ZA200203539B - Method for preparing conjugated linoleic acid. - Google Patents

Method for preparing conjugated linoleic acid. Download PDF

Info

Publication number: ZA200203539B
Authority: ZA; South Africa
Prior art keywords: linoleic acid; cla; terized; acid; charac
Prior art date: 1999-11-19

Application number

ZA200203539A

Other languages

English (en)

Inventor

Simo Laakso

Marjatta Vahvaselkae

Soile Tynkkynen

Auli Rainio

Annika Maeyrae-Maekinen

Tarja Suomalainen

Original Assignee

Valio Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-11-19

Filing date

2002-05-03

Publication date

2003-08-04

2002-05-03 Application filed by Valio Ltd filed Critical Valio Ltd

2003-08-04 Publication of ZA200203539B publication Critical patent/ZA200203539B/en

Links

OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 title claims description 264
JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 title claims description 129
229940108924 conjugated linoleic acid Drugs 0.000 title claims description 127
238000000034 method Methods 0.000 title claims description 41
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 136
235000020778 linoleic acid Nutrition 0.000 claims description 136
229960004232 linoleic acid Drugs 0.000 claims description 107
241000894006 Bacteria Species 0.000 claims description 42
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 40
230000012010 growth Effects 0.000 claims description 25
235000019260 propionic acid Nutrition 0.000 claims description 20
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 18
239000000693 micelle Substances 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 16
241000186428 Propionibacterium freudenreichii Species 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 14
230000001580 bacterial effect Effects 0.000 claims description 12
239000004094 surface-active agent Substances 0.000 claims description 12
235000013305 food Nutrition 0.000 claims description 9
239000001963 growth medium Substances 0.000 claims description 9
229940049964 oleate Drugs 0.000 claims description 8
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 7
-1 polyoxyethylene Polymers 0.000 claims description 4
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
244000005700 microbiome Species 0.000 claims description 2
241000736839 Chara Species 0.000 claims 1
239000003599 detergent Substances 0.000 description 41
239000002609 medium Substances 0.000 description 28
235000010633 broth Nutrition 0.000 description 24
210000004027 cell Anatomy 0.000 description 24
238000004519 manufacturing process Methods 0.000 description 24
239000000243 solution Substances 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
235000014113 dietary fatty acids Nutrition 0.000 description 18
239000000194 fatty acid Substances 0.000 description 18
229930195729 fatty acid Natural products 0.000 description 18
150000004665 fatty acids Chemical class 0.000 description 18
239000005862 Whey Substances 0.000 description 16
108010046377 Whey Proteins Proteins 0.000 description 16
102000007544 Whey Proteins Human genes 0.000 description 16
230000000694 effects Effects 0.000 description 16
238000000855 fermentation Methods 0.000 description 16
230000004151 fermentation Effects 0.000 description 16
239000000047 product Substances 0.000 description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
238000007792 addition Methods 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
230000002401 inhibitory effect Effects 0.000 description 10
235000013336 milk Nutrition 0.000 description 10
239000008267 milk Substances 0.000 description 10
210000004080 milk Anatomy 0.000 description 10
241000030538 Thecla Species 0.000 description 9
230000010261 cell growth Effects 0.000 description 9
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 9
229920000053 polysorbate 80 Polymers 0.000 description 9
239000012466 permeate Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
235000019485 Safflower oil Nutrition 0.000 description 7
235000005713 safflower oil Nutrition 0.000 description 7
239000003813 safflower oil Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
206010028980 Neoplasm Diseases 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000007853 buffer solution Substances 0.000 description 6
238000002156 mixing Methods 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
239000011550 stock solution Substances 0.000 description 6
239000002253 acid Substances 0.000 description 5
235000013361 beverage Nutrition 0.000 description 5
201000011510 cancer Diseases 0.000 description 5
239000003925 fat Substances 0.000 description 5
235000019197 fats Nutrition 0.000 description 5
239000000843 powder Substances 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
239000000126 substance Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
230000000845 anti-microbial effect Effects 0.000 description 4
229940041514 candida albicans extract Drugs 0.000 description 4
235000013351 cheese Nutrition 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000007789 gas Substances 0.000 description 4
229920000136 polysorbate Polymers 0.000 description 4
238000007127 saponification reaction Methods 0.000 description 4
239000012138 yeast extract Substances 0.000 description 4
206010006187 Breast cancer Diseases 0.000 description 3
208000026310 Breast neoplasm Diseases 0.000 description 3
102000004195 Isomerases Human genes 0.000 description 3
108090000769 Isomerases Proteins 0.000 description 3
240000002129 Malva sylvestris Species 0.000 description 3
235000006770 Malva sylvestris Nutrition 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000003556 assay Methods 0.000 description 3
235000015278 beef Nutrition 0.000 description 3
235000005911 diet Nutrition 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
239000012071 phase Substances 0.000 description 3
229920001817 Agar Polymers 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
201000001320 Atherosclerosis Diseases 0.000 description 2
241000605900 Butyrivibrio fibrisolvens Species 0.000 description 2
208000005623 Carcinogenesis Diseases 0.000 description 2
102000015779 HDL Lipoproteins Human genes 0.000 description 2
108010010234 HDL Lipoproteins Proteins 0.000 description 2
241000186660 Lactobacillus Species 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
210000000577 adipose tissue Anatomy 0.000 description 2
239000008272 agar Substances 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
