WO2015183069A1 - A process to enhance the concentration of tocols from palm oil - Google Patents
A process to enhance the concentration of tocols from palm oil Download PDFInfo
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- WO2015183069A1 WO2015183069A1 PCT/MY2015/000037 MY2015000037W WO2015183069A1 WO 2015183069 A1 WO2015183069 A1 WO 2015183069A1 MY 2015000037 W MY2015000037 W MY 2015000037W WO 2015183069 A1 WO2015183069 A1 WO 2015183069A1
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- tocols
- oil layer
- mixture
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- water soluble
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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
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
-
- 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
- C11B11/00—Recovery or refining of other fatty substances, e.g. lanolin or waxes
-
- 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
- C11B3/00—Refining fats or fatty oils
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
-
- 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
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
Definitions
- the present invention relates to a process to enhance the concentration of tocols from palm oil. More particularly, the present invention relates to a process to enhance the concentration of tocols from palm oil to at least more than 50%, preferably at least 70%.
- Tocotrienols rich fraction that is obtained from various palm sources, i.e. palm fatty acid distillates and crude palm oil, consists mainly of tocols (tocopherols and tocotrienols) as well as other impurities.
- the concentration of tocols in the TRF ranges from 10 - 50%. This is termed as "low range TRF". Higher concentration (>70%) of the tocols are favourable for various applications; cosmetics, nutraceuticals, food and pharmaceuticals.
- TRF of high concentrations is also the pre-cursor for the isolation and recovery of individual tocotrienols ( ⁇ -, ⁇ - and ⁇ -) in high purity (>90%).
- the present invention provides a process to enhance the concentration of tocols from palm oil to at least more than 50%, preferably at least 70%, the process involves the steps of (a) reacting a low range tocotrienols rich fraction (TRF] with tocols content of 10-50% with an alcohol, a base and antioxidant in the dark at atmospheric pressure with temperature not more than 80°C, preferably 50-70°C, to form water soluble compounds, (b) adding a hydrophobic solvent to the mixture, (c) separating the water soluble compounds from the oil layer, (d) discarding the water soluble compounds from the oil layer, (e) rinsing tocols remained in the oil layer, (f) removing excess solvents from the tocols and (g) drying the tocols.
- TRF low range tocotrienols rich fraction
- the present invention relates to a process to produce tocols rich fraction (TRF) which contain tocols of no less than 70%.
- TRF tocols rich fraction
- the enhancement in the tocols content is necessary and brings with it much commercial value as the tocols are highly sought after compounds due to their anti-cancer, anti-oxidative and anti-inflammatory properties.
- the present invention relates to a process to enhance the concentration of tocols from palm oil to at least more than 50%, preferably at least 70%.
- TRF that is obtained from various palm sources, i.e. palm fatty acid distillates and crude palm oil, consists mainly of tocols (tocopherols and tocotrienols) as well as other impurities.
- the content of tocols in the TRF ranges from 10 - 50%. This is termed as 'low range TRF'.
- TRF of high tocols content is also the pre-cursor for the isolation and recovery of individual tocotrienols ( ⁇ -, ⁇ - and ⁇ -) in high purity (>90%). These individual tocotrienols, each play an important role in combating various cancers such as prostate, breasts and skin cancers.
- the present invention provides a process to enhance the concentration of tocols from palm oil to at least more than 50%, preferably at least 70%, the process involves the steps of [a] reacting a low range tocotrienols rich fraction (TRF) with tocols content of 10- 50% with an alcohol, a base and antioxidant in the dark at atmospheric pressure with temperature not more than 80°C, preferably 50-70°C, to form water soluble compounds, (b) adding a hydrophobic solvent to the mixture, (c) separating the water soluble compounds from the oil layer, (d) discarding the water soluble compounds from the oil layer, (e) rinsing tocols remained in the oil layer, (f) removing excess solvents from the tocols and (g) drying the tocols.
- TRF low range tocotrienols rich fraction
- the tocols may be derived from palm oil, palm based products or its derivatives.
- the tocols may be a mixture or an individual compound.
- the alcohol may be methanol, ethanol and/or isopropanol.
- the base may be a hydroxide.
- the hydrophobic solvent may be hexane, heptane and/or cyclohexane.
- low range TRF with tocols content of 10 - 50% reacts with an alcohol, a base and antioxidant in the dark. Reaction is carried out at atmospheric pressure with temperature not more than 80°C. As a result from the reaction, water soluble compounds are formed. These water soluble compounds were then separated from the oil layer and discarded. The tocols remained in the oil layer was then rinsed and dried. Analyses reveals that the tocols content in the final product is more than 70%.
