WO1993006735A1 - Post-harvest fruit protection using components of natural essential oils in combination with coating waxes - Google Patents
Post-harvest fruit protection using components of natural essential oils in combination with coating waxes Download PDFInfo
- Publication number
- WO1993006735A1 WO1993006735A1 PCT/GR1992/000018 GR9200018W WO9306735A1 WO 1993006735 A1 WO1993006735 A1 WO 1993006735A1 GR 9200018 W GR9200018 W GR 9200018W WO 9306735 A1 WO9306735 A1 WO 9306735A1
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- WIPO (PCT)
- Prior art keywords
- fruits
- natural
- combination
- waxes
- trans
- Prior art date
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Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
- A23B7/153—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of liquids or solids
- A23B7/154—Organic compounds; Microorganisms; Enzymes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/16—Coating with a protective layer; Compositions or apparatus therefor
Definitions
- TITLE POST- HARVEST FRUIT PROTECTION USING COMPONENTS OF NATURAL ESSENTIAL OILS IN COMBINATION WITH COATING
- This invention constitutes a new method of pre- or post-harvest fruit protection based on the use of components of essential oils in combination with natural or artificial coating substances such as polyethylene, natural waxes, mono-di- or tri-glycerides, esters of saccharose etc.
- Components of essential oils are considered to be the products of the natural catabolism of linolenic and linolenic acid which are hexanal, trans-2-hexanal, trans-2-nonenal, trans-2-cis-6-nonadienal, nonanal, cis-3-hexanal, the corresponding alcohols and acids, eneaic acid, trans-10-dodecanoic acid and the corresponding aldehydes or alcohols and of course all the esters of the above compounds and the protected forms of aldehydes. These compounds will be mentioned form now on as C6-C9 compounds. Fruits that are destined for consumption by humans should possess the following properties :
- Fruits and vegetables will be classified according to means of preservation in order to clearly define the field of this inventions application. 1) Fruits and vegetables that can be preserved only by means of refrigeration. 2) Fruits and vegetables that can be preserve only through used of chemical preservatives in combination with one of the above mentioned techniques and that are concerned usually in time and place different than that of their harvest.
- fruits such as citrus fruits, bananas, pineapples, melons, several tropical fruits and generally all fruits and vegetable whose peel is not consumed, can be classified.
- step of fruit processing a significant percentage of natural coating wax of fruits is removed, resulting in decrease resistance to microbial infections.
- the same process causes scratches and cuts to the fruit which is one of the reasons for premature, microbial putrefaction.
- fungicides are used, which are applied together with the coating wax in order to fully protect the fruit from microbial putrefaction.
- Such fungicides are thiobenzanole and others.
- This synthetic, wide range fungicides cannot replace the natural defence of the plant in no way, for two reasons:
- C6-Ca natural component of essential oils
- the wax of the substance of fruit coating with the objective of substituting the synthetic wide-range, anti-microbial pesticide It also consists of their use, combined or not with variable atmospheres, in order to inhibit the microbial development in stored fruits and vegetables.
- the fruits that are subjected to this procedure are cleaned before if this is necessary and then they are sprayed with coating wax, that can be a poly-ethylene of high density or natural wax, or a synthetic wax of mineral origin (paraffins or others) or chemical substances, such as monoglycerides, di-glycerides or tri-glycerides of organic acids or finally esters of mono- or poly- saccharides with fatty acids.
- coating wax can be a poly-ethylene of high density or natural wax, or a synthetic wax of mineral origin (paraffins or others) or chemical substances, such as monoglycerides, di-glycerides or tri-glycerides of organic acids or finally esters of mono- or poly- saccharides with fatty acids
- C6-C9 substances has been added to the coating wax at levels that range from 0.0012. to 1%, depending of the fruit the time period and temperature of the preservation.
- the same C6-C9 substances can be added to the fruits independently, before or after the coating the protective wax.
- the simultaneous coating of the fruit with protective wax and antimicrobial mixture of C6-C9 substances has been proven to give the best results.
- C6-C9 compounds can be mixed with the above mentioned esters of sugars with fatty acids and this mixture can be used for immersing the fruits into it. Pineapples, bananas and melons are some of the fruits that can be classified under this preservation category.
