US20030159176A1 - Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability - Google Patents
Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability Download PDFInfo
- Publication number
- US20030159176A1 US20030159176A1 US10/274,092 US27409202A US2003159176A1 US 20030159176 A1 US20030159176 A1 US 20030159176A1 US 27409202 A US27409202 A US 27409202A US 2003159176 A1 US2003159176 A1 US 2003159176A1
- Authority
- US
- United States
- Prior art keywords
- oil
- seed
- imc
- less
- content
- 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.)
- Abandoned
Links
- KRHYYFGTRYWZRS-UHFFFAOYSA-N *.F Chemical compound *.F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- A01H1/00—Processes for modifying genotypes ; Plants characterised by associated natural traits
- A01H1/10—Processes for modifying non-agronomic quality output traits, e.g. for industrial processing; Value added, non-agronomic traits
- A01H1/101—Processes for modifying non-agronomic quality output traits, e.g. for industrial processing; Value added, non-agronomic traits involving biosynthetic or metabolic pathways, i.e. metabolic engineering, e.g. nicotine or caffeine
- A01H1/104—Processes for modifying non-agronomic quality output traits, e.g. for industrial processing; Value added, non-agronomic traits involving biosynthetic or metabolic pathways, i.e. metabolic engineering, e.g. nicotine or caffeine involving modified lipid metabolism, e.g. seed oil composition
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
- A01H5/00—Angiosperms, i.e. flowering plants, characterised by their plant parts; Angiosperms characterised otherwise than by their botanic taxonomy
- A01H5/10—Seeds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
-
- 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
-
- 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
- C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation
- C11C3/123—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation using catalysts based principally on nickel or derivates
Definitions
- This invention relates to improved canola seeds, plants and oil having advantageous properties, that is, a low glucosinolates content and a very low ⁇ -linolenic acid (C 18:3 ) content, which produce an oil with low sulfur content, improved sensory characteristics and oxidative stability.
- Canola oil has the lowest level of saturated fatty acids of all vegetable oils.
- “Canola” refers to rapeseed (Brassica) which has an erucic acid (C 22:1 ) content of at most 2 percent by weight based on the total fatty acid content of a seed, preferably at most 0.5 percent by weight and most preferably essentially 0 percent by weight and which produces, after crushing, an air-dried meal containing less than 30 micromoles ( ⁇ mol) per gram of defatted (oil-free) meal.
- ⁇ mol micromoles
- Canola oil extracted from natural and previously commercially useful varieties of rapeseed contains a relatively high (8%-10%) ⁇ -linolenic acid content (C 18:3 ) (ALA).
- This trienoic fatty acid is unstable and easily oxidized during cooking, which in turn creates off-flavors of the oil (Gailliard, 1980, Vol. 4, pp. 85-116 In: Stumpf, P. K., ed., The Biochemistry of Plants, Academic Press, New York). It also develops off odors and rancid flavors during storage (Hawrysh, 1990, Stability of canola oil, Chapter 7, pp. 99-122 In: F. Shahidi, ed.
- Canola and Rapeseed Production, Chemistry, Nutrition, and Processing Technology, Van Nostrand Reinhold, New York).
- Brassica napus i.e., spring canola, a type of rapeseed.
- M57 and M364 disclose two ⁇ -linolenic acid mutants, M57 and M364, produced by treating rapeseed with X-ray or ethylmethane sulfonate.
- M57 had reduced ⁇ -linolenic acid while M364 had increased ⁇ -linolenic acid.
- the instability of the fatty acid traits between generations was unacceptable for commercial purposes.
- BC 0 and BC 1 of M57 contained 29.4-33.3% of linoleic acid (C 18:2 ) and 4.9-10.8% of ⁇ -linolenic acid (C 18:3 ).
- the oleic acid (C 18:1 ) content was not reported, but by extrapolation could not have exceeded 60%.
- Stellar reported by Scarth et al. ( Can. J. Plant Sci., 68:509-511, 1988), is a Canadian cultivar with lower ⁇ -linolenic acid (also 3%) derived from M57. Its ⁇ -linolenic acid trait was generated by seed mutagenesis. S85-1426, a Stellar derivative with improved agronomic characteristics, also has lower (1.4%) ⁇ -linolenic acid (Report of 1990 Canola/Rapeseed Strain Test A, Western Canada Canola Rapeseed Recommending Committee).
- IXLIN another lower ⁇ -linolenic acid (1.8%) line described by Roy et al. ( Plant Breed., 98:89-96, 1987), originated from an interspecific selection.
- EP-A 323 753 (Allelix) discloses rape plants, seeds, and oil with reduced ⁇ -linolenic acid content linked to limitations in the content of oleic acid, erucic acid, and glucosinolate.
- glucosinolates a sulfur-based compound.
- isothiocyanate esters are produced by the action of myrosinase on glucosinolates. These products inhibit synthesis of thyroxine by the thyroid and have other anti-metabolic effects (Paul et al., Theor. Appl. Genet. 72:706-709, 1986).
- Brassica varieties with reduced glucosinolates content were developed to increase the nutritional value of canola meal (Stefansson et al., Can. J.
- This invention comprises a Brassica napus canola yielding seed having a total glucosinolates content of about 18 ⁇ mol/g or less of defatted, air-dried meal; the seed yielding extractable oil having 1) an ⁇ -linolenic acid content of about 7% or less relative to total fatty acid content of the seed, and 2) a very low sulfur content of less than or equal to 3.00 ppm.
- the invention also includes a Brassica napus yielding canola oil having, when hydrogenated, a significantly reduced overall room-odor intensity relative to the overall room-odor intensity of generic canola oil.
- the new variety more particularly yields non-hydrogenated oil significantly reduced in fishy odor relative to the fishy odor of generic canola oil, such odor being characteristic of Brassica seed oil.
- the seed of such canola variety has an ⁇ -linolenic acid content of less than or equal to 7%, more preferably less than or equal to about 4.1% ( ⁇ -linolenic acid (C 18:3 ) relative to total fatty acid content of said seed and a total glucosinolates content of less than 18 ⁇ mol/g, more preferably less than or equal to about 15 ⁇ mol/g and most preferably less than or equal to 13 ⁇ mol/g and belongs to a line in which these traits have been stable for both the generation to which the seed belongs and that of its parent.
- This invention further includes processes of making crosses using IMC 01 as at least one parent of the progeny of the above-described seeds and oil derived from said seeds.
- This invention further comprises a seed designated IMC 01 deposited with the American Type Culture Collection, 12301 Parklawn Drive, Rockville, Md., USA 20852 and bearing accession number ATCC 40579, the progeny of such seed and oil of such a seed possessing the quality traits of interest.
- a spring canola ( Brassica napus L.) variety was developed with improved sensory characteristics and oxidative stability in the seed oil.
- This variety designated IMC 01, has very low levels of ⁇ -linolenic acid (CH 3 CH 2 CH ⁇ CHCH 2 CH ⁇ CHCH 2 CH ⁇ CH (CH 2 ) 7 COOH) in the seed oil and very low levels of glucosinolates in the seed.
- the oil produced from the seed of this variety has very low levels of sulfur and was shown to have significantly improved sensory characteristics over generic canola oils.
- the IMC 01 is a line in which these traits have been stabilized for both the generation to which the seed belongs and that of its parent generation.
- Particularly desirable lines of this invention from an agronomic point of view can be derived by conventionally crossing lines producing seeds meeting the definitions of this invention with agronomically well-proven lines such as Westar.
- a “line” is a group of plants that display little or no genetic variation between individuals for at least one trait. Such lines may be created by several generations of self-pollination and selection, or vegetative propagation from a single parent using tissue or cell culture techniques.
- the terms “cultivar” and “variety” are synonymous and refer to a line which is used for commercial production. “Stability” or “stable” means that with respect to the given component, the component is maintained from generation to generation and, preferably, at least three generations at substantially the same level, e.g., preferably ⁇ 15%, more preferably ⁇ 10%, most preferably ⁇ 5%.
- Compute Utility is defined as having good plant vigor and high fertility, such that the crop can be produced by farmers using conventional farming equipment, and the oil with the described components can be extracted from the seed using conventional crushing and extraction equipment. To be commercially useful, the yield, as measured by both seed weight, oil content, and total oil produced per acre, is within 15% of the average yield of an otherwise comparable commercial canola variety without the premium value traists grown in the same region.
- Agronomically elite means that a line has desirable agronomic characteristics such as yield, maturity, disease resistance, standability.
- the amount of fatty acids, such as oleic and linolenic acids, that are characteristic of the oil is expressed as a percentage of the total fatty acid content of the oil.
- “Saturated fatty acid” refers to the combined content of palmitic acid and stearic acid.
- Polyunsaturated fatty acid refers to the combined content of linoleic-and ⁇ -linolenic acids.
- the term “shortening” refers to an oil that is a solid at room temperature.
- room odor refers to the characteristic odor of heated oil as determined using the room-odor evaluation method described in Mounts ( J. Am. Oil Chem. Soc., 56:659-663, 1979).
- Generic canola oil refers to a composite oil extracted from commercial varieties of rapeseed currently known as of the priority date of this application, which varieties generally exhibited at a minimum 8-10% ⁇ -linolenic acid content, a maximum of 2% erucic acid and a maximum of 30 ⁇ mol/g total glucosinolate level.
- the seed from each growing region is graded and blended at the grain elevators to produce an acceptably uniform product.
- the blended seed is then crushed and refined, the resulting oil being sold for use.
- Table A shows the distribution of canola varieties seeded as percentage of all canola seeded in Western Canada in 1990.
- Source Quality of Western Canadian Canola—1990 Crop Year. Bull. 187, DeClereg et al., Grain Research Laboratory, Canadian Grain Commission, 1404-303 Main Street, Winnipeg, Manitoba, R3C 3G8.
- IMC 01 is a very low ⁇ -linolenic acid ( ⁇ 4.1% C 18:3 ) line selected during an extensive germplasm screening effort. Its parentage is unknown. IMC 01 was self-pollinated and selected for low ⁇ -linolenic acid ( ⁇ 4.1%) over four consecutive generations. At each generation, seeds from individually pollinated plants were analyzed for fatty acid composition. Data showed no genetic segregation for ⁇ -linolenic acid content over five generations of self-pollinations (Table I). Breeder seed was derived from a bulk seed increase of selected plants from the fourth self-crossed generation.
- IMC 01 was planted-in replicated field trials in North Dakota, South Dakota, Minnesota, Washington, Idaho and Montana in 1989 and 1990, under both irrigated and nonirrigated conditions. These tests showed that the ⁇ -linolenic acid content of IMC 01 was sensitive to temperature (Table II). This was further supported by growing IMC 01 under controlled temperature conditions in growth chambers. Whether or not the observed temperature sensitivity of IMC 01 is common to other low ⁇ -linolenic acid canola lines is unknown.
- IMC 01 is also characterized by very low levels of glucosinolates.
- Glucosinolates are sulfur-based compounds common to all Brassica seeds. Glucosinolates exist in aliphatic or indolyl forms. Aliphatic glucosinolates can be analyzed via gas chromatography (GC) (Daun, Glucosinolate analysis of rapeseed (canola), Method of the Canadian Grain Commission, Grain Research Laboratory, Canadian Grain Commission, Winnipeg, 1981). Indolyl glucosinolates have only recently been analyzed via high performance liquid chromatograph (HPLC).
- HPLC high performance liquid chromatograph
- total glucosinolates were calculated by multiplying the aliphatic glucosinolates by a correction factor.
- Canola quality in the seed is defined as having ⁇ 30 ⁇ mol/g of glucosinolates in the defatted meal.
- IMC 01 and Westar were tested in five locations in southeastern Idaho in 1990. Three of the locations were irrigated (I) and two were dryland (D) conditions. Table IIIa shows the difference in total aliphatic glucosinolate between IMC 01 and Westar grown at these locations. The aliphatic glucosinolate values are reported as ⁇ mol/gm of defatted meal.
- IMC 01 has the lowest level of total seed glucosinolates (Table V). TABLE III Glucosinolates Profiles of IMC 01 and Westar Varieties GLUCOSINOLATES ( ⁇ mol/g) IMC 01 WESTAR 3-butenyl 1.2 4.2 4-pentenyl 0.1 0.2 2-OH-3-butenyl 3.1 7.0 2-OH-4-pentenyl 0.9 0.4 Total Aliphatics 5.3 11.8 4-OH-3-indolylmethyl 6.2 6.1 3-indolylmethyl 0.8 1.0 4-methoxyindolyl 0.1 tr 1-methoxyindolyl 0.1 0.2 Total Indolyls 7.2 7.3 Total Glucosinolates 12.5 19.1
- IMC 01 was produced, using normal production practices for spring canola, in Idaho and North Dakota in 1988, in Idaho, Washington State and Montana in 1989, in Idaho, Washington State, Montana, Oregon, and Wyoming in 1990.
- the oil contains ⁇ 4.1% ⁇ -linolenic acid.
- a normal fatty acid profile was produced at Casselton, N. Dak.
- the crop produced in Ashton, Id. was subject to extremely cool conditions and had higher levels of ⁇ -linolenic acid.
- the room-odor characteristics of cooking oils can be reproducibly characterized by trained test panels in room-odor tests (Mounts, J. Am. Oil Chem. Soc. 56:659-663, 1979).
- a standardized technique for the sensory evaluation of edible vegetable oils is presented in AOCS' Recommended Practice Cg 2-83 for the Flavor Evaluation of Vegetable Oils (Methods and Standard Practices of the AOCS, 4th Edition (1989)).
- the technique encompasses standard sample preparation and presentation, as well as reference standards and method for scoring oils.
- When heated, generic canola oil has reduced stability and produces offensive room odors.
- Refined-Bleached-Deodorized (RBD) canola oil is characterized by a fishy flavor in such tests.
- canola oil Due to its relatively low stability, canola oil is often hydrogenated for frying. However, hydrogenation produces a characteristic (hydrogenated) room odor which is unacceptable to food manufacturers. Surprisingly, hydrogenated IMC 01 oil also has reduced levels of the characteristic hydrogenated room odor (Table VII). Table VII shows that the overall room-odor intensity of hydrogenated IMC 01 is significantly less than that of hydrogenated generic oil as indicated by a difference is scores of greater than 1.0 in standardized flavor evaluation trials.
- IMC 01 produces an oil which has improved sensory characteristics. Such improvements have been predicted for low ⁇ -linolenic acid canola oils (Ulrich et al., J. Am. Oil Chem. Soc., 8:1313-1317, 1988). However, the improved sensory characteristics of IMC 01 appears not to be related solely to its low ⁇ -linolenic acid content. Surprisingly, IMC 01 canola oils with both high and low levels of ⁇ -linolenic acid showed similar degrees of improvement. Sensory tests have shown that IMC 01 oil maintains its improved quality at both 2% and 6.8% ⁇ -linolenic acid.
