NZ500698A - Conjugated linolenic acid-base synthetic triglycerides - Google Patents
Conjugated linolenic acid-base synthetic triglyceridesInfo
- Publication number
- NZ500698A NZ500698A NZ500698A NZ50069898A NZ500698A NZ 500698 A NZ500698 A NZ 500698A NZ 500698 A NZ500698 A NZ 500698A NZ 50069898 A NZ50069898 A NZ 50069898A NZ 500698 A NZ500698 A NZ 500698A
- Authority
- NZ
- New Zealand
- Prior art keywords
- acid
- conjugated linoleic
- triglycerides
- linoleic acid
- weight
- Prior art date
Links
- 150000003626 triacylglycerols Chemical class 0.000 title claims abstract description 31
- 229940108924 conjugated linoleic acid Drugs 0.000 claims abstract description 38
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims abstract description 37
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 22
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 20
- 239000000194 fatty acid Substances 0.000 claims abstract description 20
- 229930195729 fatty acid Natural products 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 230000032050 esterification Effects 0.000 claims abstract description 14
- 238000005886 esterification reaction Methods 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 9
- 239000011541 reaction mixture Substances 0.000 claims abstract description 9
- 239000011261 inert gas Substances 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 claims abstract 2
- 239000003963 antioxidant agent Substances 0.000 claims description 7
- 230000003078 antioxidant effect Effects 0.000 claims description 5
- JBYXPOFIGCOSSB-XBLVEGMJSA-N 9E,11E-octadecadienoic acid Chemical group CCCCCC\C=C\C=C\CCCCCCCC(O)=O JBYXPOFIGCOSSB-XBLVEGMJSA-N 0.000 description 40
- 235000013305 food Nutrition 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 241000282414 Homo sapiens Species 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 9
- 239000002253 acid Substances 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000000825 pharmaceutical preparation Substances 0.000 description 6
- 229940127557 pharmaceutical product Drugs 0.000 description 6
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- -1 for example Chemical class 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 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 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 235000016709 nutrition Nutrition 0.000 description 3
- 230000035764 nutrition Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 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
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- SIOLDWZBFABPJU-UHFFFAOYSA-N isotridecanoic acid Chemical compound CC(C)CCCCCCCCCC(O)=O SIOLDWZBFABPJU-UHFFFAOYSA-N 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000003346 palm kernel oil Substances 0.000 description 2
- 235000019865 palm kernel oil Nutrition 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- ADHNUPOJJCKWRT-JLXBFWJWSA-N (2e,4e)-octadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C(O)=O ADHNUPOJJCKWRT-JLXBFWJWSA-N 0.000 description 1
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- CUXYLFPMQMFGPL-WPOADVJFSA-N (9Z,11E,13E)-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C/CCCCCCCC(O)=O CUXYLFPMQMFGPL-WPOADVJFSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- 241000558306 Gynocardia odorata Species 0.000 description 1
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 241001072282 Limnanthes Species 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019728 animal nutrition Nutrition 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 230000003217 anti-cancerogenic effect Effects 0.000 description 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- 239000010480 babassu oil Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000010495 camellia oil Substances 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000001925 catabolic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000010636 coriander oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- LQJBNNIYVWPHFW-QXMHVHEDSA-N gadoleic acid Chemical compound CCCCCCCCCC\C=C/CCCCCCCC(O)=O LQJBNNIYVWPHFW-QXMHVHEDSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000010699 lard oil Substances 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 208000020442 loss of weight Diseases 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- CNVZJPUDSLNTQU-SEYXRHQNSA-N petroselinic acid Chemical compound CCCCCCCCCCC\C=C/CCCCC(O)=O CNVZJPUDSLNTQU-SEYXRHQNSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 235000020748 rosemary extract Nutrition 0.000 description 1
- IUEMQUIQAPPJDL-UHFFFAOYSA-M sodium;2,3-dihydroxypropanoate Chemical compound [Na+].OCC(O)C([O-])=O IUEMQUIQAPPJDL-UHFFFAOYSA-M 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 150000003700 vitamin C derivatives Chemical class 0.000 description 1
- 150000003712 vitamin E derivatives Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/08—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with fatty acids
-
- 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
-
- 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
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3481—Organic compounds containing oxygen
- A23L3/3508—Organic compounds containing oxygen containing carboxyl groups
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3481—Organic compounds containing oxygen
- A23L3/3508—Organic compounds containing oxygen containing carboxyl groups
- A23L3/3517—Carboxylic acid esters
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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Abstract
A process for the production of synthetic triglycerides by esterification of glycerol or transesterification of triglycerides with fatty acid mixtures, characterized in that. a) fatty acid mixtures containing at least 50% by weight of conjugated linoleic acid are used, b) the reaction is carried out in an inert gas atmosphere and c) the reaction mixture is heated to a reaction temperature of 180 to 240C at a heating rate of 0.5 to 3K per minute.