- C6-C9 compounds An other way of application of C6-C9 compounds is in combination with other polishing and protective substances of fruit surface, such as several monoglycerides, di-giycerides and tri-glycerides of organic acids. Coating substances for fruits that are consumed with their outer skin, such as grapes, can be classified under this category.
- An other application category consists of fruits and vegetables that are preserved under variable atmospheres. Fruits package in bags may from synthetic polymers belong to this category.
- variable atmospheres are mixtures of oxygen, carbon dioxide and nitrogen in percentages different from those that exist in air. If one of these C6-C9 substances is added to these mixtures or even to air,. Greater inhibition of mycelial development or better fungistatic or fungicide activity, can be achieved.
- E x a m p l e 1 40 kgs of oranges are divided in 8 groups of 5 kgs each. All of them are washed according to the technique that is used at the citrus, packaging companies. This technique involves washing of the oranges with NaOH 1-2% and then washing with water for NaOH to be removed.
- the oranges of the first group are washed and are covered with a protective, synthetic wax layer without fungistatic compounds (Group 1).
- the oranges of the second group are washed and then Biphenyl (ONP) is applied. Finally they are covered with a protective synthetic wax layer without any wide-range fungistatic compound (Group 2).
- the oranges of the third group are washed. ONP is applied and then they are covered with the protective synthetic wax layer that contains a wide-range fungistatic substance (Group 3).
- the oranges of the fourth group are washed and then they are covered with a protective synthetic wax layer that contains 0.5% Hexanal (Group 4).
- the oranges of the fifth group are washed ana then they are covered with a protective, synthetic wax layer that contains trans-2-hexanal 0.5 % (Group 5).
- the oranges of the sixth group are washed and covered with a protective synthetic wax layer that also contains hexanal 0.25% and trans-2-hexanal 0.2 ⁇ % (Group 6).
- the oranges of the seventh group are washed and covered with a protective synthetic wax that contains 0.5% trans-2-cis-6-nonadienale (Group 7).
- the waxes that were used were the synthetic waxes : Luwax 0A2 Basf, or the Citrus Wax, Hoechst in several types PEP 121 or 154 In both cases the wax consists of polyethylene of high densit that has been emulsified in water (17 % w/w) at temperature o 120oC in the presence of base and elaic acid. The coating quantity did not exceeded 140 mg/Kg of fruits of all the groups.
- the following fungi Botritis cinerea, Rhizopus stolonifer, Pythium ultimo, Aspergillus nigger and Penicillium digitatum are grown in Petri dishes with PDA as a nutritious medium.
- PDA discs of those mycelia are taken and places in the above mentioned Petri dishes where the compounds that are to be tested are included.
- the Petri dishes that contain these compounds are closed aseptically and the inhibition percentage is measured by using the Dikshit equation (1983), which is :
- [C] compond concentration in Petri dishes with PDA medium.
Abstract
A method of protection of fruits and vegetables from microbial infections, by using protective waxes and other concealing means in combination with essential oil constituents. As essential oil constituents, are used the products of degradation of linoleic and linolenic acids, thereby the saturated and unsaturated linear chain aldehydes with six, nine and twelve carbon atoms, as well as their corresponding acids and alcohols. The method is characterized by the usage of one or two essential oil constituents in varying percentages ranging from 0.001 to 10 % by weight of the covering medium or in parts ranging from 10 to 1000 ppm of the conservation atmosphere. Therefore it is used for the post-harvest protection of fruits and vegetables.
Description
TITLE: POST- HARVEST FRUIT PROTECTION USING COMPONENTS OF NATURAL ESSENTIAL OILS IN COMBINATION WITH COATING
WAXES . This invention constitutes a new method of pre- or post-harvest fruit protection based on the use of components of essential oils in combination with natural or artificial coating substances such as polyethylene, natural waxes, mono-di- or tri-glycerides, esters of saccharose etc.
Components of essential oils are considered to be the products of the natural catabolism of linolenic and linolenic acid which are hexanal, trans-2-hexanal, trans-2-nonenal, trans-2-cis-6-nonadienal, nonanal, cis-3-hexanal, the corresponding alcohols and acids, eneaic acid, trans-10-dodecanoic acid and the corresponding aldehydes or alcohols and of course all the esters of the above compounds and the protected forms of aldehydes. These compounds will be mentioned form now on as C6-C9 compounds. Fruits that are destined for consumption by humans should possess the following properties :
1) They should preserve the natural form and chemical composition they possessed when they were harvested.
