WO2010151355A1 - Huile essentielle obtenue avec des baies non mûres dotée d’une plus grande stabilité et d’une meilleure qualité d’emploi, et procédé de production associé - Google Patents

Huile essentielle obtenue avec des baies non mûres dotée d’une plus grande stabilité et d’une meilleure qualité d’emploi, et procédé de production associé Download PDF

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Publication number
WO2010151355A1
WO2010151355A1 PCT/US2010/029324 US2010029324W WO2010151355A1 WO 2010151355 A1 WO2010151355 A1 WO 2010151355A1 US 2010029324 W US2010029324 W US 2010029324W WO 2010151355 A1 WO2010151355 A1 WO 2010151355A1
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WO
WIPO (PCT)
Prior art keywords
essential oil
activated carbon
unripe
treated
amount
Prior art date
Application number
PCT/US2010/029324
Other languages
English (en)
Inventor
Ad S. Olansky
Ling Lu
Jimmy L. Arnett
Sheng S. Yang
Christopher J. Smith
Dennis R. Ryan
Terence Radford
Original Assignee
The Coca-Cola Company
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from PCT/US2009/048643 external-priority patent/WO2010002696A1/fr
Application filed by The Coca-Cola Company filed Critical The Coca-Cola Company
Priority to AU2010263197A priority Critical patent/AU2010263197A1/en
Priority to EP10792474A priority patent/EP2446007A1/fr
Priority to MX2012000101A priority patent/MX2012000101A/es
Priority to CA2766255A priority patent/CA2766255A1/fr
Priority to BRPI1015065A priority patent/BRPI1015065A2/pt
Priority to CN2010800357926A priority patent/CN102459548A/zh
Publication of WO2010151355A1 publication Critical patent/WO2010151355A1/fr

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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
    • A23L27/12—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils
    • A23L27/13—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils from citrus fruits