Description
<div class="application article clearfix" id="description">
<p class="printTableText" lang="en">WO 98/49129 <br><br>
1 <br><br>
PCT/EP98/02332 <br><br>
Conjugated Linolenic Acid-Based Synthetic Triglycerides <br><br>
Field of the Invention <br><br>
This invention relates to synthetic triglycerides containing C6-24 fatty acid residues, with the proviso that at least one residue is a conjugated linoleic acid residue, and to a process for the production of the 5 triglycerides. The invention also relates to the use of the triglycerides in foods and pharmaceutical products. <br><br>
Prior Art <br><br>
Polyunsaturated co-3 and co-6 fatty acids, such as a-linolenic acid 10 and linoleic acid, are among the fatty acids essential to mammals and human beings. Besides linoleic acid, other isomeric octadecadienoic acids occur in nature. They are distinguished by conjugated double bonds at carbon atoms 9 and 11, 10 and 12 and 11 and 13. These isomeric octadecadienoic acids are collectively referred to in the scientific literature 15 as conjugated linoleic acids (abbreviation: CLAs) and have recently attracted increasing attention (NUTRITION, Vol. 19, No. 6,1995). <br><br>
Conjugated linoleic acids are present as constituents in various foods. Their main source are animal foods although significant quantities of CLA are also present in milk and milk products. In addition, CLAs have 20 been found in various oils and fats, the concentration in vegetable oils being significantly lower than the concentration in animal fats (J. Food Compos. Anal. 5, 185-197 (1992)). <br><br>
Various working groups have reported on the significance of CLAs to the organism. Recently, Shultz et al. reported on the inhibiting effect on 25 the in-vitro growth of human cancer cells (Carcinogenesis 8, 1881-1887 (1987) and Cancer Lett. 63,125-133 (1992)). <br><br>
WO 98/49129 2 PCT/EP98/02332 <br><br>
In in vitro tests, CLAs were tested for their effectiveness against the growth of malignant human melanomas, colon and breast cancer cells. In the culture media, there was a significant reduction in the growth of the cancer cells treated with CLAs by comparison with control cultures. The 5 mechanism by which CLAs exert anticarcinogenic activity is unknown. In addition, CLAs have a strong antioxidative effect so that, for example, the peroxidation of lipids can be inhibited (Atherosclerosis 108, 19-25 (1994)). <br><br>
Investigations have also been conducted, for example, into the 10 addition of conjugated linoleic acid to foods for the purpose of color stabilization (JP 06/276939 A2). <br><br>
The use of conjugated linoleic acid in animal feeds and, in this connection, also in human nutrition is known, for example, from WO 96/06605. This application is concerned with reducing body fat content in 15 animal nutrition. In the statement of problem, the specification also mentions the possibility of application to human beings. In particular, it mentions the use of a fatty emulsion containing 0.5 to 2% by weight of conjugated linoleic acid for oral or intravenous administration to human beings. <br><br>
20 EP 0 579 901 B relates to the use of conjugated linoleic acid for avoiding loss of weight or for reducing increases in weight or anorexia caused by immunostimulation in human beings or animals. <br><br>
WO 94/16690 is concerned with improving the efficiency of food utilization in animals by administering an effective quantity of conjugated 25 linoleic acid. <br><br>
In connection with the many positive effects of conjugated linoleic acid, as demonstrated in intensive studies, particularly on animals and tissue cultures, the use of conjugated linoleic acid in foods for human consumption has also been discussed. However, the use of free 30 conjugated linoleic acid in foods and pharmaceutical products is limited by <br><br>
50065*8 <br><br>
the fact that, on the one hand, unwanted reactions with other food constituents can occur where free conjugated linoleic acid is incorporated in complex foods and, on the other hand, by the unpleasant taste and odor of conjugated linoleic acid which can lead to non-acceptance by the consumer. Another disadvantage is that free fatty acids are covered by food additive legislation so that their use in foods is restricted. <br><br>