- the very low glucosinolates characteristic of IMC 01 seed is believed to contribute to the improved sensory characteristic of IMC 01 oil.
- Glucosinolates in the seed are converted to sulfur compounds. Most of the sulfur breakdown products remain in the meal, but some inevitably contaminate the oil. Lower levels of glucosinolates in the seed are believed to result in lower sulfur content in the oil, and this is believed to reduce the objectionable odor characteristics of canola oil (Abraham et al., J. Am. Oil Chem. Soc., 65:392-395, 1988). An analysis of the sulfur content of IMC 01 oil and several generic canola oils has been performed.
- IMC 01 oil has approximately one-third the sulfur content of leading generic canola oils (Table VIII). TABLE VIII Sulfur Content of Canola Oils Canola Oils Sulfur Content Acme Brand Canola Oil 3.8 ppm Hollywood Brand Canola Oil 3.8 ppm Puritan Brand Canola Oil 3.9 ppm IMC 01 Canola Oil 1.3 ppm
- IMC 01 is true breeding as are its progeny.
- the traits responsible for reduced ⁇ -linolenic acid and reduced total glucosinolates in the seed which yield an oil low in sulfur having improved sensory characteristics have a genetic basis.
- the data presented herein show that these traits are stable under different field conditions. These traits can be removed from the IMC 01 background and are transferred into other backgrounds by traditional crossing and selection techniques.
- Example 3 is a specific example of such work to develop descendents to IMC 01 which retain the desirable quality traits.
- the data of Example 3 show that the quality traits of IMC 01 are heritable in such crosses.
- IMC 01 originally designated DNAP #336, was grown in a greenhouse in Cinnaminson, N.J., over several seasons to select for a stable, very low ⁇ -linolenic line. Day/night temperatures from August through December in the greenhouse averaged 80° F./65° F. with fluctuations of ⁇ 5° F., 75° F./65° F. from January through April, and 85° F./65° F. from March through July. The plants were grown in 1-gallon pots under natural day length, except from October through May when the plants received 14 hours of supplemental lighting. Flowering racemes were covered with paper bags to prevent cross-pollination, and gently shaken to induce seed set. Watering was decreased as pods reached maturity.
- IMC 01 was planted in multi-location trials and production plots in Montana, Idaho and Washington. The trials were planted in a completely randomized block design with four replications. Each block contained eight plots of 6 meters by 8 rows. IMC 01 was also planted in large acreages (>25 acres) according to standard agronomic procedures for spring canola production, with a minimum ⁇ fraction (1/2) ⁇ -mile isolation from other Brassica napus crops. Depending on location, the fields were planted in April or May, and harvested in August or September. Plantings were made on dryland, following both fallow or recrop, or under irrigation. Mature pod samples were taken following swathing for chemical analysis.
- IMC 01 seed was harvested and processed to produce refined, bleached and deodorized (RBD) oil. Some oil was hydrogenated after refining, bleaching and deodorization, then redeodorized.
- RBD bleached and deodorized
- the seed was tempered to adjust the moisture content to 9% and flaked to 0.38 to 0.64 cm in a ribbon blender.
- the flakes were cooked in a stack cooker at 82.8° C. for 30 min (8.5% moisture) and pre-pressed with vertical and horizontal bar spacings set to 0.031 cm, vertical shaft speed at 40 rpm and horizontal shaft at 25 rpm.
- the press cake was extracted in a Crown Model 2 extractor at 37.3 kg and hexane extracted with a 2:1 solvent to solids ratio.
- the crude oil was alkali refined at 65° C.-70° C. for 30 min with 0.2% to 85% phosphoric acid, then mixed with sodium hydroxide to neutralize free fatty acids. Soaps were removed with a water wash (65° C. water, 5 min) and the oils bleached with 0.75% each by weight of Clarion and Acticil bleaching earths for 30 min to remove color bodies. The resulting oil contained no peroxides, 0.08% free fatty acids, and had a Gardner color of 10-.
- the oil was continuously deodorized at 265° C. at 300 kg/h.
- the steam rate was 1% of feed rate.
- the deodorized oil was preheated to 68-72° C. prior to deaeration.
- RBD oil was stored in food grade plastic drums or pails at 4° C. under nitrogen prior to testing.
- RBD and hydrogenated oil samples were analyzed for room-odor characteristics by a trained test panel in comparison with a generic, commercially available RBD canola oil (Proctor & Gamble) and generic, commercially available hydrogenated canola shortening as described previously.
- the testing protocol used is described in Mounts ( J. Am. Oil Chem. Soc. 56:659-663, 1979) which is hereby incorporated by reference.
- the testing controlled for temperature of the oil, distance from the oil and room volume, and required that the oil was heated in a separate chamber and pumped into the room containing the trained panelist.
- a 150 mL sample of the selected oil was heated to 190° C. for 30 min before the start of each panel test. The oil was maintained at this temperature throughout each session. For each session a fresh oil sample was used.
- the trained panelists judged the room odor for intensity of odor, quality of odor, and odor attributes.
- the intensity was ranked as: 0-4 weak, 5-7 moderate, and 8-10 strong.
- the quality of odor was judged as: 0-1 bad, 2-3 poor, 4-6 fair, 7-8 good, and 9-10 excellent.
- the odor attributes were ranked as: 0-1 bland, 2-4 weak, 5-7 moderate, and 8-10 strong.
- the flavor attributes were fried, painty, fishy, hydrogenated, burnt, cardboard, metallic, rubbery, waxy, buttery, and nutty.
- a generic, commercially available canola oil (Proctor & Gamble) was used in the IMC room odor tests as the standard or generic canola oil.
- the standard canola oil was significantly (P ⁇ 0.05) higher in room odor intensity than IMC 01 (Table IX).
- the standard canola oil odor was of “moderate” intensity while the IMC 01 was considered “weak”.
- the overall quality of the IMC 01 room odor was significantly (P ⁇ 0.05) better than the standard canola oil.
- the standard canola oil had significantly (P ⁇ 0.05) higher intensities for fried, painty, and cardboard odors than the IMC 01 oil.
- Example 2 Pilot plant-processed samples of Example 2 generic canola (low erucic acid rapeseed) oil and oil from IMC 01 canola with the fatty acid compositions modified by mutation breeding and/or hydrogenation were evaluated for frying stability ⁇ -linolenic acid contents were 10.1% for generic canola oil, 1.7% for canola modified by breeding (IMC 01) and 0.8% and 0.7% for IMC 01 oils modified by breeding and hydrogenation.
- the IMC 01 modified oils had significantly (P ⁇ 0.05) less room odor intensity that the generic canola oil after initial heating tests at 190° C. as judged by a sensory panel under conditions of AOCS Cg 2-83.
- the generic canola oil had significantly higher intensities for fishy, burnt, rubbery, smoky, and acrid odors than the modified oils.
- Foam heights of the modified oils were significantly (P ⁇ 0.05) less than those of the generic oil after 20, 30 and 40 hrs of heating and frying at 190° C.
- the flavor quality of french fried potatoes was significantly (P ⁇ 0.05) better for all the potatoes fried in modified oils than those fried in generic canola oil.
- the potatoes fried in generic canola oil were described by the sensory panel as fishy. No off-flavors were detected in potatoes fried in the modified oils.
- This Example demonstrates that the traits of very low ⁇ -linolenic acid and very low glucosinolate content are transferred to IMC 01 progeny.
- IMC 01 A deposit of seed designated IMC 01 has been made in the American Type Culture Collection (ATCC) depository (Rockville, Md. 20852) and bears accession number ATCC 40579. The deposit was made on Mar. 2, 1989 under conditions complying with the requirements of the Budapest Treaty.
- ATCC American Type Culture Collection
- IMC 01 was compared to Alto, a “generic” variety of commercial canola oil.
- Oils were processed using standard commercial refining, bleaching and deodorizing processes. TABLE X Processed Oil Analysis IMC 01 Alto Red color 0.5 0.7 Yellow color 4 5 para-anisidine value 0.97 2.32 Peroxide value, meg/g 0.6 0.7 TOTOX value ⁇ p-av + 2 (pv) 2.07 3.72 Total Polymers, % 0.02 0.01 Total Polar Material, % 0.77 0.36 Free fatty acid, % 0.022 0.013 Fatty acid composition, % C16:0 4.2 4.0 C18:0 2.2 2.0 C18:l 63.5 62.5 C18:2 22.2 18.3 C18:3 4.9 7.7
- para-Anisidine Value determined by AOCS method Cd 18-90, measures secondary oxidation by-producs in oils.
- Peroxide Value determined by AOCS method Cd 8b-90 measures the primary oxidation product in oils.
- Oxidative stability measured by Automatic Oxygen Method (AOM) hours determined by American Oil Chemists Society (AOCS) method Cd 12b-92, Fat Stability, Oil Stability Index (OSI), using an Oxidative Stability Instrument, manufactured by Omnion/Archer Daniels Midland, Decatur, Ill. IMC 01 Alto AOM hours 26.8 17.5
- Results indicate IMC 01 has greater AOM hours and therefore greater oxidative stability than Alto.
- the Schaal oven method of accelerated aging is used in the oil industry to measure the oxidative and flavor stability of oil.
- the Schaal oven method involves examining samples of oil at predetermined intervals held at 60° C. in the dark. One day under Schaal oven conditions is equivalent to one month storage in the dark at ambient temperature.
- Oxidative stability is measured by monitoring the increases in peroxides (peroxide value) and secondary oxidative by-products (para-anisidine value) in the oil held at 60° C. for twelve days.
- Flavor stability is determined by a trained sensory panel using the same oils tested for oxidative stability.
- IMC 02 was compared to Stellar, a commercially available low alpha linolenic variety of canola.
- TOTOX value p-av + 2(pv) 0.88 1.98 Total Polymers, % 0.01 0 Total Polar Material, % 0.63 0.42 Free fatty acid, % 0.026 0.014 Fatty acid composition, % C16:0 3.8 4 C18:0 2.2 2.3 C18:1 66.3 62.8 C18:2 22.3 24.4 C18:3 2.7 3.3 Oxidative Stability - pSI AOM Hours AOM hours 31.5 23.1
Abstract
A canola line has been stabilized to produce seeds having an α-linolenic acid content of less than that of generic canola oil, more preferably less than or equal to about 7% α-linolenic acid relative to total fatty acid content of said seed and a total glucosinolate content of less than 18 μmol/g of defatted meal, more preferably less than or equal to about 15 μmol/g of defatted meal. This canola line has reduced sulfur content of less than or equal to 3.0 ppm, improved sensory characteristics and increased oxidative stability.
Description
- This invention relates to improved canola seeds, plants and oil having advantageous properties, that is, a low glucosinolates content and a very low α-linolenic acid (C18:3) content, which produce an oil with low sulfur content, improved sensory characteristics and oxidative stability.
- A need exists for an improved vegetable oil with a significantly extended shelf life and greater heat stability relative to generic canola oil and a positive nutritional contribution to animal, including human, diets.
- Canola oil has the lowest level of saturated fatty acids of all vegetable oils. “Canola” refers to rapeseed (Brassica) which has an erucic acid (C22:1) content of at most 2 percent by weight based on the total fatty acid content of a seed, preferably at most 0.5 percent by weight and most preferably essentially 0 percent by weight and which produces, after crushing, an air-dried meal containing less than 30 micromoles (μmol) per gram of defatted (oil-free) meal. These types of rapeseed are distinguished by their edibility in comparison to more traditional varieties of the species.
- As consumers become more aware of the health impact of lipid nutrition, consumption of canola oil in the U.S. has increased. However, generic canola oil cannot be used in deep frying operations, an important segment of the food processing industry.
- Canola oil extracted from natural and previously commercially useful varieties of rapeseed contains a relatively high (8%-10%) α-linolenic acid content (C18:3) (ALA). This trienoic fatty acid is unstable and easily oxidized during cooking, which in turn creates off-flavors of the oil (Gailliard, 1980, Vol. 4, pp. 85-116 In: Stumpf, P. K., ed., The Biochemistry of Plants, Academic Press, New York). It also develops off odors and rancid flavors during storage (Hawrysh, 1990, Stability of canola oil, Chapter 7, pp. 99-122 In: F. Shahidi, ed. Canola and Rapeseed: Production, Chemistry, Nutrition, and Processing Technology, Van Nostrand Reinhold, New York). One such unsatisfactory species heretofore has been Brassica napus, i.e., spring canola, a type of rapeseed.
- It is known that reducing the α-linolenic content level by hydrogenation increases the oxidative stability of the oil. Hydrogenation is routinely used to reduce the polyunsaturates content of vegetable oils, thereby increasing its oxidative stability. The food industry has used hydrogenation to raise the melting point of vegetable oils, producing oil-based products with textures similar to butter, lard and tallow. Trans isomers of unsaturated fatty acids are commonly produced during hydrogenation. However, the nutritional properties of trans fatty acids mimic saturated fatty acids, thereby reducing the overall desirability of hydrogenated oils (Mensink et al.,New England J. Medicine N323:439-445, 1990; Scarth, et al., Can. J. Pl. Sci., 68:509-511, 1988). Canola oil produced from seeds having a reduced α-linolenic acid content would be expected to have improved functionality for cooking purposes with improved nutritional value, and therefore have improved value as an industrial frying oil.
- However, in general, very little variation exists for α-linolenic acid content in previously known canola qualityB. napus germplasm (Mahler et al., 1988, Fatty acid composition of Idao Misc. Ser. No. 125). Lines with levels of α-linolenic acid lower than that of generic canola oil are known, but have sensory, genetic stability, agronomic or other nutritional deficiencies. For example, Rakow et al. (J. Am. Oil Chem. Soc., 50:400-403, 1973), and Rakow (Z. Pflanzenzuchtg, 69:62-82, 1973), disclose two α-linolenic acid mutants, M57 and M364, produced by treating rapeseed with X-ray or ethylmethane sulfonate. M57 had reduced α-linolenic acid while M364 had increased α-linolenic acid. However, the instability of the fatty acid traits between generations was unacceptable for commercial purposes.
- Brunklaus-Jung et al. (Pl. Breed., 98:9-16, 1987), backcrossed M57 and other rapeseed mutants obtained by mutagenic treatment to commercial varieties. BC0 and BC1 of M57 contained 29.4-33.3% of linoleic acid (C18:2) and 4.9-10.8% of α-linolenic acid (C18:3). The oleic acid (C18:1) content was not reported, but by extrapolation could not have exceeded 60%.
