CN100532520C - Enzymatic process for preparing spice oil - Google Patents
Enzymatic process for preparing spice oil Download PDFInfo
- Publication number
- CN100532520C CN100532520C CNB2003801109552A CN200380110955A CN100532520C CN 100532520 C CN100532520 C CN 100532520C CN B2003801109552 A CNB2003801109552 A CN B2003801109552A CN 200380110955 A CN200380110955 A CN 200380110955A CN 100532520 C CN100532520 C CN 100532520C
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- CN
- China
- Prior art keywords
- enzyme
- oil
- ginger
- seasonings
- flavor oil
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/02—Recovery or refining of essential oils from raw materials
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
- A23L27/105—Natural spices, flavouring agents or condiments; Extracts thereof obtained from liliaceae, e.g. onions, garlic
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/02—Recovery or refining of essential oils from raw materials
- C11B9/027—Recovery of volatiles by distillation or stripping
Abstract
The present invention provides a process for the efficient extraction of spice oil from fresh or dry spices by enzymatic weakening of the cell wall resulting in optimized extraction of oil using an enzyme preparation, which contains cell wall degrading enzymes such as cellulase, hemicellulases, pectinase, protease etc., obtained from fungal or bacterial cultures may be adopted efficiently for this purpose.
Description
Invention field
The present invention relates to be used to prepare the enzyme method of flavor oil (spice oil).Main application of the present invention is to assist optimized extraction to reclaim volatile oil from the seasonings such as ginger, cloves and garlic with the mixture of enzyme.
Background of invention
With reference to the method for continuing to use usually that seasonings extracts that is used for, wherein seasonings is carried out mechanical disintegration, and distill with steam or water and to collect volatility flavor oil.In dry method, will be such as the fresh seasonings section of ginger, in the time of 60 ℃ dry 10 hours and in stirrer, make powder.The drying powder mixes with water with the ratio that 100g:2 rises, and distills 5 hours, collects oil.The shortcoming of this method is (a) even when fresh seasonings is used to handle, and does not reduce distillation time yet; (b) yield of flavor oil does not increase; (c) because the tough cell walls and the cell matrix of used vegetable material provides barrier, it is slow and efficient is low therefore to distill the extraction rate that carries out oil by routine.Referring to Bartley, J.P. and Foley, P (1994), Supercritical fluidextraction of Australian grown ginger (Zingiber officinale). (supercritical extraction of the ginger (Zingiber officinale) that Australia produces) J.ofthe Sci.of Food andAgri.66 (3), 365-371 wherein extracts ginger oil by the supercritical extraction method.The shortcoming of this method is described process complexity, and it relates to hi-tech, and is not suitable for all vegetable materials.Also can be referring to oily extraction element: M.Somashekar cheaply, RRL, Trivandrum wherein introduces new dehydrating step keeping needed fresh fragrance before distillation, and the shortcoming that face is the increase of the oil amount of not having extracted.
Goal of the invention
Main purpose of the present invention has been to provide the enzyme method that is used to prepare flavor oil, and this method has been avoided some above-mentioned shortcoming.
Summary of the invention
Therefore, the invention provides the enzyme method that is used to prepare flavor oil, this method comprises:
(a) preparation of use medium contains the enzyme complex of cellulase, polygalacturonase, proteolytic enzyme and zytase,
(b) in this enzyme complex solution, will be selected from the seasonings homogenizing of ginger, garlic and cloves and hatching,
(c) the seasonings enzyme solution of homogenizing is filtered obtaining clarifying liquor,
(d) distill this liquor, and
(e) collect flavor oil.
In one embodiment of this invention, use described enzyme with the amount of 0.35 unit/ml to 500 unit/ml, and enzyme is 1:16 to the ratio of aqueous medium.
In another embodiment of the present invention, the granularity of described seasonings is 300 to 700 microns and seasonings to the ratio of enzyme complex solution is 1:1 to 2:1.
In another embodiment of the present invention, described hatching is in 30 ℃ to 50 ℃ temperature, carries out 2 to 3 hours.