Accordingly, the complex problem addressed by the present invention was to find a substitute for conjugated linoleic acid, above all in human nutrition and also for pharmacological use. On the one hand, this substitute would have better organoleptic properties than conjugated linoleic acid and, on the other hand, would lend itself to incorporation in foods without initiating secondary reactions. <br><br>
Summary of the Invention <br><br>
The present invention provides a process for the production of synthetic triglycerides by esterification of glycerol or transesterificatoin of triglycerides with fatty acid mixtures, characterized in that a) fatty acid mixtures containing at least 50% by weight of conjugated linoleic acic are used. <br><br>
b)'' the reaction is carried out in an inert gas atmosphere and c). the reaction mixture is heated to a reaction temperature of 18C to 24Q°C at a heating rate of 0.5 to 3 K per minute. <br><br>
Description of the invention <br><br>
Accordingly, the present invention relates to synthetic triglycerides corresponding to formula (I): <br><br>
H2C—OR1 ~ <br><br>
I <br><br>
HC—OR2 (I) <br><br>
I <br><br>
H2C—OR3 <br><br>
in which R1, R2 and R3 independently of one another represent C&.24 fatty acid residues, with the proviso that at least one substituent R1, R2 or R3 is a conjugated linoleic acid residue. <br><br>
The present invention also relates to a process for the production of synthetic triglycerides by esterification of glycerol or transesterification of triglycerides with fatty acid mixtures by methods known from the prior art, <br><br>
with the proviso that at least 50% by weight of conjugated linoleic acid is used in the fatty acid mixture, the reaction is carried out in an inert gas <br><br>
WO 98/49129 <br><br>
4 <br><br>
PCT/EP98/02332 <br><br>
atmosphere and heating to the reaction temperature is preferably carried out at a heating rate of 0.2 to 10 K per minute. <br><br>
The present invention also relates to the use of the triglycerides according to the invention in foods and/or as active substances for the 5 production of pharmaceutical products. <br><br>
It has surprisingly been found that the triglycerides according to the invention are comparable with pure conjugated linoleic acid in their antioxidative and color-stabilizing effect in foods. In addition, they may readily be incorporated in foods and pharmaceutical products without 10 initiating any secondary reactions. In particular, their lipophilic character enables then to be readily incorporated in fat-containing products. The triglycerides according to the invention are also readily absorbed by the animal or human organism. At the same time, they have an almost neutral taste and odor They are therefore far superior in their organoleptic 15 properties to free conjugated linoleic acid. This means, for example, that the triglycerides can be used in larger quantities in foods. Even food supplements consisting of pure triglyceride of conjugated linoleic acid can be taken by mouth by virtue of their outstanding organoleptic properties. Another advantage is that they do not come under food additive legislation, 20 in other words there are no restrictions on their incorporation in foods. <br><br>
It has also been found that, surprisingly, the triglycerides according to the invention can also readily be obtained in high yields, more particularly by the direction esterification of glycerol with conjugated linoleic acid, providing the reaction is carried out in an inert gas and providing a 25 low heating rate is maintained. <br><br>
Triglycerides <br><br>
In the triglycerides of formula (I) according to the invention, at least one of the substituents R1, R2 or R3 is a conjugated linoleic acid residue 30 while the other constituents represent C6-24 fatty acid residues. However, <br><br>
WO 98/49129 <br><br>
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PCT/EP98/02332 <br><br>