Definitions

  • Essential oils are volatile oils derived from at least a part of a plant such as fruit peels and leaves, stems, flowers, bark, roots, or twigs. Essential oils usually carry the natural odor or flavor of the plant or its fruit and are thus used in the preparation of products including foods, beverages, perfumes, pharmaceuticals, air fresheners, aromatherapeutics, and cosmetics. Such oils may be extracted by various methods that release the oils from the plant structures containing them. For example, citrus oils may be derived by squeezing or pressing citrus fruit peels.
  • Essential oils may be extracted from fruits at various stages of ripeness. Depending on the type and/or origin, some unripe fruits tend to have a green coloring due to the dominant presence of chlorin-based pigments such as chlorophyll. Chlorophyll absorbs strongly in the blue and red sections of the electromagnetic spectrum, but it absorbs weakly in the green section, hence imparting a green color to chlorophyll-containing tissues such as plant leaves and unripe fruit peels. Consequently, essential oils extracted from some unripe fruits may have a green coloring. As fruits ripen, their acidities change and the pigments change, transforming the fruits into a more yellowish and/or red coloring. For example, mandarin oranges are greenish when they are unripe.
  • Maturing mandarins contain dominant yellow and red carotenoid pigments that give a yellowish tint. As the mandarins fully ripen, the red pigments become more dominant so that the ripe fruits have more of a reddish glow.
  • plant source means any part of a plant or the whole plant.
  • unripe essential oil means any essential oil extracted from an unripe fruit, which may or may not be associated with a green coloring depending on the plant source of the oil.
  • ripe essential oil means any essential oil extracted from a ripe fruit, which may or may not be associated with a yellow or red coloring depending on the plant source.
  • organoleptic property means any property associated with one or more of the organs of sense, i.e. taste, smell, touch. Some examples of organoleptic properties include but are not limited to texture, viscosity, taste, odor, and appearance.
  • shelf life means the period of time that an essential oil or a product containing an essential oil may be stored with at least intermittent exposure to artificial or natural light without a substantial change in an organoleptic property.
  • Unripe essential oils are often less expensive and more readily available than ripe essential oils. They also may contain fewer pesticides and other agricultural contaminants because unripe fruits are less prone to insect attacks and the effects of spoilage organisms. Despite these advantages, unripe essential oils are not as widely used as ripe essential oils, especially in foods and beverage applications. One reason is because products containing unripe essential oils tend to have shorter shelf lives than products containing ripe essential oils from the same plant source. For example, inventors of the present invention discovered through sensory tests that when beverages containing unripe mandarin oils were stored under artificial light, they were much more likely and quickly to develop off-tastes than beverages containing ripe mandarin oils that were stored under the same light conditions.
  • Particular embodiments of the present invention encompass a method for enhancing the stability and usability of an unripe essential oil without substantially changing an organoleptic property other than color of the unripe essential oil, comprising obtaining an unripe essential oil derived from a plant source, wherein the unripe essential oil comprises a first amount of chlorophyll, contacting the unripe essential oil with an effective amount of an activated carbon to produce a treated essential oil, and separating the activated carbon from the treated essential oil.
  • the treated essential oil comprises a second amount of chlorophyll that is less than the first amount of chlorophyll.
  • the treated essential oil may be substantially free of chlorophyll.
  • Embodiments of the present invention also encompass a first edible product comprising the treated essential oil.
  • the shelf life of the first edible product may be similar to the shelf life of a second edible product, wherein the second edible product comprises a ripe essential oil derived from the same plant source.
  • the term "similar” as used herein is intended to also encompass identical comparisons.
  • the effective amount of the activated carbon depends on multiple factors including but not limited to the plant source of the unripe essential oil, the degree of ripeness of the plant source, the origin of the plant source, the growth conditions of the plant source, the volume of the unripe essential oil, the intended application of the treated essential oil, and the amount of chlorophyll in the unripe essential oil.
  • the effective amount of the activated carbon may be at least a minimum, wherein the minimum is the lowest amount needed to make the shelf life of the treated essential oil similar to the shelf life of a ripe essential oil derived from the same plant source.
  • the minimum is the lowest amount needed to make the shelf life of the treated essential oil similar to the shelf life of a ripe essential oil derived from the same plant source.
  • One skilled in the art may determine the shelf life of an essential oil and/or a product utilizing an essential oil
  • 105 oil by various methods of detecting a change in any organoleptic property of the essential oil and/or product. Examples of such methods include but are not limited to sensory testing, spectrometry measurements, electronic nose/tongue measurements, and chromatography.
  • activated carbon has a tendency to selectively adsorb chlorophyll over most of the other components in the unripe essential oil and the oil itself. This selectivity is particularly useful for applications that exploit the natural flavors, fragrances, and/or other properties of the unripe essential oil so that components responsible for such desired properties
  • the term “desirable component” means any component in the unripe essential oil responsible for any desirable physical and/or organoleptic property in the essential oil and/or in the products containing such oil.
  • the term “threshold amount” means the amount of a desirable component at
  • the effective 130 amount of the activated carbon may be less than a maximum, wherein the maximum is the amount beyond which the activated carbon adsorbs more of the unripe essential oil and/or a desirable component than the first amount of chlorophyll.
