WO2013070058A1 - A process for extracting phytonutrients in palm oil - Google Patents
A process for extracting phytonutrients in palm oil Download PDFInfo
- Publication number
- WO2013070058A1 WO2013070058A1 PCT/MY2012/000269 MY2012000269W WO2013070058A1 WO 2013070058 A1 WO2013070058 A1 WO 2013070058A1 MY 2012000269 W MY2012000269 W MY 2012000269W WO 2013070058 A1 WO2013070058 A1 WO 2013070058A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- phytonutrients
- extracting
- mixture
- polar solvent
- palm oil
- Prior art date
Links
- 235000019482 Palm oil Nutrition 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 18
- 239000002540 palm oil Substances 0.000 title claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 15
- 238000013019 agitation Methods 0.000 claims abstract description 12
- DFUSDJMZWQVQSF-XLGIIRLISA-N (2r)-2-methyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol Chemical class OC1=CC=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 DFUSDJMZWQVQSF-XLGIIRLISA-N 0.000 claims abstract description 8
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims abstract description 8
- GJJVAFUKOBZPCB-ZGRPYONQSA-N (r)-3,4-dihydro-2-methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2h-1-benzopyran-6-ol Chemical class OC1=CC=C2OC(CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-ZGRPYONQSA-N 0.000 claims abstract description 8
- 229930182558 Sterol Natural products 0.000 claims abstract description 8
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001746 carotenes Chemical class 0.000 claims abstract description 8
- 235000005473 carotenes Nutrition 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229940031439 squalene Drugs 0.000 claims abstract description 8
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000003432 sterols Chemical class 0.000 claims abstract description 8
- 235000003702 sterols Nutrition 0.000 claims abstract description 8
- 229930003799 tocopherol Natural products 0.000 claims abstract description 8
- 239000011732 tocopherol Substances 0.000 claims abstract description 8
- 125000002640 tocopherol group Chemical class 0.000 claims abstract description 8
- 235000019149 tocopherols Nutrition 0.000 claims abstract description 8
- 229930003802 tocotrienol Natural products 0.000 claims abstract description 8
- 239000011731 tocotrienol Substances 0.000 claims abstract description 8
- 235000019148 tocotrienols Nutrition 0.000 claims abstract description 8
- 229940068778 tocotrienols Drugs 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 229930186217 Glycolipid Natural products 0.000 claims abstract description 5
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 5
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 238000001035 drying Methods 0.000 claims abstract description 3
- 238000002156 mixing Methods 0.000 claims abstract description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 8
- 230000001476 alcoholic effect Effects 0.000 claims description 7
- 239000005515 coenzyme Substances 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 abstract 1
- 235000017471 coenzyme Q10 Nutrition 0.000 abstract 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 230000008821 health effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- 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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates to a process for extracting phytonutrients in palm oil.
- Crude palm oil consists of 99% glycerides and fatty acids and 1 % of minor components.
- the minor components commonly found in CPO are namely, carotenes, tocols, tocopherols and tocotrienols, sterols, squalene, coenzyme Qjo, phospholipids and glycolipids.
- the minor components are also termed as phytonutrients as they have been found to exhibit beneficial health properties such being anti-oxidative and anti cancer.
- the minor components can be extracted and recovered from the CPO by various methods. However, these methods call for tedious and time consuming procedures. A more rapid process is thus favorable for the extraction and recovery of the palm minor components.
- the present invention relates to a process for extracting minor components in palm oil.
- the minor components are known as phytonutrients.
- the phytonutrients includes carotenes, tocols, tocopherols and tocotrienols, sterols, squalene, coenzyme Qio, phospholipids and glycolipids.
- the process for extracting phytonutrients includes the steps of: i) mixing the palm oil with alcoholic solution and base catalyst, (ii) heating the mixture obtained from step (i) between 1 to 20 minutes using microwave with frequencies between 200MHz to 300GHz; (iii) cooling the mixture obtained from step (ii) to room temperature; (iv) adding non-polar solvent into the mixture obtained from step (iii) and the mixture is agitated wherein a top layer and bottom layer are formed; (v) subjecting the bottom layer to agitation with non-polar solvent; (vi) repeating step (v) to the bottom layer formed in step (v) and subsequent bottom layers that are formed by adding non-polar solvent and followed by agitation until the upper layer turns pale yellow in color; (vii) drying the upper layers obtained from step (iv), (v) and (vi).
- the dried portion consists of the minor components.
- the minor components are such as carotenes, tocols (tocopherols and tocotrienols), sterols and squalene.
- the alcoholic solution is selected from ethanol, methanol or combination of ethanol and methanol.
- the base catalyst is selected from potassium hydroxide or sodium hydroxide.
- the non polar solvent is selected from hexane, heptane or cyclohexane.
- the present invention relates to a process for extracting minor components in palm oil.
- the minor components are such as carotenes, tocols, tocopherols and tocotrienols, sterols, squalene, coenzyme Qio, phospholipids and glycolipids.
- the minor components are known as phytonutrients.
- Crude palm oil is first mixed with an alcoholic solution and a base catalyst. The mixture is then subjected to reaction under microwave heating for several minutes (between 1-20 minutes). The microwave heating is performed using a frequency range between 200MHz to 300GHz. Crude palm oil is reacted with an alcohol solution and base catalyst, converting the crude palm oil to esters. Minor components, i.e. phytonutrients which remain un-reacted are then extracted from the resultant mixture obtained after the microwave heating through solvent extraction.
