CA1102795A - Method of isolating polar lipids from a mixture of polar and non-polar cereal lipids - Google Patents
Method of isolating polar lipids from a mixture of polar and non-polar cereal lipidsInfo
- Publication number
- CA1102795A CA1102795A CA309,300A CA309300A CA1102795A CA 1102795 A CA1102795 A CA 1102795A CA 309300 A CA309300 A CA 309300A CA 1102795 A CA1102795 A CA 1102795A
- Authority
- CA
- Canada
- Prior art keywords
- polar
- lipids
- water
- mixture
- cereal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
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
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
- A21D2/16—Fatty acid esters
Abstract
Abstract: Cereal lipids are useful as an additive to dough in baking bread.
It is desired that such cereal lipids shall contain polar lipids, whereas non-polar lipids are not desired.
Polar lipids may be separated from non-polar lipids by mixing the cereal lipids with water, subjecting the mixture to gravity separation to form two oily phases and an inter-mediate aqueous phase, and separat-ing the heaviest oily phase which contains the major portion of the polar lipids.
It is desired that such cereal lipids shall contain polar lipids, whereas non-polar lipids are not desired.
Polar lipids may be separated from non-polar lipids by mixing the cereal lipids with water, subjecting the mixture to gravity separation to form two oily phases and an inter-mediate aqueous phase, and separat-ing the heaviest oily phase which contains the major portion of the polar lipids.
Description
" 11~2~795 The invention relates to a method for isolating polar cereal lipids from a mixture of polar and non-polar cereal lipids. The mixture of polar and non-polar lipids intended here is a lipid mixture such as can be recovered from cereals using known methods, Thus, wheat contains about 2% lipids, of which approximately half are polar, such as phospholipids and galactolipids, and half are non-polar~ primarily triglycerides.
These lipids can be recovered, e.g. by the extraction of flour with an organic solvent, or by centrifuging a flour-water--mixture. An effective extraction agent is water-saturated butanol, which has the ability of releasing the lipids from the flour to about 80%. Other useful extraction agents are chloroform, benzene-chloroform in a ratio of 1:1~ ethanol, ethanol-water with up to 90% water, and ethanol-diethylether--water in the ratio of 2:2:1. In the production of wheat starch there is obtained a residue of water-soluble proteins, gluten and lipids. From this residue the lipids can be isolated by extraction. Other cereals which can provide a lipid mixture useful as starting material for the invention are rye, triti-cale, barley oats and maize.
The product of polar lipids obtained according to theinvention is primarily intended to be used as an additive to foodstuffs. The product can with advantage replace the emul-gators now used in baking, e.g. stearyl-lactyl-lactate salts, tartaric ac;d esters and monoglycerides. They give the bread an improved cereal aroma and an increased volume, as well as an improved texture and storage ability. The good effect in baking of the polar cereal lipids is previously known, e.g. from Mac Ritchie, J. Sci. Fd Agric., 28, (1977), 53-58. Other uses are as an additive to starch-based foodstuffs, such as pastes,
These lipids can be recovered, e.g. by the extraction of flour with an organic solvent, or by centrifuging a flour-water--mixture. An effective extraction agent is water-saturated butanol, which has the ability of releasing the lipids from the flour to about 80%. Other useful extraction agents are chloroform, benzene-chloroform in a ratio of 1:1~ ethanol, ethanol-water with up to 90% water, and ethanol-diethylether--water in the ratio of 2:2:1. In the production of wheat starch there is obtained a residue of water-soluble proteins, gluten and lipids. From this residue the lipids can be isolated by extraction. Other cereals which can provide a lipid mixture useful as starting material for the invention are rye, triti-cale, barley oats and maize.
The product of polar lipids obtained according to theinvention is primarily intended to be used as an additive to foodstuffs. The product can with advantage replace the emul-gators now used in baking, e.g. stearyl-lactyl-lactate salts, tartaric ac;d esters and monoglycerides. They give the bread an improved cereal aroma and an increased volume, as well as an improved texture and storage ability. The good effect in baking of the polar cereal lipids is previously known, e.g. from Mac Ritchie, J. Sci. Fd Agric., 28, (1977), 53-58. Other uses are as an additive to starch-based foodstuffs, such as pastes,
- 2 - ~ -- , : :'-. ' .