  • the maximum is the amount necessary to remove at least about 70% of the first amount of chlorophyll in the unripe essential oil.
  • the maximum is the amount necessary to remove at least about 70% of the first amount of chlorophyll in the unripe essential oil.
  • the 135 maximum is the amount necessary to remove substantially all of the first amount of chlorophyll.
  • the maximum may be the amount necessary to remove at least about 50% of the first amount of chlorophyll without removing a threshold amount of a desirable component.
  • One skilled in the art may readily determine the maximum by various methods including but not limited to visual observation and
  • chlorophyll in essential oils catalyzes the conversion of gamma terpinene to para-cymene when stored under natural or artificial light.
  • PC/GT Ratio means the ratio of para-cymene to gamma terpinene. A higher PC/GT Ratio would indicate that there has been more conversion of gamma terpinene to para-cymene.
  • Conversion Rate means the ratio of an essential oil's (or product containing the essential oil)'s PC/GT Ratio at day 25 to the PC/GT Ratio at day 2 when the
  • essential oil or the product containing the essential oil has been at least intermittently stored under natural or artificial light.
  • a higher Conversion Rate would correlate with a faster rate of conversion from gamma terpinene to para- cymene.
  • Alternative embodiments of the present invention encompass a method of extending the shelf life of a first edible product comprising an essential oil, comprising obtaining an unripe essential oil derived from a plant source, wherein the Conversion Rate of the unripe essential oil may be at least about 3.0, contacting the unripe essential oil with an effective amount of an activated carbon to produce a
  • the Conversion Rate of the treated essential oil may be less than about 2.5, separating the activated carbon from the treated essential oil, and utilizing the treated essential oil in the first edible product.
  • the Conversion Rate of the treated essential oil may be less than about 2.0. More preferably, the Conversion Rate of the treated essential oil may be less than about 165 1.5.
  • the Conversion Rate of the first edible product may be similar to the Conversion Rate of a second edible product comprising a ripe essential oil derived from the same plant source.
  • the unripe essential oil comprises a first amount of chlorophyll and the 170 treated essential oil comprises a second amount of chlorophyll, wherein the second amount of chlorophyll may be less than the first amount of chlorophyll.
  • the treated essential oil may be substantially free of chlorophyll.
  • One skilled in the art may determine the Conversion Rate of an edible product 175 containing an essential oil by various analytical methods including but not limited to purge/trap gas chromatography-mass spectrometry (GC/MS), headspace GC/MS, solid phase microextraction GC/MS, and purge/trap gas chromatography-flame ionization detector.
  • GC/MS purge/trap gas chromatography-mass spectrometry
  • headspace GC/MS headspace GC/MS
  • solid phase microextraction GC/MS solid phase microextraction GC/MS
  • purge/trap gas chromatography-flame ionization detector purge/trap gas chromatography-flame ionization detector.
  • the unripe essential oil may be a citrus oil.
  • Citrus oils suitable for use with the embodiments of this invention include lemon oil, orange oil, lime oil, grapefruit oil, tangerine oil, mandarin oil, bitter orange oil, and bergamot oil.
  • the citrus oil may be a
  • the effective amount of the activated carbon may be at least 5 wt% of the mandarin oil. Even more preferably, the effective amount of the activated carbon may be less than about 13 wt% of the mandarin oil.
  • citrus oils may also be used for other essential oils including but not limited to, peel oils, leaf oils such as mint oils, spice oils such as clove oil, flower oils such as rose oil, and other plant oils.
  • essential oils may be derived or extracted from whole fruit or portions thereof using available equipment and known methods including but not limited to
  • cold-pressing and machine abrasion techniques the plant source is manipulated to help release the oil and then pressed or otherwise manipulated to help remove the oil from the plant material.
  • the oil may then be separated from the plant material by methods such as centrifugation, filtration, decanting, distillation, and solvent extraction.
  • the second amount of chlorophyll may be substantially less than the first amount of chlorophyll.
  • the second amount of chlorophyll may be at least about 50% less or at
  • the first and second amount of chlorophyll may readily determine the first and second amount of chlorophyll by such methods including but not limited to visual assessment, liquid or gas chromatography, sensory testing, thin-layer chromatography, nuclear magnetic resonance (NMR) spectroscopy, and UV-
  • Activated Carbon a used in the present invention may be obtained from commercial sources such as Carbon Activated Corporation (Orchard Park, NY)
  • Mead/Westvaco examples include but are not limited to
  • the activated carbon may be utilized by any method that ensures intimate contact between the activated carbon and the unripe essential oil.
  • the unripe essential oil and an activated carbon may be combined in a mixer to form a slurry.
  • the treated essential oil may be separated from the activated by various methods including but not limited to filtration, sedimentation and centrifugation.
  • the unripe essential oil may be treated by passing it through a column containing the activated carbon.
  • the unripe essential oil may be injected or poured onto the column and the treated essential oil may be eluted from the column, optionally, under pressure.
  • Such methods may be performed in batch or continuous modes with replacement or 230 regeneration of the activated carbon as needed.
  • the activated carbon may have a surface area between about 150 m 2 /g to about 2000 m 2 /g.
  • the activated carbon may have a surface area between about 1400 m 2 /g and about 1800 m 2 /g.
  • adsorbent materials may be used, including but not limited to amorphous silicas, bleaching earth, fuller's earth, and diatomaceous earth (alternately known as diatomite, diahydro, kieselguhr, kieselgur and celite).
  • amorphous silicas bleaching earth, fuller's earth, and diatomaceous earth (alternately known as diatomite, diahydro, kieselguhr, kieselgur and celite).
  • diatomaceous earth alternatively known as diatomite, diahydro, kieselguhr, kieselgur and celite.
