IL43888A - History of 6-hydro-xychromane-2-carboxylic acid or 2-acetic acid, their preparation and use as antioxidants - Google Patents
History of 6-hydro-xychromane-2-carboxylic acid or 2-acetic acid, their preparation and use as antioxidantsInfo
- Publication number
- IL43888A IL43888A IL43888A IL4388873A IL43888A IL 43888 A IL43888 A IL 43888A IL 43888 A IL43888 A IL 43888A IL 4388873 A IL4388873 A IL 4388873A IL 43888 A IL43888 A IL 43888A
- Authority
- IL
- Israel
- Prior art keywords
- hydroxy
- formula
- chroman
- compound
- carboxylic acid
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 49
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 239000003963 antioxidant agent Substances 0.000 title description 4
- OEPFJOJFTVSOOI-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-2h-chromene-2-carboxylic acid Chemical compound OC1=CC=C2OC(C(=O)O)CCC2=C1 OEPFJOJFTVSOOI-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 154
- 230000007062 hydrolysis Effects 0.000 claims abstract description 46
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 31
- 125000004185 ester group Chemical group 0.000 claims abstract description 28
- 125000001033 ether group Chemical group 0.000 claims abstract description 24
- 238000007327 hydrogenolysis reaction Methods 0.000 claims abstract description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 143
- 238000000034 method Methods 0.000 claims description 89
- 239000000203 mixture Substances 0.000 claims description 60
- 239000003921 oil Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 21
- 238000007254 oxidation reaction Methods 0.000 claims description 17
- 230000003647 oxidation Effects 0.000 claims description 16
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 12
- 239000011707 mineral Substances 0.000 claims description 12
- 239000003925 fat Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 230000003301 hydrolyzing effect Effects 0.000 claims description 10
- 239000012024 dehydrating agents Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 6
- CBWWWQHHIUXXRA-UHFFFAOYSA-N 6-hydroxy-2,7,8-trimethyl-3,4-dihydrochromene-2-carboxylic acid Chemical compound C1CC(C)(C(O)=O)OC2=C(C)C(C)=C(O)C=C21 CBWWWQHHIUXXRA-UHFFFAOYSA-N 0.000 claims description 5
- PSNWPQXOZFQFSR-UHFFFAOYSA-N 6-hydroxy-2-methyl-3,4-dihydrochromene-2-carboxylic acid Chemical compound OC1=CC=C2OC(C)(C(O)=O)CCC2=C1 PSNWPQXOZFQFSR-UHFFFAOYSA-N 0.000 claims description 5
- HYGLEDCZQLKAIM-UHFFFAOYSA-N 6-hydroxy-5,7,8-trimethyl-3,4-dihydro-2h-chromene-2-carboxylic acid Chemical compound O1C(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C HYGLEDCZQLKAIM-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- IETSMPQISKAPQX-UHFFFAOYSA-N 2-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)acetic acid Chemical compound O1C(C)(CC(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C IETSMPQISKAPQX-UHFFFAOYSA-N 0.000 claims description 3
- LQQSHBJXOPYWNY-UHFFFAOYSA-N 2-(6-hydroxy-2,7,8-trimethyl-3,4-dihydrochromen-2-yl)acetic acid Chemical compound C1CC(C)(CC(O)=O)OC2=C(C)C(C)=C(O)C=C21 LQQSHBJXOPYWNY-UHFFFAOYSA-N 0.000 claims description 3
- ZMELKGICZLGPHM-UHFFFAOYSA-N 2-ethyl-6-hydroxy-5,7,8-trimethyl-3,4-dihydrochromene-2-carboxylic acid Chemical compound OC1=C(C)C(C)=C2OC(CC)(C(O)=O)CCC2=C1C ZMELKGICZLGPHM-UHFFFAOYSA-N 0.000 claims description 3
- 239000011368 organic material Substances 0.000 claims description 3
- 229910001923 silver oxide Inorganic materials 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 12
- 150000001843 chromanes Chemical class 0.000 claims 8
- RLNWRDKVJSXXPP-UHFFFAOYSA-N tert-butyl 2-[(2-bromoanilino)methyl]piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CNC1=CC=CC=C1Br RLNWRDKVJSXXPP-UHFFFAOYSA-N 0.000 claims 3
- ZLRDSYVYEYJCOU-UHFFFAOYSA-N 6-hydroxy-2-methyl-5,7-di(propan-2-yl)-3,4-dihydrochromene-2-carboxylic acid Chemical compound O1C(C)(C(O)=O)CCC2=C1C=C(C(C)C)C(O)=C2C(C)C ZLRDSYVYEYJCOU-UHFFFAOYSA-N 0.000 claims 2
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000006866 deterioration Effects 0.000 claims 1
