
[0118] 800 g of the dried, ground marc powder was placed in a 2 L extraction vessel with sintered filter discs at both ends, filling the vessel completely with a packing density of approximately 0.4 g/mL. The vessel was then pressurised with CO.sub.2 and the extraction was started. The extraction was carried out in three steps and the three extracts obtained were kept separate. The first step (extract A) was carried out at 120 bar and 40 C. until a 35:1 CO.sub.2 to feed ratio had been circulated; the plant was then boxed in overnight and the extraction was carried on the next day under the same conditions until an additional 28:1 CO.sub.2 to feed ratio had been circulated (extract 6); at this point the pressure and temperature were increased to 400 bar and 50 C. respectively and the third and last step of the extraction was carried on until an additional 15:1 CO.sub.2 to feed ratio had been circulated (extract C). The final CO.sub.2 to feed ratio was 78:1. Throughout these steps, the solvent containing the dissolved extract after passing through the bed was depressurized and passed into a separation vessel where the extract was accumulated and gas phase CO.sub.2 from the separator was condensed and recirculated. Extract accumulating in the separation vessel was recovered through a valve periodically during the run to determine the progress of the extraction. After extraction, the plant was depressurized and the residual marc was allowed to degas before being unloaded. Extraction parameters are listed in Table 1. An ethanol wash was applied to the plant following the run to estimate the amount of residual extract that remained in the lines.
TABLE-US-00001 TABLE 1 Extraction conditions (extraction 1) Step 1 Step 2 Step 3 Feed Mass (g) 800 Extraction pressure (bar) 120 120 400 Extraction temperature ( C.) 40 40 50 Separator pressure (bar) 56 55 51 Separator temperature (C) 40 40 50 Average CO2 flow rate 2.8 2.8 3.2 CO.sub.2 to feed ratio 35:1 28:1 15:1
6.2.2 Lab Scale Extraction 2
[0119] A marc was prepared by performing a first extraction step 104 as described above. The marc was subsequently processed by preparation step 104A, to produce a dried, ground marc powder. 800 g of the dried, ground marc powder was placed in a 2 L extraction vessel with sintered filter discs at both ends, filling the vessel completely with a packing density of approximately 0.4 g/mL. The vessel was then pressurised with CO.sub.2 and the extraction was started. The extraction was initially carried out at 300 bar and 40 C., and the pressure was increased to 450 bar after a 21:1 CO.sub.2 to feed ratio had been circulated. The CO.sub.2 containing the dissolved extract was first depressurized down to 90 bar at 40 C. and passed into a first separation vessel where the first (least volatile) extract fraction, S1, was accumulated. Following this, the CO.sub.2 phase was further depressurized through a second valve to approximately 54 bar and 40 C. where the second (more volatile) extract fraction, S2, was accumulated. Gas phase CO.sub.2 from the second separator was condensed and recirculated. Extract accumulating in the separation vessels was recovered through a valve periodically during the run to determine the progress of the extraction. After extraction, the plant was depressurized and the residual marc was allowed to degas before being unloaded. Extraction parameters are listed in Table 1. The final CO.sub.2 to feed ratio was 26:1. The first extract fraction, S1, was fractionated into 4 separate extracts, collected at different CO.sub.2 to feed ratios: 51(1) from 0 to 10:1, S1(2) from 10:1 to 15:1, S1(3) from 15:1 to 20:1, and S1(4) from 20:1 to the end (corresponding with an increase in extraction pressure). The second extract fraction, S2, was collected throughout the run and not fractionated. An ethanol wash was applied to the plant following the run to estimate the amount of residual extract that remained in the lines.
TABLE-US-00002 TABLE 2 Extraction conditions (Lab Scale Extraction 2) S1(1) S1(2) S1(3) S1(4) S2 Feed Mass (g) 800 Extraction pressure (bar) 300 300 300 450 300-450 Extraction temperature ( C.) 40 40 40 40 40 Separator 1 pressure (bar) 90 90 90 90 Separator 1 temperature 40 40 40 40 Separator 2 pressure (bar) 54 Separator 2 temperature 40 Average CO.sub.2 flow rate (kg/h) 2.6 2.8 3.1 3.5 2.9 CO.sub.2 to feed ratio 10:1 5:1 5:1 6:1 26:1
6.2.3 Lab Scale Extraction 3
[0120] An additional lab scale extraction was carried out, aiming to assess the colour retention of the marc as well as the effect of particle size on the extraction yield. The feed material was milled prior to the extraction using a Wiley knife mill and a 2 mm mesh attached, and the extraction was carried out using the same conditions as the Lab Scale Extraction 2 discussed in section 6.2.2 above, but with a shortened duration (10:1 CO.sub.2:feed) to avoid extraction of dark coloured compounds.