~27~S
mashed potatoes, gruel, where the product gives the foodstuff a shorter texture. The inventlon relates to the removal ofnon-polarlipids from the total extract, since these counteract the desired effects in said products.
It is therefore desirable that the isolation of the polar lipids is so effective that these will contain at most 25 percent by weight of non-polar lipids.
The present invention provides a method for isolating polar lipids from a mix~ure of polar and non-polar cereal lipids comprising mixing the lipid mixture with water to such an amount that the lipid-water mixture contains at least 50 percent by weight of water, subjecting the mixture to a gravity separation of at least about 5000 g at a temperature in the range between about 25 to 50C until the phaseshave completely separated, and separating the heaviest oily phase obtained from the gr~vity separation, said phase containing the major portion of the polar lipids.
According to the invention, water preferably distilled water, is added to the lipid mixture, in such a quantity that the lipid-water mixture contains at least 50 percent by weight of water. We have found that 70 per-cent by weight of water is a suitable water content. If the water content is greater than 80 percent by weight, the volume of the mixture will be so large that there will be difficulties in the gravitational separation. The temp-erature of the mixture is preferably kept higher than 25C so that the desired phase will have a suitable consistency for handling. However, the temperature is preferably less than 50C to avoid fat oxidation. Phase equilibrium is achieved after 3-6 hours. The mixture is now subjected to gravity separation, preferably in a centrifugal separator. The centrifugal separation should be continued until two oily phases have been formed, separated by an aqueous phase. We prefer to centrifuge at least at 5000 g, which requires approximately 1-2 ~.~
~2795 hours for a complete separation of the phases. ~ complete sepa-ration can be achieved in approximately 20-30 minutes if the speed of the separator is increased to 10 000 g. The uppermost, lightest phase is an oil which is almost entirely composed of non-polar lipids primarily triglycerides but also minor quanti-ties of fatty acids, diglycerides and sterol esters. Under this phase there is a pure water phase. The undermost, heaviest phase is a mildly yelly-coloured oily phase containing the desired polar lipids. ~e have found, by means of thin layer chromato-graphy, that this phase mainly consists of galactolipids (mainlydigalactodiglycerides and a minor quantity of monogalactodigly-cerides) and phospholipids, subh as lecithin and lysolacithin.
Surprisingly, we have found that this phase contains a high con-tent of water, namely about 50-70 percent by weight, depending on the quantity of water added. In spite of this, the phase is not water-miscible. The heavy oil phase consists of a dispersion .... _ . .. .. . .. . ..... . . ....... .. . . . . . .. . .
of a lamellar liquid-chrystalline phase in a so-called L2-phase.
The L2-phase has been extensively studied in simple systems like sodium caprylate-decanol-water, and is often described as an in-versed micellar state, with water molecule aggregates in a con-tinuous hydrocarbon environment.
The content of non-polar lipids in the oily phase contain-ing the polar lipids can be reduced somewhat, e.g. from 25 to 10 percent by weight, if salt is added to the water which is
~27~S
mashed potatoes, gruel, where the product gives the foodstuff a shorter texture. The inventlon relates to the removal ofnon-polarlipids from the total extract, since these counteract the desired effects in said products.
It is therefore desirable that the isolation of the polar lipids is so effective that these will contain at most 25 percent by weight of non-polar lipids.
The present invention provides a method for isolating polar lipids from a mix~ure of polar and non-polar cereal lipids comprising mixing the lipid mixture with water to such an amount that the lipid-water mixture contains at least 50 percent by weight of water, subjecting the mixture to a gravity separation of at least about 5000 g at a temperature in the range between about 25 to 50C until the phaseshave completely separated, and separating the heaviest oily phase obtained from the gr~vity separation, said phase containing the major portion of the polar lipids.