- 229910000510 noble metal Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims 1
- -1 chroman aldehydes Chemical class 0.000 abstract description 29
- 239000000543 intermediate Substances 0.000 abstract description 8
- 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 abstract 2
- 229940087168 alpha tocopherol Drugs 0.000 abstract 1
- 229960000984 tocofersolan Drugs 0.000 abstract 1
- 239000002076 α-tocopherol Substances 0.000 abstract 1
- 235000004835 α-tocopherol Nutrition 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 92
- 239000000243 solution Substances 0.000 description 78
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 56
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- 239000002904 solvent Substances 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000007787 solid Substances 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000003960 organic solvent Substances 0.000 description 23
- 235000019198 oils Nutrition 0.000 description 22
- 229910001868 water Inorganic materials 0.000 description 22
- 239000000843 powder Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 150000007513 acids Chemical class 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- 238000002425 crystallisation Methods 0.000 description 17
- 230000008025 crystallization Effects 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000012267 brine Substances 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 229920006395 saturated elastomer Polymers 0.000 description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 12
- 229960004132 diethyl ether Drugs 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 12
- 235000010755 mineral Nutrition 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 238000007796 conventional method Methods 0.000 description 10
- 235000019197 fats Nutrition 0.000 description 10
- AUFZRCJENRSRLY-UHFFFAOYSA-N 2,3,5-trimethylhydroquinone Chemical compound CC1=CC(O)=C(C)C(C)=C1O AUFZRCJENRSRLY-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 6
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 238000006266 etherification reaction Methods 0.000 description 6
- 229940093499 ethyl acetate Drugs 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- KCTHYRRQQNMFKC-UHFFFAOYSA-N 2-methoxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound OC1=C(C)C(C)=C2OC(OC)(C)CCC2=C1C KCTHYRRQQNMFKC-UHFFFAOYSA-N 0.000 description 5
- LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 description 5
- 239000007900 aqueous suspension Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000010502 orange oil Substances 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- LYGKSUOGJYYSOI-UHFFFAOYSA-N 2-methoxybuta-1,3-diene Chemical compound COC(=C)C=C LYGKSUOGJYYSOI-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- VOSOOUFFOIRWHT-UHFFFAOYSA-N 2-methoxy-2-methyl-6-phenylmethoxy-3,4-dihydrochromene Chemical compound C=1C=C2OC(OC)(C)CCC2=CC=1OCC1=CC=CC=C1 VOSOOUFFOIRWHT-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- 235000019502 Orange oil Nutrition 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- 238000006680 Reformatsky reaction Methods 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- VTZZDHSCRSQSST-UHFFFAOYSA-N [4-acetyloxy-3-(3-cyano-3-hydroxybutyl)-2,5,6-trimethylphenyl] acetate Chemical compound CC(=O)OC1=C(C)C(C)=C(OC(C)=O)C(CCC(C)(O)C#N)=C1C VTZZDHSCRSQSST-UHFFFAOYSA-N 0.000 description 3
- 230000021736 acetylation Effects 0.000 description 3
- 238000006640 acetylation reaction Methods 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 238000010931 ester hydrolysis Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical group [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 3
- 229910001958 silver carbonate Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 2
- LMOOKMIJTRIWEO-UHFFFAOYSA-N (2-methoxy-2,7,8-trimethyl-3,4-dihydrochromen-6-yl) benzoate Chemical compound CC=1C(C)=C2OC(OC)(C)CCC2=CC=1OC(=O)C1=CC=CC=C1 LMOOKMIJTRIWEO-UHFFFAOYSA-N 0.000 description 2