- oil soluble impurities in the low range TRF are converted into water soluble compounds through a chemical reaction.
- the chemical reaction involves the use of an alcoholic solution, alkali catalyst and mild heating.
- the impurities in the low range TRF react with the alcoholic solution, with the help of the alkali catalyst, to form derivatives which are water soluble.
- the tocols remained unaffected.
- the conditions for the reaction are mild.
- the impurities now water soluble compounds
- the impurities can be separated from the tocols. This is carried out by liquid - liquid separation. Once separated, the water soluble derivatives are discarded, leaving the tocols.
- the concentration of the tocols is greatly enhanced, preferably at least 70%.
- the process of the present invention is economical and does not require any extreme conditions for reaction, i.e. temperature and pressure.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Abstract
The present invention relates to a process to enhance the concentration of tocols from palm oil. More particularly, the present invention relates to a process to enhance the concentration of tocols from palm oil to at least more than 50%, preferably at least 70%, the process involves the steps of (a) reacting a low range tocotrienols rich fraction (TRF) with tocols content of 10-50% with an alcohol, a base and antioxidant in the dark at atmospheric pressure with temperature not more than 80°C, preferably 50-70°C, to form water soluble compounds, (b) adding a hydrophobic solvent to the mixture, (c) separating the water soluble compounds from the oil layer, (d) discarding the water soluble compounds from the oil layer, (e) rinsing tocols remained in the oil layer, (f) removing excess solvents from the tocols and (g) drying the tocols.
Description
A PROCESS TO ENHANCE THE CONCENTRATION OF TOCOLS FROM PALM OIL
FIELD OF INVENTION The present invention relates to a process to enhance the concentration of tocols from palm oil. More particularly, the present invention relates to a process to enhance the concentration of tocols from palm oil to at least more than 50%, preferably at least 70%.
BACKGROUND OF INVENTION
Tocotrienols rich fraction (TRF) that is obtained from various palm sources, i.e. palm fatty acid distillates and crude palm oil, consists mainly of tocols (tocopherols and tocotrienols) as well as other impurities. The concentration of tocols in the TRF ranges from 10 - 50%. This is termed as "low range TRF". Higher concentration (>70%) of the tocols are favourable for various applications; cosmetics, nutraceuticals, food and pharmaceuticals. TRF of high concentrations is also the pre-cursor for the isolation and recovery of individual tocotrienols (α-, γ- and δ-) in high purity (>90%). These individual tocotrienols, each play an important role in combating various cancers such as prostate, breasts and skin cancers. Processes for the production of low range tocols have been disclosed in the past using technologies such as supercritical fluid technology (as disclosed in Canada Patent No. CA 2325224 and United States Patent No. US 8,003,144) and vacuum distillation (as disclosed in United States Patent No. US 7,141,712). There were also reports on inventions which describe methods for producing tocotrienols from palm sources. These include solvent - solvent extraction, short path distillation and extraction under supercritical state. However
these methods are able to produce tocotrienols with concentration up to 10% to 50% maximum.
SUMMARY OF THE INVENTION
Therefore, there is a need to provide a process to produce tocotrienols of concentration of tocotrienols higher than 50%.
Accordingly, the present invention provides a process to enhance the concentration of tocols from palm oil to at least more than 50%, preferably at least 70%, the process involves the steps of (a) reacting a low range tocotrienols rich fraction (TRF] with tocols content of 10-50% with an alcohol, a base and antioxidant in the dark at atmospheric pressure with temperature not more than 80°C, preferably 50-70°C, to form water soluble compounds, (b) adding a hydrophobic solvent to the mixture, (c) separating the water soluble compounds from the oil layer, (d) discarding the water soluble compounds from the oil layer, (e) rinsing tocols remained in the oil layer, (f) removing excess solvents from the tocols and (g) drying the tocols.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The present invention relates to a process to produce tocols rich fraction (TRF) which contain tocols of no less than 70%. The enhancement in the tocols content is necessary and brings with it much commercial value as the tocols are highly sought after compounds due to their anti-cancer, anti-oxidative and anti-inflammatory properties.