- Four other lower α-linolenic acid canola lines have been described. Stellar, reported by Scarth et al. (Can. J. Plant Sci., 68:509-511, 1988), is a Canadian cultivar with lower α-linolenic acid (also 3%) derived from M57. Its α-linolenic acid trait was generated by seed mutagenesis. S85-1426, a Stellar derivative with improved agronomic characteristics, also has lower (1.4%) α-linolenic acid (Report of 1990 Canola/Rapeseed Strain Test A, Western Canada Canola Rapeseed Recommending Committee). IXLIN, another lower α-linolenic acid (1.8%) line described by Roy et al. (Plant Breed., 98:89-96, 1987), originated from an interspecific selection. EP-A 323 753 (Allelix) discloses rape plants, seeds, and oil with reduced α-linolenic acid content linked to limitations in the content of oleic acid, erucic acid, and glucosinolate.
- Another nutritional aspect of rapeseed, from which canola was derived, is its high (30-55 μmol/g) level of glucosinolates, a sulfur-based compound. When the foliage or seed is crushed, isothiocyanate esters are produced by the action of myrosinase on glucosinolates. These products inhibit synthesis of thyroxine by the thyroid and have other anti-metabolic effects (Paul et al.,Theor. Appl. Genet. 72:706-709, 1986). Brassica varieties with reduced glucosinolates content (<30 μmol/g defatted meal) were developed to increase the nutritional value of canola meal (Stefansson et al., Can. J. Plant Sci. 55:343-344, 1975). Meal from an ultra-low glucosinolates line, BC86-18, has 2 μmol/g total glucosinolates and significantly improved nutritional quality compared to generic canola meal (Classen, Oral presentation, GCIRC Eighth International Rapeseed Congress, Saskatoon, Saskatchewan, Jul. 9-11, 1991). Neither its fatty acid composition nor its seed glucosinolates profile is known.
- There remains a need for an improved canola seed and oil with very low α-linolenic levels in the oil and low glucosinolates in the seed to significantly reduce the need for hydrogenation. The α-linolenic content of such a desirable oil would impart increased oxidative stability, thereby reducing the requirement for hydrogenation and the production of trans fatty acids. The reduction of seed glucosinolates would significantly reduce residual sulfur content in the oil. Sulfur poisons the nickel catalyst commonly used for hydrogenation (Koseoglu et al.,
Chapter 8, pp. 123-148, In: F. Shahidi, ed. Canola and Rapeseed: Production, Chemistry, Nutrition, and Processing Technology, Van Nostrand Reinhold, New York, 1990). Additionally, oil from a canola variety with low seed glucosinolates would be less expensive to hydrogenate. - This invention comprises aBrassica napus canola yielding seed having a total glucosinolates content of about 18 μmol/g or less of defatted, air-dried meal; the seed yielding extractable oil having 1) an α-linolenic acid content of about 7% or less relative to total fatty acid content of the seed, and 2) a very low sulfur content of less than or equal to 3.00 ppm. The invention also includes a Brassica napus yielding canola oil having, when hydrogenated, a significantly reduced overall room-odor intensity relative to the overall room-odor intensity of generic canola oil. The new variety more particularly yields non-hydrogenated oil significantly reduced in fishy odor relative to the fishy odor of generic canola oil, such odor being characteristic of Brassica seed oil. The seed of such canola variety has an α-linolenic acid content of less than or equal to 7%, more preferably less than or equal to about 4.1% (α-linolenic acid (C18:3) relative to total fatty acid content of said seed and a total glucosinolates content of less than 18 μmol/g, more preferably less than or equal to about 15 μmol/g and most preferably less than or equal to 13 μmol/g and belongs to a line in which these traits have been stable for both the generation to which the seed belongs and that of its parent.
- This invention further includes processes of making
crosses using IMC 01 as at least one parent of the progeny of the above-described seeds and oil derived from said seeds. - This invention further comprises a seed designated IMC 01 deposited with the American Type Culture Collection, 12301 Parklawn Drive, Rockville, Md., USA 20852 and bearing accession number ATCC 40579, the progeny of such seed and oil of such a seed possessing the quality traits of interest.
- A spring canola (Brassica napus L.) variety was developed with improved sensory characteristics and oxidative stability in the seed oil. This variety, designated
IMC 01, has very low levels of α-linolenic acid (CH3CH2CH═CHCH2CH═CHCH2CH═CH (CH2)7COOH) in the seed oil and very low levels of glucosinolates in the seed. The oil produced from the seed of this variety has very low levels of sulfur and was shown to have significantly improved sensory characteristics over generic canola oils. TheIMC 01 is a line in which these traits have been stabilized for both the generation to which the seed belongs and that of its parent generation. Particularly desirable lines of this invention from an agronomic point of view can be derived by conventionally crossing lines producing seeds meeting the definitions of this invention with agronomically well-proven lines such as Westar. - In the context of this disclosure, a number of terms are used. As used herein, a “line” is a group of plants that display little or no genetic variation between individuals for at least one trait. Such lines may be created by several generations of self-pollination and selection, or vegetative propagation from a single parent using tissue or cell culture techniques. As used herein, the terms “cultivar” and “variety” are synonymous and refer to a line which is used for commercial production. “Stability” or “stable” means that with respect to the given component, the component is maintained from generation to generation and, preferably, at least three generations at substantially the same level, e.g., preferably ±15%, more preferably ±10%, most preferably ±5%. The stability may be affected by temperature, location, stress and the time of planting. Comparison of subsequent generations under field conditions should produce the component in a similar manner. “Commercial Utility” is defined as having good plant vigor and high fertility, such that the crop can be produced by farmers using conventional farming equipment, and the oil with the described components can be extracted from the seed using conventional crushing and extraction equipment. To be commercially useful, the yield, as measured by both seed weight, oil content, and total oil produced per acre, is within 15% of the average yield of an otherwise comparable commercial canola variety without the premium value traists grown in the same region. “Agronomically elite” means that a line has desirable agronomic characteristics such as yield, maturity, disease resistance, standability. The amount of fatty acids, such as oleic and linolenic acids, that are characteristic of the oil is expressed as a percentage of the total fatty acid content of the oil. “Saturated fatty acid” refers to the combined content of palmitic acid and stearic acid. “Polyunsaturated fatty acid” refers to the combined content of linoleic-and α-linolenic acids. The term “shortening” refers to an oil that is a solid at room temperature. The term “room odor” refers to the characteristic odor of heated oil as determined using the room-odor evaluation method described in Mounts (J. Am. Oil Chem. Soc., 56:659-663, 1979). “Generic canola oil” refers to a composite oil extracted from commercial varieties of rapeseed currently known as of the priority date of this application, which varieties generally exhibited at a minimum 8-10% α-linolenic acid content, a maximum of 2% erucic acid and a maximum of 30 μmol/g total glucosinolate level. The seed from each growing region is graded and blended at the grain elevators to produce an acceptably uniform product. The blended seed is then crushed and refined, the resulting oil being sold for use. Table A shows the distribution of canola varieties seeded as percentage of all canola seeded in Western Canada in 1990.
TABLE A Distribution of Canola Varieties Grown in Western Canada in 1990 Percent of Canola Variety Seeded Area B. campestris Candle 0.4 Colt 4.4 Horizon 8.5 Parkland 2.5 Tobin 27.1 B. napus Alto 1.1 Delta 0.9 Global 0.9 Legend 18.2 Pivot 0.1 Regent 0.5 Stellar 0.2 Tribute 0.4 Triton 0.7 Triumph 0.2 Westar 29.5 Others 4.4 - Source: Quality of Western Canadian Canola—1990 Crop Year. Bull. 187, DeClereg et al., Grain Research Laboratory, Canadian Grain Commission, 1404-303 Main Street, Winnipeg, Manitoba, R3C 3G8.
-
IMC 01 is a very low α-linolenic acid (<4.1% C18:3) line selected during an extensive germplasm screening effort. Its parentage is unknown.IMC 01 was self-pollinated and selected for low α-linolenic acid (<4.1%) over four consecutive generations. At each generation, seeds from individually pollinated plants were analyzed for fatty acid composition. Data showed no genetic segregation for α-linolenic acid content over five generations of self-pollinations (Table I). Breeder seed was derived from a bulk seed increase of selected plants from the fourth self-crossed generation.TABLE I Fatty Acid Composition of IMC 01Over Five Generations PERCENT COMPOSITION DATE OF ANALYSIS C16:0 C18:0 C18:1 C18:2 C18:3 December 1987 4.1 1.9 64.1 25.7 1.9 August 1988 4.6 2.3 72.6 14.4 2.0 January 1989 4.9 1.5 60.4 25.8 2.5 April 1989 4.8 1.8 64.3 21.4 4.0 November 1989 4.3 2.1 64.1 24.8 2.0 -
IMC 01 was planted-in replicated field trials in North Dakota, South Dakota, Minnesota, Washington, Idaho and Montana in 1989 and 1990, under both irrigated and nonirrigated conditions. These tests showed that the α-linolenic acid content ofIMC 01 was sensitive to temperature (Table II). This was further supported by growingIMC 01 under controlled temperature conditions in growth chambers. Whether or not the observed temperature sensitivity ofIMC 01 is common to other low α-linolenic acid canola lines is unknown. - A temperature effect on fatty acid compositions has been widely reported in plants, especially oilseed crops (Rennie et al.,J. Am. Oil Chem. Soc., 66:1622-1624, 1989). These reports describe general temperature effects on fatty acid composition.
- Changes in fatty acid content in seed oil under cool temperatures have been documented in plants such as soybean, peanut and sunflower (Neidleman, In: Proceedings of the World Conference on Biotechnology for the Fats and Oils Industry, Applewhite, T. H., ed., pp. 180-183. Am. Oil. Chem. Soc. 1987).
TABLE II α-Linolenic acid Content of IMC 01 inProduction in 1990 α-LINOLENIC PRODUCTION {overscore (X)} TEMPERATURE DURING ACID REGION SEED MATURATION CONTENT Eastern Washington 74° F. 1.9% Eastern Washington 74° F. 2.0% Northern Idaho 70° F. 3.0% Northern Idaho 67° F. 2.9% Eastern Idaho 62° F. 3.5% Southern Montana 66° F. 4.1% Central Montana 67° F. 4.0% - In addition to very low α-linolenic acid,
IMC 01 is also characterized by very low levels of glucosinolates. Glucosinolates are sulfur-based compounds common to all Brassica seeds. Glucosinolates exist in aliphatic or indolyl forms. Aliphatic glucosinolates can be analyzed via gas chromatography (GC) (Daun, Glucosinolate analysis of rapeseed (canola), Method of the Canadian Grain Commission, Grain Research Laboratory, Canadian Grain Commission, Winnipeg, 1981). Indolyl glucosinolates have only recently been analyzed via high performance liquid chromatograph (HPLC). Prior to the adoption of the HPLC method, total glucosinolates were calculated by multiplying the aliphatic glucosinolates by a correction factor. Canola quality in the seed is defined as having <30 μmol/g of glucosinolates in the defatted meal. -
IMC 01 and Westar were tested in five locations in southeastern Idaho in 1990. Three of the locations were irrigated (I) and two were dryland (D) conditions. Table IIIa shows the difference in total aliphatic glucosinolate betweenIMC 01 and Westar grown at these locations. The aliphatic glucosinolate values are reported as μmol/gm of defatted meal. - The aliphatic glucosinolate content of
IMC 01 by location was consistently lower and more stable than that of Westar at all locations tested. The average glucosinolate contents ofIMC 01 was 4.9 μMol/gm while Westar was 13.3 μmol/gm. A Least Significant Difference (LSD) test was used to determine if the two were significantly different at all lcoations.IMC 01 was found to be significantly different from Westar at a level of P<0.05. - HPLC analysis of
IMC 01 vs Westar, the most widely grown spring canola variety in North America, shows thatIMC 01 has much lower levels of aliphatic glucosinolates (Table III). No significant differences exist for indolyl glucosinolates. Glucosinolates content is also subject to environment influence, e.g., sulfur fertility and drought stress. However,IMC 01 consistently had the lowest and the most stable aliphatic glucosinolates levels at all locations tested (Table IV). The locations tested differ in altitude, temperature, fertility, irrigation, and other cultural practices. Among the low α-linolenic canola lines for which glucosinates analysis have been performed,IMC 01 has the lowest level of total seed glucosinolates (Table V).TABLE III Glucosinolates Profiles of IMC 01and Westar Varieties GLUCOSINOLATES (μmol/g) IMC 01WESTAR 3-butenyl 1.2 4.2 4-pentenyl 0.1 0.2 2-OH-3-butenyl 3.1 7.0 2-OH-4-pentenyl 0.9 0.4 Total Aliphatics 5.3 11.8 4-OH-3-indolylmethyl 6.2 6.1 3-indolylmethyl 0.8 1.0 4-methoxyindolyl 0.1 tr 1-methoxyindolyl 0.1 0.2 Total Indolyls 7.2 7.3 Total Glucosinolates 12.5 19.1 -
TABLE IV Aliphatic Glucosinolates of IMC 01 andWestar over Different Environments in Southeastern Idaho ALIPHATIC GLUCOSINOLATES CONTENT (μmol/g) LOCATION* IMC 01WESTAR Newdale - I 4.7 13.0 Soda Springs - D 6.3 9.9 Tetonia - D 5.0 13.5 Tetonia - I 3.7 13.3 Shelley - I 5.0 17.0 Average 4.9 13.3 Standard Deviation 0.93 2.51 -
TABLE V Glucosinolates Content of Low α-Linolenic acid Canola Varieties and Westar GLUCOSINOLATES (μmol/g) ALIPHATIC INDOLYL TOTAL IMC 01 5.3 7.2 12.5 Stellar 5.2 19.5 24.7 S85-1426 7.9 13.4 21.3 Westar 11.8 7.3 19.1 -
IMC 01 was produced, using normal production practices for spring canola, in Idaho and North Dakota in 1988, in Idaho, Washington State and Montana in 1989, in Idaho, Washington State, Montana, Oregon, and Wyoming in 1990. When grown in suitable environments, where the average daily temperature (high temperature plus low temperature divided by 2) exceeds 20° C., the oil contains <4.1% α-linolenic acid. As an example, a normal fatty acid profile was produced at Casselton, N. Dak. The crop produced in Ashton, Id., was subject to extremely cool conditions and had higher levels of α-linolenic acid. The crops obtained from the field tests were crushed and processed to produce refined, bleached and deodorized (RBD) canola oil at the Protein, Oil, Starch (POS) Pilot Plant in Saskatoon, Saskatchewan. A method of bleaching canola oil is provided in the AOCS' Recommended Practice Cc 8a-52 (AOCS Methods and Standard Practices, 4th Edition (1989)). A method for the refining of crude oils is provided in the AOCS Practice Cc 9a-52 (AOCS Methods and Standard Practices, 4th Edition (1989)). The oils were tested at the Vegetable Oil Research Laboratory, U.S.D.A./Northern Regional Research Center, for organoleptic and sensory characteristics. - Testing to assure that desirable sensory characteristics are obtained in theBrassica napus variety was essential. The evaluation of odors has been conducted in a variety of ways on low α-linolenic acid canola oils. The testing methods are based on the fact that vegetable oils emit characteristic odors upon heating. For example, Prevot et al. (J. Amer. Oil Chemists Soc. 67:161-164, 1990) evaluated the odors of a French rapeseed, “Westar”, and “low linolenic” canola oils in a test which attempted to reproduce domestic frying conditions. In these evaluations the test oils were used to fry potatoes and the odors were evaluated by a test panel. The odor tests showed that the “low linolenic” (approximately 3%) line had a significantly higher (more acceptable) odor score than the French rapeseed and “Westar” lines, which were very similar to each other. Eskin et al. (J. Amer. Oil Chemists Soc. 66:1081-1084, 1989) evaluated the odor from canola oil with a low linolenic acid content, a laboratory deodorized sample, and a commercially deodorized sample by sniffing in the presence of the oil itself. These studies demonstrated that a reduction in the linolenic acid content of canola oil from 8-9% to 1.6% reduced the development of heated odor at frying temperatures. However, the odor of the low linolenic acid oil was still unacceptable when heated in air to a majority of the panelists, suggesting that low linolenic acid alone is not sufficient to guarantee acceptable odor.
