JP2018526361A - 香料混合物 - Google Patents
香料混合物 Download PDFInfo
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- JP2018526361A JP2018526361A JP2018507589A JP2018507589A JP2018526361A JP 2018526361 A JP2018526361 A JP 2018526361A JP 2018507589 A JP2018507589 A JP 2018507589A JP 2018507589 A JP2018507589 A JP 2018507589A JP 2018526361 A JP2018526361 A JP 2018526361A
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- acid
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- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 108010075550 termamyl Proteins 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- HBPNTDBLHQHPLH-UHFFFAOYSA-N tetradecyl 16-methylheptadecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C HBPNTDBLHQHPLH-UHFFFAOYSA-N 0.000 description 1
- AVKVDDQTHIQFSC-UHFFFAOYSA-N tetradecyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC AVKVDDQTHIQFSC-UHFFFAOYSA-N 0.000 description 1
- DHZWALZKPWZSMA-UHFFFAOYSA-N tetradecyl oleate Natural products CCCCCCCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC DHZWALZKPWZSMA-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical group NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- MSLRPWGRFCKNIZ-UHFFFAOYSA-J tetrasodium;hydrogen peroxide;dicarbonate Chemical compound [Na+].[Na+].[Na+].[Na+].OO.OO.OO.[O-]C([O-])=O.[O-]C([O-])=O MSLRPWGRFCKNIZ-UHFFFAOYSA-J 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229950009883 tocopheryl nicotinate Drugs 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- NZHGWWWHIYHZNX-CSKARUKUSA-N tranilast Chemical compound C1=C(OC)C(OC)=CC=C1\C=C\C(=O)NC1=CC=CC=C1C(O)=O NZHGWWWHIYHZNX-CSKARUKUSA-N 0.000 description 1
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- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
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- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- USPJNXWHVJTDJW-UHFFFAOYSA-N tricyclo[5.2.1.02,6]decane-3-carbaldehyde Chemical compound C1CC2C3C(C=O)CCC3C1C2 USPJNXWHVJTDJW-UHFFFAOYSA-N 0.000 description 1
- HTJNEBVCZXHBNJ-XCTPRCOBSA-H trimagnesium;(2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;diphosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.OC[C@H](O)[C@H]1OC(=O)C(O)=C1O HTJNEBVCZXHBNJ-XCTPRCOBSA-H 0.000 description 1