More particularly, the present invention relates to a process to enhance the concentration of tocols from palm oil to at least more than 50%, preferably at least 70%. The following detailed description is intended to provide example implementations to one of ordinary skill in the art, and is not intended to limit the invention to the explicit disclosure in the patent application, as one or ordinary skill in the art will understand that variations can be substituted that are within the scope of the invention as described. TRF that is obtained from various palm sources, i.e. palm fatty acid distillates and crude palm oil, consists mainly of tocols (tocopherols and tocotrienols) as well as other impurities. The content of tocols in the TRF ranges from 10 - 50%. This is termed as 'low range TRF'. Higher content (>70%) of the tocols are favourable for various applications; cosmetics, nutraceuticals, food and pharmaceuticals. TRF of high tocols content is also the pre-cursor for the isolation and recovery of individual tocotrienols (α-, γ- and δ-) in high purity (>90%). These individual tocotrienols, each play an important role in combating various cancers such as prostate, breasts and skin cancers.
Generally, the present invention provides a process to enhance the concentration of tocols from palm oil to at least more than 50%, preferably at least 70%, the process involves the
steps of [a] reacting a low range tocotrienols rich fraction (TRF) with tocols content of 10- 50% with an alcohol, a base and antioxidant in the dark at atmospheric pressure with temperature not more than 80°C, preferably 50-70°C, to form water soluble compounds, (b) adding a hydrophobic solvent to the mixture, (c) separating the water soluble compounds from the oil layer, (d) discarding the water soluble compounds from the oil layer, (e) rinsing tocols remained in the oil layer, (f) removing excess solvents from the tocols and (g) drying the tocols. The tocols may be derived from palm oil, palm based products or its derivatives. The tocols may be a mixture or an individual compound. The alcohol may be methanol, ethanol and/or isopropanol. The base may be a hydroxide. The hydrophobic solvent may be hexane, heptane and/or cyclohexane.
Specifically, low range TRF with tocols content of 10 - 50% reacts with an alcohol, a base and antioxidant in the dark. Reaction is carried out at atmospheric pressure with temperature not more than 80°C. As a result from the reaction, water soluble compounds are formed. These water soluble compounds were then separated from the oil layer and discarded. The tocols remained in the oil layer was then rinsed and dried. Analyses reveals that the tocols content in the final product is more than 70%.
In this process, oil soluble impurities in the low range TRF are converted into water soluble compounds through a chemical reaction. The chemical reaction involves the use of an alcoholic solution, alkali catalyst and mild heating. Upon heating, the impurities in the low range TRF react with the alcoholic solution, with the help of the alkali catalyst, to form derivatives which are water soluble. However, the tocols remained unaffected. The conditions for the reaction are mild. Thus, the tocotrienols remain intact and not destroyed or degraded.
Upon completion of the reaction, the impurities (now water soluble compounds) can be separated from the tocols. This is carried out by liquid - liquid separation. Once separated, the water soluble derivatives are discarded, leaving the tocols. Through this process, the concentration of the tocols is greatly enhanced, preferably at least 70%.
The process of the present invention is economical and does not require any extreme conditions for reaction, i.e. temperature and pressure.
EXAMPLES
Example 1
lOg pyrogallol. 3-mL 50% potassium hydroxide and 300mL ethanol were added into a flask containing 30g low range TRF (tocols content, ca. 30%). The mixture was reacted at 60°C in the dark for 1 hour. Upon refluxed, the mixture was cooled to room temperature and transferred to a funnel using ethanol, hot water, distilled water and hexane in sequence. The mixture was mixed with hexane and agitated. The aqueous layer of the mixture was then separated and discarded. The oil layer was collected and rinse with water till the washing water turned neutral (pH7). Excess solvent was removed from the oil layer. The oil layer was then analysed for its tocols content using a known analytical method. Analyses revealed that the content of tocols in the oil layer was more than 70%.
Example 2
lOg pyrogallol. 3-mL 50% potassium hydroxide and 300mL ethanol were added into a flask containing 30g low range TRF (tocols content, ca. 30%). The mixture was reacted at 70°C in the dark for 1 hour. Upon refluxed, the mixture was cooled to room temperature and transferred to a funnel using ethanol, hot water, distilled water and hexane in sequence.
The mixture was mixed with hexane and agitated. The aqueous layer of the mixture was then separated and discarded. The oil layer was collected and rinse with water till the washing water turned neutral (pH7). Excess solvent was removed from the oil layer. The oil layer was then analysed for its tocols content using a known analytical method. Analyses revealed that the content of tocols in the oil layer was more than 70%.