- the mixture After the microwave heating, the mixture is cooled to room temperature and a known amount ( ⁇ 100mL) of non-polar solvent is then added. Upon agitation and left to rest, the mixture forms two layers in which upper layer is kept aside while lower layer is re-extracted with the non polar solvent until it turns into pale yellow in color. The pooled upper layers are then washed with water and dried to zero percent moisture content. The dried portion consists of the said minor components.
- the alcoholic solution is selected from ethanol, methanol or combination of ethanol and methanol. Any alcoholic solution can be used in the present invention.
- the base catalyst is selected from potassium hydroxide or sodium hydroxide.
- the non- polar solvent is selected from hexane, heptane or cyclohexane.
- Example 1 30mL absolute ethanol and 5mL 50% potassium hydroxide are added to 5.0g crude palm oil in a flat round bottom flask. The mixture is then placed in an 800 watt, 2450 MHz microwave oven. The mixture is then let to react in the microwave for 6 minutes. Thereafter the mixture is left to cool to room temperature. lOOmL hexane is added into the mixture and agitated and left to rest. Two layers are then formed. Upper layer is kept aside while lower layer is again subjected to agitation with hexane. This step is repeated till the upper layer of the re-extracted portion turns pale yellow in color. All the upper layers obtained are then pooled and dried. The dried portion contains the minor components as indicated in Table 1. Table 1 : Minor Components Recovered in the Dried Portion
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Mycology (AREA)
- Food Science & Technology (AREA)
- Botany (AREA)
- General Chemical & Material Sciences (AREA)
- Nutrition Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201280055427.0A CN104039169B (zh) | 2011-11-11 | 2012-11-09 | 提取棕榈油中植物营养素的方法 |
MYPI2015000742A MY192728A (en) | 2011-11-11 | 2012-11-09 | A process for extracting phytonutrients in palm oil |
SG11201402286SA SG11201402286SA (en) | 2011-11-11 | 2012-11-09 | A process for extracting phytonutrients in palm oil |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MYPI2011005478 | 2011-11-11 | ||
MYPI2011005478 | 2011-11-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2013070058A1 true WO2013070058A1 (en) | 2013-05-16 |
Family
ID=48290347
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/MY2012/000269 WO2013070058A1 (en) | 2011-11-11 | 2012-11-09 | A process for extracting phytonutrients in palm oil |
Country Status (4)
Country | Link |
---|---|
CN (1) | CN104039169B (zh) |
MY (1) | MY192728A (zh) |
SG (1) | SG11201402286SA (zh) |
WO (1) | WO2013070058A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015183069A1 (en) * | 2014-05-29 | 2015-12-03 | Malaysian Palm Oil Board (Mpob) | A process to enhance the concentration of tocols from palm oil |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6610867B2 (en) * | 2000-08-10 | 2003-08-26 | Renessen Llc | Corn oil processing and products comprising corn oil and corn meal obtained from corn |
US20050101820A1 (en) * | 2002-08-20 | 2005-05-12 | May Choo Y. | Recovery of palm phytonutrients |
US20050250953A1 (en) * | 2002-08-20 | 2005-11-10 | May Choo Y | Extraction of palm vitamin E, phytosterols and squalene from palm oil |
US7161055B2 (en) * | 2002-11-27 | 2007-01-09 | Malaysian Palm Oil Board | 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 |
-
2012
- 2012-11-09 SG SG11201402286SA patent/SG11201402286SA/en unknown
- 2012-11-09 WO PCT/MY2012/000269 patent/WO2013070058A1/en active Application Filing
- 2012-11-09 CN CN201280055427.0A patent/CN104039169B/zh not_active Expired - Fee Related
- 2012-11-09 MY MYPI2015000742A patent/MY192728A/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6610867B2 (en) * | 2000-08-10 | 2003-08-26 | Renessen Llc | Corn oil processing and products comprising corn oil and corn meal obtained from corn |
US20050101820A1 (en) * | 2002-08-20 | 2005-05-12 | May Choo Y. | Recovery of palm phytonutrients |
US20050250953A1 (en) * | 2002-08-20 | 2005-11-10 | May Choo Y | Extraction of palm vitamin E, phytosterols and squalene from palm oil |
US7161055B2 (en) * | 2002-11-27 | 2007-01-09 | Malaysian Palm Oil Board | 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 |
Non-Patent Citations (1)
Title |
---|
CHOW, MEE CHIN ET AL.: "Processing of fresh palm fruits using microwaves", JOURNAL OF MICROWAVE POWER AND ELECTROMAGNETIC ENERGY, vol. 40, no. 3, 17 April 2007 (2007-04-17), pages 165 - 173 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015183069A1 (en) * | 2014-05-29 | 2015-12-03 | Malaysian Palm Oil Board (Mpob) | A process to enhance the concentration of tocols from palm oil |
CN106661497A (zh) * | 2014-05-29 | 2017-05-10 | 马来西亚棕榈油局 | 提高源自棕榈油的母育酚的浓度的方法 |
Also Published As
Publication number | Publication date |
---|---|
MY192728A (en) | 2022-09-05 |
CN104039169A (zh) | 2014-09-10 |
SG11201402286SA (en) | 2014-10-30 |
CN104039169B (zh) | 2016-06-29 |
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