- OEIXGLMQZVLOQX-UHFFFAOYSA-N trimethyl-[3-(prop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCNC(=O)C=C OEIXGLMQZVLOQX-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- FQAZRHVERGEKOS-UHFFFAOYSA-N tripropan-2-yl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CC(C)OC(=O)CC(O)(C(=O)OC(C)C)CC(=O)OC(C)C FQAZRHVERGEKOS-UHFFFAOYSA-N 0.000 description 1
- ODHUFJLMXDXVRC-UHFFFAOYSA-N tripropyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCOC(=O)CC(O)(C(=O)OCCC)CC(=O)OCCC ODHUFJLMXDXVRC-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 230000001810 trypsinlike Effects 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- HFTAFOQKODTIJY-UHFFFAOYSA-N umbelliferone Natural products Cc1cc2C=CC(=O)Oc2cc1OCC=CC(C)(C)O HFTAFOQKODTIJY-UHFFFAOYSA-N 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- ZENOXNGFMSCLLL-UHFFFAOYSA-N vanillyl alcohol Natural products COC1=CC(CO)=CC=C1O ZENOXNGFMSCLLL-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- WXETUDXXEZHSCS-MAVITOTKSA-N vertofix coeur Chemical compound C[C@@H]1CC[C@@]2(C(/CC3)=C\C(C)=O)[C@@H]3C(C)(C)[C@@H]1C2 WXETUDXXEZHSCS-MAVITOTKSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019143 vitamin K2 Nutrition 0.000 description 1
- 239000011728 vitamin K2 Substances 0.000 description 1
- 229940041603 vitamin k 3 Drugs 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011670 zinc gluconate Substances 0.000 description 1
- 235000011478 zinc gluconate Nutrition 0.000 description 1
- 229960000306 zinc gluconate Drugs 0.000 description 1
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- 229940043810 zinc pyrithione Drugs 0.000 description 1
- GAWWVVGZMLGEIW-GNNYBVKZSA-L zinc ricinoleate Chemical compound [Zn+2].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O.CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O GAWWVVGZMLGEIW-GNNYBVKZSA-L 0.000 description 1
- 229940100530 zinc ricinoleate Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
- OJYLAHXKWMRDGS-UHFFFAOYSA-N zingerone Chemical compound COC1=CC(CCC(C)=O)=CC=C1O OJYLAHXKWMRDGS-UHFFFAOYSA-N 0.000 description 1
