JP5047507B2

JP5047507B2 - カルニチン誘導体及びその塩、皮膚外用剤ならびに化粧料

カルニチン誘導体及びその塩、皮膚外用剤ならびに化粧料 Download PDF

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Publication number: JP5047507B2
Authority: JP; Japan
Prior art keywords: group; ion; carnitine; acid; extract
Prior art date: 2005-09-30
Legal status : Active

Application number

JP2006045167A

Other languages

English (en)

Japanese (ja)

Other versions

JP2007119441A (ja

JP2007119441A5 (pl

Inventor

裕史青木

晴美蒲池

洋平倉田

Current Assignee

Resonac Holdings Corp

Original Assignee

Showa Denko KK

Priority date

2005-09-30

Filing date

2006-02-22

Publication date

2012-10-10

2006-02-22 Priority to JP2006045167A priority Critical patent/JP5047507B2/ja

2006-02-22 Application filed by Showa Denko KK filed Critical Showa Denko KK

2006-09-21 Priority to ES06810679.8T priority patent/ES2453148T3/es

2006-09-21 Priority to PCT/JP2006/319221 priority patent/WO2007043339A1/en

2006-09-21 Priority to BRPI0616650-4A priority patent/BRPI0616650B1/pt

2006-09-21 Priority to CN2006800361450A priority patent/CN101277675B/zh

2006-09-21 Priority to EP06810679.8A priority patent/EP1928402B1/en

2006-09-21 Priority to US12/088,792 priority patent/US7842726B2/en

2007-05-17 Publication of JP2007119441A publication Critical patent/JP2007119441A/ja

2009-04-02 Publication of JP2007119441A5 publication Critical patent/JP2007119441A5/ja