triglycerides which, on a statistical average, contain more than 2 conjugated linoleic acid residues per triglyceride are particularly preferred, triglycerides in which the substituents R1, R2 and R3 represent a conjugated linoleic acid residue being most particularly preferred. In the context of the 5 present invention, triglycerides are also understood to be the technical mixtures of mono-, di- and triglycerides which are obtained in particular in the direct esterification of glycerol with conjugated linoleic acid. A typical composition which is particularly preferred and which is obtained in the process according to the invention, more particularly in the esterification of 10 glycerol with conjugated linoleic acid, contains 60 to 98% by weight and preferably 80 to 98% by weight of a triglyceride of conjugated linoleic acid, 1 to 40 and preferably 1 to 20% by weight of a diglyceride of conjugated linoleic acid and at most 2% by weight and preferably at most 1% by weight of a monoglyceride of conjugated linoleic acid. At the same time, the gly-15 ceride to be used in accordance with the invention has an acid value of at most 5 and preferably of at most 3, a hydroxyl value below 40 and preferably below 30 and a peroxide number below 4 and preferably below 2. <br><br>
Fatty acids <br><br>
20 Fatty acids in the context of the present invention are aliphatic carboxylic acids corresponding to formula (II): <br><br>
R4CO-OH (II) <br><br>
25 in which R4CO is an aliphatic, linear or branched acyl group containing 6 to 24 carbon atoms and 0 and/or 1, 2 or 3 double bonds. <br><br>
Typical examples are caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, 30 petroselic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, <br><br>
WO 98/49129 6 PCT/EP98/02332 <br><br>
gadoleic acid, behenic acid and erucic acid and the technical mixtures thereof obtained, for example, in the pressure hydrolysis of natural fats and oils, in the reduction of aldehydes from Roelen's oxosynthesis or in the dimerization of unsaturated fatty acids. <br><br>
5 Technical C12-18 fatty acids such as, for example, cocofatty acid, <br><br>
palm oil fatty acid, palm kernel oil fatty acid or tallow fatty acid, are preferred. <br><br>
According to the invention, conjugated linoleic acid is preferably understood to be the main isomers 9,11-octadecadienoic acid and 10,12-10 octadecadienoic acid, but also includes the isomer mixtures normally obtained in the production of conjugated linoleic acid. <br><br>
Transesterification <br><br>
The fatty acid glycerides to be used as starting materials in 15 accordance with the invention may be the usual natural vegetable or animal fats and oils. These include, for example, palm oil, palm kernel oil, cottonseed oil, rapeseed oil, coconut oil, peanut oil, olive oil, linseed oil, babassu oil, tea oil, olive kernel oil, meadow foam oil, chaulmoogra oil, coriander oil, soybean oil, castor oil, lard oil, beef tallow, lard, fish oil and 20 also sunflower oil and rapeseed oil from old and new plants. The main constituents of these fats and oils are glycerides of various types of fatty acids which contain considerable quantities of impurities such as, for example, aldehyde compounds, phospholipid compounds and free fatty acids. These materials may be used either directly or after purification. In 25 some cases, it is particularly advisable to esterify the free fatty acids with lower alcohols in a preliminary reaction. These triglycerides are transesterified with fatty acid mixtures containing at least 50, more especially 70 to 100% by weight of conjugated linoleic acid in an inert gas atmosphere by methods known from the prior art, i.e. by acidic and/or basic 30 transesterification. Nitrogen is preferably used as the inert gas. The <br><br>
WO 98/49129 <br><br>
7 <br><br>
PCT/EP98/02332 <br><br>