- Mounts (J. Am. Oil Chem. Soc., 56:659-663, 1979) describe a distinct room-odor evaluation method that is used to reproducibly assess the odor characteristics of a cooking oil upon heating. This is the evaluation method of choice owing to its reproducibility and its approximation of odors emitted upon heating the oil. In this method, the oil is heated in a separate chamber and the odor pumped into the room containing the trained evaluators. As noted elsewhere, where the term “room-odor” is used herein, it refers to this method of Mounts. This method is distinct from earlier described tests where the oil and evaluator are within the same room. Such same room testing is referred to as “uncontrolled bench top odor tests” and is considered less accurate and less reliable than the Mounts' room odor evaluation method.
- The room-odor characteristics of cooking oils can be reproducibly characterized by trained test panels in room-odor tests (Mounts,J. Am. Oil Chem. Soc. 56:659-663, 1979). A standardized technique for the sensory evaluation of edible vegetable oils is presented in AOCS' Recommended Practice Cg 2-83 for the Flavor Evaluation of Vegetable Oils (Methods and Standard Practices of the AOCS, 4th Edition (1989)). The technique encompasses standard sample preparation and presentation, as well as reference standards and method for scoring oils. When heated, generic canola oil has reduced stability and produces offensive room odors. Refined-Bleached-Deodorized (RBD) canola oil is characterized by a fishy flavor in such tests. This characteristic is commonly ascribed to its high polyunsaturated fatty acid content, particularly α-linolenic acid, relative to other vegetable oils. The individual fragrance notes (odor attributes) of the oils are evaluated by Least Significant Difference Analysis. Notes which differ by greater than 1.0 can be reproducibly measured by a sensory panel. In these tests,
IMC 01 oil expressed significantly reduced levels of the offensive odors (Table VI).TABLE VI Room Odor Intensity of IMC 01and Generic Canola Oil GENERIC ODOR ATTRIBUTES IMC 01CANOLA OIL Overall 4.6a 7.4b Fried Foods 1.8 3.5 Doughy 1.0 0 Fishy 0a 5.5b Burnt 0a 0.9b Acrid 0a 2.3b Woody/Cardboard 1.9 0 Hydrogenated 0 0 Pastry/Sugary 0 0 Waxy 0 0 Chemical 0 0 - Due to its relatively low stability, canola oil is often hydrogenated for frying. However, hydrogenation produces a characteristic (hydrogenated) room odor which is unacceptable to food manufacturers. Surprisingly, hydrogenated
IMC 01 oil also has reduced levels of the characteristic hydrogenated room odor (Table VII). Table VII shows that the overall room-odor intensity ofhydrogenated IMC 01 is significantly less than that of hydrogenated generic oil as indicated by a difference is scores of greater than 1.0 in standardized flavor evaluation trials.TABLE VII Room Odor Intensity and Individual Odor Descriptions for Hydrogenated Canola Oils HYDROGENATED HYDROGENATED IMC 01 HYDROGENATED, IMC 01SHORTENING GENERIC SHORTENING (2% (6.8% CANOLA α-LINOLENIC α-LINOLENIC ODOR ATTRIBUTE SHORTENING ACID) ACID) Overall Intensity 6.6b 3.8a 3.9a Fried Food 2.7 1.1 1.5 Doughy 1.2 0.6 0.8 Fishy 0.6 0 0 Burnt 0.5 0 0 Acrid 0.8 0 0 Hydrogenated 3.2 1.8 2.3 Waxy 0.5 0.6 0. Other 4.5 2.4 2.8 rubbery fruity fruity flowery smoky flowery weedy sweet soapy pastry -
IMC 01 produces an oil which has improved sensory characteristics. Such improvements have been predicted for low α-linolenic acid canola oils (Ulrich et al., J. Am. Oil Chem. Soc., 8:1313-1317, 1988). However, the improved sensory characteristics ofIMC 01 appears not to be related solely to its low α-linolenic acid content. Surprisingly,IMC 01 canola oils with both high and low levels of α-linolenic acid showed similar degrees of improvement. Sensory tests have shown thatIMC 01 oil maintains its improved quality at both 2% and 6.8% α-linolenic acid. - The very low glucosinolates characteristic of
IMC 01 seed is believed to contribute to the improved sensory characteristic ofIMC 01 oil. Glucosinolates in the seed are converted to sulfur compounds. Most of the sulfur breakdown products remain in the meal, but some inevitably contaminate the oil. Lower levels of glucosinolates in the seed are believed to result in lower sulfur content in the oil, and this is believed to reduce the objectionable odor characteristics of canola oil (Abraham et al., J. Am. Oil Chem. Soc., 65:392-395, 1988). An analysis of the sulfur content ofIMC 01 oil and several generic canola oils has been performed.IMC 01 oil has approximately one-third the sulfur content of leading generic canola oils (Table VIII).TABLE VIII Sulfur Content of Canola Oils Canola Oils Sulfur Content Acme Brand Canola Oil 3.8 ppm Hollywood Brand Canola Oil 3.8 ppm Puritan Brand Canola Oil 3.9 ppm IMC 01 Canola Oil 1.3 ppm - The biochemical, molecular and genetic mechanisms responsible for the room-odor quality of vegetable oils are not fully understood. Improvements in vegetable oil processing technology, i.e., preferential removal of sulfur during processing, less abusive oil extraction procedures, minimal processing, gentler deodorization, etc., may improve the overall quality of vegetable oils, including both sensory and functional characteristics (Daun et al.,J. Am. Oil Chem. Soc., 53:169-171, 1976).
IMC 01 will benefit from any such processing improvements, and will maintain its improved sensory characteristics over generic canola oil under equivalent processing conditions. -
IMC 01 is true breeding as are its progeny. The traits responsible for reduced α-linolenic acid and reduced total glucosinolates in the seed which yield an oil low in sulfur having improved sensory characteristics have a genetic basis. The data presented herein show that these traits are stable under different field conditions. These traits can be removed from theIMC 01 background and are transferred into other backgrounds by traditional crossing and selection techniques. - Crosses have been made with
IMC 01 as one parent to demonstrate that thesuperior IMC 01 quality/sensory traits are transferred along with the superior agronomic traists of another parent such as the Canadian canola line, Westar, into descendents. The parent to whichIMC 01 is crossed is chosen on the basis of desirable characteristics such as yield, maturity, disease resistance, and standability. Conventional breeding techniques employed in such crossings are well known by those skilled in the art. Thus, a method of using theIMC 01 Brassica napus is to cross it with agronomically elite lines to produce plants yielding seeds having the characteristics listed above. - The general protocol is:
- a. cross
IMC 01 to a selected parent; - b. produce a “gametic array” using microsphores of the F1 plants to produce dihaploid (DH) individuals;
- c. field trial DH2 individuals for yield and select from
IMC 01 α-linolenic acid and glucosinolate levels; and - d. test selected individuals for oil quality using RBD oil.
- Example 3 is a specific example of such work to develop descendents to
IMC 01 which retain the desirable quality traits. The data of Example 3 show that the quality traits ofIMC 01 are heritable in such crosses. - The present invention is further defined in the following Examples, in which all parts and percentages are by weight and degrees are Celsius, unless otherwise stated. It should be understood that this Example, while indicating preferred embodiments of the invention, is given by way of illustration only. From the above discussion and this Example, one skilled in the art can ascertain the essential characteristics of this invention, and without departing from the spirit and scope thereof, can make various changes and modifications of the invention to adapt it to various usages and conditions.
-
IMC 01, originally designated DNAP #336, was grown in a greenhouse in Cinnaminson, N.J., over several seasons to select for a stable, very low α-linolenic line. Day/night temperatures from August through December in the greenhouse averaged 80° F./65° F. with fluctuations of ±5° F., 75° F./65° F. from January through April, and 85° F./65° F. from March through July. The plants were grown in 1-gallon pots under natural day length, except from October through May when the plants received 14 hours of supplemental lighting. Flowering racemes were covered with paper bags to prevent cross-pollination, and gently shaken to induce seed set. Watering was decreased as pods reached maturity. - For field testing,
IMC 01 was planted in multi-location trials and production plots in Montana, Idaho and Washington. The trials were planted in a completely randomized block design with four replications. Each block contained eight plots of 6 meters by 8 rows.IMC 01 was also planted in large acreages (>25 acres) according to standard agronomic procedures for spring canola production, with a minimum {fraction (1/2)}-mile isolation from other Brassica napus crops. Depending on location, the fields were planted in April or May, and harvested in August or September. Plantings were made on dryland, following both fallow or recrop, or under irrigation. Mature pod samples were taken following swathing for chemical analysis. - For fatty acid analysis, 10-50 seed samples were ground in 15-mL polypropylene tubes and extracted in 1.2 mL 0.25 N KOH in 1:1 ether/methanol. The sample was vortexed for 10 sec and heated for 60 sec and in 60° C. water bath. Four mL of saturated NaCl and 2.4 mL of iso-octane were added, and the mixture was vortexed again. After phase separation, 600 μL of the upper organic phase was pipetted into individual vials and stored under nitrogen. One μL sample was injected into a Supelco SP-2330 fused silica capillary column (0.25 mm ID, 30 m length, 0.20 μm df, Bellfonte, Pa.).
- The gas chromatograph was set at 180° C. for 5.5 min, then programmed for a 2° C./min increase to 212° C., and held at this temperature for 1.5 min. Chromatography settings were: Column head pressure—15 psi, Column flow (He)—0.7 mL/min, Auxiliary and Column flow—33 mL/min, Hydrogen flow=33 mL/min, Air flow—400 mL/min, Injector temperature—250° C., Detector temperature—300° C., Split vent—{fraction (1/15)}.
- A standard industry procedure for HPLC analysis of glucosinolates was used to analyze the glucosinolates composition of the seed (Daun et al., In: Glucosinolate Analysis of Rapeseed (Canola). Method of the Canadian Grain Commission, Grain Research Laboratory, 1981).
-
IMC 01 seed was harvested and processed to produce refined, bleached and deodorized (RBD) oil. Some oil was hydrogenated after refining, bleaching and deodorization, then redeodorized. - Before extraction, the seed was tempered to adjust the moisture content to 9% and flaked to 0.38 to 0.64 cm in a ribbon blender. The flakes were cooked in a stack cooker at 82.8° C. for 30 min (8.5% moisture) and pre-pressed with vertical and horizontal bar spacings set to 0.031 cm, vertical shaft speed at 40 rpm and horizontal shaft at 25 rpm. The press cake was extracted in a
Crown Model 2 extractor at 37.3 kg and hexane extracted with a 2:1 solvent to solids ratio. - The crude oil was alkali refined at 65° C.-70° C. for 30 min with 0.2% to 85% phosphoric acid, then mixed with sodium hydroxide to neutralize free fatty acids. Soaps were removed with a water wash (65° C. water, 5 min) and the oils bleached with 0.75% each by weight of Clarion and Acticil bleaching earths for 30 min to remove color bodies. The resulting oil contained no peroxides, 0.08% free fatty acids, and had a Gardner color of 10-.
- The oil was continuously deodorized at 265° C. at 300 kg/h. The steam rate was 1% of feed rate. The deodorized oil was preheated to 68-72° C. prior to deaeration. RBD oil was stored in food grade plastic drums or pails at 4° C. under nitrogen prior to testing.
- For hydrogenation, RBD oil was heated to 350° F. under vacuum in a stainless steel pressure reactor. A 0.5% sulfur-poisoned nickel catalyst, Englehardt SP-7, was added to the oil at 80.1° C., and hydrogen gas was introduced at 40 psi. Periodic samples were analyzed until an oil with a 30.5° C. melting point was achieved. The hydrogenated oil was redeodorized and stored by the methods described previously.
- The RBD and hydrogenated oil samples were analyzed for room-odor characteristics by a trained test panel in comparison with a generic, commercially available RBD canola oil (Proctor & Gamble) and generic, commercially available hydrogenated canola shortening as described previously. The testing protocol used is described in Mounts (J. Am. Oil Chem. Soc. 56:659-663, 1979) which is hereby incorporated by reference. The testing controlled for temperature of the oil, distance from the oil and room volume, and required that the oil was heated in a separate chamber and pumped into the room containing the trained panelist.
- Specifically, room odor profiles of
IMC 01 and a generic canola oil were obtained as follows: - A. Room Odor Protocol
- A 150 mL sample of the selected oil was heated to 190° C. for 30 min before the start of each panel test. The oil was maintained at this temperature throughout each session. For each session a fresh oil sample was used.
- Panelists visited each odor room for approximately 15 sec. A five min rest was required between visits. Visitation to each odor room was randomized among the panelists.
- The trained panelists judged the room odor for intensity of odor, quality of odor, and odor attributes. The intensity was ranked as: 0-4 weak, 5-7 moderate, and 8-10 strong. The quality of odor was judged as: 0-1 bad, 2-3 poor, 4-6 fair, 7-8 good, and 9-10 excellent. The odor attributes were ranked as: 0-1 bland, 2-4 weak, 5-7 moderate, and 8-10 strong. The flavor attributes were fried, painty, fishy, hydrogenated, burnt, cardboard, metallic, rubbery, waxy, buttery, and nutty.