2) They should have note been infected by microorganisms or subjected to putrefaction.
3) They should not be sub.jected to oxidization or other chemical
alterations.
4) Generally they should possess and attractive appearance.
Nowadays in order to fulfil all those requirements chemical preservatives are used, which in combination with coating waxes preserve the natural composition, that the fruits possess during harvest period, for a long period.
Up till now, fruits that were going to be consumed during a time period different than that of their harvest, were preserved either by means of refrigeration or through use of chemical preservatives or several wide-range pesticides. Recently, the use of special modified atmospheres has also started to be developed. All these preservation techniques usually involve the use of pesticides or chemical preservatives in order to improve the result. There is a growing demand, though for restricted use of pesticides because they have been characterized as dangerous for man and the environment.
Fruits and vegetables will be classified according to means of preservation in order to clearly define the field of this inventions application. 1) Fruits and vegetables that can be preserved only by means of refrigeration.
2) Fruits and vegetables that can be preserve only through used of chemical preservatives in combination with one of the above mentioned techniques and that are concerned usually in time and place different than that of their harvest.
Under the second category, fruits such as citrus fruits, bananas, pineapples, melons, several tropical fruits and generally all fruits and vegetable whose peel is not consumed, can be classified.
Packaging and trade companies that are involved in the distribution of fruits and vegetables of the second category are obliged by the growing demand of consumers and by the demand of great urban areas for consumption of fresh products regardless of season and origin to proceed in washing of fruits in order to remove pesticides, dirt or other unwanted objects. D u r i n g this
step of fruit processing a significant percentage of natural coating wax of fruits is removed, resulting in decrease resistance to microbial infections. The same process causes scratches and cuts to the fruit which is one of the reasons for premature, microbial putrefaction.
Packaging and transportation company use synthetic or natural wax to cover washed fruits by spraying them or by immersing them into it. However, the coverage of fruits with synthetic or natural
waxes, mono-or polyglycerides of organic acids or any other coating means, cannot protect the fruits effectively. This is due to the fact that together with the natural wax lays or any other protected layer, part of the natural essential oils or other secondary metabolites which consist the natural defence of the plant, is removed, as well. For this reason wide range
fungicides are used, which are applied together with the coating wax in order to fully protect the fruit from microbial putrefaction. Such fungicides are thiobenzanole and others. Unfortunately this synthetic, wide range fungicides cannot replace the natural defence of the plant in no way, for two reasons:
1) They are not metabolized and consequent they are not be degraded to secondary products in order to contribute to the natural functions of the plant, and
2) They consist a continuous threat for man and ecological environment. By studying the post-harvest physiology of the plant the applicant came to the conclusion that is possible to use natural secondary metabolites such as the degradation products of linoleic and linolenic acid, which are the saturated or mono- and poly- unsaturated aldehydes with six and nine carbon atoms and the corresponding alcohols or acids such as hexanal, trans-2-hexanal, hexanol, hexanoic acid and the corresponding esters of
the above mentioned acids. Under the same category are the compounds with nine carbon atoms, aldehydes, alcohols, acids, saturated or unsaturated with one or two unsaturated double bonds, such as nonanale, nonadienale, nonenenale and the corresponding alcohols or acids, free or esterified. Apart of the above compounds all the combinations of them have been studied and proved to be effected. The above mentioned compounds can be
also applied in the case of fruit and vegetable preservation
unde r modi f ied atmosphere s . So , thi s inventi on c ons i s t s the
combined use of a natural component of essential oils (C6-Ca) and the wax of the substance of fruit coating with the objective of substituting the synthetic wide-range, anti-microbial pesticide It also consists of their use, combined or not with variable atmospheres, in order to inhibit the microbial development in stored fruits and vegetables. The fruits that are subjected to this procedure, are cleaned before if this is necessary and then they are sprayed with coating wax, that can be a poly-ethylene of high density or natural wax, or a synthetic wax of mineral origin (paraffins or others) or chemical substances, such as monoglycerides, di-glycerides or tri-glycerides of organic acids or finally esters of mono- or poly- saccharides with fatty acids. One of the above
mentioned C6-C9 substances has been added to the coating wax at levels that range from 0.0012. to 1%, depending of the fruit the time period and temperature of the preservation. The same C6-C9 substances can be added to the fruits independently, before or after the coating the protective wax. The simultaneous coating of the fruit with protective wax and antimicrobial mixture of C6-C9 substances has been proven to give the best results.