  • One skilled in the art may determine the preferred adsorbent material
  • the activated carbon may be used to extract other components (desirable or not) in the unripe essential oils, some of which may be separated from the activated carbon and used in other applications.
  • Particular embodiments of the present invention encompass a method for extracting a component from an unripe essential oil, comprising obtaining an 255 unripe essential oil, wherein the unripe essential oil comprises at least one component, contacting the unripe essential oil with an effective amount of an activated carbon to produce a treated essential oil, wherein the at least one component is adsorbed by the activated carbon, and separating the activated carbon from the treated essential oil.
  • the at least one component may be 260 selected from a chlorophyll, a flavonoid, and a desirable component. More preferably, the method comprises recovering the at least one component from the activated carbon. Even more preferably, the method further comprises utilizing the at least one component recovered from the activated carbon in an edible product. In some embodiments, the at least one component may be a flavonoid. Preferably,
  • the method comprises recovering the flavonoid from the activated carbon with a polar solvent.
  • the polar solvent may be selected from an acetone, an ethanol, and a dichloromethane.
  • the method further comprises washing the activated carbon with a nonpolar solvent prior to recovering the flavonoid from the activated carbon.
  • the at least one component may be a desirable component and the effective amount of the activated carbon may be less than a maximum, wherein the maximum is the amount necessary to remove a threshold amount of the desirable component.
  • the method comprises recovering the desirable
  • the method further comprises washing the activated carbon with a nonpolar solvent prior to recovering the desirable component from the activated carbon.
  • one skilled in the art may also consider additional factors such as the amount of the component desired to be removed from the unripe essential oil, the adsorption efficiency, and the degree of difficulty or costs or time for recovering the component from the activated carbon. Similar to the detection and measurement of chlorophyll, one skilled in the art may 285 readily determine the amount of the component adsorbed by the activated carbon or the amount of the component in the unripe essential oil and/or the treated essential oil by various methods including but not limited to visual assessment, sensory testing, liquid or gas chromatography, UV-Vis spectrophotometry.
  • embodiments of the present invention may encompass a one -stage treatment method comprising removing a first predetermined amount of the chlorophyll and a second predetermined amount of a component other than chlorophyll with an effective amount of activated carbon.
  • embodiments of the present invention may encompass a two-stage treatment method comprising removing a first predetermined amount of the chlorophyll with an effective amount of a first activated carbon and then removing a second predetermined amount of a component other than chlorophyll with an effective amount of a second activated carbon or another suitable adsorbent material.
  • 300 stage treatments may also be set up if more than one component other than chlorophyll is desired to be removed from the unripe essential oil.
  • the first activated carbon and the second activated carbon may be the same activated carbon if the first activated carbon comprising the chlorophyll would be
  • Another advantage of the present invention is that the chlorophyll adsorbed by the activated carbon is not easily extracted from the activated carbon. Hence, the same activated carbon may be used to adsorb both chlorophyll and other components without chlorophyll reoccurring in the unripe essential oil or the other
  • the treated essential oils or the components of the treated essential oil are preserved by drying, cooling, or freezing for subsequent use or are immediately added to other compositions, e.g., drinks, foods, perfumes, medications, or the like.
  • the 315 components of the essential oil composition can be further prepared or treated, for example, by concentration, separation, or purification (if more than one component is present).
  • Table 1 shows the Conversion Rate and PC/GT Ratio of each sample at day 2, day 5, day 15, day 22, and day 25.
  • Samples 1 to 4 reveal that beverages utilizing unripe mandarin oils had Conversion Rates greater than 3.0 when they were stored under light while identical samples stored without exposure to light had Conversion Rates less than 2.0.
  • the content of the chlorophyll varies and thus the
  • Table 2 shows the Conversion Rate and PC/GT Ratio of each sample at day 2, day 5, day 15, day 22, and day 25.
  • Table 2 PC/GT Ratio and Conversion Rate of Beverages Made with Treated Mandarin Oils at Varying Amount of Activated Carbon
  • Table 2 shows that the Conversion Rates of unripe mandarin oil treated with at least 5 wt% of activated carbon are lower than 2.0, regardless of whether the samples were stored with or without exposure to light.
  • the Conversion Rates of samples containing the treated unripe mandarin oils are significantly lower than the Conversion Rates of samples containing untreated unripe mandarin oils.
  • the Conversion Rates of samples containing the treated unripe mandarin oils are similar to the Conversion Rates of samples containing the ripe mandarin oils.
  • the treated unripe mandarin oils can be a viable substitute for the more expensive ripe mandarin oils in many products without affecting the organoleptic properties of the products.
  • Table 2 also shows that the higher the amount of activated carbon used, the lower the Conversion Rate. Depending on the applications, one skilled in the art may readily adjust the amount of activated carbon for contacting the unripe essential oil to produce a treated essential oil suitable for the application. It should be understood that the foregoing relates to particular embodiments of the present invention and that numerous changes may be made therein without departing from the scope of the invention as defined by the following claims.
  • compositions, apparatus, and methods of the appended claims are not limited in scope by the specific compositions, apparatus, methods, and examples described herein, which are intended as illustrations of a few aspects of the compositions, apparatus, and methods of the claims and any compositions, apparatus, and methods

