JPH0571236B2 - - Google Patents

Info

Publication number

JPH0571236B2

JPH0571236B2 JP20993384A JP20993384A JPH0571236B2 JP H0571236 B2 JPH0571236 B2 JP H0571236B2 JP 20993384 A JP20993384 A JP 20993384A JP 20993384 A JP20993384 A JP 20993384A JP H0571236 B2 JPH0571236 B2 JP H0571236B2

Authority

JP

Japan

Prior art keywords

group

ring

phosphorylcholine

propanol

residue

Prior art date

1984-10-08

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 - Fee Related

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• -1 pregnane steroid compound Chemical group 0.000 claims description 212
• 125000001424 substituent group Chemical group 0.000 claims description 82
• 150000001875 compounds Chemical class 0.000 claims description 45
• 229910052736 halogen Inorganic materials 0.000 claims description 42
• 150000002367 halogens Chemical group 0.000 claims description 42
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
• 125000003277 amino group Chemical group 0.000 claims description 40
• 230000001476 alcoholic effect Effects 0.000 claims description 39
• 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 39
• 229920006395 saturated elastomer Polymers 0.000 claims description 39
• 229910019142 PO4 Inorganic materials 0.000 claims description 35
• 102000011420 Phospholipase D Human genes 0.000 claims description 35
• 108090000553 Phospholipase D Proteins 0.000 claims description 35
• 239000010452 phosphate Substances 0.000 claims description 34
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
• 125000003545 alkoxy group Chemical group 0.000 claims description 26
• 239000000126 substance Substances 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 20
• 125000002252 acyl group Chemical group 0.000 claims description 17
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
• 125000004414 alkyl thio group Chemical group 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 14
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
• 125000003386 piperidinyl group Chemical group 0.000 claims description 12
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 11
• 125000004193 piperazinyl group Chemical group 0.000 claims description 11
• 238000006276 transfer reaction Methods 0.000 claims description 11
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 9
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 9
• 150000003014 phosphoric acid esters Chemical class 0.000 claims description 9
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• 125000004043 oxo group Chemical group O=* 0.000 claims description 8
• 235000000346 sugar Nutrition 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 125000005543 phthalimide group Chemical group 0.000 claims description 7
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 6
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
• 125000002560 nitrile group Chemical group 0.000 claims description 6
• 125000006830 (C1-C24) aliphatic hydrocarbon group Chemical group 0.000 claims description 5
• ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical group C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims description 5
• GIIGHSIIKVOWKZ-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine Chemical group N1=CN=CC2=NNN=C21 GIIGHSIIKVOWKZ-UHFFFAOYSA-N 0.000 claims description 5
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 5
• 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical group OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 4
• 125000000204 (C2-C4) acyl group Chemical group 0.000 claims description 4
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 4
• HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical group C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 4
• SPAMRUYRVYMHPV-UHFFFAOYSA-N 3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical group C1=CCCC2C(=O)NC(=O)C21 SPAMRUYRVYMHPV-UHFFFAOYSA-N 0.000 claims description 4
• SHZGCJCMOBCMKK-UHFFFAOYSA-N 6-methyloxane-2,3,4,5-tetrol Chemical group CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 4
• 125000003892 C18 acyl group Chemical group 0.000 claims description 4
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
• 125000001931 aliphatic group Chemical group 0.000 claims description 4
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 125000006501 nitrophenyl group Chemical group 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
• HNXQXTQTPAJEJL-UHFFFAOYSA-N 2-aminopteridin-4-ol Chemical group C1=CN=C2NC(N)=NC(=O)C2=N1 HNXQXTQTPAJEJL-UHFFFAOYSA-N 0.000 claims description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical group C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 238000003763 carbonization Methods 0.000 claims description 3
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
• AHKZTVQIVOEVFO-UHFFFAOYSA-N oxide(2-) Chemical group [O-2] AHKZTVQIVOEVFO-UHFFFAOYSA-N 0.000 claims description 3
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical group C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 2
• 150000001408 amides Chemical class 0.000 claims description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 3
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims 1
• 229910052799 carbon Inorganic materials 0.000 claims 1
• 125000000600 disaccharide group Chemical group 0.000 claims 1
• 125000002017 heptosyl group Chemical group 0.000 claims 1
• 125000000625 hexosyl group Chemical group 0.000 claims 1
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
• 125000001805 pentosyl group Chemical group 0.000 claims 1
• 229950004354 phosphorylcholine Drugs 0.000 description 338
• 239000000758 substrate Substances 0.000 description 72
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
• 238000006243 chemical reaction Methods 0.000 description 36
• 238000000034 method Methods 0.000 description 35
• ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 34
• 102000015439 Phospholipases Human genes 0.000 description 34
• 108010064785 Phospholipases Proteins 0.000 description 34
• 239000000243 solution Substances 0.000 description 34
• 235000021317 phosphate Nutrition 0.000 description 33
• NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 30
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