In another embodiment of the present invention, described distillation is in 95 ℃ to 100 ℃ temperature, carries out 2 to 3 hours.
In another embodiment of the present invention, the yield of described flavor oil is for being 0.86 to 1.9ml flavor oil with respect to the ginger of 100g dry weight, is 1.69 to 2.53ml flavor oil with respect to the garlic of 100g dry weight, is 10 to 15ml flavor oil with respect to the cloves of 100g dry weight.
In another embodiment of the present invention, described flavor oil, in ginger oil, contain maximum 73% zingiberene, curcumene and sesquiterpene alcohols, in garlic oil, contain maximum 76% diallyl trisulfide, allyl methyl trisulfide thing and diallyl disulfide, and in Syzygium aromaticum stem oil, contain maximum 80% oxymethoxyallylbenzenes.
In another embodiment of the present invention, cellulase uses with 0.35 to 4.6 units/ml amount, and polygalacturonase uses with 80 to 500 units/ml amount, and proteolytic enzyme uses with 30 to 150 units/ml amount and zytase uses with 17.5 to 125 units/ml amount.
Detailed description of the invention
The invention provides the enzyme method that is used to prepare flavor oil, this method comprises the ratio with 1:16, utilizes aqueous medium to prepare the enzyme complex that contains cellulase, polygalacturonase, proteolytic enzyme and zytase that content is 0.35 unit/ml to 500 unit/ml.With ginger, garlic and the cloves of 300 to 700 micron granularities ratio homogenizing in this enzyme complex solution, and in 30 ℃ to 50 ℃ temperature, hatched 2 to 3 hours with 1:1 to 2:1.The seasonings enzyme solution of homogenizing is filtered to obtain clarifying liquor, under 95 to 100 ℃ temperature, distilled 2 to 3 hours subsequently, obtain flavor oil, its yield is a 0.86-1.9ml flavor oil for the ginger with respect to the 100g dry weight, produced 30% than untreated ginger, be 1.69-2.53ml flavor oil with respect to the garlic of 100g dry weight more, produced 50% than untreated garlic more, cloves with respect to the 100g dry weight is a 10-15ml flavor oil, has produced 50% than untreated cloves more.The total concn of main component is for containing maximum 73% zingiberene, curcumene and sesquiterpene alcohols in ginger oil in above-mentioned gained oil, in garlic oil, contain maximum 76% diallyl trisulfide, allyl methyl trisulfide thing and diallyl disulfide, and in Syzygium aromaticum stem oil, contain maximum 80% oxymethoxyallylbenzenes.
Described cellulase uses with the level of 0.35-4.6 unit/ml, and polygalacturonase is 80-500 unit/ml, and proteolytic enzyme is that 30-150 unit/ml and zytase are 17.5-125 unit/ml.The fungal enzyme that contains above-mentioned enzyme complex can be used for extracting flavor oil.Fresh seasoning material such as ginger or garlic is cleaned and mixed with enzyme solution, in the warring stirrer, evenly turn to 300-700 micron size then with the ratio of 1:1 to 2:1, and in 30-50 ℃ of maximum hydrolysis 3 hours.To wear into the powder of 300-700 micron size such as the dried seasonings of cloves, and be suspended in the enzyme solution hydrolysis.Subsequently hydrolysate is passed through water pressure engine and collects filtrate.This filtrate is left standstill 2-3 hour with the deposition starch material in 10-25 ℃, with the water distillation of the upper strata stillness of night to obtain volatility flavor oil.Novelty of the present invention is that described method provides the approach that extracts effectively flavor oil by described enzyme reduction cell walls from fresh or exsiccant seasonings, causes the optimized extraction of oil.Contain the zymin that is obtained from fungi or bacterial cultures and can be applicable to this purpose effectively such as the enzyme of degradation of cell walls such as cellulase, hemicellulase, polygalacturonase, proteolytic enzyme.
Following examples have exemplarily been described the present invention, therefore should not be construed as limitation of the scope of the invention.
