JPS6339568B2 - - Google Patents
Info
- Publication number
- JPS6339568B2 JPS6339568B2 JP52014533A JP1453377A JPS6339568B2 JP S6339568 B2 JPS6339568 B2 JP S6339568B2 JP 52014533 A JP52014533 A JP 52014533A JP 1453377 A JP1453377 A JP 1453377A JP S6339568 B2 JPS6339568 B2 JP S6339568B2
- Authority
- JP
- Japan
- Prior art keywords
- composition
- fatty acid
- group
- edible
- polyol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 claims description 242
- 229920000728 polyester Polymers 0.000 claims description 168
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 132
- 239000000194 fatty acid Substances 0.000 claims description 132
- 229930195729 fatty acid Natural products 0.000 claims description 132
- 239000007788 liquid Substances 0.000 claims description 91
- 229940125714 antidiarrheal agent Drugs 0.000 claims description 88
- 239000003793 antidiarrheal agent Substances 0.000 claims description 88
- 229920005862 polyol Polymers 0.000 claims description 88
- 229930006000 Sucrose Natural products 0.000 claims description 69
- 239000005720 sucrose Substances 0.000 claims description 69
- 229940088594 vitamin Drugs 0.000 claims description 69
- 229930003231 vitamin Natural products 0.000 claims description 69
- 235000013343 vitamin Nutrition 0.000 claims description 69
- 239000011782 vitamin Substances 0.000 claims description 69
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 63
- -1 polyol fatty acid Chemical class 0.000 claims description 63
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 55
- 150000004665 fatty acids Chemical class 0.000 claims description 55
- 150000003077 polyols Chemical class 0.000 claims description 49
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 43
- 235000019197 fats Nutrition 0.000 claims description 42
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- 235000019155 vitamin A Nutrition 0.000 claims description 39
- 239000011719 vitamin A Substances 0.000 claims description 39
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 37
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 35
- 235000013305 food Nutrition 0.000 claims description 34
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 claims description 33
- 229940045997 vitamin a Drugs 0.000 claims description 33
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 32
- 235000000346 sugar Nutrition 0.000 claims description 31
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 24
- 150000005846 sugar alcohols Chemical class 0.000 claims description 23
- 150000008163 sugars Chemical class 0.000 claims description 23
- 150000003626 triacylglycerols Chemical class 0.000 claims description 23
- 206010012735 Diarrhoea Diseases 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 239000011709 vitamin E Substances 0.000 claims description 22
- 235000019165 vitamin E Nutrition 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 21
- 235000019166 vitamin D Nutrition 0.000 claims description 21
- 239000011710 vitamin D Substances 0.000 claims description 21
- 239000011712 vitamin K Substances 0.000 claims description 20
- 235000019168 vitamin K Nutrition 0.000 claims description 20
- 241001465754 Metazoa Species 0.000 claims description 19
- 235000012000 cholesterol Nutrition 0.000 claims description 18
- 125000005313 fatty acid group Chemical group 0.000 claims description 18
- 239000004615 ingredient Substances 0.000 claims description 18
- 229930003427 Vitamin E Natural products 0.000 claims description 17
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 17
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 claims description 17
- 229940046009 vitamin E Drugs 0.000 claims description 17
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims description 16
- 229930003448 Vitamin K Natural products 0.000 claims description 16
- 150000003721 vitamin K derivatives Chemical class 0.000 claims description 16
- 229940046010 vitamin k Drugs 0.000 claims description 16
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 15
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 15
- 229930003316 Vitamin D Natural products 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 235000010356 sorbitol Nutrition 0.000 claims description 15
- 239000000600 sorbitol Substances 0.000 claims description 15
- 150000003710 vitamin D derivatives Chemical class 0.000 claims description 15