reaction is preferably carried out at a temperature of 180 to 240°C. In one particularly preferred embodiment, heating to that temperature is carried out at a low rate of 0.2 to 10 and preferably 0.5 to 3 K per minute. Suitable catalysts are any of the usual catalysts known from the prior art for 5 esterification or transesterification reactions. Such catalysts are, for example, alkali metal and/or alkaline earth metal alcoholates or hydroxides, more especially sodium methanolate and sodium glycerate. It is also preferred to use acetates, such as zinc and/or magnesium acetate, or even titanates and, in particular, tin compounds, organotin compounds, such as 10 dibutyl tin diacetate for example, or tin salts. <br><br>
Esterification <br><br>
In one particularly preferred embodiment, the triglycerides according to the invention are not produced by transesterification, but rather by the 15 direct esterification of glycerol with a fatty acid mixture containing at least 50 and preferably 70 to 100% by weight of conjugated linoleic acid in an inert gas atmosphere, again preferably nitrogen, by methods known from the prior art. The esterification of glycerol with 100% by weight of conjugated linoleic acid is particularly preferred. Technical mixtures of 20 mono-, di- and triglycerides of conjugated linoleic acid are normally obtained. According to the invention, these mixtures may be used both directly and after further purification. The foregoing observations on the temperature, heating rate and catalyst used for the transesterification apply similarly to esterification. <br><br>
25 After esterification or transesterification, 0.01 to 1% by weight of an antioxidant is preferably added. In another preferred embodiment, the triglyceride obtained is purified using a thin-layer evaporator, after which another 0.01 to 1 % by weight of an antioxidant is added. <br><br>
30 Antioxidants <br><br>
WO 98/49129 <br><br>
8 <br><br>
PCT/EP98/02332 <br><br>
Antioxidants in the context of the present invention are any of the usual natural antioxidants which are used in particular in pharmaceutical products and in foods, including vitamin C and vitamin C derivatives such as, for example, ascorbyl palmitate, carotinoids, rosemary extracts and/or 5 synthetic antioxidants such as, for example, BHA, BHT, TB.HQ or gallates and, in particular, various vitamin E derivatives, such as Coviox® T 70 for example. <br><br>
Uses <br><br>
10 The triglycerides according to the invention are particularly suitable for use in foods, preferably so-called functional foods, and in pharmaceutical products, more especially as a supporting agent in the treatment of tumors or even in the treatment of patients suffering from catabolic conditions. Since the physiological properties of the triglycerides <br><br>
15 according to the invention are comparable with those of free conjugated linoleic acid both in human beings and in animals, the triglycerides are suitable for use in all those areas which are already known from the literature for conjugated linoleic acid. <br><br>
20 Examples <br><br>
Production of a conjugated linoleic acid triglyceride <br><br>
Example 1 <br><br>
25 92.1 kg of glycerol and 841.5 kg of conjugated linoleic acid were preheated under nitrogen to around 80°C and introduced into a reactor, after which 0.62 kg of tin grindings were added with stirring. The reactor was then evacuated to 30 mbar, stirred for 10 minutes and blanketed with nitrogen. Heating was carried out under nitrogen at a rate of 1 K per <br><br>
30 minute, the temperature reaching 150°C after 1 hour. At the same time, <br><br>
WO 98/49129 <br><br>
9 <br><br>
PCT/EP98/02332 <br><br>
the pressure was reduced to 800 mmbar. The temperature was then increased to 210°C over a period of another hour and the reaction mixture was stirred at that temperature for 2 hours. The reaction mixture was then re-evacuated to 30 mmbar over a period of 30 minutes and stirred until an 5 acid value of 15 had been reached. The reaction mixture was then cooled in vacuo to 90°C and purged with nitrogen, after which phosphoric acid was added to precipitate the catalyst. After stirring for 15 minutes and after the addition of Perlite, the reaction mixture was filtered through a filter press into a nitrogen-purged receiver to which 0.1% by weight of Coviox T-70 10 was added as stabilizer. <br><br>
Example 2 <br><br>