2012-10-10 Application granted granted Critical

2012-10-10 Publication of JP5047507B2 publication Critical patent/JP5047507B2/ja

Status Active legal-status Critical Current

2026-02-22 Anticipated expiration legal-status Critical

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PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical class C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 title claims description 153
238000002360 preparation method Methods 0.000 title claims description 61
150000003839 salts Chemical class 0.000 title claims description 52
239000002537 cosmetic Substances 0.000 title claims description 48
-1 n-octyl group Chemical group 0.000 claims description 271
125000004432 carbon atom Chemical group C* 0.000 claims description 38
229960004203 carnitine Drugs 0.000 claims description 38
150000001450 anions Chemical class 0.000 claims description 37
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 27
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 24
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 21
150000001768 cations Chemical class 0.000 claims description 20
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 19
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 16
229920006395 saturated elastomer Polymers 0.000 claims description 14
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 9
229960005070 ascorbic acid Drugs 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
229910001414 potassium ion Inorganic materials 0.000 claims description 8
229910001415 sodium ion Inorganic materials 0.000 claims description 8
DBSABEYSGXPBTA-RXSVEWSESA-N (2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;phosphoric acid Chemical compound OP(O)(O)=O.OC[C@H](O)[C@H]1OC(=O)C(O)=C1O DBSABEYSGXPBTA-RXSVEWSESA-N 0.000 claims description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 7
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 7
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 7
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 7
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims description 7
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims description 7
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 7
235000010323 ascorbic acid Nutrition 0.000 claims description 7
239000011668 ascorbic acid Substances 0.000 claims description 7
229940071097 ascorbyl phosphate Drugs 0.000 claims description 7
229910001424 calcium ion Inorganic materials 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 7
229910001425 magnesium ion Inorganic materials 0.000 claims description 7
150000004670 unsaturated fatty acids Chemical class 0.000 claims description 7
235000021122 unsaturated fatty acids Nutrition 0.000 claims description 7
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 6
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 6
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 4
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
150000004671 saturated fatty acids Chemical class 0.000 claims description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 claims 2
239000000284 extract Substances 0.000 description 136
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
229920003171 Poly (ethylene oxide) Polymers 0.000 description 61
210000003491 skin Anatomy 0.000 description 58
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
235000002639 sodium chloride Nutrition 0.000 description 55
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
235000014113 dietary fatty acids Nutrition 0.000 description 47
229930195729 fatty acid Natural products 0.000 description 47
239000000194 fatty acid Substances 0.000 description 47
238000003756 stirring Methods 0.000 description 43
239000000203 mixture Substances 0.000 description 42
125000000217 alkyl group Chemical group 0.000 description 40
150000004665 fatty acids Chemical class 0.000 description 38
239000008213 purified water Substances 0.000 description 37
239000011734 sodium Substances 0.000 description 35
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 34
229910052708 sodium Inorganic materials 0.000 description 33
ABWFEAGHHZSUSC-KDKNQRMFSA-N 2-hexyldecanoic acid;(3r)-3-hydroxy-4-(trimethylazaniumyl)butanoate;hydrochloride Chemical compound Cl.C[N+](C)(C)C[C@H](O)CC([O-])=O.CCCCCCCCC(C(O)=O)CCCCCC ABWFEAGHHZSUSC-KDKNQRMFSA-N 0.000 description 30
239000003921 oil Substances 0.000 description 30
235000019198 oils Nutrition 0.000 description 30
238000009472 formulation Methods 0.000 description 29
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 27
239000000126 substance Substances 0.000 description 27
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 26
125000001931 aliphatic group Chemical group 0.000 description 25
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 25
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 24
235000019864 coconut oil Nutrition 0.000 description 22
239000003240 coconut oil Substances 0.000 description 22
125000002252 acyl group Chemical group 0.000 description 20
239000000499 gel Substances 0.000 description 19
238000004949 mass spectrometry Methods 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000002253 acid Substances 0.000 description 18
230000015572 biosynthetic process Effects 0.000 description 18
230000037356 lipid metabolism Effects 0.000 description 18
239000007788 liquid Substances 0.000 description 18
238000012360 testing method Methods 0.000 description 18
PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 17
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 17
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 17
229960002216 methylparaben Drugs 0.000 description 17
238000003786 synthesis reaction Methods 0.000 description 17
239000004359 castor oil Substances 0.000 description 16
235000019438 castor oil Nutrition 0.000 description 16
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 16
229920001223 polyethylene glycol Polymers 0.000 description 16
235000019482 Palm oil Nutrition 0.000 description 15
239000002202 Polyethylene glycol Substances 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
239000002540 palm oil Substances 0.000 description 15
JXXCENBLGFBQJM-UHFFFAOYSA-N (3-carboxy-2-hydroxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)CC(O)=O JXXCENBLGFBQJM-UHFFFAOYSA-N 0.000 description 14
125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 14
230000007935 neutral effect Effects 0.000 description 14
229920001451 polypropylene glycol Polymers 0.000 description 14
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 13
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 13
229960003237 betaine Drugs 0.000 description 13
229920001577 copolymer Polymers 0.000 description 13
235000011187 glycerol Nutrition 0.000 description 13
TYIJJCSQTQSIPX-KDKNQRMFSA-N (3r)-3-hydroxy-4-(trimethylazaniumyl)butanoate;2-methylhexadecanoic acid;hydrochloride Chemical compound Cl.C[N+](C)(C)C[C@H](O)CC([O-])=O.CCCCCCCCCCCCCCC(C)C(O)=O TYIJJCSQTQSIPX-KDKNQRMFSA-N 0.000 description 12