- 239000001841 zingiber officinale Substances 0.000 description 1
- VLCYCQAOQCDTCN-ZCFIWIBFSA-N α-difluoromethylornithine Chemical compound NCCC[C@@](N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-ZCFIWIBFSA-N 0.000 description 1
- UZFLPKAIBPNNCA-FPLPWBNLSA-N α-ionone Chemical compound CC(=O)\C=C/C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-FPLPWBNLSA-N 0.000 description 1
- WHNFPRLDDSXQCL-UAZQEYIDSA-N α-msh Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(N)=O)NC(=O)[C@H](CO)NC(C)=O)C1=CC=C(O)C=C1 WHNFPRLDDSXQCL-UAZQEYIDSA-N 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
- 108020001612 μ-opioid receptors Proteins 0.000 description 1
Classifications
-
- 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
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- 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
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
本発明の第1の目的は、香料混合物であって、
(a)少なくとも1つの一般式(I)の化合物
(b)少なくとも1つの一般式(II)の化合物
(c)化合物(I)および(II)とは異なる、少なくとも1つの追加の香料;および
(d)任意に少なくとも1つの溶媒
を含む、前記混合物である。
を含む。
・[(1R,5R)−5−イソプロペニル−2−メチル−シクロヘキサ−2−エン−1−イル]アセテート、
・[(1R,5R)−5−イソプロペニル−2−メチル−シクロヘキサ−2−エン−1−イル]プロピオネート、
・[(1R,5R)−5−イソプロペニル−2−メチル−シクロヘキサ−2−エン−1−イル]メチルカーボネート、
・[(1R、5R)−5−イソプロペニル−2−メチル−シクロヘキサ−2−エン−1−イル]エチルカーボネート。
・[(1S,5R)−5−イソプロペニル−2−メチル−シクロヘキシル]アセテート、
・[(1S,5R)−5−イソプロペニル−2−メチル−シクロヘキシル]プロピオネート、
・[(1S,5R)−5−イソプロペニル−2−メチル−シクロヘキシル]メチルカーボネート、
・[(1S,5R)−5−イソプロペニル−2−メチル−シクロヘキシル]エチルカーボネート。
・[(1R,2R,5R)−5−イソプロペニル−2−メチル−シクロヘキシル]アセテート、
・[(1R,2R,5R)−5−イソプロペニル−2−メチル−シクロヘキシル]プロピオネート、
・[(1R,2R,5R)−5−イソプロペニル−2−メチル−シクロヘキシル]メチルカーボネート、
・[(1R,2R,5R)−5−イソプロペニル−2−メチル−シクロヘキシル]エチルカルボネート。
(i)約62〜約67重量%(%b.w.)の少なくとも1つの化合物(I)の1R,5R異性体;
(ii)約14〜約18重量%の少なくとも1つの化合物(IIa)の1R,2R,5R異性体;
(iii)約6.0〜約7.0重量%の少なくとも1つの化合物(II)の1S,2R,5S異性体;
(iv)約7.0〜約9.0重量%の少なくとも1つの化合物(III)の1R,5S異性体;
(v)約4.0〜約6.0重量%の少なくとも1つの式(III)の1R,2S,5S異性体;および
(vi)約0.5〜約1.0重量%の少なくとも1つの式(III)の1R,2R,5S異性体
を、前記した量の合計が100重量%であることを条件として、
含む、混合物に関する。
(A)(−)−カルベオールおよび/または(−)−ジヒドロカルベオールの供給源を準備するステップ;
(B)(−)−カルベオールおよび/または(−)−ジヒドロカルベオールの前記供給源を、一般式(IV)の化合物
と反応させてエステルを形成するステップ。
・直鎖C8〜22の脂肪族アルコールへの、C12〜22の脂肪酸への、およびアルキル基中に8〜15個の炭素原子を含むアルキルフェノールへの、2〜30モルのエチレンオキシドおよび/または0〜5モルのプロピレンオキシドの付加生成物;