Example 3
lOg pyrogallol. 3-mL 50% potassium hydroxide and 300mL ethanol were added into a flask containing 30g low range TRF (tocols content, ca. 50%) . The mixture was reacted at 60°C in the dark for 1 hour. Upon refluxed, the mixture was cooled to room temperature and transferred to a funnel using ethanol, hot water, distilled water and hexane in sequence. The mixture was mixed with hexane and agitated. The aqueous layer of the mixture was then separated and discarded. The oil layer was collected and rinse with water till the washing water turned neutral (pH7). Excess solvent was removed from the oil layer. The oil layer was then analysed for its tocols content using a known analytical method. Analyses revealed that the content of tocols in the oil layer was more than 80%.
Example 4
lOg pyrogallol. 3-mL 50% potassium hydroxide and 300mL ethanol were added into a flask containing 30g low range TRF (tocols content, ca. 50%) . The mixture was reacted at 70°C in the dark for 1 hour. Upon refluxed, the mixture was cooled to room temperature and transferred to a funnel using ethanol, hot water, distilled water and hexane in sequence. The mixture was mixed with hexane and agitated. The aqueous layer of the mixture was then separated and discarded. The oil layer was collected and rinse with water till the washing water turned neutral (pH7). Excess solvent was removed from the oil layer. The oil
layer was then analysed for its tocols content using a known analytical method. Analyses revealed that the content of tocols in the oil layer was more than 80%.
Example 5
lOg pyrogallol. 3-mL 50% potassium hydroxide and 300mL methanol were added into a flask containing 30g low range TRF (tocols content, ca. 50%) . The mixture was reacted at 70°C in the dark for 1 hour. Upon refluxed, the mixture was cooled to room temperature and transferred to a funnel using ethanol, hot water, distilled water and hexane in sequence. The mixture was mixed with hexane and agitated. The aqueous layer of the mixture was then separated and discarded. The oil layer was collected and rinse with water till the washing water turned neutral (pH7). Excess solvent was removed from the oil layer. The oil layer was then analysed for its tocols content using a known analytical method. Analyses revealed that the content of tocols in the oil layer was more than 80%. Example 6
lOg pyrogallol. 3-mL 50% potassium hydroxide and 300mL isopropanol were added into a flask containing 30g low range TRF (tocols content, ca. 50%) . The mixture was reacted at 70°C in the dark for 1 hour. Upon refluxed, the mixture was cooled to room temperature and transferred to a funnel using ethanol, hot water, distilled water and hexane in sequence. The mixture was mixed with hexane and agitated. The aqueous layer of the mixture was then separated and discarded. The oil layer was collected and rinse with water till the washing water turned neutral (pH7). Excess solvent was removed from the oil layer. The oil layer was then analysed for its tocols content using a known analytical method. Analyses revealed that the content of tocols in the oil layer was more than 80%.
Example 7
lOg pyrogallol. 3-mL 50% potassium hydroxide and 300mL ethanol were added into a flask containing 30g low range TRF (tocols content, ca. 50%) . The mixture was reacted at 70°C in the dark for 1 hour. Upon refluxed, the mixture was cooled to room temperature and transferred to a funnel using ethanol, hot water, distilled water and hexane in sequence. The mixture was mixed with heptane and agitated. The aqueous layer of the mixture was then separated and discarded. The oil layer was collected and rinse with water till the washing water turned neutral (pH7). Excess solvent was removed from the oil layer. The oil layer was then analysed for its tocols content using a known analytical method. Analyses revealed that the content of tocols in the oil layer was more than 80%.
Example 8
lOg pyrogallol. 3-mL 50% potassium hydroxide and 300mL ethanol were added into a flask containing 30g low range TRF (tocols content, ca. 50%) . The mixture was reacted at 70°C in the dark for 1 hour. Upon refluxed, the mixture was cooled to room temperature and transferred to a funnel using ethanol, hot water, distilled water and hexane in sequence. The mixture was mixed with cyclohexane and agitated. The aqueous layer of the mixture was then separated and discarded. The oil layer was collected and rinse with water till the washing water turned neutral (pH7). Excess solvent was removed from the oil layer. The oil layer was then analysed for its tocols content using a known analytical method. Analyses revealed that the content of tocols in the oil layer was more than 80%.
As will be understood by those familiar with the art, the invention may be embodied in other specific forms without departing from essential characteristics thereof. Likewise, the particular naming and division of the components, procedures, methodologies and other
aspects are not mandatory or significant, and the mechanisms that implement the invention or its features may have different names, divisions and/or formats.