- B. Generic Oil—
IMC 01 Profile Comparison - A generic, commercially available canola oil (Proctor & Gamble) was used in the IMC room odor tests as the standard or generic canola oil. In a comparative test, the standard canola oil was significantly (P<0.05) higher in room odor intensity than IMC 01 (Table IX). The standard canola oil odor was of “moderate” intensity while the
IMC 01 was considered “weak”. The overall quality of theIMC 01 room odor was significantly (P<0.05) better than the standard canola oil. The standard canola oil had significantly (P<0.05) higher intensities for fried, painty, and cardboard odors than theIMC 01 oil.TABLE IX Room Odor Profile of Generic (Proctor & Gamble) and IMC 01 OilEvaluation* IMC 01Generic A. Intensity 3.4a 5.2b B. Quality 5.8a 4.9b C. Odor Attributes Fried 1.9a 2.9b Painty 0.4 1.3 Fishy 0.8a 1.9b Hydrogenated 1.1 0.6 Rancid 0.7 0.9 Burnt 0.8 1.4 Cardboard 0.1a 1.5b Metallic 0.5 0.1 Rubbery 0.0 0.0 Waxy 0.6 0.0 Buttery 0.7 0.3 - Pilot plant-processed samples of Example 2 generic canola (low erucic acid rapeseed) oil and oil from
IMC 01 canola with the fatty acid compositions modified by mutation breeding and/or hydrogenation were evaluated for frying stability α-linolenic acid contents were 10.1% for generic canola oil, 1.7% for canola modified by breeding (IMC 01) and 0.8% and 0.7% forIMC 01 oils modified by breeding and hydrogenation. TheIMC 01 modified oils had significantly (P<0.05) less room odor intensity that the generic canola oil after initial heating tests at 190° C. as judged by a sensory panel under conditions of AOCS Cg 2-83. The generic canola oil had significantly higher intensities for fishy, burnt, rubbery, smoky, and acrid odors than the modified oils. Foam heights of the modified oils were significantly (P<0.05) less than those of the generic oil after 20, 30 and 40 hrs of heating and frying at 190° C. The flavor quality of french fried potatoes was significantly (P<0.05) better for all the potatoes fried in modified oils than those fried in generic canola oil. The potatoes fried in generic canola oil were described by the sensory panel as fishy. No off-flavors were detected in potatoes fried in the modified oils. -
- The pre-production will be crushed and the oil refined for quality.
- Once a canola line has been stabilized, fully conventional methods of plant biotechnology, breeding and selection are used to further enhance, for example, the agronomic properties of the resultant line in order to improve important factors such as yield; hardiness, etc. Such techniques are also well known and include, e.g., somaclonal variation, seed mutagenesis, anther and microspore culture, protoplast fusion, etc. See, e.g., Brunklaus-Jung et al.,Pl. Breed., 98:9-16, 1987; Hoffmann et al., Theor. Appl. Genet, 61, 225-232 (1982), each herein incorporated by reference).
- A deposit of seed designated
IMC 01 has been made in the American Type Culture Collection (ATCC) depository (Rockville, Md. 20852) and bears accession number ATCC 40579. The deposit was made on Mar. 2, 1989 under conditions complying with the requirements of the Budapest Treaty. -
IMC 01 was compared to Alto, a “generic” variety of commercial canola oil. - Oils were processed using standard commercial refining, bleaching and deodorizing processes.
TABLE X Processed Oil Analysis IMC 01 Alto Red color 0.5 0.7 Yellow color 4 5 para-anisidine value 0.97 2.32 Peroxide value, meg/g 0.6 0.7 TOTOX value − p-av + 2 (pv) 2.07 3.72 Total Polymers, % 0.02 0.01 Total Polar Material, % 0.77 0.36 Free fatty acid, % 0.022 0.013 Fatty acid composition, % C16:0 4.2 4.0 C18:0 2.2 2.0 C18:l 63.5 62.5 C18:2 22.2 18.3 C18:3 4.9 7.7 - Colors determined by American Oil Chemists' Society (AOCS) method Cc 13b-43, using American Oil Tintometer, Model AF715, The Tintometer LTD., Salisbury, England.
- para-Anisidine Value (p-av) determined by AOCS method Cd 18-90, measures secondary oxidation by-producs in oils.
- Peroxide Value determined by AOCS method Cd 8b-90, measures the primary oxidation product in oils.
- Total polymers determined by AOCS method Cd 22-91, gel-permeation HPLC.
- Total Polar Materials determined by AOCS method Cd 20-91, packed column method adpated to HPLC.
- Free fatty acid determined by AOCS method Ca 5a-40.
- Fatty acid composition determined by AOCS method Ce 1e-91, capillary gas liquid chromatography.
- Oxidative Stability by Oxidative Stability Instrument (OSI)
- Oxidative stability measured by Automatic Oxygen Method (AOM) hours determined by American Oil Chemists Society (AOCS) method Cd 12b-92, Fat Stability, Oil Stability Index (OSI), using an Oxidative Stability Instrument, manufactured by Omnion/Archer Daniels Midland, Decatur, Ill.
IMC 01Alto AOM hours 26.8 17.5 - Results indicate
IMC 01 has greater AOM hours and therefore greater oxidative stability than Alto. - Oxidative Stability and Flavor Stability by Accelerated Aging
- The Schaal oven method of accelerated aging is used in the oil industry to measure the oxidative and flavor stability of oil. The Schaal oven method involves examining samples of oil at predetermined intervals held at 60° C. in the dark. One day under Schaal oven conditions is equivalent to one month storage in the dark at ambient temperature.
- Oxidative stability is measured by monitoring the increases in peroxides (peroxide value) and secondary oxidative by-products (para-anisidine value) in the oil held at 60° C. for twelve days.
- Flavor stability is determined by a trained sensory panel using the same oils tested for oxidative stability.
- Sample Preparation:
- 400 g of oil placed in 500 mL amber glass bottles (80 mm wide, 140 mm high, with a 42 mm opening), uncapped, held in 60° C. (range 59 to 61° C.) convection oven (Blue M, manufactured by Blue M Electric) for 3, 6, 9 and 12 days. One bottle of oil per day per type of oil.
- Samples were frozen immediately after removing from the oven. Peroxide value, para-anisidine value and sensory evaluation were made within seven days after samples were frozen.
- Oxidative Stability by Accelerated Aging
TABLE XI Changes in Peroxide Value and para-Anisidine Value PV p- AV Days IMC 01 Alto IMC 01 Alto 0 .6 0.7 0.97 2.32 3 0.9 5.33 0.99 2.52 6 5.48 11.8 1.36 5.02 9 10.3 15.7 2.45 6.5 12 14.1 18.8 3.42 7.49 - Flavor Stability by Accelerated Aging:
- Sensory panel trained in evaluation of vegetable oils according to protocol of AOCS method Cg 2-83, Flavor Panel Evaluation of Vegetable Oils. Using AOCS flavor standards panel members were trained to identify the following off flavors; fishy, green, cardboard, plastic and painty.
TABLE XII Overall Acceptance Scores and Total Off-Flavor Intensities Overall Acceptance1 Total Off-Flavors2 Day IMC 01 Alto IMC 01 Alto 0 7.53 6.01 0.59 2.32 3 7.04 3.2 0.87 8.29 6 5.44 3.10 4.17 9.46 9 3.81 1.78 6.22 10.15 12 4.00 2.00 7.16 12.89 - Correlation between overall acceptance score and total off-flavors r2-0.9485 (see FIG. 5).
- Significantly lower overall acceptance scores and lower total off-flavor intensities indicates
IMC 01 has significantly better flavor stability than Alto. -
IMC 02 was compared to Stellar, a commercially available low alpha linolenic variety of canola.TABLE XIII IMC 02 Stellar Processed Oil Analysis Red color 0.2 0.3 Yellow color 3 3 para-Anisidine value 0.48 0.78 Peroxide value, meq/g 0.2 0.6 TOTOX value = p-av + 2(pv) 0.88 1.98 Total Polymers, % 0.01 0 Total Polar Material, % 0.63 0.42 Free fatty acid, % 0.026 0.014 Fatty acid composition, % C16:0 3.8 4 C18:0 2.2 2.3 C18:1 66.3 62.8 C18:2 22.3 24.4 C18:3 2.7 3.3 Oxidative Stability - pSI AOM Hours AOM hours 31.5 23.1 - Results indicate
IMC 02 has greater AOM hours and therefore greater oxidative stability than Stellar. - Oxidative Stability by Accelerated Aging
TABLE XIV Changes in Peroxide Value and para-Anisidine Value PV p- Av Days IMC 02 Stellar IMC 02 Stellar 0 0.2 0.6 0.48 0.78 3 0.7 1.39 0.76 0.84 6 1.5 3.77 0.26 0.99 9 4.4 7.37 0.82 2.07 12 9.6 13.3 1.18 2.56 -
TABLE XV Overall Acceptance Scores and Total Off-Flavor Intensities Overall Acceptance1 Total Off-Flavors2 Day IMC 01 Alto IMC 01 Alto 0 8.66 7.75 0.66 0.73 3 6.87 4.18 1.98 7.16 6 7.01 4.57 1.44 6.07 9 6.10 3.67 2.79 8.41 12 4.16 3.67 5.73 7.83 - Correlation between overall acceptance score and total off-flavor intensities is r2-0.9428 (see FIG. 10).
- Significantly lower overall acceptance scores and lower off-flavor intensities indicates
IMC 02 has significantly better flavor stability than Stellar.
Claims (19)
1. A Brassica napus plant comrising seed having a total glucosinolates content of about 18 μmol/g or less of defatted, air-dried meal;
the seed yielding oil having an α-linolenic acid content of 7% or less relative to total fatty acid content of said seed and a sulfur content of less than or equal to 3.0 ppm; and
the plant belonging to a line in which these traits have been stabilized for both the generation to which the seed belongs and that of its parent generation.
2. The seed produced by the plant of claim 1 .
3. The seed produced by the plant of claim 1 wherein total glucosinate content is about 15 μmol/g or less of defatted, air-dried meal.
4. The oil of the seed produced by the plant of claim 1 .
5. A Brassica napus plant designated IMC 01 represented by seed deposited with the ATCC and bearing accession number 40579.
6. The oil produced from the variety of claim 5 .
7. A Brassica napus seed yielding canola oil having, when hydrogenated, significantly reduced overall room-odor intensity relative to the overall room-odor intensity of generic canola oil, a significant difference in overall room odor-intensity indicated by a difference of greater than 1.0 obtained in a standardized sensory evaluation.
8. A Brassica napus comprising oil, which when non-hydrogenated, is significantly reduced in fishy odor intensity relative to the fishy odor intensity of generic canola oil, a significant difference in fishy odor intensity indicated by a difference of greater than 1.0 obtained in standardized sensory evaluation.
9. A Brassica napus plant wherein at least one parent was the variety of claims 1 or 5.
10. The progeny of the plant of claims 1, 5 or 9.
11. A plant produced from the crossing of IMC 01 with an agronomically elite variety of Brassica napus, the plant yielding a seed having a total glucosinolates content of about 18 μmol/g or less of defatted, air-dried meal, said seed yielding extractable oil having (1) an α-linolenic acid content of about 7% or less relative to total fatty acid content of said seed, and (2) a sulfur content of less than or equal to 3.0 ppm.
12. The plant of claim 11 , wherein the agronomically elite parent is the Canadian canola line, Westar.
13. A process for producing a canola of enhanced commercial utility comprising:
(a) crossing the Brassica napus IMC 01 with an agronomically elite variety;
(b) selecting the off-spring of step (a) which yield a seed having a total glucosinolates content of about 18 μmol/g or less of defatted, air-dried meal, said seed yielding extractable oil having (1) an α-linolenic acid content of about 7% or less relative to total fatty acid content of said seed, and (2) a sulfur content of less than or equal to 3.0 ppm.
14. The oil extracted from the seed produced by the process of claim 13 .
15. A method of using the Brassica napus IMC 01 comprising:
(a) crossing IMC 01 with an agronomically elite variety;
(b) selecting the off-spring of step (a) which yield a seed having a total glucosinolates content of about 18 μmol/g or less of defatted, air-dried meal, said seed yielding extractable oil having (1) an α-linolenic acid content of about 7% or less relative to total fatty acid content of said seed, and (2) a sulfur content of less than or equal to 3.0 ppm;
(c) producing sufficient progeny of the seed selected in step (b) to extract oil.
16. The Brassica napus designated HW 3.001, a progeny line of the cross of IMC 01 with Westar.
17. An improved vegetable oil extracted from Brassica napus seeds, said seeds having:
(1) an oil which exhibits following crushing and extraction
(a) an α-linolenic acid content of 7% or less relative to total fatty acid content of said seed;
(b) a sulfur content of less than or equal to 3.0 ppm; and
(2) a total glucosinolates content of about 18 μmol/g or less of defatted, air-dried meal.
18. The oil produced from the progeny of claim 1 , 5 or 9, as described in claim 10 , wherein the stability of such oil measured in AOM hours is from about 25.0 to about 35.0.