According to the invention, water preferably distilled water, is added to the lipid mixture, in such a quantity that the lipid-water mixture contains at least 50 percent by weight of water. We have found that 70 per-cent by weight of water is a suitable water content. If the water content is greater than 80 percent by weight, the volume of the mixture will be so large that there will be difficulties in the gravitational separation. The temp-erature of the mixture is preferably kept higher than 25C so that the desired phase will have a suitable consistency for handling. However, the temperature is preferably less than 50C to avoid fat oxidation. Phase equilibrium is achieved after 3-6 hours. The mixture is now subjected to gravity separation, preferably in a centrifugal separator. The centrifugal separation should be continued until two oily phases have been formed, separated by an aqueous phase. We prefer to centrifuge at least at 5000 g, which requires approximately 1-2 ~.~
~2795 hours for a complete separation of the phases. ~ complete sepa-ration can be achieved in approximately 20-30 minutes if the speed of the separator is increased to 10 000 g. The uppermost, lightest phase is an oil which is almost entirely composed of non-polar lipids primarily triglycerides but also minor quanti-ties of fatty acids, diglycerides and sterol esters. Under this phase there is a pure water phase. The undermost, heaviest phase is a mildly yelly-coloured oily phase containing the desired polar lipids. ~e have found, by means of thin layer chromato-graphy, that this phase mainly consists of galactolipids (mainlydigalactodiglycerides and a minor quantity of monogalactodigly-cerides) and phospholipids, subh as lecithin and lysolacithin.
Surprisingly, we have found that this phase contains a high con-tent of water, namely about 50-70 percent by weight, depending on the quantity of water added. In spite of this, the phase is not water-miscible. The heavy oil phase consists of a dispersion .... _ . .. .. . .. . ..... . . ....... .. . . . . . .. . .
of a lamellar liquid-chrystalline phase in a so-called L2-phase.
The L2-phase has been extensively studied in simple systems like sodium caprylate-decanol-water, and is often described as an in-versed micellar state, with water molecule aggregates in a con-tinuous hydrocarbon environment.
The content of non-polar lipids in the oily phase contain-ing the polar lipids can be reduced somewhat, e.g. from 25 to 10 percent by weight, if salt is added to the water which is
3 added to the lipid extract. The salt content of the water is suitably 0 4 - 4 percent by weight, and the salt is suitably a halogen salt of an alkali metal.
~xample This example deals with the production of a lipid mixture from wheat flour, isolatlon of polar lipids, and use of the polar .
.
- , : :
- .,, - - . . ':
' ' ' ' ' ' ' - ~
,, : - : .
lipids in bal~ -A._ _ro(ll_t;on of lip;ds _om wheat flour.
10 kg of wheat flour was mixed in a mixer with 40 kg water-saturated butanol. The mixer was run for 2 hours. The temperature of the mixture was 20-25C. The mixture was trans-ferred to a centrifugal separator and centrifu~ed at 1800 g for one hour, after which time about 35 liters of liquid was - obtained. The liquid was evaporated by heating at 50C, and a dry residue weighing about 16~ g was obtained. With regard to use in foodsturfs it is important that the evaporation is com-plete, so that no organic solvent remains in the lipid mixture.
B. Isolation of polar lipids.
300 g of a lipid mixture of the kind produced according to step A was mixed with 700 g distilled water and agitated un-til an apparently homogenous mixture was obtained. The mixture was allowed to stand for 4 hours at 30C without stirring. It was subsequently transferred to a centrifugal separator and centrifuged at 5~00 g for 1 hour. Two oily phases were obtained, separated by a water stratum. The heaviest oily phase was sepa-rated and was found to have a volume of 750 ml and a water con-tent of 70 %.
C Baking.
Baking experiments were carried out according to the standardized method prescribed by the Swedish Seed Association, Or Svalov ? Sweden. The w~leat f]our was a so-called bakery mix-ture produced by the Swedish milling Iirm of Kungsornen. The fermenting and bakin~ ovens used were made by the British firm of Simons. The polar wheat lipids produced according to step B
were added to an amount of 0.83 percent by weight of the amount of flour. For comparison~ bread was baked (1) with an equally large addition of sodium stearyl-lactyl-lactate, and (2) with-. . ., . ~ .. . ... . . . _ . .. _ -. .
. . , , - , . ., ~ :
, . . - . . . . . , . - .
` 1'1~Z73S
out any ext,ra emulgator additive. The following results were obtained. Porosity is given in a scale of 1-8, where the high-est numeral denotes fine porosity. The elasticity of the crumb, i.e. the soft-inner portion of the bread, is given in a scale of 1-6, where 6 denotes very good elasticity. The appearance of the bread is given in a scale of 1-4 where 1 is the best value and denotes a faultless appearance.
Bread additive Bread Poro- Crumb Appear- Time to un-volume sity elasti- ance acceptable city hardness ml days -No additive 410 6 4 1 4 - Sodium stearyl-lactyl-lactate o.83% of flour quantity 480 6 2 1 4 Polar wheat lipids according to invention 0.83% of flour quantity 490 6 6 1 6 It was also noted that the texture of the crumb and the taste of the baked bread was superior for the baking batch containing the polar wheat lipids. It is well known that the addition of a con-ventional emulgator reduces the elasticity of the crumb, which was very clearly demonstrated by our comparative experiment. The polar wht?at lipitls gave no such bad effects, but produced a superior elasticity of the crumb.
.
: -: - : . .
:, .. . ~ -... . - .:
.. . . . :.
- : . . . . . . . . .
:
.
,
~xample This example deals with the production of a lipid mixture from wheat flour, isolatlon of polar lipids, and use of the polar .
.
- , : :
- .,, - - . . ':
' ' ' ' ' ' ' - ~
,, : - : .
lipids in bal~ -A._ _ro(ll_t;on of lip;ds _om wheat flour.
10 kg of wheat flour was mixed in a mixer with 40 kg water-saturated butanol. The mixer was run for 2 hours. The temperature of the mixture was 20-25C. The mixture was trans-ferred to a centrifugal separator and centrifu~ed at 1800 g for one hour, after which time about 35 liters of liquid was - obtained. The liquid was evaporated by heating at 50C, and a dry residue weighing about 16~ g was obtained. With regard to use in foodsturfs it is important that the evaporation is com-plete, so that no organic solvent remains in the lipid mixture.
B. Isolation of polar lipids.
300 g of a lipid mixture of the kind produced according to step A was mixed with 700 g distilled water and agitated un-til an apparently homogenous mixture was obtained. The mixture was allowed to stand for 4 hours at 30C without stirring. It was subsequently transferred to a centrifugal separator and centrifuged at 5~00 g for 1 hour. Two oily phases were obtained, separated by a water stratum. The heaviest oily phase was sepa-rated and was found to have a volume of 750 ml and a water con-tent of 70 %.
C Baking.
Baking experiments were carried out according to the standardized method prescribed by the Swedish Seed Association, Or Svalov ? Sweden. The w~leat f]our was a so-called bakery mix-ture produced by the Swedish milling Iirm of Kungsornen. The fermenting and bakin~ ovens used were made by the British firm of Simons. The polar wheat lipids produced according to step B
were added to an amount of 0.83 percent by weight of the amount of flour. For comparison~ bread was baked (1) with an equally large addition of sodium stearyl-lactyl-lactate, and (2) with-. . ., . ~ .. . ... . . . _ . .. _ -. .
. . , , - , . ., ~ :
, . . - . . . . . , . - .
` 1'1~Z73S
out any ext,ra emulgator additive. The following results were obtained. Porosity is given in a scale of 1-8, where the high-est numeral denotes fine porosity. The elasticity of the crumb, i.e. the soft-inner portion of the bread, is given in a scale of 1-6, where 6 denotes very good elasticity. The appearance of the bread is given in a scale of 1-4 where 1 is the best value and denotes a faultless appearance.
Bread additive Bread Poro- Crumb Appear- Time to un-volume sity elasti- ance acceptable city hardness ml days -No additive 410 6 4 1 4 - Sodium stearyl-lactyl-lactate o.83% of flour quantity 480 6 2 1 4 Polar wheat lipids according to invention 0.83% of flour quantity 490 6 6 1 6 It was also noted that the texture of the crumb and the taste of the baked bread was superior for the baking batch containing the polar wheat lipids. It is well known that the addition of a con-ventional emulgator reduces the elasticity of the crumb, which was very clearly demonstrated by our comparative experiment. The polar wht?at lipitls gave no such bad effects, but produced a superior elasticity of the crumb.