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- BTFSFQNWGHJWJH-UHFFFAOYSA-N 2,5,7,8-tetramethyl-3,4-dihydrochromene-2,6-diol Chemical compound O1C(C)(O)CCC2=C1C(C)=C(C)C(O)=C2C BTFSFQNWGHJWJH-UHFFFAOYSA-N 0.000 description 2
- LCWQRJPASJXXJU-UHFFFAOYSA-N 2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromen-2-ol Chemical compound CC1=C(C)C=2OC(C)(O)CCC=2C(C)=C1OCC1=CC=CC=C1 LCWQRJPASJXXJU-UHFFFAOYSA-N 0.000 description 2
- VYKNZRLGBLRHSC-UHFFFAOYSA-N 2-(2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromen-2-yl)acetaldehyde Chemical compound CC1=C(C)C=2OC(C)(CC=O)CCC=2C(C)=C1OCC1=CC=CC=C1 VYKNZRLGBLRHSC-UHFFFAOYSA-N 0.000 description 2
- CKCVCAIYCFAOOA-UHFFFAOYSA-N 2-(2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromen-2-yl)ethyl acetate Chemical compound CC=1C(C)=C2OC(CCOC(=O)C)(C)CCC2=C(C)C=1OCC1=CC=CC=C1 CKCVCAIYCFAOOA-UHFFFAOYSA-N 0.000 description 2
- OKICZKRKWSIBSU-JOCHJYFZSA-N 2-[(2r)-2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromen-2-yl]acetic acid Chemical compound C([C@](C)(CC(O)=O)OC=1C(C)=C2C)CC=1C(C)=C2OCC1=CC=CC=C1 OKICZKRKWSIBSU-JOCHJYFZSA-N 0.000 description 2
- TWPCJMOQTUTRRS-UHFFFAOYSA-N 2-ethoxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound OC1=C(C)C(C)=C2OC(OCC)(C)CCC2=C1C TWPCJMOQTUTRRS-UHFFFAOYSA-N 0.000 description 2
- QESBMELDVUHSDM-UHFFFAOYSA-N 2-methyl-3,4-dihydrochromene-2,6-diol Chemical compound OC1=CC=C2OC(C)(O)CCC2=C1 QESBMELDVUHSDM-UHFFFAOYSA-N 0.000 description 2
- LJGJWQMMAANWJR-UHFFFAOYSA-N 4-(2,5-dihydroxy-3,4,6-trimethylphenyl)-2-ethyl-2-hydroxybutanoic acid Chemical compound CCC(O)(C(O)=O)CCC1=C(C)C(O)=C(C)C(C)=C1O LJGJWQMMAANWJR-UHFFFAOYSA-N 0.000 description 2
- YZMUECYFRYYUAZ-UHFFFAOYSA-N 6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carbonitrile Chemical compound O1C(C)(C#N)CCC2=C1C(C)=C(C)C(O)=C2C YZMUECYFRYYUAZ-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
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- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
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- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
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- 235000007586 terpenes Nutrition 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
- C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
- C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Emergency Medicine (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Edible Oils And Fats (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31756672A | 1972-12-22 | 1972-12-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43888A0 IL43888A0 (en) | 1974-03-14 |
| IL43888A true IL43888A (en) | 1977-02-28 |
Family
ID=23234257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43888A IL43888A (en) | 1972-12-22 | 1973-12-21 | History of 6-hydro-xychromane-2-carboxylic acid or 2-acetic acid, their preparation and use as antioxidants |
Country Status (21)
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH618695A5 (en) * | 1975-01-27 | 1980-08-15 | Hoffmann La Roche | Process for the preparation of chromane derivatives |
| DE2820861A1 (de) * | 1977-05-16 | 1978-11-23 | Hoffmann La Roche | Chromanderivate |
| US4150050A (en) * | 1978-01-30 | 1979-04-17 | Hoffmann-La Roche Inc. | 3,6-Dioxo-1,4-cyclohexadien-1-yl-butandate esters |
| EP0003484B1 (de) * | 1978-01-30 | 1981-10-14 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Verfahren zur Herstellung von Chromanderivaten |
| DE2909601A1 (de) * | 1979-03-12 | 1980-09-25 | Basf Ag | Verfahren zur herstellung von chromanderivaten |
| DE3010505A1 (de) * | 1980-03-19 | 1981-10-01 | Basf Ag, 6700 Ludwigshafen | Chromanderivate, verfahren zu ihrer herstellung, ihre verwendung als stabilisatoren von organischen materialien sowie diese stabilisatoren enthaltende organische materialien |
| DE3010504A1 (de) * | 1980-03-19 | 1981-10-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 2-hydroxyalkylchromanen |
| DE3103740A1 (de) * | 1981-02-04 | 1982-08-19 | Basf Ag, 6700 Ludwigshafen | Chromanderivate |
| DE3103707A1 (de) * | 1981-02-04 | 1982-08-19 | Basf Ag, 6700 Ludwigshafen | Chromanderivate |