・グリセロールへの1〜30モルのエチレンオキシドの付加生成物のC12/18脂肪酸モノエステルおよびジエステル;
・6〜22個の炭素原子を含有する飽和および不飽和脂肪酸およびそれらのエチレンオキシド付加物のグリセロールモノおよびジエステルおよびソルビタンモノおよびジエステル;
・ヒマシ油および/または硬化ヒマシ油への15〜60モルのエチレンオキシドの付加生成物;
・ポリオールエステル、特にポリグリセロールエステル、例えばポリグリセロールポリリシノレート、ポリグリセロールポリ−12−ヒドロキシステアレートまたはポリグリセロールジメレートイソステアレートなど。これらのクラスのいくつかに由来の化合物の混合物も適切である;
・ヒマシ油および/または硬化ヒマシ油への2〜15モルのエチレンオキシドの付加生成物;
・直鎖状、分岐した、不飽和または飽和のC6/22の脂肪酸、リシノール酸および12−ヒドロキシステアリン酸およびグリセロール、ポリグリセロール、ペンタエリスリトール、ジペンタエリスリトール、糖アルコール(例えば、ソルビトール)、アルキルグルコシド(例えば、メチルグルコシド、ブチルグルコシド、ラウリルグルコシド)およびポリグルコシド(例えば、セルロース)に基づく部分エステル;
・モノ−、ジ−およびトリアルキルホスフェートおよびモノ−、ジ−および/またはトリ−PEG−アルキルホスフェートおよびそれらの塩;
・ウールワックスアルコール;
・ポリシロキサン/ポリアルキルポリエーテル・コポリマーおよび対応する誘導体;
・ペンタエリスリトール、脂肪酸、クエン酸および脂肪族アルコールの混合エステルおよび/またはC6−22の脂肪酸、メチルグルコースおよびポリオール、好ましくはグリセロールまたはポリグリセロールの混合エステル、
・ポリアルキレングリコールおよび
・グリセロールカーボネート。
・p−アミノ安息香酸
・エトキシル化したp−アミノ安息香酸エチルエステル(25モル)(INCI名:PEG−25PABA)
・p−ジメチルアミノ安息香酸−2−エチルヘキシルエステル
・N−プロポキシル化したp−アミノ安息香酸エチルエステル(2モル)
・p−アミノ安息香酸グリセロールエステル
・サリチル酸ホモメンチルエステル(ホモサレート)(Neo Heliopan(登録商標)HMS)
・サリチル酸−2−エチルヘキシルエステル(Neo Heliopan(登録商標)OS)
・サリチル酸トリエタノールアミン
・4−イソプロピルベンジルサリチレート
・アントラニル酸メンチルエステル(Neo Heliopan(登録商標)MA)
・ジイソプロピル桂皮酸エチルエステル
・p−メトキシ桂皮酸−2−エチルヘキシルエステル(Neo Heliopan(登録商標)AV)
・ジイソプロピル桂皮酸メチルエステル
・p−メトキシ桂皮酸イソアミルエステル(Neo Heliopan(登録商標)E1000)
・p−メトキシ桂皮酸ジエタノールアミン塩
・p−メトキシ桂皮酸イソプロピルエステル
・2−フェニルベンズイミダゾールスルホン酸および塩(Neo Heliopan(登録商標)Hydro)
・3−(4’−トリメチルアンモニウム)ベンジリデンボルナン−2−オンメチルスルフェート
・ベータ−イミダゾール−4(5)−アクリル酸(ウロカニン酸)
・3−(4’−スルホ)ベンジリデンボルナン−2−オンおよび塩
・3−(4’−メチルベンジリデン)−D,L−カンファー(Neo Heliopan(登録商標)MBC)
・3−ベンジリデン−D,L−カンファー
・N−[(2および4)−[2−(オキソボルン−3−イリデン)メチル]ベンジル]アクリルアミドポリマー
・4,4’−[(6−[4−(1,1−ジメチル)アミノカルボニル)フェニルアミノ]−1,3,5−トリアジン−2,4−ジイル)ジイミノ]−ビス−(安息香酸−2−エチルヘキシルエステル)(Uvasorb(登録商標)HEB)
・ベンジリデンマロネートポリシロキサン(Parsol(登録商標)SLX)
・グリセリルエチルヘキサノエートジメトキシシンナメート
・ジプロピレングリコールサリチレート
・トリス(2−エチルヘキシル)−4,4’,4’’−(1,3,5−トリアジン−2,4,6−トリイルトリイミノ)トリベンゾエート(=2,4,6−トリアニリノ−(p−カルボ−2’−エチルヘキシル−1’−オキシ)−1,3,5−トリアジン)(Uvinul(登録商標)T150)。
・2−エチルヘキシル−2−シアノ−3,3−ジフェニルアクリレート(Neo Heliopan(登録商標)303)
・エチル−2−シアノ−3,3’−ジフェニルアクリレート
・2−ヒドロキシ−4−メトキシベンゾフェノン(Neo Heliopan(登録商標)BB)
・2−ヒドロキシ−4−メトキシベンゾフェノン−5−スルホン酸
・ジヒドロキシ−4−メトキシベンゾフェノン
・2,4−ジヒドロキシベンゾフェノン
・テトラヒドロキシベンゾフェノン
・2,2’−ジヒドロキシ−4,4’−ジメトキシベンゾフェノン
・2−ヒドロキシ−4−n−オクトキシベンゾフェノン
・2−ヒドロキシ−4−メトキシ−4’−メチルベンゾフェノン