Embodiment 1
Between fresh ginger and exsiccant ginger powder, compared the organic efficiency of volatile oil.The extracting method that follows conventional lines is used for the extraction of rhizoma zingiberis powder, wherein the 100g material is suspended in 2 premium on currency, distills 5 hours, collects volatile oil and mensuration.Clean new fresh ginger (625g is equivalent to based on dry weight 100g) is mixed with water (2:1), and in the warring stirrer, evenly turn to the 300-700 granularity.In water pressure engine, extract the material of homogenizing.In low temperature, filtrate is left standstill so that sedimentation (10 ℃ left standstill 2-3 hour).Incline and supernatant and, collect volatile oil and mensuration through the water distillation.With obtained 1.3ml oil phase ratio with rhizoma zingiberis, obtain 1.44ml volumetrical oil with new fresh ginger.
Described result shows preparation and the extract phase ratio with drying material, and the volatile oil rate of recovery of fresh material and treatment process are effectively and easier.
Embodiment 2
From at Mysore, obtain to be used to prepare the fungi Aspergillus ustus (Aspergillus ustus) (registration number is 1134) of described enzyme complex in the culture collection product of the food microbiology of C.F.T.R.I. system.This fungi is maintained in the potato dextrose agar inclined-plane (Hi-Media, Mumbai, India).The cultural characteristic that is grown in the Aspergillus ustus on the potato dextrose agar is: have the light brown bacterium colony of a large amount of sporulations, slick conidium and erose head.The wheat bran that is used for the enzyme generation is taken from the local market.Other pharmaceutical chemicals and reagent used in this substratum are India AG and that derive from standard company.
The degreasing ground nut meal (nutmeal) that will be used to cultivate the wheat bran and 1% (w/w) of Aspergillus ustus mixes, and with pH be 4.5, contain MgSO
47H
2O, 0.05; KCl, 0.05; K
2HPO
4, 0.1; And FeSO
47H
2O, 0.0001 substratum is moistening to 60%.
Cultivate in the 500ml flask, this flask contains wheat bran (weight in wet base) that 50g has 60% water content and sterilization 45 minutes in 151bs.Will be in these flasks from the spore inoculating of the culture in 7 day age, thorough mixing, and growth 96 hours in envrionment temperature (26-30 ℃).Come from wheat bran, to squeeze out described enzyme by water extraction (1:4), and the various enzymic activitys of following evaluation:
Cellulase: (0.1M pH4.8) is placed on to contain and curls that (No. 1, Ward door (Whatman), 1 * 6cm bar is in 18mm test tube 50mg) for the filter paper bar with 0.5ml enzyme solution and 1ml citrate buffer.Sample was hatched 1 hour in the time of 50 ℃, and added the 3ml edlefsen's reagent, and this test tube is placed on 5 minutes and cooling in the boiling water bath.Make blank sample with the enzyme solution that boils, and do parallel test.By in spectrophotometer, the color of measuring this sample at the 540nm place is assessed the glucose (mg) of release.With glucose (micromole)/enzyme (ml) of discharging/minute come calculated activity.
Zytase: the reaction mixture that will contain the enzyme solution of 1ml larchwood xylan solution (Sigma chemical company, the U.S., 1% solution), 0.5ml acetate buffer (0.05M pH5.5) and 0.5ml dilution was hatched 30 minutes in the time of 55 ℃.Gone back original hase with what the assessment of above-mentioned edlefsen's reagent discharged, and with wood sugar (the micromole)/enzyme (ml) of release/minute represent activity.
Polygalacturonase: will be under given conditions, the per-cent that the viscosity of 1% pectin solution reduces is thought of as the activity of polygalacturonase.In the pectin solution (prepare, pH is 4) of 1% purifying of 20ml, add the 2ml enzyme solution in the 0.1M citrate buffer, and in the time of 40 ℃, hatched 30 minutes.The enzyme solution that will boil is with comparing.By using Ostwald viscosimeter (Ostwald viscometer) to come with minute flowing time of definite this reaction mixture and the flowing time of contrast.Calculate the per-cent that viscosity reduces by the flowing time difference of compare and this sample.