TABLE-US-00003 TABLE 3 Extraction conditions (Lab Scale Extraction 3) Feed Mass (g) 365 Extraction pressure (bar) 300 Extraction temperature ( C.) 40 Separator 1 pressure (bar) 90 Separator 1 temperature 40 Separator 2 pressure (bar) 52 Separator 2 temperature 40 Average CO.sub.2 flow rate (kg/h) 2.0 CO.sub.2 to feed ratio 10:1
6.2.4 Commercial Scale Extraction
[0121] A marc was prepared by performing a first extraction step 104 as described above. The marc was subsequently processed by preparation step 104A, to produce a dried, ground marc.
[0122] 360 kg of the dried, ground marc was extracted using Pharmalink's manufacturing plant (3 by 850 L capacity). The beans were extracted with supercritical CO2 at 300 bar and 40 C. using a single 850 L vessel, with a final solvent to feed ratio of 40:1 (i.e. 40 kg of CO.sub.2 were circulated per kg of beans). The extraction was carried out over a 4 hour period. The extract was fractionated into a first separator fraction (i.e. S401, 90 bar and 40 C.) and a second separator fraction (i.e. S403, approximately 45 bar and 40 C.). The first separator fraction was further fractionated into two separate fractions: the first one (interim) was collected after a 10:1 CO.sub.2:feed had been circulated, and the second one (final) was collected at the end of the run. The second separator fraction was collected at the end of the run and the water present in this fraction was decanted off and kept separate. Samples of feed, marc and all extract fractions were sent to PFR for analysis.
6.3 Results and Discussion of Extraction Examples
6.3.1 Lab Scale Extractions
[0123] The total extraction yield obtained in Lab Scale Extraction 1 and Lab Scale Extraction 2 were relatively similar (Table 4), with Lab Scale Extraction 1 being slightly higher possibly due to the longer overall extraction time and higher extraction pressure used in the final step. In Lab Scale Extraction 2, the pressure was also increased to 450 bar at the final step but the total extraction time was shorter than for Lab Scale Extraction 1.
[0124] The extraction curves (
TABLE-US-00004 TABLE 4 Extraction yields Wet basis Dry basis Extraction Extract A 9.6% 9.7% 1 Extract B 2.1% 2.2% Extract C 3.1% 3.3% Total Yield 14.9% 15.2% Extraction S1(1) 8.8% 9.4% 2 S1(2) 1.0% 1.1% S1(3) 0.4% 0.4% S1(4) 0.6% 0.6% S2 3.5% 2.9% Total Yield 14.3% 14.4% Extraction S1 9.7% 10.3% 3 S2 2.5% 2.7% Total Yield 12.2% 13.0%
[0125] The extract obtained in Lab Scale Extraction 1 was initially pale yellow with an appearance very similar to whipped butter, but as the extraction progressed the colour gradually darkened, and turned green when the pressure was increased to 400 bar (
[0126] The moisture content of the feed was measured at 5.85% 1, and a small amount of water was co-extracted in both extractions. In extraction 1, 3.7 g free water were decanted off extract A (4.8% of the total extract A mass), and 0.67 g were recovered from extract B (3.9% of total extract B mass). In extraction 2, water was collected in S2, and 5.9 g free water was decanted (21.3% of S2 mass). The S2 fraction is noticeably more fragrant with a characteristic Vanilla aroma.
[0127] The analytical results from Lab Scale Extraction 1 (see
[0128] As seen in
6.3.2 Commercial Scale Extraction
[0129] The total extraction yield obtained in the extraction carried out at Pharmalink was 11.9% (13.0% including the water phase). A comparison between the lab and commercial extraction curves is shown in
[0130] The total 51 yield obtained in the commercial extraction was slightly lower (9.5% vs 10.3%), even though the extraction was run for a longer solvent:feed ratio (
[0131] The analytical results for the commercial scale extraction (see Appendix) show a 10.2% residual lipid content in the marc, which is consistent with the lab scale findings. The lipid mass balance is 104.8% (note that this was obtained with an estimated value of the marc, calculated by mass difference between the feed and the extract fractions).
TABLE-US-00005 TABLE 5 Commercial extraction yields S1 Interim Final S2 Feed (0-10:1) (10:1-40:1) Product Water Mass (kg) 360.5 27.67 6.64 8.6 3.9 Yield 7.7% 1.8% 2.4% 1.1%
[0132] Subsamples (3.6 g) of the marc produced by Lab Scale Extraction 1 and the Commercial Scale Up were milled through 0.25 mm screen (Retsch ZM 100 mill) to a fine powder and photographed under uniform light conditions (an are shown as
6.4 Efficacy Investigations
6.4.1 Introduction
[0133] The activity of a lipid-soluble extract of vanilla (ISF) manufactured according to the method 100 on beneficial collagen synthesis was investigated.