• 239000007858 starting material Substances 0.000 description 22
• 239000000203 mixture Substances 0.000 description 21
• 239000002904 solvent Substances 0.000 description 21
• 239000007864 aqueous solution Substances 0.000 description 19
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 17
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
• 150000001298 alcohols Chemical class 0.000 description 16
• 229960001231 choline Drugs 0.000 description 15
• 239000000370 acceptor Substances 0.000 description 14
• 239000003153 chemical reaction reagent Substances 0.000 description 14
• 230000000694 effects Effects 0.000 description 14
• 239000000047 product Substances 0.000 description 14
• RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 13
• 235000012239 silicon dioxide Nutrition 0.000 description 13
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 150000004945 aromatic hydrocarbons Chemical group 0.000 description 12
• 150000003904 phospholipids Chemical class 0.000 description 12
• 238000012546 transfer Methods 0.000 description 12
• PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
• 239000000787 lecithin Substances 0.000 description 11
• 229940067606 lecithin Drugs 0.000 description 11
• 235000002639 sodium chloride Nutrition 0.000 description 11
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• 235000010445 lecithin Nutrition 0.000 description 10
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 230000009471 action Effects 0.000 description 9
• 150000002402 hexoses Chemical group 0.000 description 9
• 159000000000 sodium salts Chemical class 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 8
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 8
• 229910052757 nitrogen Inorganic materials 0.000 description 8
• PYJNAPOPMIJKJZ-UHFFFAOYSA-N phosphorylcholine chloride Chemical compound [Cl-].C[N+](C)(C)CCOP(O)(O)=O PYJNAPOPMIJKJZ-UHFFFAOYSA-N 0.000 description 8
• 150000003138 primary alcohols Chemical class 0.000 description 8
• 238000003756 stirring Methods 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
• NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 7
• 240000007124 Brassica oleracea Species 0.000 description 7
• 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 7
• 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 7
• 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 7
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
• 239000002994 raw material Substances 0.000 description 7
• 150000003527 tetrahydropyrans Chemical group 0.000 description 7
• 238000004809 thin layer chromatography Methods 0.000 description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• MCSYNJVXRZLTKA-UHFFFAOYSA-O CCCCCCCCCCCCCCP(=O)=C(O)C[N+](C)(C)C Chemical compound CCCCCCCCCCCCCCP(=O)=C(O)C[N+](C)(C)C MCSYNJVXRZLTKA-UHFFFAOYSA-O 0.000 description 6
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
• 238000006911 enzymatic reaction Methods 0.000 description 6
• ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
• 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 6
• 150000002972 pentoses Chemical class 0.000 description 6
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
• 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
• UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 5
• 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 description 5
• 102000004190 Enzymes Human genes 0.000 description 5
• 108090000790 Enzymes Proteins 0.000 description 5
• 241000203622 Nocardiopsis Species 0.000 description 5
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
• 239000003125 aqueous solvent Substances 0.000 description 5
• 239000000872 buffer Substances 0.000 description 5
• 239000001110 calcium chloride Substances 0.000 description 5
• 229910001628 calcium chloride Inorganic materials 0.000 description 5
• 238000005119 centrifugation Methods 0.000 description 5
• 230000002255 enzymatic effect Effects 0.000 description 5
• 150000002327 glycerophospholipids Chemical class 0.000 description 5
• 238000002329 infrared spectrum Methods 0.000 description 5
• 239000012528 membrane Substances 0.000 description 5
• 239000003960 organic solvent Substances 0.000 description 5
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 5
• 239000000600 sorbitol Substances 0.000 description 5
• 235000010356 sorbitol Nutrition 0.000 description 5
• 238000001308 synthesis method Methods 0.000 description 5
• KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
• WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 4
• BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
• IHPYMWDTONKSCO-UHFFFAOYSA-N 2,2'-piperazine-1,4-diylbisethanesulfonic acid Chemical compound OS(=O)(=O)CCN1CCN(CCS(O)(=O)=O)CC1 IHPYMWDTONKSCO-UHFFFAOYSA-N 0.000 description 4
• MLKJAWRTVVIMAO-UHFFFAOYSA-N 3-octadecylsulfanylpropan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCSCCCO MLKJAWRTVVIMAO-UHFFFAOYSA-N 0.000 description 4
• 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 description 4
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
• WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
• 239000008351 acetate buffer Substances 0.000 description 4
• 229960000583 acetic acid Drugs 0.000 description 4
• 125000002947 alkylene group Chemical group 0.000 description 4
• 230000008901 benefit Effects 0.000 description 4
• 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 description 4
• WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
• WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
• 239000013078 crystal Substances 0.000 description 4
• GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 4
• 125000003438 dodecyl group Chemical group [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])* 0.000 description 4
• 239000003995 emulsifying agent Substances 0.000 description 4
• 239000008103 glucose Substances 0.000 description 4
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
• 239000002244 precipitate Substances 0.000 description 4
• LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 4
• 239000000741 silica gel Substances 0.000 description 4
• 229910002027 silica gel Inorganic materials 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
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