Proteolytic enzyme: to the pH of 1ml is to add the enzyme of 1m dilution in 7 1% casein solution, and hatches 20 minutes in the time of 37 ℃.Left standstill 30 minutes to this adding 3ml 5% trichoroacetic acid(TCA) solution and in room temperature.Described sample is filtered through No. 1 circular filter paper of Ward door.In 1ml filtrate, add 2ml 0.2N NaOH and 0.6ml Folin reagent (Folin reagent), and after 20 minutes, measure the color that produces at the 620nm place.The above-mentioned simply dealt enzyme solution that boils is used as blank reagent.Tyrosine is as standard substance.The product (mg) that discharges with the 1ml enzyme solution comes calculated activity.Be shown in the table 1 by mycetogenetic different enzymic activity.
Table 1: the enzymic activity of in the Aspergillus ustus enzyme complex, assessing
| Enzyme | Active (u/ml) |
| Cellulase | 0.35 |
| Zytase | 17.5 |
| Proteolytic enzyme | 30 |
| Polygalacturonase | 80 |
The fresh ginger (100g dry weight) that reaches that a collection of 625g is clean is suspended in the 312ml enzyme solution, and evenly turns to the granularity of 300-700 micron.Comprise above-mentioned enzyme solution of 142ml and 170ml water in this enzyme suspension.Only aqueous usefulness compares.Then the ginger of homogenizing was hatched 2.5 hours and extracted in water pressure engine 450 ℃ the time.As among the embodiment 1 this filtrate being handled and the water distillation.The yield of oil is that the sample that enzyme is handled is a 1.9ml oil, and reference substance is a 1.4ml oil.
Embodiment 3
Commercial enzyme complex (Ex.Trizyme 50)) also can be used for hydrolysis ginger discharges volatile oil.This enzyme comprises 4.6 units/ml cellulase, 125 units/ml zytase, 150 units/ml proteolytic enzyme and 500 units/ml polygalacturonase.In this embodiment, in view of the described material of 500-3500 zytase units activity/100g dry weight, described substrate remains on 2:1 to the ratio of enzyme solution, with the new fresh ginger part (100g dry weight) of multiple volumetrical enzyme solution hydrolysis 625g.Prepare enzyme solution by in 308-284ml water, mixing the 4-28ml enzyme, the ginger homogenizing in this enzyme solution, and was hatched 2.5 hours in the time of 40 ℃.Obtain extracting solution and as described in the embodiment 1, by water distillation refiltered oil.The oil recovery rate increases with the increase of enzyme concn, is 2500 zytase units/100g ginger (dry weight) until enzyme concn, and after this yield no longer increases (table 2).
Table 2: enzyme concn is to the effect of oil recovery rate
Embodiment 4
Under 30 ℃ to 50 ℃ different incubation temperature, as described in embodiment 3, the fresh clean ginger (based on dry weight 100g) that reaches of a collection of 625g was handled 2.5 hours with the enzyme solution that contains 2500 unit zytases.Such as embodiment 1 detailed description, reclaim described oil.The oil recovery rate increases with the increase of temperature, is 40 ℃ until temperature, and after this rate of recovery reduces (table 3).This is possible because described volatile oil evaporate with the increase of incubation temperature, and is also possible because of enzyme partially denaturing when comparatively high temps, so the degraded of pair cell wall becomes invalid.Because oil volatility, the method for handling when low temperature is suitable.