230000036952 cancer formation Effects 0.000 description 2
231100000504 carcinogenesis Toxicity 0.000 description 2
108010079058 casein hydrolysate Proteins 0.000 description 2
238000004113 cell culture Methods 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
235000013365 dairy product Nutrition 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
230000037213 diet Effects 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
235000021588 free fatty acids Nutrition 0.000 description 2
235000013376 functional food Nutrition 0.000 description 2
239000003102 growth factor Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000002054 inoculum Substances 0.000 description 2
229940049918 linoleate Drugs 0.000 description 2
150000002632 lipids Chemical class 0.000 description 2
235000013372 meat Nutrition 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
BDXAHSJUDUZLDU-UHFFFAOYSA-N methyl nonadecanoate Chemical compound CCCCCCCCCCCCCCCCCCC(=O)OC BDXAHSJUDUZLDU-UHFFFAOYSA-N 0.000 description 2
239000006872 mrs medium Substances 0.000 description 2
238000002703 mutagenesis Methods 0.000 description 2
231100000350 mutagenesis Toxicity 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
238000012545 processing Methods 0.000 description 2
238000011160 research Methods 0.000 description 2
210000004767 rumen Anatomy 0.000 description 2
239000000523 sample Substances 0.000 description 2
239000012064 sodium phosphate buffer Substances 0.000 description 2
OYHQOLUKZRVURQ-KQHSAVHASA-N (9Z,12E)-octadecadienoic acid Chemical compound CCCCC\C=C\C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-KQHSAVHASA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000186012 Bifidobacterium breve Species 0.000 description 1
108010076119 Caseins Proteins 0.000 description 1
206010009944 Colon cancer Diseases 0.000 description 1
241000186427 Cutibacterium acnes Species 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000186604 Lactobacillus reuteri Species 0.000 description 1
241000194036 Lactococcus Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
101100192881 Neosartorya fumigata (strain ATCC MYA-4609 / Af293 / CBS 101355 / FGSC A1100) pyr8 gene Proteins 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
102000004316 Oxidoreductases Human genes 0.000 description 1
108090000854 Oxidoreductases Proteins 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000282849 Ruminantia Species 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
208000005718 Stomach Neoplasms Diseases 0.000 description 1
241000194017 Streptococcus Species 0.000 description 1
235000019486 Sunflower oil Nutrition 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000010420 art technique Methods 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000013405 beer Nutrition 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
235000015155 buttermilk Nutrition 0.000 description 1
230000000711 cancerogenic effect Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
231100000315 carcinogenic Toxicity 0.000 description 1
239000012159 carrier gas Substances 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
208000029742 colonic neoplasm Diseases 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
239000000470 constituent Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
235000015140 cultured milk Nutrition 0.000 description 1
235000014048 cultured milk product Nutrition 0.000 description 1
238000012258 culturing Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000000378 dietary effect Effects 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
235000019387 fatty acid methyl ester Nutrition 0.000 description 1
206010017758 gastric cancer Diseases 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
230000009422 growth inhibiting effect Effects 0.000 description 1
235000015220 hamburgers Nutrition 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
210000005260 human cell Anatomy 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000000413 hydrolysate Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
229940001447 lactate Drugs 0.000 description 1
229940039696 lactobacillus Drugs 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
235000021243 milk fat Nutrition 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000003471 mutagenic agent Substances 0.000 description 1
231100000707 mutagenic chemical Toxicity 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical class O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 description 1
230000002265 prevention Effects 0.000 description 1
229940055019 propionibacterium acne Drugs 0.000 description 1
229940070376 protein Drugs 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000005180 public health Effects 0.000 description 1
238000005070 sampling Methods 0.000 description 1
235000011888 snacks Nutrition 0.000 description 1
239000001540 sodium lactate Substances 0.000 description 1
229940005581 sodium lactate Drugs 0.000 description 1
235000011088 sodium lactate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000021262 sour milk Nutrition 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
201000011549 stomach cancer Diseases 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000013595 supernatant sample Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013618 yogurt Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6409—Fatty acids
- C12P7/6427—Polyunsaturated fatty acids [PUFA], i.e. having two or more double bonds in their backbone
- C12P7/6431—Linoleic acids [18:2[n-6]]
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Zoology (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Wood Science & Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Biotechnology (AREA)
Oil, Petroleum & Natural Gas (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Microbiology (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

ZA200203539A 1999-11-19 2002-05-03 Method for preparing conjugated linoleic acid. ZA200203539B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FI992477A FI108730B (fi)	1999-11-19	1999-11-19	Menetelmä konjugoidun linolihapon valmistamiseksi

Publications (1)

Publication Number	Publication Date
ZA200203539B true ZA200203539B (en)	2003-08-04

Family

ID=8555617

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200203539A ZA200203539B (en)	1999-11-19	2002-05-03	Method for preparing conjugated linoleic acid.