The procedure was as in Example 1, except that the crude product was deodorized in a thin-evaporator at 230°C in the presence of stripping 15 steam. Another 0.2% by weight of Coviox T-70 was added to the end product for stabilization. <br><br>
Glvceride composition <br><br>
20 Example 3 <br><br>
A glyceride prepared as described in Example 1 has the following composition: <br><br>
triglyceride of conjugated linoleic acid: 95% by weight <br><br>
25 diglyceride of conjugated linoleic acid 3% by weight monoglyceride of conjugated linoleic acid: 2% by weight <br><br>
The acid value was 2, the hydroxyl value 25 and the peroxide number 2. <br><br></p>
</div>
Claims (4)
1. A process for the production of synthetic triglycerides by esterification of glycerol or transesterification of triglycerides with fatty acid mixtures, characterized in that a) fatty acid mixtures containing at least 50% by weight of conjugated linoleic acid are used.<br><br> b) the reaction is carried out in an inert gas atmosphere and c) the reaction mixture is heated to a reaction temperature of 18C to 24Q°C at a heating rate of 0.5 to 3 K per minute.<br><br>
2. A process as claimed in claim 1, characterized in that, after the esterification or transesterification, 0.01 to 1% by weight of an antioxidant is added to the reaction mixture.<br><br>
3. A process as claimed in claims 1 and 2, characterized in that the crude reaction mixture is purified in a thin-layer evaporator. v<br><br>
4. A process as claimed in claim 1 substantially as herein described with reference to any example thereof.<br><br> i intellectual property i office of n.z.<br><br> I 1 4 MAH 20(m<br><br> I RECEIVED<br><br> J+.<br><br> t-<br><br> END<br><br> </p> </div>
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE19718245A DE19718245C5 (en) | 1997-04-30 | 1997-04-30 | Synthetic triglycerides based on conjugated linoleic acid, process for their preparation and their use |
PCT/EP1998/002332 WO1998049129A1 (en) | 1997-04-30 | 1998-04-21 | Conjugated linolenic acid-based synthetic triglycerides |
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NZ500698A NZ500698A (en) | 1997-04-30 | 1998-04-21 | Conjugated linolenic acid-base synthetic triglycerides |
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EP (5) | EP1135998B1 (en) |
JP (1) | JP4217798B2 (en) |
KR (1) | KR100483247B1 (en) |
AT (5) | ATE211126T1 (en) |
AU (1) | AU735493B2 (en) |
BR (1) | BR9809421A (en) |
CA (1) | CA2287476C (en) |
DE (6) | DE19718245C5 (en) |
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ES (5) | ES2169515T3 (en) |
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ATE350028T1 (en) | 1998-03-17 | 2007-01-15 | Natural Asa | CONJUGATED LINOLIC ACID COMPOSITION |
US7776353B1 (en) | 1998-03-17 | 2010-08-17 | Aker Biomarine Asa | Conjugated linoleic acid compositions |
US6015833A (en) | 1998-03-17 | 2000-01-18 | Conlinco., Inc. | Conjugated linoleic acid compositions |
US7078051B1 (en) | 1998-08-11 | 2006-07-18 | Natural Asa | Conjugated linoleic acid alkyl esters in feedstuffs and food |
US7101914B2 (en) | 1998-05-04 | 2006-09-05 | Natural Asa | Isomer enriched conjugated linoleic acid compositions |
US6060514A (en) * | 1998-05-04 | 2000-05-09 | Conlin Co., Inc. | Isomer enriched conjugated linoleic acid compositions |
MX228618B (en) | 1998-05-04 | 2005-06-21 | Conlinco Inc | Methods of using isomer enriched conjugated linoleic acid compositions. |
US6214372B1 (en) | 1998-05-04 | 2001-04-10 | Con Lin Co., Inc. | Method of using isomer enriched conjugated linoleic acid compositions |
KR100350432B1 (en) * | 1998-09-02 | 2002-08-28 | 하영래 | Derivatives of conjugated linoleic acid and method for synthesizing thereof |
JP4565750B2 (en) * | 1999-04-27 | 2010-10-20 | 株式会社ヤクルト本社 | Method for producing conjugated linoleic acid ester |
EP1231913A2 (en) * | 1999-07-09 | 2002-08-21 | Pharmacia Corporation | Treatment of cyclooxygenase-2 mediated disorders using conjugated fatty acid compounds |
GB9918028D0 (en) * | 1999-07-30 | 1999-09-29 | Unilever Plc | Skin care composition |
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