Table 3: temperature is to the effect of oil recovery rate
Embodiment 5
The clean ginger (800g dry weight) that reaches that a collection of 5kg is fresh mixes with enzyme solution to comprise the ginger of 2500 units zytase/100g dry weight.160ml embodiment 3 described commercial enzymes are mixed with 2.34 premium on currency prepare enzyme solution.Hatched 2.5 hours with this mixture homogenizing and 40 ℃ the time subsequently.Obtain extracting solution and as distilling as illustrated in the embodiment 1.With obtain the 15ml ethereal oil in the ginger that enzyme is handled and compare, control sample (handling without enzyme) produces the 11.5ml ethereal oil.Carry out gas-chromatography: SE 30 posts (10% dia solid L, 60-80 sieve mesh) with following condition; Injection temperature is 200 ℃; Detector temperature is 235 ℃; Nitrogen flow rate is 40ml/min.The gas-liquid chromatograph characteristic spectrum of the main ingredient of the oil shown in the table 4 shows that main peak area is zingiberene, curcumene and sesquiterpene alcohols, amounts to about 65% contrast ginger (doing) extraction.The rate of recovery of these materials increases to the 11.0ml (from 15ml) that enzyme is handled from the 8.72ml (from 11.5ml oil) of reference substance.
Table 4: through the volatile oil concentration of the ginger of gas-chromatography assessment
1,2 and 3=zingiberene, curcumene and sesquiterpene alcohols, other material of 4=
*Ordinary method
Peak area % among the a=GC
B=is for the component (ml) of 100g ginger (based on dry weight matter)
Embodiment 6
As embodiment 5 described methods, a collection of 260g fresh garlic (100g dry weight) also carries out enzymic hydrolysis, and refiltered oil is also analyzed.Compare with reference substance (1.69ml), in the sample that enzyme is handled, the yield of the oil that is obtained higher (is 2.35ml for the 100g dry weight).Resulting thus main body of oil comprises maximum 76% diallyl trisulfide, allyl methyl trisulfide thing and diallyl disulfide.
Embodiment 7
Repeat embodiment 5 described steps to obtain oil from cloves.This seasonings is ground to form the 300-700 micron granularity,, obtain oil with handling as embodiment 5 described enzyme complexs.Resulting oily yield is to be 10ml (to the 100g dry weight) with respect to contrast, and the sample of handling with respect to enzyme is 15ml.The main component that obtains is an oxymethoxyallylbenzene, adds up to maximum 80%.
Major advantage of the present invention is:
2. compare with conventional method, the yield of volatility flavored oils has increased about 30-50%.
3. because described multienzyme complex has been hydrolyzed the barrier that the cell membrane by fresh or dry seasoning material provides, so compare with conventional method, this extracts and more effectively discharges more oil.
Claims (9)
1. enzyme method that is used to prepare flavor oil, it comprises:
(a) preparation of use medium contains the enzyme complex of cellulase, polygalacturonase, proteolytic enzyme and zytase,
(b) in described enzyme complex solution, will be selected from the seasonings homogenizing of ginger, garlic and cloves and hatching,
(c) the seasonings enzyme solution of homogenizing is filtered obtaining clarifying liquor,
(d) distill described liquor, and
(e) collect flavor oil.
2. the method for claim 1, wherein said enzyme is to use with the amount of 0.35 unit/ml to 500 unit/ml, and enzyme is 1:16 to the ratio of aqueous medium.
3. the method for claim 1, wherein said seasonings has 300 to 700 microns granularity, and seasonings is 1:1 to 2:1 to the ratio of enzyme complex solution.
4. the method for claim 1, wherein said hatching is under 30 ℃ to 50 ℃ temperature, carries out 2 to 3 hours.
5. the method for claim 1, wherein said distillation is in 95 ℃ to 100 ℃ temperature, carries out 2 to 3 hours.
6. the method for claim 1, the yield of wherein said flavor oil is 0.86 to 1.9ml flavor oil for the ginger with respect to the 100g dry weight, garlic with respect to the 100g dry weight is 1.69 to 2.53ml flavor oil, is 10 to 15ml flavor oil with respect to the cloves of 100g dry weight.
7. the method for claim 1, wherein said flavor oil is included in contains maximum 73% zingiberene, curcumene and sesquiterpenoid in the ginger oil, in garlic oil, contain maximum 76% diallyl trisulfide, allyl methyl trisulfide thing and diallyl disulfide, and in Syzygium aromaticum stem oil, contain maximum 80% oxymethoxyallylbenzenes.