19. The oil as described by claim 18 wherein the stability in AOM hours is from 26.8 to 31.5.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/274,092 US20030159176A1 (en) | 1993-11-12 | 2002-10-17 | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
US10/976,585 US20050114922A1 (en) | 1992-09-30 | 2004-10-26 | Conola variety IMC 02 with reduced linolenic acid |
US11/754,923 US20080034457A1 (en) | 1992-09-30 | 2007-05-29 | Canola variety imc 02 with reduced linolenic acid |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14020593A | 1993-11-12 | 1993-11-12 | |
US08/290,660 US5750827A (en) | 1991-09-30 | 1994-08-15 | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
US08/850,279 US6270828B1 (en) | 1993-11-12 | 1997-05-05 | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
US09/861,905 US6562397B2 (en) | 1991-09-30 | 2001-05-21 | Canola meal having reduced glucosinolates |
US10/274,092 US20030159176A1 (en) | 1993-11-12 | 2002-10-17 | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/861,905 Continuation US6562397B2 (en) | 1991-09-30 | 2001-05-21 | Canola meal having reduced glucosinolates |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/976,585 Continuation US20050114922A1 (en) | 1992-09-30 | 2004-10-26 | Conola variety IMC 02 with reduced linolenic acid |
Publications (1)
Publication Number | Publication Date |
---|---|
US20030159176A1 true US20030159176A1 (en) | 2003-08-21 |
Family
ID=26837966
Family Applications (8)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/850,279 Expired - Fee Related US6270828B1 (en) | 1991-09-30 | 1997-05-05 | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
US09/861,905 Expired - Fee Related US6562397B2 (en) | 1991-09-30 | 2001-05-21 | Canola meal having reduced glucosinolates |
US10/034,698 Abandoned US20020092042A1 (en) | 1991-09-30 | 2001-12-27 | Canola oil from seeds with reduced glucosinolates and linolenic acid |
US10/143,432 Expired - Fee Related US6680396B2 (en) | 1991-09-30 | 2002-05-09 | Canola oil with reduced linolenic acid |
US10/274,092 Abandoned US20030159176A1 (en) | 1992-09-30 | 2002-10-17 | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
US10/274,312 Expired - Fee Related US6689409B2 (en) | 1991-09-30 | 2002-10-17 | Canola oil with reduced linolenic acid |
US10/976,585 Abandoned US20050114922A1 (en) | 1992-09-30 | 2004-10-26 | Conola variety IMC 02 with reduced linolenic acid |
US11/754,923 Abandoned US20080034457A1 (en) | 1992-09-30 | 2007-05-29 | Canola variety imc 02 with reduced linolenic acid |
Family Applications Before (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/850,279 Expired - Fee Related US6270828B1 (en) | 1991-09-30 | 1997-05-05 | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
US09/861,905 Expired - Fee Related US6562397B2 (en) | 1991-09-30 | 2001-05-21 | Canola meal having reduced glucosinolates |
US10/034,698 Abandoned US20020092042A1 (en) | 1991-09-30 | 2001-12-27 | Canola oil from seeds with reduced glucosinolates and linolenic acid |
US10/143,432 Expired - Fee Related US6680396B2 (en) | 1991-09-30 | 2002-05-09 | Canola oil with reduced linolenic acid |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/274,312 Expired - Fee Related US6689409B2 (en) | 1991-09-30 | 2002-10-17 | Canola oil with reduced linolenic acid |
US10/976,585 Abandoned US20050114922A1 (en) | 1992-09-30 | 2004-10-26 | Conola variety IMC 02 with reduced linolenic acid |
US11/754,923 Abandoned US20080034457A1 (en) | 1992-09-30 | 2007-05-29 | Canola variety imc 02 with reduced linolenic acid |
Country Status (1)
Country | Link |
---|---|
US (8) | US6270828B1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007016521A3 (en) * | 2005-08-01 | 2007-04-26 | Ca Minister Agriculture & Food | Low fiber yellow canola seeds comprising high oleic, low linolenic oil |
Families Citing this family (198)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6270828B1 (en) * | 1993-11-12 | 2001-08-07 | Cargrill Incorporated | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
ES2735987T3 (en) | 2000-01-19 | 2019-12-23 | Dsm Ip Assets Bv | Extraction procedure without solvent |
JP3970513B2 (en) * | 2000-11-06 | 2007-09-05 | 花王株式会社 | Crisps |
AU2011202620B2 (en) * | 2002-05-03 | 2013-09-26 | Dsm Ip Assets B.V. | High-quality lipids and methods for producing by enzymatic liberation from biomass |
CA2484334C (en) * | 2002-05-03 | 2013-01-22 | Martek Biosciences Corporation | High-quality lipids and methods for producing by enzymatic liberation from biomass |
CA2535310C (en) | 2003-08-21 | 2015-06-09 | Monsanto Technology Llc | Fatty acid desaturases from primula |
US20050154069A1 (en) * | 2004-01-13 | 2005-07-14 | Syntroleum Corporation | Fischer-Tropsch process in the presence of nitrogen contaminants |
US6974788B2 (en) * | 2004-03-12 | 2005-12-13 | Chevron Oronite Company Llc. | Zeolite Y alkylation catalysts |
EP1734947B1 (en) | 2004-04-16 | 2015-04-15 | Monsanto Technology, LLC | Expression of fatty acid desaturases in corn |
US20080260933A1 (en) * | 2004-10-08 | 2008-10-23 | Dow Agroscience Llc | Certain Plants with "No Saturate" or Reduced Saturate Levels of Fatty Acids in Seeds, and Oil Derived from the Seeds |
AU2005294298C1 (en) | 2004-10-08 | 2017-03-09 | Corteva Agriscience Llc | Oil and seeds with reduced saturate levels of fatty acids |
CA2586309C (en) | 2004-11-04 | 2014-05-27 | Monsanto Technology Llc | High pufa oil compositions |
US20070065565A1 (en) * | 2005-08-10 | 2007-03-22 | Frank Kincs | Edible oils and methods of making edible oils |
WO2007030253A2 (en) * | 2005-09-02 | 2007-03-15 | Bunge Oils, Inc. | Edible oils and methods of making edible oils |
US20070148194A1 (en) * | 2005-11-29 | 2007-06-28 | Amiji Mansoor M | Novel nanoemulsion formulations |
EP3133162B1 (en) | 2006-03-10 | 2021-04-21 | Monsanto Technology LLC | Soybean seed and oil compositions and methods of making same |
UA97127C2 (en) * | 2006-12-06 | 2012-01-10 | Бандж Ойлз, Инк. | Method and system for the enzymatic treatment of lipid containing feedstock |
CL2007003743A1 (en) | 2006-12-22 | 2008-07-11 | Bayer Cropscience Ag | COMPOSITION THAT INCLUDES FENAMIDONA AND AN INSECTICIDE COMPOUND; AND METHOD TO CONTROL FITOPATOGENOS CULTURES AND INSECTS FACING OR PREVENTIVELY. |
CL2007003744A1 (en) | 2006-12-22 | 2008-07-11 | Bayer Cropscience Ag | COMPOSITION THAT INCLUDES A 2-PYRIDILMETILBENZAMIDE DERIVATIVE AND AN INSECTICIDE COMPOUND; AND METHOD TO CONTROL FITOPATOGENOS CULTURES AND INSECTS FACING OR PREVENTIVELY. |
EP1969930A1 (en) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Phenoxy phenylamidines and their use as fungicides |
EP1969934A1 (en) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | 4-cycloalkyl or 4-aryl substituted phenoxy phenylamidines and their use as fungicides |
US8080688B2 (en) * | 2007-03-12 | 2011-12-20 | Bayer Cropscience Ag | 3, 4-disubstituted phenoxyphenylamidines and use thereof as fungicides |
EP1969929A1 (en) | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Substituted phenylamidines and their use as fungicides |
EP2136628B1 (en) * | 2007-03-12 | 2015-07-01 | Bayer Intellectual Property GmbH | Phenoxy substituted phenylamidine derivatives and their use as fungicides |
EP1969931A1 (en) | 2007-03-12 | 2008-09-17 | Bayer CropScience Aktiengesellschaft | Fluoroalkyl phenylamidines and their use as fungicides |
EP2136627B1 (en) * | 2007-03-12 | 2015-05-13 | Bayer Intellectual Property GmbH | Dihalophenoxyphenylamidines and use thereof as fungicides |
EP2146975B1 (en) | 2007-04-19 | 2015-06-17 | Bayer Intellectual Property GmbH | Thiadiazolyl oxyphenyl amidines and the use thereof as a fungicide |
DE102007045920B4 (en) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistic drug combinations |
DE102007045922A1 (en) * | 2007-09-26 | 2009-04-02 | Bayer Cropscience Ag | Drug combinations with insecticidal and acaricidal properties |
DE102007045953B4 (en) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Drug combinations with insecticidal and acaricidal properties |
DE102007045919B4 (en) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Drug combinations with insecticidal and acaricidal properties |
DE102007045956A1 (en) * | 2007-09-26 | 2009-04-09 | Bayer Cropscience Ag | Combination of active ingredients with insecticidal and acaricidal properties |
EP2090168A1 (en) | 2008-02-12 | 2009-08-19 | Bayer CropScience AG | Method for improving plant growth |
WO2009046837A2 (en) * | 2007-10-02 | 2009-04-16 | Bayer Cropscience Ag | Methods of improving plant growth |
EP2072506A1 (en) | 2007-12-21 | 2009-06-24 | Bayer CropScience AG | Thiazolyloxyphenylamidine or thiadiazolyloxyphenylamidine und its use as fungicide |
EP2113172A1 (en) * | 2008-04-28 | 2009-11-04 | Bayer CropScience AG | Method for improved utilisation of the production potential of transgene plants |
EP2168434A1 (en) | 2008-08-02 | 2010-03-31 | Bayer CropScience AG | Use of azols to increase resistance of plants of parts of plants to abiotic stress |
BRPI0918430A2 (en) | 2008-08-14 | 2015-11-24 | Bayer Cropscience Ag | 4-phenyl-1h-pyrazols insecticides. |
DE102008041695A1 (en) * | 2008-08-29 | 2010-03-04 | Bayer Cropscience Ag | Methods for improving plant growth |
WO2010044648A1 (en) | 2008-10-16 | 2010-04-22 | Ragasa Industrias S.A. De C.V. | Vegetable oil of high dielectric purity, method for obtaining same and use thereof in an electrical device |
EP2201838A1 (en) | 2008-12-05 | 2010-06-30 | Bayer CropScience AG | Active ingredient-beneficial organism combinations with insecticide and acaricide properties |
EP2198709A1 (en) | 2008-12-19 | 2010-06-23 | Bayer CropScience AG | Method for treating resistant animal pests |
EP2381781B1 (en) | 2008-12-29 | 2016-06-08 | Bayer Intellectual Property GmbH | Method for improved use of the production potential of genetically modified plants |
EP2204094A1 (en) | 2008-12-29 | 2010-07-07 | Bayer CropScience AG | Method for improved utilization of the production potential of transgenic plants Introduction |
EP2223602A1 (en) | 2009-02-23 | 2010-09-01 | Bayer CropScience AG | Method for improved utilisation of the production potential of genetically modified plants |
EP2039771A2 (en) | 2009-01-06 | 2009-03-25 | Bayer CropScience AG | Method for improved utilization of the production potential of transgenic plants |
EP2039770A2 (en) | 2009-01-06 | 2009-03-25 | Bayer CropScience AG | Method for improved utilization of the production potential of transgenic plants |
EP2039772A2 (en) | 2009-01-06 | 2009-03-25 | Bayer CropScience AG | Method for improved utilization of the production potential of transgenic plants introduction |
EP2387309A2 (en) | 2009-01-19 | 2011-11-23 | Bayer CropScience AG | Cyclic diones and their use as insecticides, acaricides and/or fungicides |
EP2227951A1 (en) | 2009-01-23 | 2010-09-15 | Bayer CropScience AG | Application of enaminocarbonyl compounds for combating viruses transmitted by insects |
JP5592398B2 (en) | 2009-01-28 | 2014-09-17 | バイエル・クロップサイエンス・アーゲー | Disinfectant N-cycloalkyl-N-bicyclic methylene-carboxamide derivatives |
AR075126A1 (en) | 2009-01-29 | 2011-03-09 | Bayer Cropscience Ag | METHOD FOR THE BEST USE OF THE TRANSGENIC PLANTS PRODUCTION POTENTIAL |
WO2010094666A2 (en) | 2009-02-17 | 2010-08-26 | Bayer Cropscience Ag | Fungicidal n-(phenylcycloalkyl)carboxamide, n-(benzylcycloalkyl)carboxamide and thiocarboxamide derivatives |
EP2218717A1 (en) | 2009-02-17 | 2010-08-18 | Bayer CropScience AG | Fungicidal N-((HET)Arylethyl)thiocarboxamide derivatives |
TW201031331A (en) | 2009-02-19 | 2010-09-01 | Bayer Cropscience Ag | Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance |
WO2010108508A2 (en) | 2009-03-25 | 2010-09-30 | Bayer Cropscience Ag | Active ingredient combinations with insecticidal and acaricidal properties |
JP5462354B2 (en) | 2009-03-25 | 2014-04-02 | バイエル・クロップサイエンス・アーゲー | Active ingredient combinations with insecticidal and acaricidal properties |
AU2009342807B2 (en) | 2009-03-25 | 2015-04-02 | Bayer Cropscience Aktiengesellschaft | Synergistic combinations of active ingredients |
EP2232995A1 (en) | 2009-03-25 | 2010-09-29 | Bayer CropScience AG | Method for improved utilisation of the production potential of transgenic plants |
EP2410849A1 (en) | 2009-03-25 | 2012-02-01 | Bayer CropScience AG | Active ingredient combinations having insecticidal and acaricidal properties |
CN102448304B (en) | 2009-03-25 | 2015-03-11 | 拜尔农作物科学股份公司 | Active ingredient combinations having insecticidal and acaricidal properties |
EP2239331A1 (en) | 2009-04-07 | 2010-10-13 | Bayer CropScience AG | Method for improved utilization of the production potential of transgenic plants |
BRPI1015543A8 (en) | 2009-05-06 | 2016-05-24 | Bayer Cropscience Ag | CYCLOPENTANEDIONE COMPOUNDS AND THEIR USE AS INSECTICIDES, ACARICIDES AND/OR FUNGICIDES. |
AR076839A1 (en) | 2009-05-15 | 2011-07-13 | Bayer Cropscience Ag | FUNGICIDE DERIVATIVES OF PIRAZOL CARBOXAMIDAS |