6.4.2 Objective
[0134] The aim of the investigation was to evaluate the effect of the LSF on the synthesis of collagen type I in vitro using the full thickness human 3D skin model EpiDermFT..sup.1 .sup.1(MatTek Corporation) [1], which has been widely used for a wide range of applications including anti-aging studies [2,3]
6.4.3 Methods
[0135] EpiDerm FT tissues were randomly allocated to groups (N=4 tissues/group) and were treated with 0.5% LSF in base cream or 1% LSF in base cream. Two further groups of tissues (N=4 each) were treated with just the base cream vehicle (negative control group), or with 0.5% retinol in base cream (positive control group [4,5]). Following administration of 100 L of each cream treatment the tissues were cultured for three hours and the creams were then rinsed off using sterile phosphate-buffered saline (PBS). The tissues were cultured overnight for a further 21 hours, after which the conditioned cell culture media were collected for determination of procollagen I C-peptide (PICP). PICP is a marker of fresh collagen synthesis and was measured using an EIA kit (TaKaRa) following the manufacturer's instructions.
6.4.4 Results
[0136] The mean levels of PICP measured in the conditioned media of each treatment group are shown in
6.4.5 Conclusions
[0137] The LSF increased the production of PICP, and thus collagen type I, by the EpiDermFT full-thickness human skin model tissues. [0138] 0.5% LSF in base cream was as effective as 1% LSF. [0139] Both LSF treatments were as effective as the 0.5% retinol cream positive control treatment. [0140] The results demonstrate that the LSF could be an effective anti-aging ingredient for cosmetic formulations.
7. COSMETIC FORMULATION
[0141] The lipid soluble fraction obtained according to the method 100 may be sold as either an ingredient for use in subsequent cosmetic formulation e.g. to manufacturers of cosmetics, or formulated into a cosmetic formulation and sold to retailers or consumers.
[0142] A representative formulation for a cosmetic according to the technology is summarised in table 6 below,
TABLE-US-00006 TABLE 6 Representative formulation of a cosmetic according to the present invention. Part Trade name INCI Description Supplier % wt A Marula oil Sclerocarya Birrea (Marula) Seed Oil Pure Ingredients 4.00 Kakaduplum oil Terminalia Ferdinandiana (Kakadu Pure Ingredients 4.00 plum) seed oil Safflower oil Carthamus Tinctorius (Safflower) Pure Ingredients 4.00 Seed Oil Lipid soluble fraction Vanilla Planifolia (Vanilla) Fruit Heilala Vanilla 0.50 Extract Vitamin E natural Tocopherol various 1.00 Avocado oil Persea gratissima (Avocado) Oil various 1.00 Jojoba oil Simmondsia Chinensis (Jojoba) Seed Pure Ingredients 69.70 Oil Rosehip oil Rosa Canina Fruit Oil Pure Ingredients 4.00 L 22 Jojoba Oil/Macadamia Seed Oil Esters Verital 2.50 (and) Squalene (and) Phytosteryl Macadamiate (and) Phytosterols (and) Tocopherol Sytenol A Bakuchiol DKSH 0.80 Oleosoft-4 OLIVE GLYCERIDES, ALMOND Connell 5.00 GLYCERIDES, LINSEED GLYCERIDES, Australasia BORAGE SEED GLYCERIDES, TOCOPHERYL ACETATE Nikko VC IPV Ascorbyl Tetraisopalmitate CeeChem 2.50 Vitamin C TBC Fragrance Innovaction 1.00
[0143] Unless the context clearly requires otherwise, throughout the description and the claims, the words comprise, comprising, and the like, are to be construed in an inclusive sense as opposed to an exclusive or exhaustive sense, that is to say, in the sense of including, but not limited to.
[0144] The entire disclosures of all applications, patents and publications cited above and below, if any, are herein incorporated by reference.
[0145] Reference to any prior art in this specification is not, and should not be taken as, an acknowledgement or any form of suggestion that that prior art forms part of the common general knowledge in the field of endeavour in any country in the world.
[0146] The invention may also be said broadly to consist in the parts, elements, characteristics and features referred to or indicated in the specification of the application, individually or collectively, in any or all combinations of two or more of said parts, elements, characteristics or features.
[0147] Aspects of the present invention have been described by way of example only and it should be appreciated that modifications and additions may be made thereto without departing from the scope thereof as defined herein.
[0148] Where in the foregoing description reference has been made to integers or components having known equivalents thereof, those integers are herein incorporated as if individually set forth.
[0149] It should be noted that various changes and modifications to the presently preferred embodiments described herein will be apparent to those skilled in the art. Such changes and modifications may be made without departing from the spirit and scope of the invention and without diminishing its attendant advantages. It is therefore intended that such changes and modifications be included within the present invention.