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Edible Oils And Fats (AREA)
  • Fats And Perfumes (AREA)

Abstract

Cette invention concerne des procédés permettant d’améliorer la stabilité et la durée de conservation des huiles essentielles obtenues avec des baies non mûres sans changer sensiblement les propriétés organoleptiques autres que la couleur du produit. Les procédés consistent à obtenir une huile essentielle obtenue avec des baies non mûres à l’aide d’une première quantité de chlorophylle, à mettre en contact cette huile essentielle avec du charbon activé pour obtenir une huile essentielle traitée à l’aide d’une seconde quantité de chlorophylle qui est inférieure à la première quantité de chlorophylle, et à séparer l’huile essentielle traitée du charbon activé.
PCT/US2010/029324 2009-06-25 2010-03-31 Huile essentielle obtenue avec des baies non mûres dotée d’une plus grande stabilité et d’une meilleure qualité d’emploi, et procédé de production associé WO2010151355A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU2010263197A AU2010263197A1 (en) 2009-06-25 2010-03-31 Unripe essential oil with enhanced stability and usability and method for producing such oil
EP10792474A EP2446007A1 (fr) 2009-06-25 2010-03-31 Huile essentielle obtenue avec des baies non mûres dotée d une plus grande stabilité et d une meilleure qualité d emploi, et procédé de production associé
MX2012000101A MX2012000101A (es) 2009-06-25 2010-03-31 Aceite esencial de frutos sin madurar con estabilidad y utilidad mejoradas y metodo para producir dicho aceite.
CA2766255A CA2766255A1 (fr) 2009-06-25 2010-03-31 Huile essentielle obtenue avec des baies non mures dotee d'une plus grande stabilite et d'une meilleure qualite d'emploi, et procede de production associe
BRPI1015065A BRPI1015065A2 (pt) 2009-06-25 2010-03-31 óleo essencial não maduro com estabilidade e usabilidade itensificadas e método para produzir esse óleo
CN2010800357926A CN102459548A (zh) 2009-06-25 2010-03-31 具有增强的稳定性和可用性的未成熟的精油和制备这种油的方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
PCT/US2009/048643 WO2010002696A1 (fr) 2008-06-30 2009-06-25 Traitement d’huiles essentielles
USPCT/US2009/048643 2009-06-25

Publications (1)

Publication Number Publication Date
WO2010151355A1 true WO2010151355A1 (fr) 2010-12-29

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PCT/US2010/029324 WO2010151355A1 (fr) 2009-06-25 2010-03-31 Huile essentielle obtenue avec des baies non mûres dotée d’une plus grande stabilité et d’une meilleure qualité d’emploi, et procédé de production associé

Country Status (7)

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EP (1) EP2446007A1 (fr)
CN (1) CN102459548A (fr)
AU (1) AU2010263197A1 (fr)
BR (1) BRPI1015065A2 (fr)
CA (1) CA2766255A1 (fr)
MX (1) MX2012000101A (fr)
WO (1) WO2010151355A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106922844B (zh) * 2015-12-30 2021-05-04 丰益(上海)生物技术研发中心有限公司 具有减少油烟的浓香菜籽油油脂组合物

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4049520A (en) * 1976-03-19 1977-09-20 Petrolite Corporation Color improvement process for organic liquid
US5336794A (en) * 1986-05-14 1994-08-09 W. R. Grace & Co.-Conn. Dual phase adsorption and treatment of glyceride oils
US5433949A (en) * 1992-03-11 1995-07-18 Skw Trostberg Aktiengesellschaft Process for the production of natural antioxidants
JPH07197076A (ja) * 1993-12-30 1995-08-01 Honen Corp 食用植物原油の精製法
WO2007001697A1 (fr) * 2005-06-21 2007-01-04 The Coca-Cola Company Procede d'elimination de contaminants dans des huiles essentielles

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4049520A (en) * 1976-03-19 1977-09-20 Petrolite Corporation Color improvement process for organic liquid
US5336794A (en) * 1986-05-14 1994-08-09 W. R. Grace & Co.-Conn. Dual phase adsorption and treatment of glyceride oils
US5433949A (en) * 1992-03-11 1995-07-18 Skw Trostberg Aktiengesellschaft Process for the production of natural antioxidants
JPH07197076A (ja) * 1993-12-30 1995-08-01 Honen Corp 食用植物原油の精製法
WO2007001697A1 (fr) * 2005-06-21 2007-01-04 The Coca-Cola Company Procede d'elimination de contaminants dans des huiles essentielles

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Publication number Publication date
CA2766255A1 (fr) 2010-12-29
CN102459548A (zh) 2012-05-16
AU2010263197A1 (en) 2012-01-19
MX2012000101A (es) 2012-02-28
EP2446007A1 (fr) 2012-05-02
BRPI1015065A2 (pt) 2016-04-19

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