・ヒドロキシメトキシベンゾフェノンスルホン酸ナトリウム
・二ナトリウム−2,2’−ジヒドロキシ−4,4’−ジメトキシ−5,5’−ジスルホベンゾフェノン
・フェノール、2−(2H−ベンゾトリアゾール−2−イル)−4−メチル−6−(2−メチル−3(1,3,3,3−テトラメチル−1−(トリメチルシリル)オキシ)ジシロキシアニル)プロピル)(Mexoryl(登録商標)XL)
・2,2’−メチレンビス−(6−(2H−ベンゾトリアゾール−2−イル)−4−1,1,3,3−テトラメチルブチル)フェノール)(Tinosorb(登録商標)M)
・2,4−ビス−〔4−(2−エチルヘキシルオキシ)−2−ヒドロキシフェニル〕−1,3,5−トリアジン
・2,4−ビス−〔{(4−(2−エチルヘキシルオキシ)−2−ヒドロキシ}フェニル〕−6−(4−メトキシフェニル)−1,3,5−トリアジン(Tinosorb(登録商標)S)
・2,4−ビス−〔{(4−(3−スルホナト)−2−ヒドロキシプロピルオキシ)−2−ヒドロキシ}フェニル〕−6−(4−メトキシフェニル)−1,3,5−トリアジンナトリウム塩
・2,4−ビス−〔{(3−(2−プロピルオキシ)−2−ヒドロキシプロピルオキシ)−2−ヒドロキシ}フェニル〕−6−(4−メトキシフェニル)−1,3,5−トリアジン
・2,4−ビス−〔{4−(2−エチルヘキシルオキシ)−2−ヒドロキシ}フェニル〕−6−〔4−(2−メトキシエチルカルボニル)フェニルアミノ〕−1,3,5−トリアジン
・2,4−ビス−〔{4−(3−(2−プロピルオキシ)−2−ヒドロキシプロピルオキシ)−2−ヒドロキシ}フェニル〕−6−〔4−(2−エチルカルボキシ)フェニルアミノ〕−1,3,5−トリアジン
・2,4−ビス−〔{4−(2−エチルヘキシルオキシ)−2−ヒドロキシ}フェニル〕−6−(1−メチルピロール−2−イル)−1,3,5−トリアジン
・2,4−ビス−[{4−トリス−(トリメチルシロキシシリルプロピルオキシ)−2−ヒドロキシ}フェニル]−6−(4−メトキシフェニル)−1,3,5−トリアジン
・2,4−ビス−[{4−(2’’−メチルプロペニルオキシ)−2−ヒドロキシ}フェニル]−6−(4−メトキシフェニル)−1,3,5−トリアジン
・2,4−ビス−〔{4−(1’,1’,1’,3’,5’,5’,5’−ヘプタメチルシロキシ−2’’−メチルプロピルオキシ)−2−ヒドロキシ}フェニル]−6−(4−メトキシフェニル)−1,3,5−トリアジン。
・4−イソプロピルジベンゾイルメタン
・テレフタリリデンジボルナンスルホン酸および塩(Mexoryl(登録商標)SX)
・4−t−ブチル−4’−メトキシジベンゾイルメタン(アボベンゾン)/(Neo Heliopan(登録商標)357)
・フェニレンビスベンズイミダジルテトラスルホン酸二ナトリウム塩(Neo Heliopan(登録商標)AP)
・2,2’−(1,4−フェニレン)−ビス−(1H−ベンゾイミダゾール−4,6−ジスルホン酸)、一ナトリウム塩
・2−(4−ジエチルアミノ−2−ヒドロキシベンゾイル)安息香酸ヘキシルエステル(Uvinul(登録商標) A Plus)
・独国特許出願公開第100 55 940 A1号明細書(=国際公開第2002/038537 A1号パンフレット)によるインダニリデン化合物。
・p−アミノ安息香酸
・3−(4’−トリメチルアンモニウム)ベンジリデンボルナン−2−オンメチルスルフェート
・サリチル酸ホモメンチルエステル(Neo Heliopan(登録商標)HMS)
・2−ヒドロキシ−4−メトキシベンゾフェノン(Neo Heliopan(登録商標)BB)
・2−フェニルベンズイミダゾールスルホン酸(Neo Heliopan(登録商標)Hydro)
・テレフタリリデンジボルナンスルホン酸および塩(Mexoryl(登録商標)SX)
・4−tert−ブチル−4’−メトキシジベンゾイルメタン(Neo Heliopan(登録商標)357)
・3−(4’−スルホ)ベンジリデンボルナン−2−オンおよび塩
・2−エチルヘキシル−2−シアノ−3,3−ジフェニルアクリレート(Neo Heliopan(登録商標)303)
・N−[(2および4)−[2−(オキソボルン(oxoborn)−3−イリデン)メチル]ベンジル]アクリルアミドポリマー
・p−メトキシ桂皮酸−2−エチルヘキシルエステル(Neo Heliopan(登録商標)AV)
・エトキシル化したp−アミノ安息香酸エチルエステル(25モル)(INCI名:PEG−25PABA)
・p−メトキシ桂皮酸イソアミルエステル(Neo Heliopan(登録商標)E1000)
・2,4,6−トリアニリノ−(p−カルボ−2’−エチルヘキシル−1’−オキシ)−1,3,5−トリアジン(Uvinul(登録商標)T150)
・フェノール、2−(2H−ベンゾトリアゾール−2−イル)−4−メチル−6−(2−メチル−3(1,3,3,3−テトラメチル−1−(トリメチルシリル)オキシ)ジシロキシアニル)プロピル)(Mexoryl(登録商標)XL)