.
: -: - : . .
:, .. . ~ -... . - .:
.. . . . :.
- : . . . . . . . . .
:
.
,
Claims (6)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A method for isolating polar lipids from a mixture of polar and non-polar cereal lipids comprising mixing the lipid mixture with water to such an amount that the lipid-water mixture contains at least 50 percent by weight of water, subjecting the mixture to a gravity separation of at least about 5000 g at a temperature in the range between about 25 to 50°C until the phases have completely separated, and separating the heaviest oily phase obtained from the gravity separation, said phase containing the major portion of the polar lipids.
2. A method according to claim 1, wherein the lipid water mixture contains no more than 80 percent by weight water.
3. A method according to claim 2 wherein the lipid water mixture contains 70 % by weight water.
4. A method according to claim 1, 2 or 3 wherein the lipid water mixture is subject to a gravity separation of about 10,000 g.
5. A method according to claim 1, 2 or 3 wherein the water contains from about 0.4 to 4 percent by weight of a salt.
6. A method according to claim 1, 2 or 3 wherein the water contains from about 0.4 to 4 percent by weight of a halogen salt of an alkali metal.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7709374A SE417441B (en) | 1977-08-19 | 1977-08-19 | PROCEDURE FOR INSULATING POLERA LIPIDES FROM A MIXTURE OF POLERA AND OPOLERA CEREALICLIPIDES BY MIXING WITH THE WATER AND THEIR FOLLOWING Gravity Separation |
| SE77-09374-8 | 1977-08-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1102795A true CA1102795A (en) | 1981-06-09 |
Family
ID=20332052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA309,300A Expired CA1102795A (en) | 1977-08-19 | 1978-08-14 | Method of isolating polar lipids from a mixture of polar and non-polar cereal lipids |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5452003A (en) |
| AU (1) | AU522378B2 (en) |
| CA (1) | CA1102795A (en) |
| DE (1) | DE2834999A1 (en) |
| FI (1) | FI782477A (en) |
| FR (1) | FR2400552A1 (en) |
| SE (1) | SE417441B (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003089620A2 (en) | 2002-04-19 | 2003-10-30 | Diversa Corporation | Phospholipases, nucleic acids encoding them and methods for making and using them |
| WO2006009676A2 (en) | 2004-06-16 | 2006-01-26 | Diversa Corporation | Compositions and methods for enzymatic decolorization of chlorophyll |
| WO2008036863A2 (en) | 2006-09-21 | 2008-03-27 | Verenium Corporation | Phospholipases, nucleic acids encoding them and methods for making and using them |
| EP2216403A2 (en) | 2006-02-02 | 2010-08-11 | Verenium Corporation | Esterases and related nucleic acids and methods |
| WO2011046815A1 (en) | 2009-10-16 | 2011-04-21 | Bunge Oils, Inc. | Oil degumming methods |
| WO2011046812A1 (en) | 2009-10-16 | 2011-04-21 | Verenium Corporation | Phospholipases, nucleic acids encoding them and methods for making and using them |
| EP2853593A1 (en) | 2003-03-07 | 2015-04-01 | DSM IP Assets B.V. | Hydrolases, nucleic acids encoding them and mehods for making and using them |
| US9017990B2 (en) | 2004-09-10 | 2015-04-28 | Dsm Ip Assets B.V. | Methods for enzymatic decolorization of chlorophyll |
| EP3190182A1 (en) | 2004-03-08 | 2017-07-12 | DSM IP Assets B.V. | Phospholipases, nucleic acids encoding them and methods for making and using them |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2676936B1 (en) * | 1991-05-27 | 1993-11-05 | Inocosm Laboratoires | PROCESS FOR SEPARATING A COMPOUND RICH IN GLYCOLIPIDES LYSOPHOSPHOLIPIDES SHINGOLIPIDES AND CERAMIDES OF PLANT ORIGIN, AS WELL AS COSMETIC PRODUCTS OBTAINED BY THE IMPLEMENTATION OF THIS PROCESS. |