- 229940046008 vitamin d Drugs 0.000 claims description 15
- 238000010521 absorption reaction Methods 0.000 claims description 14
- 235000019482 Palm oil Nutrition 0.000 claims description 13
- 230000000741 diarrhetic effect Effects 0.000 claims description 13
- 239000002540 palm oil Substances 0.000 claims description 13
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 13
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 12
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 12
- 239000000811 xylitol Substances 0.000 claims description 12
- 235000010447 xylitol Nutrition 0.000 claims description 12
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 12
- 229960002675 xylitol Drugs 0.000 claims description 12
- 239000004386 Erythritol Substances 0.000 claims description 11
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 11
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 11
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 11
- 235000019868 cocoa butter Nutrition 0.000 claims description 11
- 229940110456 cocoa butter Drugs 0.000 claims description 11
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 11
- 235000019414 erythritol Nutrition 0.000 claims description 11
- 229940009714 erythritol Drugs 0.000 claims description 11
- 239000008103 glucose Substances 0.000 claims description 11
- 210000005070 sphincter Anatomy 0.000 claims description 11
- 230000001906 cholesterol absorption Effects 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 229960002920 sorbitol Drugs 0.000 claims description 7
- 229960001031 glucose Drugs 0.000 claims description 6
- 235000001727 glucose Nutrition 0.000 claims description 6
- 229960004793 sucrose Drugs 0.000 claims description 6
- 235000013861 fat-free Nutrition 0.000 claims description 4
- 230000037406 food intake Effects 0.000 claims description 4
- 230000002452 interceptive effect Effects 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- GFAZGHREJPXDMH-UHFFFAOYSA-N 1,3-dipalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCC GFAZGHREJPXDMH-UHFFFAOYSA-N 0.000 claims 12
- 125000005907 alkyl ester group Chemical group 0.000 claims 6
- GYNODFLZPXTEPN-UHFFFAOYSA-N 3-(docosanoyloxy)-2-hydroxypropyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCCCCCC GYNODFLZPXTEPN-UHFFFAOYSA-N 0.000 claims 4
- VFEKBHKRXKVKGN-UHFFFAOYSA-N 2-hydroxy-3-(icosanoyloxy)propyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCCCC VFEKBHKRXKVKGN-UHFFFAOYSA-N 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 description 37
- 239000002775 capsule Substances 0.000 description 25
- 239000003925 fat Substances 0.000 description 23
- 230000000694 effects Effects 0.000 description 19
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- 208000035150 Hypercholesterolemia Diseases 0.000 description 13
- 235000005911 diet Nutrition 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- 239000003549 soybean oil Substances 0.000 description 11
- 235000012424 soybean oil Nutrition 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000001142 anti-diarrhea Effects 0.000 description 10
- MVLVMROFTAUDAG-UHFFFAOYSA-N ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC MVLVMROFTAUDAG-UHFFFAOYSA-N 0.000 description 10
- 239000003778 fat substitute Substances 0.000 description 10
- 210000001035 gastrointestinal tract Anatomy 0.000 description 10
- 230000037213 diet Effects 0.000 description 9
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 235000012343 cottonseed oil Nutrition 0.000 description 8
- 239000002385 cottonseed oil Substances 0.000 description 8
- 235000013341 fat substitute Nutrition 0.000 description 8
- 229930182830 galactose Natural products 0.000 description 8
- 239000000344 soap Substances 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 7
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 7
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- 239000005642 Oleic acid Substances 0.000 description 7
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 7
- 235000021355 Stearic acid Nutrition 0.000 description 7
- 239000007903 gelatin capsule Substances 0.000 description 7
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 7
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 7