EP2251331A1 (en) | 2009-05-15 | 2010-11-17 | Bayer CropScience AG | Fungicide pyrazole carboxamides derivatives |
EP2255626A1 (en) | 2009-05-27 | 2010-12-01 | Bayer CropScience AG | Use of succinate dehydrogenase inhibitors to increase resistance of plants or parts of plants to abiotic stress |
PL2437595T3 (en) | 2009-06-02 | 2019-05-31 | Bayer Cropscience Ag | Use of fluopyram for controlling sclerotinia ssp |
KR20120051015A (en) | 2009-07-16 | 2012-05-21 | 바이엘 크롭사이언스 아게 | Synergistic active substance combinations containing phenyl triazoles |
WO2011015524A2 (en) | 2009-08-03 | 2011-02-10 | Bayer Cropscience Ag | Fungicide heterocycles derivatives |
EP2292094A1 (en) | 2009-09-02 | 2011-03-09 | Bayer CropScience AG | Active compound combinations |
US9480271B2 (en) | 2009-09-15 | 2016-11-01 | Monsanto Technology Llc | Soybean seed and oil compositions and methods of making same |
CN102712911B (en) | 2009-11-20 | 2016-01-13 | 拜尔作物科学公司 | Comprise the allelic Brassica plants of sudden change FAD3 |
EP2343280A1 (en) | 2009-12-10 | 2011-07-13 | Bayer CropScience AG | Fungicide quinoline derivatives |
CA3041371A1 (en) | 2009-12-18 | 2011-06-23 | Cargill Incorporated | Brassica plants yielding oils with a low total saturated fatty acid content |
WO2011080256A1 (en) | 2009-12-28 | 2011-07-07 | Bayer Cropscience Ag | Fungicide hydroximoyl-tetrazole derivatives |
EP2519516A2 (en) | 2009-12-28 | 2012-11-07 | Bayer CropScience AG | Fungicidal hydroximoyl-tetrazole derivatives |
US9000012B2 (en) | 2009-12-28 | 2015-04-07 | Bayer Cropscience Ag | Fungicide hydroximoyl-heterocycles derivatives |
BR112012018108A2 (en) | 2010-01-22 | 2015-10-20 | Bayer Ip Gmbh | acaricidal and / or insecticidal combinations of active ingredients |
JP2013521255A (en) | 2010-03-04 | 2013-06-10 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | Fluoroalkyl-substituted 2-amidobenzimidazoles and their use to enhance stress tolerance in plants |
JP2013523795A (en) | 2010-04-06 | 2013-06-17 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | Use of 4-phenylbutyric acid and / or salt thereof to enhance stress tolerance of plants |
CA2795838A1 (en) | 2010-04-09 | 2011-10-13 | Bayer Intellectual Property Gmbh | Use of derivatives of the(1-cyanocyclopropyl)phenylphosphinic acid, the esters thereof and/or the salts thereof for enhancing the tolerance of plants to abiotic stress |
US20130116287A1 (en) | 2010-04-28 | 2013-05-09 | Christian Beier | Fungicide hydroximoyl-heterocycles derivatives |
WO2011134912A1 (en) | 2010-04-28 | 2011-11-03 | Bayer Cropscience Ag | Fungicide hydroximoyl-heterocycles derivatives |
WO2011134911A2 (en) | 2010-04-28 | 2011-11-03 | Bayer Cropscience Ag | Fungicide hydroximoyl-tetrazole derivatives |
US9695434B2 (en) | 2010-05-25 | 2017-07-04 | Cargill, Incorporated | Brassica plants yielding oils with a low alpha linolenic acid content |
CA2837011C (en) | 2010-05-25 | 2023-01-17 | Cargill Incorporated | Brassica plants yielding oils with a low alpha linolenic acid content |
WO2011153246A2 (en) | 2010-06-01 | 2011-12-08 | Martek Biosciences Corporation | Extraction of lipid from cells and products therefrom |
UA110703C2 (en) | 2010-06-03 | 2016-02-10 | Байєр Кропсайнс Аг | Fungicidal n-[(trisubstitutedsilyl)methyl]carboxamide |
EP2576516B1 (en) | 2010-06-03 | 2014-12-17 | Bayer Intellectual Property GmbH | N-[(het)arylethyl)]pyrazole(thio)carboxamides and their heterosubstituted analogues |
WO2011151370A1 (en) | 2010-06-03 | 2011-12-08 | Bayer Cropscience Ag | N-[(het)arylalkyl)] pyrazole (thio)carboxamides and their heterosubstituted analogues |
JP2013532648A (en) | 2010-07-20 | 2013-08-19 | バイエル・クロップサイエンス・アーゲー | Benzocycloalkenes as antibacterial agents |
PL2611300T3 (en) | 2010-09-03 | 2016-10-31 | Substituted annelated dihydropyrimidinone compounds | |
EP2460406A1 (en) | 2010-12-01 | 2012-06-06 | Bayer CropScience AG | Use of fluopyram for controlling nematodes in nematode resistant crops |
BR112013006611B1 (en) | 2010-09-22 | 2021-01-19 | Bayer Intellectual Property Gmbh | method for the control of soy cyst nematode (heterodera glycines) by infesting a nematode resistant soy plant comprising the application of n- {2- [3-chloro-5- (trifluoromethyl) -2-pyridinyl] ethyl} -2 - (trifluoromethyl) benzamide (fluoride |
PE20131399A1 (en) | 2010-10-07 | 2013-12-16 | Bayer Cropscience Ag | FUNGICIDAL COMPOSITION INCLUDING A TETRAZOLILOXIMA DERIVATIVE AND A THIAZOLYLPIPERIDINE DERIVATIVE |
JP2013541553A (en) | 2010-10-21 | 2013-11-14 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | 1- (Heterocycliccarbonyl) piperidines |
CN103313973B (en) | 2010-10-21 | 2015-09-16 | 拜耳知识产权有限责任公司 | N-benzyl heterocyclic carboxamide |
JP2013542215A (en) | 2010-11-02 | 2013-11-21 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | N-hetarylmethylpyrazolyl carboxamides |
CN103313971B (en) | 2010-11-15 | 2015-12-02 | 拜耳知识产权有限责任公司 | N-arylpyrazole (sulfo-) methane amide |
EP2640191A1 (en) | 2010-11-15 | 2013-09-25 | Bayer Intellectual Property GmbH | 5-halogenopyrazole(thio)carboxamides |
WO2012065947A1 (en) | 2010-11-15 | 2012-05-24 | Bayer Cropscience Ag | 5-halogenopyrazolecarboxamides |
CN102090320B (en) * | 2010-11-18 | 2013-11-13 | 李先明 | Method for cultivating and breeding cabbage (partially one-stalk and multi-pod gregarious type)-series hybrid rape |
EP2460407A1 (en) | 2010-12-01 | 2012-06-06 | Bayer CropScience AG | Agent combinations comprising pyridylethyl benzamides and other agents |
CN103281900A (en) | 2010-12-01 | 2013-09-04 | 拜耳知识产权有限责任公司 | Use of fluopyram for controlling nematodes in crops and for increasing yield |
US20130289077A1 (en) | 2010-12-29 | 2013-10-31 | Juergen Benting | Fungicide hydroximoyl-tetrazole derivatives |
EP2474542A1 (en) | 2010-12-29 | 2012-07-11 | Bayer CropScience AG | Fungicide hydroximoyl-tetrazole derivatives |
EP2471363A1 (en) | 2010-12-30 | 2012-07-04 | Bayer CropScience AG | Use of aryl-, heteroaryl- and benzylsulfonamide carboxylic acids, -carboxylic acid esters, -carboxylic acid amides and -carbonitriles and/or its salts for increasing stress tolerance in plants |
EP2494867A1 (en) | 2011-03-01 | 2012-09-05 | Bayer CropScience AG | Halogen-substituted compounds in combination with fungicides |
CA2823999C (en) | 2011-03-10 | 2020-03-24 | Bayer Intellectual Property Gmbh | Use of lipochito-oligosaccharide compounds for safeguarding seed safety of treated seeds |
CN103502238A (en) | 2011-03-14 | 2014-01-08 | 拜耳知识产权有限责任公司 | Fungicide hydroximoyl-tetrazole derivatives |
BR112013025871A2 (en) | 2011-04-08 | 2016-07-26 | Bayer Ip Gmbh | compound of formula (i) and its use, composition for controlling phytopathogenic fungi, method for controlling phytopathogenic fungi of crops and process for producing compositions |
AR090010A1 (en) | 2011-04-15 | 2014-10-15 | Bayer Cropscience Ag | 5- (CICLOHEX-2-EN-1-IL) -PENTA-2,4-DIENOS AND 5- (CICLOHEX-2-EN-1-IL) -PENT-2-EN-4-INOS REPLACED AS ACTIVE PRINCIPLES AGAINST THE ABIOTIC STRESS OF PLANTS, USES AND TREATMENT METHODS |
AR085585A1 (en) | 2011-04-15 | 2013-10-09 | Bayer Cropscience Ag | VINIL- AND ALQUINILCICLOHEXANOLES SUBSTITUTED AS ACTIVE PRINCIPLES AGAINST STRIPS ABIOTIQUE OF PLANTS |
AR085568A1 (en) | 2011-04-15 | 2013-10-09 | Bayer Cropscience Ag | 5- (BICYCLE [4.1.0] HEPT-3-EN-2-IL) -PENTA-2,4-DIENOS AND 5- (BICYCLE [4.1.0] HEPT-3-EN-2-IL) -PENT- 2-IN-4-INOS REPLACED AS ACTIVE PRINCIPLES AGAINST ABIOTIC STRESS OF PLANTS |
EP2511255A1 (en) | 2011-04-15 | 2012-10-17 | Bayer CropScience AG | Substituted prop-2-in-1-ol and prop-2-en-1-ol derivatives |
HUE043158T2 (en) | 2011-04-22 | 2019-08-28 | Bayer Cropscience Ag | Active compound compositions comprising a (thio)carboxamide derivative and a fungicidal compound |
JP2014520776A (en) | 2011-07-04 | 2014-08-25 | バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー | Use of substituted isoquinolinones, isoquinoline diones, isoquinoline triones and dihydroisoquinolinones or their salts in each case as active agents against abiotic stresses in plants |
US9265252B2 (en) | 2011-08-10 | 2016-02-23 | Bayer Intellectual Property Gmbh | Active compound combinations comprising specific tetramic acid derivatives |
CN103748092A (en) | 2011-08-22 | 2014-04-23 | 拜耳知识产权有限责任公司 | Fungicide hydroximoyl-tetrazole derivatives |
EP2561759A1 (en) | 2011-08-26 | 2013-02-27 | Bayer Cropscience AG | Fluoroalkyl-substituted 2-amidobenzimidazoles and their effect on plant growth |
CN103781353B (en) | 2011-09-09 | 2016-10-19 | 拜耳知识产权有限责任公司 | For improveing the acyl homoserine lactones derivant of plant products |
WO2013037717A1 (en) | 2011-09-12 | 2013-03-21 | Bayer Intellectual Property Gmbh | Fungicidal 4-substituted-3-{phenyl[(heterocyclylmethoxy)imino]methyl}-1,2,4-oxadizol-5(4h)-one derivatives |
AR087872A1 (en) | 2011-09-16 | 2014-04-23 | Bayer Ip Gmbh | USE OF 5-PHENYL-OR 5-BENCIL-2 ISOXAZOLIN-3 CARBOXYLATES TO IMPROVE THE PERFORMANCE OF PLANTS |
EA029005B1 (en) | 2011-09-16 | 2018-01-31 | Байер Интеллектчуал Проперти Гмбх | Use of phenylpyrazolin-3-carboxylates for improving plant yield |
AU2012307321B2 (en) | 2011-09-16 | 2016-07-14 | Bayer Intellectual Property Gmbh | Use of acylsulfonamides for improving plant yield |
WO2013041602A1 (en) | 2011-09-23 | 2013-03-28 | Bayer Intellectual Property Gmbh | Use of 4-substituted 1-phenyl-pyrazole-3-carboxylic-acid derivatives as agents against abiotic plant stress |
CN103842507A (en) | 2011-10-04 | 2014-06-04 | 拜耳知识产权有限责任公司 | Rnai for the control of fungi and oomycetes by inhibiting saccharopine dehydrogenase gene |
WO2013050324A1 (en) | 2011-10-06 | 2013-04-11 | Bayer Intellectual Property Gmbh | Combination, containing 4-phenylbutyric acid (4-pba) or a salt thereof (component (a)) and one or more selected additional agronomically active compounds (component(s) (b)), that reduces abiotic plant stress |
MX2014005976A (en) | 2011-11-21 | 2014-08-27 | Bayer Ip Gmbh | Fungicide n-[(trisubstitutedsilyl)methyl]-carboxamide derivatives. |
WO2013079566A2 (en) | 2011-11-30 | 2013-06-06 | Bayer Intellectual Property Gmbh | Fungicidal n-bicycloalkyl and n-tricycloalkyl (thio)carboxamide derivatives |
IN2014CN04325A (en) | 2011-12-19 | 2015-09-04 | Bayer Cropscience Ag | |
CN104039769B (en) | 2011-12-29 | 2016-10-19 | 拜耳知识产权有限责任公司 | 3-[(1,3-thiazole-4-yl methoxyimino) (phenyl) methyl]-2-substituted-1,2,4-diazole-5 (2H) the-one derivant of antifungal |
US9556158B2 (en) | 2011-12-29 | 2017-01-31 | Bayer Intellectual Property Gmbh | Fungicidal 3-[(pyridin-2-ylmethoxyimino)(phenyl)methyl]-2-substituted-1,2,4-oxadiazol-5(2H)-one derivatives |
ES2664230T3 (en) | 2012-02-22 | 2018-04-18 | Bayer Cropscience Ag | Use of fluopiram for the control of diseases of wood in the vine |
CN104244716B (en) | 2012-02-27 | 2017-05-03 | 拜耳知识产权有限责任公司 | Active compound combinations containing a thiazoylisoxazoline and a fungicide |
WO2013139949A1 (en) | 2012-03-23 | 2013-09-26 | Bayer Intellectual Property Gmbh | Compositions comprising a strigolactame compound for enhanced plant growth and yield |
US9357778B2 (en) | 2012-04-12 | 2016-06-07 | Bayer Cropscience Ag | N-acyl-2-(cyclo)alkypyrrolidines and piperidines useful as fungicides |
EP2838893B1 (en) | 2012-04-20 | 2019-03-13 | Bayer Cropscience AG | N-cycloalkyl-n-[(heterocyclylphenyl)methylene]-(thio)carboxamide derivatives |
US20150080337A1 (en) | 2012-04-20 | 2015-03-19 | Bayer Cropscience | N-cycloalkyl-n-[(trisubstitutedsilylphenyl)methylene]-(thio)carboxamide derivatives |
EP2662361A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | Pyrazol indanyl carboxamides |
MX2014013489A (en) | 2012-05-09 | 2015-02-12 | Bayer Cropscience Ag | 5-halogenopyrazole indanyl carboxamides. |
EP2662360A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | 5-Halogenopyrazole indanyl carboxamides |
JP6262208B2 (en) | 2012-05-09 | 2018-01-17 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | Pyrazole indanyl carboxamides |
EP2662363A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | 5-Halogenopyrazole biphenylcarboxamides |
EP2662370A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | 5-Halogenopyrazole benzofuranyl carboxamides |
EP2662362A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | Pyrazole indanyl carboxamides |
EP2662364A1 (en) | 2012-05-09 | 2013-11-13 | Bayer CropScience AG | Pyrazole tetrahydronaphthyl carboxamides |
AR091104A1 (en) | 2012-05-22 | 2015-01-14 | Bayer Cropscience Ag | COMBINATIONS OF ACTIVE COMPOUNDS THAT INCLUDE A LIPO-CHYTOOLIGOSACARIDE DERIVATIVE AND A NEMATICIDE, INSECTICIDE OR FUNGICIDE COMPOUND |
WO2014009322A1 (en) | 2012-07-11 | 2014-01-16 | Bayer Cropscience Ag | Use of fungicidal combinations for increasing the tolerance of a plant towards abiotic stress |
AU2013311826A1 (en) | 2012-09-05 | 2015-03-26 | Bayer Cropscience Ag | Use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles or salts thereof as active substances against abiotic plant stress |
US9801374B2 (en) | 2012-10-19 | 2017-10-31 | Bayer Cropscience Ag | Active compound combinations comprising carboxamide derivatives |