| PL179737B1 (en) * | 1994-08-16 | 2000-10-31 | Drfrische Gmbh | Method of obtaining water-insoluble natural products from mixtures by centrifuging them |
| WO1997010050A1 (en) * | 1995-09-14 | 1997-03-20 | Unilever N.V. | Surface-active composition |
| FR2836335B1 (en) * | 2002-02-27 | 2004-12-03 | Intersnack Knabber Geback Gmbh | STARCH-BASED DEHYDRATED FLAKES COMPRISING 0.05% GLYCOLIPIDE (S) |
| CA2754707C (en) | 2009-03-11 | 2016-11-22 | Swedish Oat Fiber Ab | Method for separating neutral and polar lipids and an oil rich in polar lipids |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1469392A (en) * | 1965-02-20 | 1967-02-10 | Inst Przemyslu Tluszczowego | Continuous process for the degumming of vegetable oils and for the production of lecithin from the phosphatide sludge obtained, and device for implementing this process |
| DE1923971B1 (en) * | 1969-05-10 | 1970-11-26 | Heinz Schumacher | Method and device for degumming vegetable oils |
-
1977
- 1977-08-19 SE SE7709374A patent/SE417441B/en not_active IP Right Cessation
-
1978
- 1978-08-04 AU AU38631/78A patent/AU522378B2/en not_active Expired
- 1978-08-10 DE DE19782834999 patent/DE2834999A1/en active Granted
- 1978-08-14 CA CA309,300A patent/CA1102795A/en not_active Expired
- 1978-08-14 FI FI782477A patent/FI782477A/en unknown
- 1978-08-17 FR FR7824047A patent/FR2400552A1/en active Granted
- 1978-08-18 JP JP10136578A patent/JPS5452003A/en active Granted
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003089620A2 (en) | 2002-04-19 | 2003-10-30 | Diversa Corporation | Phospholipases, nucleic acids encoding them and methods for making and using them |
| EP2298871A1 (en) | 2002-04-19 | 2011-03-23 | Verenium Corporation | Phospholipases, nucleic acids encoding them and methods for making and using them |
| EP2853593A1 (en) | 2003-03-07 | 2015-04-01 | DSM IP Assets B.V. | Hydrolases, nucleic acids encoding them and mehods for making and using them |
| EP3190182A1 (en) | 2004-03-08 | 2017-07-12 | DSM IP Assets B.V. | Phospholipases, nucleic acids encoding them and methods for making and using them |
| WO2006009676A2 (en) | 2004-06-16 | 2006-01-26 | Diversa Corporation | Compositions and methods for enzymatic decolorization of chlorophyll |
| EP2468853A1 (en) | 2004-06-16 | 2012-06-27 | Verenium Corporation | Composition and methods for enzymatic decolorization of chlorophyll |
| US9017990B2 (en) | 2004-09-10 | 2015-04-28 | Dsm Ip Assets B.V. | Methods for enzymatic decolorization of chlorophyll |
| EP2216403A2 (en) | 2006-02-02 | 2010-08-11 | Verenium Corporation | Esterases and related nucleic acids and methods |
| WO2008036863A2 (en) | 2006-09-21 | 2008-03-27 | Verenium Corporation | Phospholipases, nucleic acids encoding them and methods for making and using them |
| WO2011046815A1 (en) | 2009-10-16 | 2011-04-21 | Bunge Oils, Inc. | Oil degumming methods |
| WO2011046812A1 (en) | 2009-10-16 | 2011-04-21 | Verenium Corporation | Phospholipases, nucleic acids encoding them and methods for making and using them |
| US9512382B2 (en) | 2009-10-16 | 2016-12-06 | Bunge Global Innovation, Llc | Oil degumming methods |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2400552B1 (en) | 1983-08-05 |
| SE417441B (en) | 1981-03-16 |
| FR2400552A1 (en) | 1979-03-16 |
| AU3863178A (en) | 1980-02-07 |
| JPS5452003A (en) | 1979-04-24 |
| AU522378B2 (en) | 1982-06-03 |
| SE7709374L (en) | 1979-02-20 |
| DE2834999A1 (en) | 1979-03-01 |
| DE2834999C2 (en) | 1989-04-20 |
| JPS626558B2 (en) | 1987-02-12 |
| FI782477A (en) | 1979-02-20 |
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