8. the method for claim 1, wherein said cellulase uses with 0.35 to 4.6 units/ml amount, polygalacturonase uses with 80 to 500 units/ml amount, and proteolytic enzyme uses with 30 to 150 units/ml amount and zytase uses with 17.5 to 126 units/ml amount.
9. the method for claim 1 wherein realizes the filtration of the seasonings suspension of described homogenizing and hydrolysis through water pressure engine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2003/000451 WO2005063953A1 (en) | 2003-12-31 | 2003-12-31 | Enzymatic process for preparing spice oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1886491A CN1886491A (en) | 2006-12-27 |
| CN100532520C true CN100532520C (en) | 2009-08-26 |
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|---|---|---|---|
| CNB2003801109552A Expired - Fee Related CN100532520C (en) | 2003-12-31 | 2003-12-31 | Enzymatic process for preparing spice oil |
Country Status (4)
| Country | Link |
|---|---|
| CN (1) | CN100532520C (en) |
| AU (1) | AU2003300708A1 (en) |
| BR (1) | BR0318671A (en) |
| WO (1) | WO2005063953A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101979522A (en) * | 2010-09-27 | 2011-02-23 | 赵岩 | Complex enzyme formula for improving extraction rate of sodium alginate and application |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008062431A2 (en) * | 2006-08-08 | 2008-05-29 | Advanced Enzyme Technologies Limited | Synergistic anthelmintic composition |
| CN102517259A (en) * | 2011-12-28 | 2012-06-27 | 天津滨海诺奥酶工程技术有限公司 | Enzyme preparation and application and method of enzyme preparation for extracting ginger oleoresin |
| US8986977B2 (en) * | 2011-12-30 | 2015-03-24 | Alliance For Sustainable Energy, Llc | Disruption of cell walls for enhanced lipid recovery |
| CN104543914B (en) * | 2015-01-09 | 2017-07-07 | 无锡商业职业技术学院 | The preparation method of allium sesame oil |
| CN109536282A (en) * | 2017-09-22 | 2019-03-29 | 江苏智谋科技有限公司 | A kind of garlic oil extraction process |
| CN111388636B (en) * | 2020-03-13 | 2021-09-24 | 山东德信生物科技有限公司 | Ginger formula oral liquid for livestock and preparation method thereof |
| CN111394188B (en) * | 2020-04-20 | 2022-05-27 | 广东蔚莱生物科技有限公司 | Preparation method of oregano oil, oregano oil and application thereof |
| CN113831967A (en) * | 2021-11-08 | 2021-12-24 | 福建省农业科学院农业质量标准与检测技术研究所 | Method for enzyme-assisted extraction of turmeric essential oil |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57192318A (en) * | 1981-05-19 | 1982-11-26 | Riken Kagaku Kogyo Kk | Preventing method of filarial disease |
| SU1701738A1 (en) * | 1989-12-07 | 1991-12-30 | Научно-Производственное Объединение "Арагил" Госагропрома Армсср | Method of producing estragon oil |
| JPH11222410A (en) * | 1998-02-03 | 1999-08-17 | Riken Health Kk | Control of plant withering and activating agent |
-
2003
- 2003-12-31 WO PCT/IN2003/000451 patent/WO2005063953A1/en active Application Filing
- 2003-12-31 AU AU2003300708A patent/AU2003300708A1/en not_active Abandoned
- 2003-12-31 CN CNB2003801109552A patent/CN100532520C/en not_active Expired - Fee Related
- 2003-12-31 BR BRPI0318671-7A patent/BR0318671A/en not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101979522A (en) * | 2010-09-27 | 2011-02-23 | 赵岩 | Complex enzyme formula for improving extraction rate of sodium alginate and application |
| CN101979522B (en) * | 2010-09-27 | 2012-05-23 | 赵岩 | Complex enzyme formula for improving extraction rate of sodium alginate and application |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1886491A (en) | 2006-12-27 |
| WO2005063953A1 (en) | 2005-07-14 |
| BR0318671A (en) | 2006-11-28 |
| AU2003300708A1 (en) | 2005-07-21 |
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