In the case of fruits that are protected by immersion in esters fatty acids with sugars, C6-C9 compounds can be mixed with the above mentioned esters of sugars with fatty acids and this mixture can be used for immersing the fruits into it. Pineapples, bananas and melons are some of the fruits that can be classified under this preservation category.
An other way of application of C6-C9 compounds is in combination with other polishing and protective substances of fruit surface, such as several monoglycerides, di-giycerides and tri-glycerides of organic acids. Coating substances for fruits that are consumed with their outer skin, such as grapes, can be classified under this category. An other application category consists of fruits and vegetables that are preserved under variable atmospheres. Fruits package in
bags may from synthetic polymers belong to this category.
These variable atmospheres are mixtures of oxygen, carbon dioxide and nitrogen in percentages different from those that exist in air. If one of these C6-C9 substances is added to these mixtures or even to air,. Greater inhibition of mycelial development or better fungistatic or fungicide activity, can be achieved.
In order to illustrate the effects of this invention, the activity of the C6-C9 will be illustrated through the following examples:
E x a m p l e 1. 40 kgs of oranges are divided in 8 groups of 5 kgs each. All of them are washed according to the technique that is used at the citrus, packaging companies. This technique involves washing of the oranges with NaOH 1-2% and then washing with water for NaOH to be removed.
The oranges of the first group are washed and are covered with a protective, synthetic wax layer without fungistatic compounds (Group 1). The oranges of the second group are washed and then Biphenyl (ONP) is applied. Finally they are covered with a protective
synthetic wax layer without any wide-range fungistatic compound (Group 2).
The oranges of the third group are washed. ONP is applied and then they are covered with the protective synthetic wax layer that contains a wide-range fungistatic substance (Group 3).
The oranges of the fourth group are washed and then they are covered with a protective synthetic wax layer that contains 0.5% Hexanal (Group 4).
The oranges of the fifth group are washed ana then they are covered with a protective, synthetic wax layer that contains trans-2-hexanal 0.5 % (Group 5).
The oranges of the sixth group are washed and covered with a protective synthetic wax layer that also contains hexanal 0.25% and trans-2-hexanal 0.2δ% (Group 6). The oranges of the seventh group are washed and covered with a protective synthetic wax that contains 0.5% trans-2-cis-6-nonadienale (Group 7).
The oranges of the eighth group are not washed and are not treated with any protective wax (Group 8).
The results of the effect of the above mentioned compounds combined or not with wax, are shown at Table 1.
The waxes that were used were the synthetic waxes : Luwax 0A2 Basf, or the Citrus Wax, Hoechst in several types PEP 121 or 154 In both cases the wax consists of polyethylene of high densit that has been emulsified in water (17 % w/w) at temperature o 120ºC in the presence of base and elaic acid. The coating quantity did not exceeded 140 mg/Kg of fruits of all the groups.
T A B L E 1
The amount (%) of Fungi inhibition
15 days 60 days
Group 1 38 0
Group 2 50 0
Group 3 95 90
Group 4 93 87
Group δ 96 92
Group 6 97 98
Group 7 94 80
Group 8 0 0
The oranges that were used. during the experiments of Table 1 were of the variety VALENCIA H has been observed that different varieties react in a different way to the fungi influence. However in general terms all the oranges regardless the variety react in the same way to the fungi influence.
E x a m p l e 2 The Grover and Moove (1960) technique was used to test the wide- range inhibition of C6-C9 compounds. This technique is used to determine the minimum concentration that exerts inhibition (MIC).
According to this technique : Solutions of these compounds (100- 1000ppm) in PDA oxide (Potato-Dextrose Ag r) are prepared which are then poured in Petri dishes.