・4,4’−[(6−[4−(1,1−ジメチル)アミノカルボニル)フェニルアミノ]−1,3,5−トリアジン−2,4−ジイル)ジイミノ]−ビス−(安息香酸−2−エチルヘキシルエステル)(Uvasorb HEB)
・3−(4’−メチルベンジリデン)−D,L−カンファー(Neo Heliopan(登録商標)MBC)
・3−ベンジリデンカンファー
・サリチル酸−2−エチルヘキシルエステル(Neo Heliopan(登録商標)OS)
・4−ジメチルアミノ安息香酸−2−エチルヘキシルエステル(Padimate O)
・ヒドロキシ−4−メトキシベンゾフェノン−5−スルホン酸およびNa塩
・2,2’−メチレンビス−(6−(2H−ベンゾトリアゾール−2−イル)−4−1,1,3,3−テトラメチルブチル)フェノール)(Tinosorb(登録商標)M)
・フェニレンビスベンズイミダジルテトラスルホン酸二ナトリウム塩(Neo Heliopan(登録商標)AP)
・2,4−ビス−[{4−(2−エチルヘキシルオキシ)−2−ヒドロキシ}フェニル]−6−(4−メトキシフェニル)−1,3,5−トリアジン(Tinosorb(登録商標)S)
・ベンジリデンマロネートポリシロキサン(Parsol(登録商標)SLX)
・アントラニル酸メンチル(Neo Heliopan(登録商標)MA)
・2−(4−ジエチルアミノ−2−ヒドロキシベンゾイル)安息香酸ヘキシルエステル(Uvinul(登録商標) A Plus)
・独国特許出願公開第100 55 940号明細書(=国際公開第2002/038537号パンフレット)によるインダニリデン化合物。
・剥離促進による直接の落屑作用、例えばβ‐ヒドロキシ酸、特にサリチル酸およびその誘導体(5−n−オクタノイルサリチル酸を含む);α−ヒドロキシ酸、例えばグリコール酸、クエン酸、乳酸、酒石酸、リンゴ酸またはマンデル酸;尿素;ゲンチシン酸;オリゴフコース;桂皮酸;ソフォラ ジャポニカ(エンジュ)の抽出物;レスベラトロールおよびジャスモン酸の所定の誘導体による作用;
・またはコルネオデスモソーム、グリコシダーゼ、角質層キモトリプシン酵素(SCCE)またはその他のプロテアーゼ(トリプシン様、キモトリプシン様)の落屑または分解に関係する酵素による作用のいずれか。無機塩キレート剤には以下のものが挙げられ得る:EDTA;N−アシル−N,N’,N’−エチレンジアミン三酢酸;アミノスルホン化合物および特に(N−2−ヒドロキシエチルピペラジン−N−2−エタン)スルホン酸(HEPES);2−オキソチアゾリジン−4−カルボン酸(プロシステイン)の誘導体;グリシン型のアルファ−アミノ酸の誘導体(欧州特許出願公開第0 852 949号明細書に記載されるような、および商標名TRILON MとしてBASF社より市販されているメチルグリシンジアセタートナトリウム);蜂蜜;糖誘導体、例えばO−オクタノイル−6−D−マルトースおよびN−アセチルグルコサミン;クリ抽出物、例えばSILAB社よりRecoverine(登録商標)という商品名で市販されているもの、ウチワサボテン抽出物、例えばSILAB社よりExfolactive(登録商標)という商品名で市販されているもの、またはDegussa社よりPhytosphingosine SLC(登録商標)(サリチル酸を付加したフィトスフィンゴシン)という商品名で市販されているもの。
(i)コルチコステロイド型のステロイド系抗炎症物質、特にヒドロコルチゾン、ヒドロコルチゾン誘導体、例えばヒドロコルチゾン17−ブチレート、デキサメタゾン、リン酸デキサメタゾン、メチルプレドニゾロンまたはコルチゾン;
(ii)非ステロイド系抗炎症物質、特にオキシカム、例えばピロキシカムまたはテノキシカム、サリチレート、例えばアスピリン、ジスラシッド、ソルプリンまたはフェンドサル、酢酸誘導体、例えばジクロフェナク、フェンクロフェナック、インドメタシン、スリンダク、トルメチンまたはクリンダナック、フェナメート、例えばメフェナム、メクロフェナム、フルフェナムまたはニフルム、プロピオン酸誘導体、例えばイブプロフェン、ナプロキセンまたはベノキサプロフェン、ピラゾール、例えばフェニルブタゾン、オキシフェニルブタゾン、フェブラゾンまたはアザプロパゾン;
(iii)天然のまたは天然に存在する抗炎症物質または発赤および/または痒みを軽減する物質、特にカモミール、アロエベラ、コミフォラ種、ルビア種、ヤナギ、アカバナ、オートムギ、キンセンカ、アルニカ、セイヨウオトギリソウ、スイカズラ、ローズマリー、パッシフロラ インカルナタ(チャボトケイソウ)、マンサク、ショウガまたはエキナシアからの抽出物または画分、またはそれらの単一活性化合物、
(iv)ヒスタミン受容体アンタゴニスト、セリンプロテアーゼ阻害剤(例えばダイズ抽出物のセリンプロテアーゼ阻害剤)、TRPV1アンタゴニスト(例えば4−t−ブチルシクロヘキサノール)、NK1アンタゴニスト(例えば、アプレピタント、ヒドロキシフェニルプロパミド安息香酸)、カンナビノイド受容体アゴニスト(例えばパルミトイルエタノールアミン)およびTRPV3アンタゴニスト。
メントール、メントングリセロールアセタール、メントングリセリルケタール、乳酸メンチル、好ましくはl−メンチルラクテート、特にl−メンチルl−乳酸)、メンチルエチルオキサメート、置換メンチル−3−カルボン酸アミド(例えばメンチル−3−カルボン酸N−エチルアミド、Na−(L−メンタンカルボニル)グリシンエチルエステル、2−イソプロピル−N−2,3−トリメチルブタンアミド、置換シクロヘキサンカルボン酸アミド、3−メントキシプロパン−1,2−ジオール、2−ヒドロキシエチルメンチルカーボネート、2−ヒドロキシプロピルメンチルカーボネート、N−アセチルグリシンメンチルエステル、イソプレゴール、メンチルヒドロキシカルボン酸エステル(例えば3−ヒドロキシ酪酸メンチル)、コハク酸モノメンチル、グルタル酸モノメンチル、2−メルカプトシクロデカノン、メンチル2−ピロリジン−5−オンカルボキシレート、2,3−ジヒドロキシ−p−メンタン、3,3,5−トリメチルシクロヘキサノングリセロールケタール、3−メンチル3,6−ジ−およびトリオキサアルカノアート、3−メンチルメトキシアセテートおよびイシリン。
・グリセロール;
・アルキレングリコール、例えばエチレングリコール、ジエチレングリコール、プロピレングリコール、ブチレングリコール、ヘキシレングリコールおよびポリエチレングリコール(100〜1000ダルトンの平均分子量を有する)など;
・1.5〜10の自己縮合度を有する工業用オリゴグリセロール混合物、例えば40〜50重量%のジグリセロール含量を有する工業用ジグリセロール混合物など;
・メチロール化合物、例えば、特に、トリメチロールエタン、トリメチロールプロパン、トリメチロールブタン、ペンタエリスリトールおよびジペンタエリスリトール;
・低級アルキルグルコシド、特にアルキル基中に1〜8個の炭素原子を含むもの、例えばメチルおよびブチルグルコシド;
・5〜12個の炭素原子を含む糖アルコール、例えばソルビトールまたはマンニトール;
・5〜12個の炭素原子を含む糖、例えばグルコースまたはスクロース;
・アミノ糖、例えばグルカミン;
・ジアルコールアミン、例えばジエタノールアミンまたは2−アミノプロパン−1,3−ジオール。
前記組成物は、通常の増粘剤および付着防止組成物ならびに粘度調整剤、例えば、ポリアクリレート、ポリカルボン酸、多糖類およびそれらの誘導体、ポリウレタン、ポリビニルピロリドン、ヒマシ油誘導体、第四級化および/またはエトキシル化ヘキサメチレンジアミンなどのポリアミン誘導体、ならびにそれらの任意の混合物も含むことができる。好ましい組成物はBrookfield粘度計を用いて、20℃の温度で、50min−1の剪断速度で測定した場合に、10,000mPa*s未満の粘度を有する。
実施例
実施例1
121.6gの(−)−カルベオール(CAS 99−48−9)、30.8gの(−)−ジヒドロカルベオール(CAS 20549−47−7)および3gの炭酸ナトリウムを、KPGスターラー、滴下漏斗および冷却器を備えた2L容の3つ口フラスコに入れ、150mlのトルエンに溶解した。その後、得られた混合物を加熱還流した。1時間以内に112.2g(1.1mol)の無水酢酸を滴下し、反応を120℃の温度でさらに2時間継続した。エステル化が終了した時点で、生成物を約75〜80℃に冷却し、10mlの水を徐々に滴下した。このようにして得た有機相を50mlの水、50mlの炭酸ナトリウム溶液(5重量%(%b.w.))および塩化ナトリウム溶液(5重量%(%b.w.))の一部で洗浄した。最後に、前記有機相を真空下で除去した(70℃、15mbar)。残った固体は、本質的に[(1R,5R)−5−イソプロペニル−2−メチル−シクロヘキス−2−エン−1−イル]アセテートおよび[(1R,5R)−5−イソプロぺニル−2−メチル−シクロヘキシル]アセテートで構成され、82.5:17.5の重量比であった。
実施例2
以下の混合物A、BおよびCを、以下の表Iに従って成分をブレンドすることにより得た。
Claims (15)
- 香料混合物であって、
(a)少なくとも1つの一般式(I)の化合物
(b)少なくとも1つの一般式(II)の化合物
(c)化合物(I)および(II)とは異なる、少なくとも1つの追加の香料;および
(d)任意に少なくとも1つの溶媒
を含む、前記混合物。 - 成分(b)として、一般式(IIa)の化合物
を含む、請求項1に記載の前記混合物。 - 前記追加の香料(成分c)はテルペン、アルデヒド、ニトリル、エステル、ラクトンおよびそれらの混合物からなる群から選択される、請求項1に記載の前記混合物。
- 前記香料は約100〜約250ダルトンの分子量を示す、請求項3に記載の前記混合物。
- 前記溶媒(成分d)はアルコール、エーテルおよびエステルからなる群から選択される、請求項1に記載の前記混合物。
- 前記混合物は成分(a)および(b)を約1:99から約99:1の重量比で含む、請求項1に記載の前記混合物。
- 前記混合物はさらに少なくとも1つの式(III)の化合物
を含む、請求項1に記載の前記混合物。 - 前記混合物は
(i)約62〜約67重量%(%b.w.)の少なくとも1つの化合物(I)の1R,5R異性体;
(ii)約14〜約18重量%の少なくとも1つの化合物(IIa)の1R,2R,5R異性体;
(iii)約6.0〜約7.0重量%の少なくとも1つの化合物(II)の1S,2R,5S異性体;
(iv)約7.0〜約9.0重量%の少なくとも1つの化合物(III)の1R,5S異性体;
(v)約4.0〜約6.0重量%の少なくとも1つの式(III)の1R,2S,5S異性体;および
(vi)約0.5〜約1.0重量%の少なくとも1つの式(III)の1R,2R,5S異性体
を、前記した量の合計が100重量%であることを条件として、
含む、請求項1に記載の前記混合物。 - 以下のステップを含む化合物(I)、(II)および/または(III)のいずれかを製造する方法:
(A)(−)−カルベオールおよび/または(−)−ジヒドロカルベオールの供給源を準備するステップ;
(B)(−)−カルベオールおよび/または(−)−ジヒドロカルベオールの前記供給源を、一般式(IV)の化合物
と反応させてエステルを形成するステップ。 - (−)−カルベオールおよび(−)−ジヒドロカルベオールの混合物をメチルクロロホルメート、エチルクロロホルメート、無水酢酸または無水プロピオン酸と反応させてエステルを形成し、前記(−)−カルベオールおよび(−)−ジヒドロカルベオールは約1:99から約99:1の重量比で存在し、そのエステル化の間のpH値は約6から約9の間に維持される、請求項9に記載の方法。
- 請求項1に記載の香料混合物を含むかまたはからなる香水組成物。
- 前記組成物は約0.001〜約75重量%(%b.w.)の請求項1に記載の前記混合物を含む、請求項11に記載の前記組成物。
- 請求項1に記載の前記混合物または請求項11に記載の香水組成物を含む化粧品用組成物または家庭用組成物。
- 香料の嗅覚側面を改善しかつ/または不快な嗅覚側面を抑える方法であって、嗅覚サポートを必要とする香料を準備するステップと、少なくとも1つの式(I)の化合物および少なくとも1つの式(II)の化合物を前記香料に適用するステップを含む、方法。
- 香料の嗅覚側面を改善しかつ/または不快な嗅覚側面を抑えるための、請求項1に記載の前記混合物の使用。
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WO2017146182A2 (en) * | 2016-02-24 | 2017-08-31 | Takasago International Corporation | Household product delivering warming and/or tingling sensations |
CH712470A2 (de) * | 2016-05-18 | 2017-11-30 | Apomedica Sagl | Erzeugnis zum Therapieren und Vorbeugen von Burnout-Syndromen der Kopfhaut und der Haut. |
JP7463110B2 (ja) * | 2017-06-29 | 2024-04-08 | ユニヴァーシティ オブ ワシントン | N-オキシド及びエクトインモノマー、ポリマー、それらの組成物及び関連方法 |
CN108384673B (zh) * | 2018-05-08 | 2020-06-09 | 杭州妙洁日化科技有限公司 | 环保洗衣液 |
CN108410596B (zh) * | 2018-05-08 | 2020-04-07 | 福州秘庄日化有限公司 | 多功能洗衣液及其制备工艺 |
CN109371094A (zh) * | 2018-12-19 | 2019-02-22 | 湖南杰萃生物技术有限公司 | 一种从橄榄叶中提取脱氢山楂酸的方法 |
CN109337884B9 (zh) * | 2018-12-21 | 2021-10-29 | 中国农业科学院北京畜牧兽医研究所 | 一种丙酮酸激酶基因及其应用 |
US20210022462A1 (en) | 2019-07-15 | 2021-01-28 | Paul Ashley | Compositions for temporarily enhancing the luster and brilliance of jewelry and gem stones and methods for making and using same |
CN112625018A (zh) * | 2020-12-10 | 2021-04-09 | 河南中烟工业有限责任公司 | 2,3-二氢-3-羟基-6-甲基-4h-吡喃-4-酮-5-o-碳酸芳樟醇酯及应用 |
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