Country Status (19)

Country	Link
US (1)	US6960456B1 (et)
EP (1)	EP1240348A1 (et)
JP (1)	JP2003514535A (et)
KR (1)	KR20020065523A (et)
CN (1)	CN1391613A (et)
AU (1)	AU770113B2 (et)
BR (1)	BR0015663A (et)
CA (1)	CA2390572A1 (et)
CZ (1)	CZ20021637A3 (et)
EE (1)	EE200200253A (et)
FI (1)	FI108730B (et)
HR (1)	HRP20020427B1 (et)
HU (1)	HU224704B1 (et)
NO (1)	NO20022361L (et)
NZ (1)	NZ518902A (et)
PL (1)	PL355658A1 (et)
RU (1)	RU2265664C2 (et)
WO (1)	WO2001036653A1 (et)
ZA (1)	ZA200203539B (et)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI115842B (fi) *	2002-03-27	2005-07-29	Valio Oy	Menetelmä konjugoidun linolihapon valmistamiseksi
KR100686557B1 (ko) *	2004-08-16	2007-02-23	씨제이 주식회사	체지방 저하 기능성 락토바실러스 람노서스와 이를 함유한 식품
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1999
- 1999-11-19 FI FI992477A patent/FI108730B/fi active
2000
- 2000-11-16 HU HU0204173A patent/HU224704B1/hu not_active IP Right Cessation
- 2000-11-16 US US10/130,426 patent/US6960456B1/en not_active Expired - Fee Related
- 2000-11-16 CN CN00815851A patent/CN1391613A/zh active Pending
- 2000-11-16 CA CA002390572A patent/CA2390572A1/en not_active Abandoned
- 2000-11-16 WO PCT/FI2000/001004 patent/WO2001036653A1/en not_active Ceased
- 2000-11-16 HR HR20020427 patent/HRP20020427B1/xx not_active IP Right Cessation
- 2000-11-16 KR KR1020027006376A patent/KR20020065523A/ko not_active Ceased
- 2000-11-16 JP JP2001538531A patent/JP2003514535A/ja active Pending
- 2000-11-16 CZ CZ20021637A patent/CZ20021637A3/cs unknown
- 2000-11-16 AU AU17093/01A patent/AU770113B2/en not_active Ceased
- 2000-11-16 PL PL00355658A patent/PL355658A1/xx not_active Application Discontinuation
- 2000-11-16 EE EEP200200253A patent/EE200200253A/et unknown
- 2000-11-16 RU RU2002116367/13A patent/RU2265664C2/ru not_active IP Right Cessation
- 2000-11-16 NZ NZ518902A patent/NZ518902A/en unknown
- 2000-11-16 BR BR0015663-9A patent/BR0015663A/pt not_active IP Right Cessation
- 2000-11-16 EP EP00979692A patent/EP1240348A1/en not_active Withdrawn
2002
- 2002-05-03 ZA ZA200203539A patent/ZA200203539B/en unknown
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Also Published As

Publication number	Publication date
AU1709301A (en)	2001-05-30
US6960456B1 (en)	2005-11-01
CZ20021637A3 (cs)	2002-11-13
HUP0204173A3 (en)	2004-07-28
RU2002116367A (ru)	2004-02-10
WO2001036653A1 (en)	2001-05-25
EP1240348A1 (en)	2002-09-18
BR0015663A (pt)	2002-07-23
HRP20020427A2 (en)	2003-08-31
HUP0204173A2 (hu)	2003-03-28
HRP20020427B1 (en)	2004-12-31
NO20022361D0 (no)	2002-05-16
CA2390572A1 (en)	2001-05-25
NZ518902A (en)	2003-07-25
KR20020065523A (ko)	2002-08-13
RU2265664C2 (ru)	2005-12-10
FI19992477L (fi)	2001-05-20
HU224704B1 (en)	2006-01-30
JP2003514535A (ja)	2003-04-22
CN1391613A (zh)	2003-01-15
AU770113B2 (en)	2004-02-12
EE200200253A (et)	2003-06-16
FI108730B (fi)	2002-03-15
PL355658A1 (en)	2004-05-04
NO20022361L (no)	2002-07-10

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US5856149A (en)	1999-01-05	Method of producing conjugated fatty acids
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Rainio et al.	2002	Production of conjugated linoleic acid by Propionibacterium freudenreichii ssp. shermanii
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FI115842B (fi)	2005-07-29	Menetelmä konjugoidun linolihapon valmistamiseksi
WO1999029886A1 (en)	1999-06-17	Formation of conjugated unsaturated fatty acids
Das et al.	2005	Effect of yeast and bacterial adjuncts on the CLA content and flavour of a washed-curd, dry-salted cheese
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CN120888620B (zh)	2026-01-30	一种增强裂殖壶菌磷脂dha生产能力的发酵方法和应用
MATULOVÁ et al.	2009	Composition of conjugated linoleic acid isomers formed by Lactobacillus and Bifidobacterium spp. in conversion media
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