The following fungi Botritis cinerea, Rhizopus stolonifer, Pythium ultimo, Aspergillus nigger and Penicillium digitatum are grown in Petri dishes with PDA as a nutritious medium. When these mycelia have fully developed, PDA discs of those mycelia (diameter of 5mm ) are taken and places in the above mentioned Petri dishes where the compounds that are to be tested are included. For each compound there is also a control Petri dish with the medium PDA only, without the compound that will be tested. The Petri dishes that contain these compounds are closed
aseptically and the inhibition percentage is measured by using the Dikshit equation (1983), which is :
dt : colony diameter in Petri dishes with the corresponding compounds.
In order for the antimicrobial effect to be determined, in other words, in order for this effect to be characterized as
fungistatic or fungicide, the following experiment has been carried out.
Mycelia disks from Petri dishes where 100% inhibition of growth has been observed, were transferred To Petri dishes, with only PDA and the behaviour of the disk was observed. If growth was observed after 7 days, the effect of the compound was fungistatic. If no growth was observed, the effect was fungicide the results of these experiments are shown at Table 2.
Determination of fungistatic or fungicide effect
In the above table.
[C] = compond concentration in Petri dishes with PDA medium.
Claims
C L A I M S 1. Method of pre- and post- harvest protection of fruits and vegetables form microbial and other biochemical infections by using products of the natural catabolism of linolenic and linoleic acid, in combination with natural or artificial waxes or substances for coating or polishing fruits and vegetables.
2. Method according to claim 1, that is characterized by the fact that natural catobilism products of linoleic and linoleic acid are considered to be : hexanal, trans-2- haxanal, trans-2-nonanal, cis-3-hexenal, the corresponding alcohols and acids, eneanic acid, trans-10-dodecanoic acid and the corresponding aldehydes and alcohols and of course all the esters of the above compounds and the protected forms of aldehydes.
3. Method according to which natural or artificial waxes are considered to be substances like waxes of mineral origin, paraffins and other by-products of petroleum, polyethylene, colophony or other related compounds, gommalaca, mono- or poly-glycerides, esters of saccharose with fatty acids.
4. Method according to claims 1, 2, 3 in combination with variable, preservation atmospheres.
5. Method according to claims 1, 2, 3, where the compounds mentioned at claims 1 and 2 are used, independently or combined at levels of 0.001 - 10 % and mainly at 0.01- 1 % of the coating wax weight that is described at claim 3.
6. Method according to claim 2, where the substances are added to the surroundings in concentration of 0.1 - 10000 ppm and mainly from 10 to 1000 ppm.
7. Method according to claims 1, 2, 3, 4, 5, 6, combined with freezing, hat contains a wide-range fungistatic substance (Group 3).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GR910100417 | 1991-10-10 | ||
| GR91100417 | 1991-10-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1993006735A1 true WO1993006735A1 (en) | 1993-04-15 |
Family
ID=10940791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GR1992/000018 WO1993006735A1 (en) | 1991-10-10 | 1992-10-09 | Post-harvest fruit protection using components of natural essential oils in combination with coating waxes |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU2693292A (en) |
| WO (1) | WO1993006735A1 (en) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1106070A2 (en) * | 1999-11-11 | 2001-06-13 | Inabonos, S.A. | Natural source composition for the control of post-harvest pathologies and method of application |
| WO2004037006A1 (en) * | 2002-10-23 | 2004-05-06 | Keating Vernon P | Post harvest treatment of crops |
| CN1314331C (en) * | 2005-07-14 | 2007-05-09 | 甘肃省润源农产品开发公司 | Nano-silicon oxide (SiO2) type wax for fruit preservation, and its prodn. method |
| JP2008520638A (en) * | 2004-11-22 | 2008-06-19 | スタンフォード ルック リミテッド | Immunotherapy |
| WO2012095486A1 (en) * | 2011-01-12 | 2012-07-19 | Dsm Ip Assets B.V. | Reduction of weight loss of fruits |