- 239000008117 stearic acid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XPXWDKLKEOUSOD-UHRUCXANSA-N [(2S,4R)-2,3,4,5-tetrakis[[(Z)-octadec-9-enoyl]oxy]pentyl] (Z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)C(OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H](COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC XPXWDKLKEOUSOD-UHRUCXANSA-N 0.000 description 6
- 230000000326 anti-hypercholesterolaemic effect Effects 0.000 description 6
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
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- QSQLTHHMFHEFIY-UHFFFAOYSA-N methyl behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OC QSQLTHHMFHEFIY-UHFFFAOYSA-N 0.000 description 4
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- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 4
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- LYAKYODQZBHMCI-YSVXLPCPSA-N [(2r,3r,4s,5r,6r)-6-[(2s,3s,4r,5r)-3,4-di(octadecanoyloxy)-2,5-bis(octadecanoyloxymethyl)oxolan-2-yl]oxy-3,4,5-tri(octadecanoyloxy)oxan-2-yl]methyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@H]1[C@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@@H](COC(=O)CCCCCCCCCCCCCCCCC)O[C@@]1(COC(=O)CCCCCCCCCCCCCCCCC)O[C@@H]1[C@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@@H](COC(=O)CCCCCCCCCCCCCCCCC)O1 LYAKYODQZBHMCI-YSVXLPCPSA-N 0.000 description 3
- GQPAMKBZEBGASK-LVVDDXEGSA-N [(2r,3s)-2,3,4-tris[[(z)-octadec-9-enoyl]oxy]butyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC GQPAMKBZEBGASK-LVVDDXEGSA-N 0.000 description 3
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- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 3
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- DLQDPUCZIABCES-VZBBZXSKSA-N CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)[C@H](OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)[C@@H](OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)C=O Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)[C@H](OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)[C@@H](OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)C=O DLQDPUCZIABCES-VZBBZXSKSA-N 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
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- 206010056474 Erythrosis Diseases 0.000 description 2
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- 230000036541 health Effects 0.000 description 1
- 206010019692 hepatic necrosis Diseases 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000008173 hydrogenated soybean oil Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 231100000149 liver necrosis Toxicity 0.000 description 1
- 235000020845 low-calorie diet Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000011772 phylloquinone Substances 0.000 description 1
- MBWXNTAXLNYFJB-NKFFZRIASA-N phylloquinone Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)=C(C)C(=O)C2=C1 MBWXNTAXLNYFJB-NKFFZRIASA-N 0.000 description 1
- 229960001898 phytomenadione Drugs 0.000 description 1
- 235000002378 plant sterols Nutrition 0.000 description 1
- 239000006223 plastic coating Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 208000007442 rickets Diseases 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 150000004370 vitamin A ester derivatives Chemical class 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- 208000016794 vitamin K deficiency hemorrhagic disease Diseases 0.000 description 1
- 150000003714 vitamin K1 derivatives Chemical class 0.000 description 1
- 235000019143 vitamin K2 Nutrition 0.000 description 1
- 239000011728 vitamin K2 Substances 0.000 description 1
- 235000012711 vitamin K3 Nutrition 0.000 description 1
- 239000011652 vitamin K3 Substances 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 235000019195 vitamin supplement Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
-
- 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
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
- A23D9/013—Other fatty acid esters, e.g. phosphatides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
- A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
- A23L33/25—Synthetic polymers, e.g. vinylic or acrylic polymers
- A23L33/26—Polyol polyesters, e.g. sucrose polyesters; Synthetic sugar polymers, e.g. polydextrose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Obesity (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Nutrition Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Mycology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Edible Oils And Fats (AREA)
- General Preparation And Processing Of Foods (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/657,528 US4005195A (en) | 1976-02-12 | 1976-02-12 | Compositions for treating hypercholesterolemia |
| US05/657,529 US4005196A (en) | 1976-02-12 | 1976-02-12 | Vitaminized compositions for treating hypercholesterolemia |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52120131A JPS52120131A (en) | 1977-10-08 |
| JPS6339568B2 true JPS6339568B2 (el) | 1988-08-05 |
Family
ID=27097425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1453377A Granted JPS52120131A (en) | 1976-02-12 | 1977-02-12 | Treating composition for rercholesterol disease |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS52120131A (el) |
| DE (1) | DE2705105A1 (el) |
| FR (1) | FR2340737A1 (el) |
| GB (1) | GB1579241A (el) |
| IE (1) | IE44458B1 (el) |
| IT (1) | IT1075126B (el) |
| LU (1) | LU76751A1 (el) |
| NL (1) | NL188503C (el) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4368213A (en) * | 1981-06-23 | 1983-01-11 | The Procter & Gamble Company | Emulsion concentrate for palatable polyester beverage |
| DE3788443T2 (de) * | 1986-02-20 | 1994-04-28 | Procter & Gamble | Kalorienarme Fettprodukte, die die laxierenden Nebeneffekte ausschliessen. |
| DE3788661T2 (de) * | 1986-02-20 | 1994-05-19 | Procter & Gamble | Kalorienarme Fettprodukte mit verbessertem Geschmack. |
| US4849222A (en) * | 1987-03-24 | 1989-07-18 | The Procter & Gamble Company | Mixtures for treating hypercholesterolemia |
| JPH07108184B2 (ja) * | 1987-11-25 | 1995-11-22 | 三菱化学株式会社 | チヨコレートの製造法 |
| US5006360B1 (en) * | 1988-06-27 | 1992-04-28 | Low calorie fat substitute compositions resistant to laxative side effect | |
| CA2004723C (en) * | 1988-12-22 | 1997-03-04 | James Anthony Letton | Fatty compositions with high solids content |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2458732A1 (de) * | 1973-12-14 | 1975-06-26 | Procter & Gamble | Pharmazeutische zubereitung zur hemmung der cholesterinabsorption |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2997492A (en) * | 1959-02-17 | 1961-08-22 | Procter & Gamble | Method for preparing fatty esters of straight chain hexitols |
| US2997491A (en) * | 1959-09-29 | 1961-08-22 | Procter & Gamble | Method for preparing partial fatty esters of inositol |
| US3059009A (en) * | 1961-09-21 | 1962-10-16 | Proeter & Gamble Company | Fat crystallization process |
| US3158490A (en) * | 1962-03-27 | 1964-11-24 | Procter & Gamble | Salad oils and method of making them |
| US3600186A (en) * | 1968-04-23 | 1971-08-17 | Procter & Gamble | Low calorie fat-containing food compositions |
| US3809711A (en) * | 1972-04-07 | 1974-05-07 | Procter & Gamble | Process for synthesizing specific complete mixed polyol esters |
| US3963699A (en) * | 1974-01-10 | 1976-06-15 | The Procter & Gamble Company | Synthesis of higher polyol fatty acid polyesters |
| US4034083A (en) * | 1975-11-03 | 1977-07-05 | The Procter & Gamble Company | Compositions for inhibiting absorption of cholesterol |
| EP0236288B1 (en) * | 1986-02-20 | 1993-12-15 | The Procter & Gamble Company | Low calorie fat materials that eliminate laxative side effect |
-
1977
- 1977-02-02 IE IE213/77A patent/IE44458B1/en not_active IP Right Cessation
- 1977-02-08 DE DE19772705105 patent/DE2705105A1/de active Granted
- 1977-02-11 LU LU76751A patent/LU76751A1/xx unknown
- 1977-02-11 NL NL7701460A patent/NL188503C/xx not_active IP Right Cessation
- 1977-02-11 FR FR7703892A patent/FR2340737A1/fr active Granted
- 1977-02-11 GB GB5716/77A patent/GB1579241A/en not_active Expired
- 1977-02-11 IT IT20238/77A patent/IT1075126B/it active
- 1977-02-12 JP JP1453377A patent/JPS52120131A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2458732A1 (de) * | 1973-12-14 | 1975-06-26 | Procter & Gamble | Pharmazeutische zubereitung zur hemmung der cholesterinabsorption |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2705105C2 (el) | 1987-06-11 |
| FR2340737A1 (fr) | 1977-09-09 |
| JPS52120131A (en) | 1977-10-08 |
| DE2705105A1 (de) | 1977-08-18 |
| NL188503B (nl) | 1992-02-17 |
| NL188503C (nl) | 1995-05-16 |
| NL7701460A (nl) | 1977-08-16 |
| IT1075126B (it) | 1985-04-22 |
| FR2340737B1 (el) | 1981-01-09 |
| LU76751A1 (el) | 1977-08-19 |
| GB1579241A (en) | 1980-11-19 |
| IE44458L (en) | 1977-08-12 |
| IE44458B1 (en) | 1981-12-02 |
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