BXJKNWIZYMNDEJ-KDKNQRMFSA-N 2-butyloctanoic acid;(3r)-3-hydroxy-4-(trimethylazaniumyl)butanoate;hydrochloride Chemical compound Cl.C[N+](C)(C)C[C@H](O)CC([O-])=O.CCCCCCC(C(O)=O)CCCC BXJKNWIZYMNDEJ-KDKNQRMFSA-N 0.000 description 12
235000019437 butane-1,3-diol Nutrition 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
238000013329 compounding Methods 0.000 description 12
229940058015 1,3-butylene glycol Drugs 0.000 description 11
125000003136 n-heptyl 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])* 0.000 description 11
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 11
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
229920002125 Sokalan® Polymers 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
150000001875 compounds Chemical class 0.000 description 10
229930195712 glutamate Natural products 0.000 description 10
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 9
AXPAUZGVNGEWJD-UHFFFAOYSA-N 2-methylhexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(C)C(O)=O AXPAUZGVNGEWJD-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
239000006071 cream Substances 0.000 description 9
230000000694 effects Effects 0.000 description 9
239000000839 emulsion Substances 0.000 description 9
150000002632 lipids Chemical class 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
239000000843 powder Substances 0.000 description 9
239000012736 aqueous medium Substances 0.000 description 8
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 8
239000011591 potassium Substances 0.000 description 8
229910052700 potassium Inorganic materials 0.000 description 8
229940032094 squalane Drugs 0.000 description 8
229960004418 trolamine Drugs 0.000 description 8
FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 7
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 7
XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 7
238000005481 NMR spectroscopy Methods 0.000 description 7
229910019142 PO4 Inorganic materials 0.000 description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 7
150000001449 anionic compounds Chemical class 0.000 description 7
150000001767 cationic compounds Chemical class 0.000 description 7
238000000921 elemental analysis Methods 0.000 description 7
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235000019197 fats Nutrition 0.000 description 7
229910001411 inorganic cation Inorganic materials 0.000 description 7
239000006210 lotion Substances 0.000 description 7
239000002609 medium Substances 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
150000002891 organic anions Chemical class 0.000 description 7
150000002892 organic cations Chemical class 0.000 description 7
239000010452 phosphate Substances 0.000 description 7
230000001737 promoting effect Effects 0.000 description 7
239000002453 shampoo Substances 0.000 description 7
229920001285 xanthan gum Polymers 0.000 description 7
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ASKIVFGGGGIGKH-UHFFFAOYSA-N 2,3-dihydroxypropyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(O)CO ASKIVFGGGGIGKH-UHFFFAOYSA-N 0.000 description 6
235000021355 Stearic acid Nutrition 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
235000015278 beef Nutrition 0.000 description 6
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 6
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
JMOLZNNXZPAGBH-UHFFFAOYSA-N hexyldecanoic acid Chemical compound CCCCCCCCC(C(O)=O)CCCCCC JMOLZNNXZPAGBH-UHFFFAOYSA-N 0.000 description 6
229950004531 hexyldecanoic acid Drugs 0.000 description 6
229910001412 inorganic anion Inorganic materials 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 6
229920001296 polysiloxane Polymers 0.000 description 6
FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 6
239000008117 stearic acid Substances 0.000 description 6
229960000984 tocofersolan Drugs 0.000 description 6
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NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 5
FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 5
RZRILSWMGXWSJY-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;sulfuric acid Chemical compound OS(O)(=O)=O.OCCN(CCO)CCO RZRILSWMGXWSJY-UHFFFAOYSA-N 0.000 description 5
JMOLZNNXZPAGBH-UHFFFAOYSA-M 2-hexyldecanoate Chemical compound CCCCCCCCC(C([O-])=O)CCCCCC JMOLZNNXZPAGBH-UHFFFAOYSA-M 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
150000001348 alkyl chlorides Chemical class 0.000 description 5
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 description 5
GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
238000000132 electrospray ionisation Methods 0.000 description 5
239000003480 eluent Substances 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000000047 product Substances 0.000 description 5
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 5
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 5
229960003415 propylparaben Drugs 0.000 description 5
239000002994 raw material Substances 0.000 description 5
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NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
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FHHPUSMSKHSNKW-SMOYURAASA-M sodium deoxycholate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 FHHPUSMSKHSNKW-SMOYURAASA-M 0.000 description 1
BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
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KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
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RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
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PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
239000011755 sodium-L-ascorbate Substances 0.000 description 1
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DSOWAKKSGYUMTF-GZOLSCHFSA-M sodium;(1e)-1-(6-methyl-2,4-dioxopyran-3-ylidene)ethanolate Chemical compound [Na+].C\C([O-])=C1/C(=O)OC(C)=CC1=O DSOWAKKSGYUMTF-GZOLSCHFSA-M 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
KNYAZNABVSEZDS-UHFFFAOYSA-M sodium;2-octadecanoyloxypropanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC(=O)OC(C)C([O-])=O KNYAZNABVSEZDS-UHFFFAOYSA-M 0.000 description 1
HWCHICTXVOMIIF-UHFFFAOYSA-M sodium;3-(dodecylamino)propanoate Chemical compound [Na+].CCCCCCCCCCCCNCCC([O-])=O HWCHICTXVOMIIF-UHFFFAOYSA-M 0.000 description 1
NHZIBLPDGIARQC-UHFFFAOYSA-M sodium;4-hydroxy-5-(2-hydroxy-4-methoxybenzoyl)-2-methoxybenzenesulfonate Chemical compound [Na+].OC1=CC(OC)=CC=C1C(=O)C1=CC(S([O-])(=O)=O)=C(OC)C=C1O NHZIBLPDGIARQC-UHFFFAOYSA-M 0.000 description 1
MWZFQMUXPSUDJQ-KVVVOXFISA-M sodium;[(z)-octadec-9-enyl] sulfate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCOS([O-])(=O)=O MWZFQMUXPSUDJQ-KVVVOXFISA-M 0.000 description 1
GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 1
GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
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