| WO2012123904A1 (en) | 2011-03-17 | 2012-09-20 | Ica Laboratories Cc | A fungicidal composition |
| CN103283828A (en) * | 2013-06-24 | 2013-09-11 | 湖南工业大学 | Preparation method for essential oil/beta-cyclodextrin inclusion based antibacterial fruit wax |
| WO2017132281A1 (en) * | 2016-01-26 | 2017-08-03 | Apeel Technology, Inc. | Method for preparing and preserving sanitized products |
| WO2017172951A1 (en) * | 2016-04-01 | 2017-10-05 | Apeel Technology, Inc. | Method of reducing spoilage in harvested produce during storage and shipping |
| WO2018009846A1 (en) * | 2016-07-08 | 2018-01-11 | Apeel Technology, Inc. | Methods of controlling the rate of ripening in harvested produce |
| US9957215B2 (en) | 2015-12-10 | 2018-05-01 | Apeel Technology, Inc. | Plant extract compositions for forming protective coatings |
| US10239069B2 (en) | 2013-07-29 | 2019-03-26 | Apeel Technology, Inc. | Agricultural skin grafting |
| US10266708B2 (en) | 2015-09-16 | 2019-04-23 | Apeel Technology, Inc. | Precursor compounds for molecular coatings |
| US10517310B2 (en) | 2015-05-20 | 2019-12-31 | Apeel Technology, Inc. | Plant extract compositions and methods of preparation thereof |
| US10843997B2 (en) | 2016-11-17 | 2020-11-24 | Apeel Technology, Inc. | Compositions formed from plant extracts and methods of preparation thereof |
| US11582979B2 (en) | 2020-06-07 | 2023-02-21 | Comestaag Llc | Selectively treating plant items |
| US11641865B2 (en) | 2020-03-04 | 2023-05-09 | Apeel Technology, Inc. | Compounds and formulations for protective coatings |
| US11827591B2 (en) | 2020-10-30 | 2023-11-28 | Apeel Technology, Inc. | Compositions and methods of preparation thereof |
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1992
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- 1992-10-09 WO PCT/GR1992/000018 patent/WO1993006735A1/en active Application Filing
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| US2856294A (en) * | 1954-05-28 | 1958-10-14 | Best Foods Inc | Mold inhibiting processes and products thereof |
| US4312766A (en) * | 1979-10-17 | 1982-01-26 | International Flavors & Fragrances Inc. | Derivatives of cis-3-hexenol and process for producing compositions of matter containing cis-3-hexenal and products produced thereby and organoleptic uses thereof |
| DD283565A5 (en) * | 1986-04-17 | 1990-10-17 | Inst. Fuer Pflanzenschutz Forschung Kleinmachnow,Dd | DISINFECTANT AND PRESERVATIVE |
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Cited By (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1106070A2 (en) * | 1999-11-11 | 2001-06-13 | Inabonos, S.A. | Natural source composition for the control of post-harvest pathologies and method of application |
| WO2004037006A1 (en) * | 2002-10-23 | 2004-05-06 | Keating Vernon P | Post harvest treatment of crops |
| JP2008520638A (en) * | 2004-11-22 | 2008-06-19 | スタンフォード ルック リミテッド | Immunotherapy |
| CN1314331C (en) * | 2005-07-14 | 2007-05-09 | 甘肃省润源农产品开发公司 | Nano-silicon oxide (SiO2) type wax for fruit preservation, and its prodn. method |
| WO2012095486A1 (en) * | 2011-01-12 | 2012-07-19 | Dsm Ip Assets B.V. | Reduction of weight loss of fruits |
| WO2012123904A1 (en) | 2011-03-17 | 2012-09-20 | Ica Laboratories Cc | A fungicidal composition |
| CN103283828A (en) * | 2013-06-24 | 2013-09-11 | 湖南工业大学 | Preparation method for essential oil/beta-cyclodextrin inclusion based antibacterial fruit wax |
| US10239069B2 (en) | 2013-07-29 | 2019-03-26 | Apeel Technology, Inc. | Agricultural skin grafting |
| US10537130B2 (en) | 2013-07-29 | 2020-01-21 | Apeel Technology, Inc. | Agricultural skin grafting |
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| US11472970B2 (en) | 2015-09-16 | 2022-10-18 | Apeel Technology, Inc. | Precursor compounds for molecular coatings |
| US10266708B2 (en) | 2015-09-16 | 2019-04-23 | Apeel Technology, Inc. | Precursor compounds for molecular coatings |
| US11447646B2 (en) | 2015-09-16 | 2022-09-20 | Apeel Technology, Inc. | Precursor compounds for molecular coatings |
| US10561155B2 (en) | 2015-12-10 | 2020-02-18 | Apeel Technology, Inc. | Plant extract compositions for forming protective coatings |
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