Accordingly, the disclosure of the present invention is intended to be illustrative, but not limiting, of the scope of the invention, which is set forth in the following claims.
Claims
1. A process to enhance the concentration of tocols from palm oil to at least more than 50%, preferably at least 70%, the process involves the steps of:
(a) reacting a low range tocotrienols rich fraction (TRF] with tocols content of 10-50% with an alcohol, a base and antioxidant in the dark at atmospheric pressure with temperature not more than 80°C, preferably 50-70°C, to form water soluble compounds;
(b) adding a hydrophobic solvent to the mixture;
(c) separating the water soluble compounds from the oil layer;
(d) discarding the water soluble compounds from the oil layer;
(e) rinsing tocols remained in the oil layer;
(f) removing excess solvents from the tocols; and
(g) drying the tocols.
2. The process as claimed in claim 1, wherein the tocols are derived from palm oil, palm based products or its derivatives.
3. The process as claimed in claim 1, wherein the tocols are a mixture or an individual compound.
4. The process as claimed in claim 1, whereby the alcohol is methanol, ethanol and/or isopropanol.
5. The process as claimed in claim 1, whereby the base is a hydroxide.
6. The process as claimed in claim 1, whereby the hydrophobic solvent is hexane, heptane and/or cyclohexane.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SG11201609983VA SG11201609983VA (en) | 2014-05-29 | 2015-05-22 | A process to enhance the concentration of tocols from palm oil |
CN201580031740.4A CN106661497A (en) | 2014-05-29 | 2015-05-22 | A process to enhance the concentration of tocols from palm oil |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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MYPI2014001558 | 2014-05-29 | ||
MYPI2014001558 | 2014-05-29 |
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WO2015183069A1 true WO2015183069A1 (en) | 2015-12-03 |
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PCT/MY2015/000037 WO2015183069A1 (en) | 2014-05-29 | 2015-05-22 | A process to enhance the concentration of tocols from palm oil |
Country Status (4)
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CN (1) | CN106661497A (en) |
MY (1) | MY178344A (en) |
SG (1) | SG11201609983VA (en) |
WO (1) | WO2015183069A1 (en) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4122094A (en) * | 1976-06-09 | 1978-10-24 | Lever Brothers Company | Separation of the isomers of tocopherol by liquid/solid chromatography |
US20040158083A1 (en) * | 2002-11-27 | 2004-08-12 | Choo Yuen May | Method of extracting and isolating minor components from vegetable oil |
US20070238886A1 (en) * | 2003-11-19 | 2007-10-11 | Ho David S S | Recovery of Phytonutrients from Oils |
WO2012039599A2 (en) * | 2010-09-22 | 2012-03-29 | Malaysian Palm Oil Board | Extraction of crude palm oil and phenolic compounds from oil palm fruitlets |
WO2013070058A1 (en) * | 2011-11-11 | 2013-05-16 | Malaysian Palm Oil Board | A process for extracting phytonutrients in palm oil |
-
2015
- 2015-05-22 WO PCT/MY2015/000037 patent/WO2015183069A1/en active Application Filing
- 2015-05-22 MY MYPI2016002070A patent/MY178344A/en unknown
- 2015-05-22 SG SG11201609983VA patent/SG11201609983VA/en unknown
- 2015-05-22 CN CN201580031740.4A patent/CN106661497A/en active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4122094A (en) * | 1976-06-09 | 1978-10-24 | Lever Brothers Company | Separation of the isomers of tocopherol by liquid/solid chromatography |
US20040158083A1 (en) * | 2002-11-27 | 2004-08-12 | Choo Yuen May | Method of extracting and isolating minor components from vegetable oil |
US20070238886A1 (en) * | 2003-11-19 | 2007-10-11 | Ho David S S | Recovery of Phytonutrients from Oils |
WO2012039599A2 (en) * | 2010-09-22 | 2012-03-29 | Malaysian Palm Oil Board | Extraction of crude palm oil and phenolic compounds from oil palm fruitlets |
WO2013070058A1 (en) * | 2011-11-11 | 2013-05-16 | Malaysian Palm Oil Board | A process for extracting phytonutrients in palm oil |
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Publication number | Publication date |
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MY178344A (en) | 2020-10-08 |
SG11201609983VA (en) | 2016-12-29 |
CN106661497A (en) | 2017-05-10 |
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