| JPS57136582A (en) * | 1981-02-19 | 1982-08-23 | Eisai Co Ltd | Preparation of optically active alpha-tocopherol |
| JPS57145871A (en) * | 1981-03-05 | 1982-09-09 | Eisai Co Ltd | Chromanolcarboxylic derivative |
| DE3139238A1 (de) * | 1981-10-02 | 1983-04-21 | Basf Ag, 6700 Ludwigshafen | Optisch aktive bausteine fuer die synthese der seitenkette von (r,r,r)-(alpha)-tocopherol sowie verfahren zu deren herstellung |
| EP0115142B1 (en) * | 1982-12-23 | 1986-11-05 | Ici Americas Inc. | Chroman compounds |
| ZA844519B (en) * | 1983-06-24 | 1985-02-27 | Hoffmann La Roche | Dihydrobenzopyran derivatives |
| ATE41151T1 (de) * | 1986-01-23 | 1989-03-15 | Hoffmann La Roche | 3,4-dihydro-2,5,7,8-tetramethyl-2h-1benzopyranderivate und verfahren zu ihrer herstellung. |
| US4987231A (en) * | 1989-08-04 | 1991-01-22 | Pfizer Inc. | Optical resolution method for 3R-(3-carboxybenzyl)-6-(5-fluoro-2-benzothiazolyl)methoxy-4R-chromanol |
| CA2082004A1 (en) * | 1991-11-20 | 1993-05-21 | David Laffan | Substituted pentaalkylchromans |
| DE19859251A1 (de) * | 1998-12-22 | 2000-06-29 | Basf Ag | Verfahren zur Herstellung von substituierten Chromanderivaten |
| WO2002012221A1 (fr) * | 2000-08-03 | 2002-02-14 | Kuraray Co., Ltd. | Procede de resolution optique de l'acide (±)-6-hydroxy-2,5,7,8,-tetramethyle de coumarone-2-carboxylique |
| WO2005073212A1 (ja) * | 2004-01-30 | 2005-08-11 | Mitsubishi Gas Chemical Company, Inc. | クロマン化合物の製造方法 |
| KR101233223B1 (ko) * | 2004-12-21 | 2013-02-14 | 제이엔씨 석유 화학 주식회사 | 크로만환을 가지는 액정 화합물, 액정 조성물 및 이 액정조성물을 함유하는 액정 표시소자 |
| EP2522647B1 (en) * | 2011-05-10 | 2014-04-30 | DSM IP Assets B.V. | Process of separating chiral isomers of chroman compounds and their derivatives and precursors |
| NL2010010C2 (en) | 2012-12-19 | 2014-06-23 | Sulfateq B V | Compounds for protection of cells. |
| KR20220143897A (ko) * | 2020-02-21 | 2022-10-25 | 스미토모 파마 가부시키가이샤 | 광학 분할된 트롤록스 중간체 및 그 제조 방법 |
-
1973
- 1973-12-13 ZA ZA739471*A patent/ZA739471B/xx unknown
- 1973-12-19 CH CH1777173A patent/CH603617A5/xx not_active IP Right Cessation
- 1973-12-19 CH CH1777073A patent/CH605892A5/xx not_active IP Right Cessation
- 1973-12-20 PH PH15347A patent/PH11133A/en unknown
- 1973-12-20 DD DD175557A patent/DD109624A5/xx unknown
- 1973-12-21 GB GB5929673A patent/GB1456827A/en not_active Expired
- 1973-12-21 SE SE7317421A patent/SE406912B/xx unknown
- 1973-12-21 CA CA188,762A patent/CA1022562A/en not_active Expired
- 1973-12-21 BE BE139129A patent/BE808943A/xx not_active IP Right Cessation
- 1973-12-21 AR AR251651A patent/AR200751A1/es active
- 1973-12-21 NL NL7317587A patent/NL7317587A/xx not_active Application Discontinuation
- 1973-12-21 GB GB2227175A patent/GB1456829A/en not_active Expired
- 1973-12-21 FR FR7346000A patent/FR2284604A1/fr active Granted
- 1973-12-21 DE DE2364141A patent/DE2364141A1/de not_active Ceased
- 1973-12-21 SU SU1978253A patent/SU518135A3/ru active
- 1973-12-21 JP JP48142526A patent/JPS4988876A/ja active Pending
- 1973-12-21 HU HUHO1637A patent/HU168043B/hu unknown
- 1973-12-21 IE IE2317/73A patent/IE38671B1/xx unknown
- 1973-12-21 DE DE2364165A patent/DE2364165A1/de not_active Ceased
- 1973-12-21 IL IL43888A patent/IL43888A/en unknown
- 1973-12-21 JP JP48142527A patent/JPS5946233B2/ja not_active Expired
- 1973-12-21 LU LU69067A patent/LU69067A1/xx unknown
- 1973-12-21 GB GB2227275A patent/GB1456830A/en not_active Expired
- 1973-12-21 BE BE139128A patent/BE808942A/xx unknown
- 1973-12-21 GB GB5929873A patent/GB1456828A/en not_active Expired
- 1973-12-21 ES ES421683A patent/ES421683A1/es not_active Expired
- 1973-12-21 AT AT1076973A patent/AT333755B/de not_active IP Right Cessation
- 1973-12-21 NL NLAANVRAGE7317590,A patent/NL178968C/xx not_active IP Right Cessation
- 1973-12-21 FR FR7346001A patent/FR2255299B1/fr not_active Expired
- 1973-12-22 KR KR7302219A patent/KR780000008B1/ko not_active Expired
-
1976
- 1976-11-19 CH CH1457976A patent/CH622257A5/de not_active IP Right Cessation
-
1984
- 1984-01-18 JP JP59005854A patent/JPS6026795B2/ja not_active Expired
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