JP6262747B2 (en) | 2012-10-19 | 2018-01-17 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | Plant growth promotion method using carboxamide derivatives |
UA114647C2 (en) | 2012-10-19 | 2017-07-10 | Байєр Кропсайнс Аг | Method for enhancing tolerance to abiotic stress in plants using carboxamide or thiocarboxamide derivatives |
DK2908641T3 (en) | 2012-10-19 | 2018-04-23 | Bayer Cropscience Ag | PROCEDURE FOR TREATING PLANTS AGAINST FUNGI RESISTANT TO FUNGICIDES USING CARBOXAMIDE OR THIOCARBOXAMIDE DERIVATIVES |
EP2735231A1 (en) | 2012-11-23 | 2014-05-28 | Bayer CropScience AG | Active compound combinations |
WO2014079957A1 (en) | 2012-11-23 | 2014-05-30 | Bayer Cropscience Ag | Selective inhibition of ethylene signal transduction |
BR112015012055B1 (en) | 2012-11-30 | 2021-01-12 | Bayer Cropscience Ag | ternary fungicidal composition, its preparation process, method to control one or more harmful microorganisms, seed resistant to harmful microorganisms and its treatment method |
UA116222C2 (en) | 2012-11-30 | 2018-02-26 | Байєр Кропсайєнс Акцієнгезелльшафт | Ternary fungicidal and pesticidal mixtures |
EA030020B1 (en) | 2012-11-30 | 2018-06-29 | Байер Кропсайенс Акциенгезельшафт | Binary fungicidal mixtures |
UA116223C2 (en) | 2012-11-30 | 2018-02-26 | Байєр Кропсайєнс Акцієнгезелльшафт | Binary fungicidal mixtures |
MX2015006328A (en) | 2012-11-30 | 2015-09-07 | Bayer Cropscience Ag | Binary fungicidal or pesticidal mixture. |
EP2740720A1 (en) | 2012-12-05 | 2014-06-11 | Bayer CropScience AG | Substituted bicyclic and tricyclic pent-2-en-4-inic acid derivatives and their use for enhancing the stress tolerance in plants |
CN105072903A (en) | 2012-12-05 | 2015-11-18 | 拜耳作物科学股份公司 | Use of substituted 1-(aryl ethynyl)-, 1-(heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cyloalkenyl ethynyl)-cyclohexanols as active agents against abiotic plant stress |
EP2740356A1 (en) | 2012-12-05 | 2014-06-11 | Bayer CropScience AG | Substituted (2Z)-5(1-Hydroxycyclohexyl)pent-2-en-4-inic acid derivatives |
WO2014090765A1 (en) | 2012-12-12 | 2014-06-19 | Bayer Cropscience Ag | Use of 1-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-5-amino-3-trifluoromethyl)-1 h-1,2,4 tfia zole for controlling nematodes in nematode-resistant crops |
AR093996A1 (en) | 2012-12-18 | 2015-07-01 | Bayer Cropscience Ag | BACTERICIDAL COMBINATIONS AND BINARY FUNGICIDES |
EP2935218A1 (en) | 2012-12-19 | 2015-10-28 | Bayer CropScience AG | Difluoromethyl-nicotinic- tetrahydronaphtyl carboxamides |
CN105705490A (en) | 2013-03-07 | 2016-06-22 | 拜耳作物科学股份公司 | Fungicidal 3-{phenyl[(heterocyclylmethoxy)imino]methyl}-heterocycle derivatives |
JP2016522800A (en) | 2013-04-12 | 2016-08-04 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | New triazoline thione derivatives |
MX2015014365A (en) | 2013-04-12 | 2015-12-07 | Bayer Cropscience Ag | Novel triazole derivatives. |
BR112015026235A2 (en) | 2013-04-19 | 2017-10-10 | Bayer Cropscience Ag | method for improving utilization of the potential of transgenic plant production involving the application of a phthaldiamide derivative |
WO2014170364A1 (en) | 2013-04-19 | 2014-10-23 | Bayer Cropscience Ag | Binary insecticidal or pesticidal mixture |
WO2014177514A1 (en) | 2013-04-30 | 2014-11-06 | Bayer Cropscience Ag | Nematicidal n-substituted phenethylcarboxamides |
TW201507722A (en) | 2013-04-30 | 2015-03-01 | Bayer Cropscience Ag | N-(2-halogen-2-phenethyl)carboxamides as nematicides and endoparasiticides |
WO2014206953A1 (en) | 2013-06-26 | 2014-12-31 | Bayer Cropscience Ag | N-cycloalkyl-n-[(bicyclylphenyl)methylene]-(thio)carboxamide derivatives |
MX2016000141A (en) | 2013-07-09 | 2016-03-01 | Bayer Cropscience Ag | Use of selected pyridone carboxamides or salts thereof as active substances against abiotic plant stress. |
EP2837287A1 (en) | 2013-08-15 | 2015-02-18 | Bayer CropScience AG | Use of prothioconazole for increasing root growth of Brassicaceae |
WO2015082586A1 (en) | 2013-12-05 | 2015-06-11 | Bayer Cropscience Ag | N-cycloalkyl-n-{[2-(1-substitutedcycloalkyl)phenyl]methylene}-(thio)carboxamide derivatives |
TW201607929A (en) | 2013-12-05 | 2016-03-01 | 拜耳作物科學公司 | N-cycloalkyl-N-{[2-(1-substitutedcycloalkyl) phenyl]methylene}-(thio)carboxamide derivatives |
MX2016008228A (en) | 2013-12-20 | 2016-11-28 | Dsm Ip Assets Bv | Processes for obtaining microbial oil from microbial cells. |
NZ721415A (en) | 2013-12-20 | 2022-08-26 | Dsm Ip Assets Bv | Processes for obtaining microbial oil from microbial cells |
KR102426988B1 (en) | 2013-12-20 | 2022-07-28 | 디에스엠 아이피 어셋츠 비.브이. | Processes for obtaining microbial oil from microbial cells |
JP2017501709A (en) | 2013-12-20 | 2017-01-19 | ディーエスエム アイピー アセッツ ビー.ブイ. | Method for obtaining microbial oil from microbial cells |
AR101214A1 (en) | 2014-07-22 | 2016-11-30 | Bayer Cropscience Ag | CIANO-CICLOALQUILPENTA-2,4-DIENOS, CIANO-CICLOALQUILPENT-2-EN-4-INAS, CIANO-HETEROCICLILPENTA-2,4-DIENOS AND CYANO-HETEROCICLILPENT-2-EN-4-INAS REPLACED AS ACTIVE PRINCIPLES PLANTS ABIOTIC |
AR103024A1 (en) | 2014-12-18 | 2017-04-12 | Bayer Cropscience Ag | SELECTED PYRIDONCARBOXAMIDS OR ITS SALTS AS ACTIVE SUBSTANCES AGAINST ABIOTIC PLANTS STRESS |
BR112017022000A2 (en) | 2015-04-13 | 2018-07-03 | Bayer Cropscience Ag | n-cycloalkyl-n- (biheterocyclylethylene) - (thio) carboxamide derivatives. |
CN105245286B (en) * | 2015-07-08 | 2018-04-03 | 天津理工大学 | Apparatus and method caused by a kind of double width degree pulse position modulation signal |
WO2018019676A1 (en) | 2016-07-29 | 2018-02-01 | Bayer Cropscience Aktiengesellschaft | Active compound combinations and methods to protect the propagation material of plants |
US20190211002A1 (en) | 2016-09-22 | 2019-07-11 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives |
WO2018054829A1 (en) | 2016-09-22 | 2018-03-29 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives and their use as fungicides |
EP3531833A2 (en) | 2016-10-26 | 2019-09-04 | Bayer CropScience Aktiengesellschaft | Use of pyraziflumid for controlling sclerotinia spp in seed treatment applications |
BR112019011616A2 (en) | 2016-12-08 | 2019-10-22 | Bayer Ag | use of insecticides to control larvae |
WO2018108627A1 (en) | 2016-12-12 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Use of substituted indolinylmethyl sulfonamides, or the salts thereof for increasing the stress tolerance of plants |
EP3332645A1 (en) | 2016-12-12 | 2018-06-13 | Bayer Cropscience AG | Use of substituted pyrimidine diones or their salts as agents to combat abiotic plant stress |
WO2019025153A1 (en) | 2017-07-31 | 2019-02-07 | Bayer Cropscience Aktiengesellschaft | Use of substituted n-sulfonyl-n'-aryl diaminoalkanes and n-sulfonyl-n'-heteroaryl diaminoalkanes or salts thereof for increasing the stress tolerance in plants |
US20210323950A1 (en) | 2018-06-04 | 2021-10-21 | Bayer Aktiengesellschaft | Herbicidally active bicyclic benzoylpyrazoles |
CN112689457A (en) | 2018-07-26 | 2021-04-20 | 拜耳公司 | Use of fluopyram as succinate dehydrogenase inhibitor for preventing and treating root rot complex disease and/or seedling disease complex disease caused by rhizoctonia solani, fusarium species and pythium species in cruciferae species |
CN116998520A (en) * | 2019-11-13 | 2023-11-07 | 云南省热带作物科学研究所 | Preparation method of nut crisp compounded by moringa oleifera and macadimia nut kernels |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4948881A (en) * | 1982-12-28 | 1990-08-14 | Sanofi | Process for the depolymerization and sulfation of polysaccharides |
US4627192B1 (en) | 1984-11-16 | 1995-10-17 | Sigco Res Inc | Sunflower products and methods for their production |
US4889921A (en) | 1987-04-29 | 1989-12-26 | The University Of Toronto Innovations Foundation | Production of rapeseed protein materials |
US5638637A (en) * | 1987-12-31 | 1997-06-17 | Pioneer Hi-Bred International, Inc. | Production of improved rapeseed exhibiting an enhanced oleic acid content |
ATE110224T1 (en) | 1987-12-31 | 1994-09-15 | Pioneer Hi Bred Int | PRODUCTION OF RAPESEED WITH HIGH OIL ACID CONTENT. |
US4948811A (en) * | 1988-01-26 | 1990-08-14 | The Procter & Gamble Company | Salad/cooking oil balanced for health benefits |
US5494650A (en) * | 1989-01-19 | 1996-02-27 | Societe Nationale Elf Aquitaine (Production) | Process for improving the sulphur yield of a complex for producing sulphur from a sour gas containing H2 S, the said complex comprising a sulphur plant and then an oxidation and hydrolysis unit followed by a purification unit |
JPH05505512A (en) | 1989-03-06 | 1993-08-19 | パイオニア ハイ―ブレッド インターナショナル インコーポレイテッド | Production of improved rapeseed showing increased oleic acid content |
US4970084A (en) * | 1989-06-30 | 1990-11-13 | The Procter & Gamble Company | Process for making potato-based chip products containing intact non-potato pieces |
US5077071A (en) | 1989-09-06 | 1991-12-31 | Epe Incorporated | Oil extrusion process |
ATE195053T1 (en) | 1990-08-30 | 2000-08-15 | Cargill Inc | BRASSICA OILS WITH MODIFIED FATTY ACID CONTENTS |
US5260077A (en) * | 1991-02-12 | 1993-11-09 | The Lubrizol Corporation | Vegetable oil compositions |
US6270828B1 (en) * | 1993-11-12 | 2001-08-07 | Cargrill Incorporated | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
US5750827A (en) * | 1991-09-30 | 1998-05-12 | Cargill Incorporated | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability |
US5536900A (en) | 1991-12-16 | 1996-07-16 | Ciba-Geigy Corporation | Inbred corn line |
US5912041A (en) * | 1993-06-17 | 1999-06-15 | Cargill, Incorporated | Canola shortening for food applications |
AU692791B2 (en) | 1993-10-12 | 1998-06-18 | Agrigenetics, Inc. | Brassica napus variety AG019 |
-
1997
- 1997-05-05 US US08/850,279 patent/US6270828B1/en not_active Expired - Fee Related
-
2001
- 2001-05-21 US US09/861,905 patent/US6562397B2/en not_active Expired - Fee Related
- 2001-12-27 US US10/034,698 patent/US20020092042A1/en not_active Abandoned
-
2002
- 2002-05-09 US US10/143,432 patent/US6680396B2/en not_active Expired - Fee Related
- 2002-10-17 US US10/274,092 patent/US20030159176A1/en not_active Abandoned
- 2002-10-17 US US10/274,312 patent/US6689409B2/en not_active Expired - Fee Related
-
2004
- 2004-10-26 US US10/976,585 patent/US20050114922A1/en not_active Abandoned
-
2007
- 2007-05-29 US US11/754,923 patent/US20080034457A1/en not_active Abandoned
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007016521A3 (en) * | 2005-08-01 | 2007-04-26 | Ca Minister Agriculture & Food | Low fiber yellow canola seeds comprising high oleic, low linolenic oil |
US20100303999A1 (en) * | 2005-08-01 | 2010-12-02 | Her Majesty The Queen in Right of Canada as Repre- sented by the Minister of Agriculture and Agri-Fo | Low Fiber Yellow Canola Seeds Comprising High Oleic, Low Linolenic Oil |
US9066483B2 (en) | 2005-08-01 | 2015-06-30 | Her Majesty The Queen In Right Of Canada As Represented By The Minister Of Agriculture And Agri-Food | Low fiber yellow canola seeds comprising high, oleic, low linolenic oil |
Also Published As
Publication number | Publication date |
---|---|
US6689409B2 (en) | 2004-02-10 |
US6680396B2 (en) | 2004-01-20 |
US6270828B1 (en) | 2001-08-07 |
US6562397B2 (en) | 2003-05-13 |
US20020129408A1 (en) | 2002-09-12 |
US20030066105A1 (en) | 2003-04-03 |
US20080034457A1 (en) | 2008-02-07 |
US20020092042A1 (en) | 2002-07-11 |
US20030154514A1 (en) | 2003-08-14 |
US20050114922A1 (en) | 2005-05-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6680396B2 (en) | Canola oil with reduced linolenic acid | |
EP0779024B1 (en) | A canola producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur | |
US5750827A (en) | Canola variety producing a seed with reduced glucosinolates and linolenic acid yielding an oil with low sulfur, improved sensory characteristics and increased oxidative stability | |
US7238852B2 (en) | Non-hydrogenated canola oil for food applications | |
CA2089265C (en) | Seeds, plants and oils with altered fatty acid profiles | |
US6303849B1 (en) | Brassica juncea lines bearing endogenous edible oils | |
JPH11501513A (en) | Improved oilseed rape with desired levels of unsaturated fatty acids and endogenous oils containing saturated fatty acids | |
US6953882B2 (en) | Oil from seeds with a modified fatty acid composition | |
US5912416A (en) | Safflower products with very high levels of unsaturated fatty acids | |
US7569712B2 (en) | Plant, seeds and oil with increased saturated triacylglycerols content and oil having a high stearic acid content | |
CA2253984C (en) | Brassica juncea lines bearing endogenous edible oils | |
DE DK et al. | AUS SAATEN GEWONNENES ÖL MIT MODIFIZIERTER FETTSÄUREZUSAMMENSETZUNG HUILE PROVENANT DE GRAINES A TENEUR EN ACIDES GRAS MODIFIEE | |
MXPA97006836A (en) | Brazilian oil seed improved with an endogenous oil with desirable concentrations of saturated fatty acids and insatura |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |