JP2021091656A - 抗酸化活性を有するヒドロキシチロソールジヒドロカフェアートとその調製方法 - Google Patents
抗酸化活性を有するヒドロキシチロソールジヒドロカフェアートとその調製方法 Download PDFInfo
- Publication number
- JP2021091656A JP2021091656A JP2020155642A JP2020155642A JP2021091656A JP 2021091656 A JP2021091656 A JP 2021091656A JP 2020155642 A JP2020155642 A JP 2020155642A JP 2020155642 A JP2020155642 A JP 2020155642A JP 2021091656 A JP2021091656 A JP 2021091656A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- reaction mixture
- hydroxytyrosol
- crude product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- JUUBCHWRXWPFFH-UHFFFAOYSA-N Hydroxytyrosol Chemical compound OCCC1=CC=C(O)C(O)=C1 JUUBCHWRXWPFFH-UHFFFAOYSA-N 0.000 title abstract description 88
- DZAUWHJDUNRCTF-UHFFFAOYSA-N 3-(3,4-dihydroxyphenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(O)C(O)=C1 DZAUWHJDUNRCTF-UHFFFAOYSA-N 0.000 title abstract description 47
- 229940095066 hydroxytyrosol Drugs 0.000 title abstract description 43
- 235000003248 hydroxytyrosol Nutrition 0.000 title abstract description 43
- 230000003078 antioxidant effect Effects 0.000 title abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 72
- 239000011541 reaction mixture Substances 0.000 claims description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000012043 crude product Substances 0.000 claims description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- -1 1-butyl-3-methylimidazolium tetrafluoroborate Chemical compound 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 12
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 12
- 239000003208 petroleum Substances 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000003480 eluent Substances 0.000 claims description 8
- 239000002608 ionic liquid Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 6
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 claims description 4
- NGHMEZWZOZEZOH-UHFFFAOYSA-N silicic acid;hydrate Chemical compound O.O[Si](O)(O)O NGHMEZWZOZEZOH-UHFFFAOYSA-N 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 abstract description 9
- 238000011160 research Methods 0.000 abstract description 3
- 238000002474 experimental method Methods 0.000 abstract description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical group CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 10
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical class [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 235000006708 antioxidants Nutrition 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 230000001681 protective effect Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003925 fat Substances 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 230000002000 scavenging effect Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000012488 sample solution Substances 0.000 description 3
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 2
- 229930003268 Vitamin C Natural products 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 235000019154 vitamin C Nutrition 0.000 description 2
- 239000011718 vitamin C Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 241000092665 Atractylodes macrocephala Species 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 244000019459 Cynara cardunculus Species 0.000 description 1
- 235000019106 Cynara scolymus Nutrition 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 230000002292 Radical scavenging effect Effects 0.000 description 1
- 241000304195 Salvia miltiorrhiza Species 0.000 description 1
- 235000011135 Salvia miltiorrhiza Nutrition 0.000 description 1
- 238000011481 absorbance measurement Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 235000016520 artichoke thistle Nutrition 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 244000237330 gutta percha tree Species 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002831 nitrogen free-radicals Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000000844 retinal pigment epithelial cell Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/652—Chromium, molybdenum or tungsten
- B01J23/6525—Molybdenum
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0245—Nitrogen containing compounds being derivatives of carboxylic or carbonic acids
- B01J31/0247—Imides, amides or imidates (R-C=NR(OR))
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Emergency Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
本発明は、食品化学分野、特に抗酸化活性を有するヒドロキシチロソールジヒドロカフェアートおよびその製造方法に関する。
3つの主要な栄養素のうちの1つである脂肪は、毎日の食事の必須部分である。油脂の酸化は、油の品質に影響を及ぼす重要な因子である。油脂の自動酸化は活性化されたオレフィン含有基質(例えば、不飽和油)と空気中の酸素との、室温での完全な自然酸化反応であり、いかなる直接照射またはいかなる触媒も必要としない。油の酸化物は油食品の風味および色に影響を及ぼし、食品の品質を低下させるだけでなく、食べる人の健康に影響を及ぼす多くの毒性物質を生成する。油の過酸化物は膜、酵素およびタンパク質を損傷し、多くの老化疾患を引き起こし、癌を引き起こすことさえあり、ヒトの健康を深刻に危険にさらす。油脂の貯蔵寿命を延長するために、油脂への酸化防止剤の添加は、最も有効な手段の1つである。しかしながら、いくつかの一般的に使用されている合成酸化防止剤はいくつかの隠れた危険性を有しており、これらは、いくつかの国の人々によって強く反対され、禁止または制限されている。抗酸化剤の研究は、天然の抗酸化剤の適用に転じ始めた。
本発明のさらなる理解を提供するために含まれ、本明細書に組み込まれ、その一部を構成する添付の図面は本発明の実施形態を示し、説明と共に本発明の原理を説明するのに役立つ。図において、
次に、本発明の実施形態を詳細に参照し、その例を添付の図面に示す。下記の実施例は本発明を説明するが、本発明は下記の実施例に限定されるものではない。
化合物3,4−ジヒドロキシフェネチル3−(3,4−ジヒドロキシフェニル)プロパノアート(ヒドロキシチロソールジヒドロカフェアート、式(I)の化合物)の調製
化合物3,4−ジヒドロキシフェネチル3−(3,4−ジヒドロキシフェニル)プロパノアートの調製
化合物3,4−ジヒドロキシフェネチル3−(3,4−ジヒドロキシフェニル)プロパノアートの調製
化合物3,4−ジヒドロキシフェネチル3−(3,4−ジヒドロキシフェニル)プロパノアートの調製
化合物3,4−ジヒドロキシフェネチル3−(3,4−ジヒドロキシフェニル)プロパノアートの調製
化合物3,4−ジヒドロキシフェネチル3−(3,4−ジヒドロキシフェニル)プロパノアートの調製
化合物3,4−ジヒドロキシフェネチル3−(3,4−ジヒドロキシフェニル)プロパノアートの調製
化合物3,4−ジヒドロキシフェネチル3−(3,4−ジヒドロキシフェニル)プロパノアートの調製
DPPHラジカル消去活性アッセイにより測定したヒドロキシチロソールジヒドロカフェアートの抗酸化活性
2,2−ジフェニル−1−ピクリルヒドラジル(DPPH)の正確な量を測定し、トルエンに溶解して、0.2mmol/LのDPPH溶液を調製し、暗所にて0℃で保存する。
Vc(ビタミンC、陽性対照)、ヒドロキシチロソールジヒドロカフェアート(試料)、ヒドロキシチロソール(対照)およびジヒドロカフェ酸(対照)。試料溶液をトルエンで勾配希釈し、一定量のトルエンで3組の対照を別々に試験管に溶解し、試料と同じ濃度勾配を調製した。対応する3群の対照溶液を得た(勾配設定を表1に示す)。
試料溶液吸光度測定:
試験溶液(表1: Vc、A、B、C)2mLをとり、2×10−4moL/Lの濃度のDPPH溶液2mLを加え、室温で30分間暗所で混合して反応させ、トルエンでゼロに調整し、517nmで測定する。吸光度Aiは、2mLの溶液と混合した2mLのトルエンの吸光度Ajと、2mLのトルエンと混合した2mLのDPPH溶液の吸光度A0とを同時に測定した(実験結果を表2に示す)。
Claims (7)
- 前記式(II)の化合物と前記式(III)の化合物との反応は、下記の工程、
前記式(II)の化合物、触媒、および有機溶媒を窒素雰囲気下で反応容器中に入れる工程であって、前記触媒はEDCである、工程と、
前記式(III)の化合物を前記反応容器に加えて反応混合物を形成する工程、
前記反応混合物を50〜85℃で1〜4時間加熱する工程と、
前記反応混合物を濃縮して粗生成物を得る工程と、
シリカゲルカラムで前記粗生成物を精製し、溶離剤として酢酸エチル/石油エーテルとして用いて溶離し、前記式(I)の化合物を得る工程と、を含む、請求項1に記載の方法。 - 有機溶媒は、トルエン、酢酸エチル、またはアセトニトリルである請求項2に記載の方法。
- 前記式(II)の化合物と前記式(III)の化合物は、1:1.1のモル比を有する請求項2に記載の方法。
- 前記式(II)の化合物と前記式(III)の化合物との反応は、下記の工程、
前記式(II)の化合物、触媒、および、イオン性液体を窒素雰囲気下で反応容器中に入れる工程であって、前記触媒は12−モリブド珪酸水和物(H6Mo12O41Si)である工程と、
前記式(III)の化合物を前記反応容器に加えて反応混合物を形成する工程と、
前記反応混合物を25〜50℃で5〜10時間加熱する工程と、
前記反応混合物を分液漏斗中に入れて粗生成物を分離する工程と、
メタノール中での再結晶により粗生成物を精製し、前記式(I)の化合物を得る工程と、を含む、請求項1に記載の方法。 - 前記イオン性液体は、1−ブチル−3−メチルイミダゾリウムテトラフルオロホウ酸塩([BMIM][BF4])である請求項5に記載の方法。
- 前記式(II)の化合物と前記式(III)の化合物は、1:1.1のモル比を有する請求項5に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201911262276.6 | 2019-12-11 | ||
CN201911262276.6A CN112094191B (zh) | 2019-12-11 | 2019-12-11 | 一种具抗氧化活性的羟基酪醇二氢咖啡酸酯及其合成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2021091656A true JP2021091656A (ja) | 2021-06-17 |
JP6940197B2 JP6940197B2 (ja) | 2021-09-22 |
Family
ID=70461451
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020155642A Active JP6940197B2 (ja) | 2019-12-11 | 2020-09-16 | 抗酸化活性を有するヒドロキシチロソールジヒドロカフェアートとその調製方法 |
Country Status (3)
Country | Link |
---|---|
US (1) | US10640450B1 (ja) |
JP (1) | JP6940197B2 (ja) |
CN (1) | CN112094191B (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023243210A1 (ja) * | 2022-06-13 | 2023-12-21 | 丸善製薬株式会社 | 筋芽細胞増殖促進剤及び筋芽細胞増殖促進用組成物、並びに筋萎縮抑制剤及び筋萎縮抑制用組成物 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114317627A (zh) * | 2021-12-08 | 2022-04-12 | 陕西师范大学 | 一种羟基酪醇油酸酯及其制备方法与它的用途 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2892923B1 (fr) * | 2005-11-08 | 2009-01-16 | Engelhard Lyon Sa | Utilisatiion des derives de l'acide para-coumarique ou para- hydroxycinnamique dans des compositions cosmetiques ou dermatologiques. |
-
2019
- 2019-12-11 CN CN201911262276.6A patent/CN112094191B/zh active Active
- 2019-12-21 US US16/724,206 patent/US10640450B1/en not_active Expired - Fee Related
-
2020
- 2020-09-16 JP JP2020155642A patent/JP6940197B2/ja active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023243210A1 (ja) * | 2022-06-13 | 2023-12-21 | 丸善製薬株式会社 | 筋芽細胞増殖促進剤及び筋芽細胞増殖促進用組成物、並びに筋萎縮抑制剤及び筋萎縮抑制用組成物 |
Also Published As
Publication number | Publication date |
---|---|
JP6940197B2 (ja) | 2021-09-22 |
CN112094191A (zh) | 2020-12-18 |
US10640450B1 (en) | 2020-05-05 |
CN112094191B (zh) | 2023-04-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2375633C (en) | Cranberry seed oil extract and compositions containing components thereof | |
JP6940197B2 (ja) | 抗酸化活性を有するヒドロキシチロソールジヒドロカフェアートとその調製方法 | |
KR20080065218A (ko) | 안트로디아 캄포라타로부터 얻은 신규 시클로헥세논 화합물및 그의 적용 | |
WO2022105726A1 (zh) | 一种具有高效抗氧化功效的含番茄红素颗粒的生产方法 | |
EP4321518A1 (en) | Novel polyphenol compound | |
Tsai et al. | Formation of samin diastereomers by acid-catalyzed transformation of sesamolin with hydrogen peroxide | |
EP1301501B1 (de) | Tocotrienolchinon- zyklisierungsprodukte mit antihypercholesterin wirkung | |
US10377702B1 (en) | Hydroxytyrosol isophorone diisocyannate derivative with antioxidant activity and a method of preparing the same | |
JP6741315B2 (ja) | 酸化防止活性を有するエスクリンリポ酸エステル及びその製造方法 | |
KR100911623B1 (ko) | 비만, 고지혈 또는 당뇨의 예방 또는 치료용 분획물 | |
CN103494806B (zh) | 苯骈α-吡喃酮类化合物的应用及其制备方法 | |
JP6934264B2 (ja) | 抗酸化活性を有するヒドロキシチロソールp−フェニレンジカルボキシレート及びその調製方法 | |
JP6923100B1 (ja) | 新規イソフラボン化合物 | |
KR101198129B1 (ko) | 한인진으로부터 추출한 항염증 조성물 | |
JP6940201B1 (ja) | 抗酸化活性を有するヒドロキシチロソールウルソデオキシコール酸エステルおよびその調製方法 | |
JP7118335B2 (ja) | 肝保護活性を有するシリビニンリポ酸エステルおよびその調製方法 | |
CN106726806B (zh) | 一种从松花粉中提取有效成分的超临界萃取方法 | |
KR100740208B1 (ko) | 미역 포자엽에서 분리한 신규한 항산화 물질과 분리 정제방법 | |
KR101001289B1 (ko) | 알러지 비유발성 우루시올 유도체, 상기 유도체를 유효성분으로 포함하는 항산화제조성물과 지질과산화억제제조성물, 및 우루시올유도체 알러지유발여부 확인방법 | |
KR100955942B1 (ko) | 알러지 비유발성 우루시올 유도체 | |
JP5040016B2 (ja) | 発癌予防剤 | |
KR101514839B1 (ko) | 황목련 유래 신규 네오리그난 및 이를 포함하는 항염증 조성물 | |
CN116425629B (zh) | 白藜芦醇神经酸酯的制备方法 | |
JP6974659B2 (ja) | 肝保護活性を有するシリビニン3,3’−チオジプロピオン酸エステルおよびその調製方法 | |
CN111909007B (zh) | 对羟基苯基丁二醇和其衍生物及其制备方法与应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20210126 |
|
A871 | Explanation of circumstances concerning accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A871 Effective date: 20210507 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20210608 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210630 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20210727 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20210826 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6940197 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |