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[ CAS No. 497-76-7 ] {[proInfo.proName]}

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Chemical Structure| 497-76-7
Chemical Structure| 497-76-7
Structure of 497-76-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 497-76-7 ]

CAS No. :497-76-7 MDL No. :MFCD00016915
Formula : C12H16O7 Boiling Point : -
Linear Structure Formula :- InChI Key :BJRNKVDFDLYUGJ-RMPHRYRLSA-N
M.W : 272.25 Pubchem ID :440936
Synonyms :
β-Arbutin;NSC 4036;Uvasol;Ursin;HSDB 7661;CCRIS 9273;BRN 0089673;Arbutyne;Arbutoside

Safety of [ 497-76-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 497-76-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 497-76-7 ]

[ 497-76-7 ] Synthesis Path-Downstream   1~85

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  • (E)-(R)-6-Hydroxy-2,6-dimethyl-octa-2,7-dienoic acid (2R,3R,4S,5R,6S)-3,4,5-triacetoxy-6-(4-acetoxy-phenoxy)-tetrahydro-pyran-2-ylmethyl ester [ No CAS ]
  • [ 83945-54-4 ]
  • [ 497-76-7 ]
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  • [ 144-48-9 ]
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  • [ 89790-23-8 ]
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  • [ 108-24-7 ]
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  • [ 100-52-7 ]
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  • [ 19896-00-5 ]
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  • [ 2644-64-6 ]
  • [ 497-76-7 ]
  • 1,2-dipalmitoyl-3-sn-phosphatidylarbutin [ No CAS ]
  • dipalmitoylphosphatidylglycerol [ No CAS ]
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  • [ 123-31-9 ]
  • [ 2816-24-2 ]
  • [ 497-76-7 ]
  • 15
  • [ 17719-70-9 ]
  • [ 497-76-7 ]
  • 6'-(2,5-dihydroxycinnamoyl)arbutin [ No CAS ]
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  • [ 76-83-5 ]
  • [ 497-76-7 ]
  • [ 180297-88-5 ]
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  • [ 50-99-7 ]
  • [ 123-31-9 ]
  • emulsin [ No CAS ]
  • [ 497-76-7 ]
  • 21
  • [ 497-76-7 ]
  • 3,4,5-trioxo-6-(4-oxo-cyclohexa-2,5-dienyloxy)-tetrahydro-pyran-2-carbaldehyde [ No CAS ]
  • 22
  • [ 5299-57-0 ]
  • [ 497-76-7 ]
  • 6-O-ω-undecylenoyl p-hydroxyphenyl β-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With water;Bacillus subtilis-derived protease; In DMF (N,N-dimethyl-formamide); at 30℃; for 168h;Product distribution / selectivity; Bacillus subtilis-derived protease (0.5 g, manufactured by Nagase ChemteX Corp.) was added to 72.6 ml of a dimethylformamide solution containing 6.8 g of <strong>[497-76-7]arbutin</strong>, 21 g of 10-undecylenic acid vinyl ester and 3.8 g of water, followed by stirring at 30C and 130 rpm for 1 week. The conversion ratio was 80%. TLC analysis of the product revealed that substantially only a monoester was formed. The enzymatic reaction mixture was filtered to remove the enzyme powder, and the filtrate was concentrated under reduced pressure to remove DMF. The concentrate was added to a column packed with 100 g of silica gel, and eluted with chloroform: methanol (8:1). The product was collected and concentrated to give crystals of 6-0-(10-undecylenoyl)<strong>[497-76-7]arbutin</strong>. The yield was 62%. 13C-NMR: delta 101.6 (C1), 76.4 (C2), 73.2 (C3), 70.1 (C4), 73.7 (C5), 63.4 (C6), 115.5, 117.7, 150.2 152.4 (phenol), 172.8 (C=O), 114.6, 138.9 (CH=CH2), 24.4, 28.3, 28.5, 28.7, 33.2, 33.6 (CH2) Anal. Calc'd for C23H34O8 (438) : C, 63.01; H, 7.76, Found: C, 63.16; H, 7.75.
10% 4-pyrrolidin-1-ylpyridine; In DMF (N,N-dimethyl-formamide); at 80℃; for 24h;Product distribution / selectivity; One gram of 4-pyrrolidinopyridine (manufactured by Wako Pure Chemical Ind. Ltd.) was added to 76.2 ml of a DMF solution containing 6.8 g of <strong>[497-76-7]arbutin</strong> and 21 g of 10-undecylenic acid vinyl ester, followed by stirring at 80C and 130 rpm for 24 hours. TLC analysis of the product revealed that mono-, di-, tri- and polyesters were produced. The reaction mixture was concentrated under reduced pressure to remove DMF, added to a column packed with 100 g of silica gel, and eluted with chloroform:methanol (8:1). The produced monoester was collected and concentrated to give crystals of 6-O-(10-undecylenoyl) <strong>[497-76-7]arbutin</strong>. The yield was 10%.13C-NMR: delta 101.6 (C1), 76.4 (C2), 73.2 (C3), 70.1 (C4), 73.7 (C5), 63.4 (C6), 115.5, 117.7, 150.2 152.4 (phenol), 172.8 (C=O), 114.6, 138.9 (CH=CH2), 24.4, 28.3, 28.5, 28.7, 33.2, 33.6 (CH2) Anal. Calcd for C23H34O8 (438) : C, 63.01; H, 7.76, Found: C, 63.06; H, 7.81.
  • 23
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  • C24H30O14 [ No CAS ]
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  • [ 50-00-0 ]
  • [ 110-70-3 ]
  • [ 497-76-7 ]
  • [ 944046-28-0 ]
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  • [ 57-50-1 ]
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  • Phosphorous acid benzyl ester (R)-4-benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-oxo-2,5-dihydro-furan-3-yl ester (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-(4-benzyloxy-phenoxy)-tetrahydro-pyran-2-ylmethyl ester [ No CAS ]
  • 36
  • [ 497-76-7 ]
  • [ 180297-91-0 ]
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  • [ 497-76-7 ]
  • [ 74522-87-5 ]
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  • [ 2444-19-1 ]
  • [ 497-76-7 ]
  • 43
  • [ 5238-38-0 ]
  • [ 497-76-7 ]
  • [ 681212-47-5 ]
YieldReaction ConditionsOperation in experiment
21% dmap; In DMF (N,N-dimethyl-formamide); at 80℃; for 3h;Product distribution / selectivity; <strong>[497-76-7]Arbutin</strong> (0.3 g) and vinyl adipate (1 g) were dissolved in 4 ml of DMF, and 10 mg of dimethylaminopyridine was added thereto, followed by stirring at 80C for 3 hours. TLC analysis of the product revealed that mono-, di-, tri- and tetraesters were produced. The reaction mixture was concentrated under reduced pressure to remove DMF, added to a column packed with 100 g of silica gel, and eluted with chloroform:methanol (8:1). The monoester was collected and concentrated to give crystals of 6-O-(vinyladipoyl)<strong>[497-76-7]arbutin</strong>. The yield was 21%.
  • 44
  • [ 112-38-9 ]
  • [ 497-76-7 ]
  • 6-O-ω-undecylenoyl p-hydroxyphenyl β-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% Candida antarctica-derived lipase; In 1,4-dioxane; dimethyl sulfoxide; at 40℃; for 168h;Molecular sieve;Product distribution / selectivity; <strong>[497-76-7]Arbutin</strong> (327 mg) and 10-undecylenic acid (885 mg) were dissolved in 4.0 ml of a 1,4-dioxane/DMSO (=9:1) mixed solvent in an Erlenmeyer flask. After adding 0.4 g of activated molecular sieves 4A, 40 mg of immobilized Candida antarctica-derived lipase (manufactured by Novozymes) was added, followed by stirring at 40C and 130 rpm for 1 week. The molecular sieve had been activated by a simple process using a microwave oven. Specifically, molecular sieves 4A placed in a flask had been heated in a microwave oven for 1 minute, and immediately thereafter, allowed to cool to room temperature under reduced pressure using a vacuum pump; this process was conducted three times. TLC analysis of the enzymatic reaction product revealed that only a monoester was produced. The enzymatic reaction mixture was filtered to remove the enzyme and molecular sieves, and then the filtrate was concentrated under reduced pressure. Methanol (4 ml) and water (2.5 ml) were added to the concentrate, and hexane (5 ml) was further added to extract unreacted undecylenic acid into the hexane layer. Such hexane extraction was carried out 6 times, and the aqueous layer was concentrated using an evaporator. After adding 8 mL of water to the concentrate to form a white precipitate, the supernatant liquid was removed by centrifugation. Such aqueous extraction was performed 3 times to remove DMSO and unreacted <strong>[497-76-7]arbutin</strong>. The white precipitate was collected and dried under reduced pressure, to give 287 mg of powder. TLC analysis of the purified product using 100% ethyl acetate confirmed that unreacted 10-undecylenic acid had been removed and that a single ester compound had been produced. The purified product was subjected to NMR analysis to thereby find that the it was the same compound as the ester obtained in Example 1-1, i.e., 6-O-(10-undecylenoyl) <strong>[497-76-7]arbutin</strong>. The yield of the ester was 91%. The process used in this Example does not involve purification with a silica gel column, and thus easy and simple.
Candida antarctica-derived lipase; In 1,4-dioxane; at 40℃; for 168h;Molecular sieve;Product distribution / selectivity; <strong>[497-76-7]Arbutin</strong> (33 mg) and 10-undecylenic acid (89 mg) were dissolved in 4.0 ml of 1,4-dioxane in an Erlenmeyer flask. After adding 0 to 15 wt.% of activated molecular sieves 4A, 40 mg of immobilized Candida anterctica-derived lipase (manufactured by Novozymes) was added, followed by stirring at 40C and 130 rpm for 1 week. The molecular sieve had been activated by the same method as in Example 1-5. The change over time in <strong>[497-76-7]arbutin</strong> conversion ratio was determined by HPLC analysis. The conditions for the HPLC analysis were as follows: Device; Shimazu LC-10, Column; TSK gel Amide-80, Mobile phase solvent; acetonitrile/water (=90:10), Flow rate; 1.0 ml, Detection; differential refraction. Fig. 1 shows the results. The addition of molecular sieves, which act as a dehydrating agent, remarkably improved the <strong>[497-76-7]arbutin</strong> conversion ratio (reaction ratio). The higher the concentration of molecular sieves, the higher the conversion ratio.
  • 45
  • [ 4074-90-2 ]
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  • [ 681212-47-5 ]
YieldReaction ConditionsOperation in experiment
85% Streptomyces sp.-derived alkaline protease; In pyridine; at 30℃; for 96h;Product distribution / selectivity; <strong>[497-76-7]Arbutin</strong> (2.8 g) and divinyl adipate (9.5 g) were dissolved in 40.5 ml of pyridine, and 5 g of Streptomyces sp.-derived alkaline protease (manufactured by Toyobo Co., Ltd.) was added, followed by stirring at 30C and 130 rpm for 4 days. TLC analysis of the product revealed that only a monoester was produced. The enzymatic reaction mixture was filtered to remove the enzyme powder, and the filtrate was concentrated under reduced pressure to remove pyridine. The concentrate was added to a column packed with 100 g of silica gel, and eluted with hexane: acetic acid ethyl ester (4:1). The product was collected and concentrated to give crystals of 6-O-(vinyladipoyl) <strong>[497-76-7]arbutin</strong>. The isolation yield was 85%. H-NMR: delta 1.556 (4H,m,-CH2CH2-), 2.320(2H,m,-COCH2-), 2.430 (2H, t, -CH2CO-), 3.12-3.29 (3H, m, H-2,3,4), 3.508 (1H, m, H-5), 4.070 (1H, q, H-6), 4.310 (1H, dd, H-6), 4.640 (1H, dd, =CH2), 4.675 (1H, d, H-1), 4.900 (1H, dd, =CH2), 5.11-5.32 (3H, m, OH-2,3,4), 6.66 (2H, m, phi), 6.83 (2H, m, phi), 7.21(1H, q, -CH=)
YieldReaction ConditionsOperation in experiment
Hydroquinone and derivatives thereof Extract of placenta Arbutin phloretin phloridzin
Kojic acid, and derivatives thereof Hydroquinone Extract of placenta Arbutin Niacin Niacinamide, and
Compounds having the structure (2) Arbutin Niacin Niacinamide, and
  • 47
  • [ 106-89-8 ]
  • [ 497-76-7 ]
  • [ 54230-69-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In ethanol; a. 27.2 g (0.1 mol) of <strong>[497-76-7]hydroquinone-beta-D-glucopyranoside</strong> and 250 ml of epichlorohydrin are dissolved in 1 liter of ethanol, 6.9 g (0.05 mol) of potassium carbonate are added and the mixture is heated for 6 hours under reflux. The precipitate which separates out is filtered off. The filtrate is concentrated in a waterpump vacuum. The residue is dissolved in ethanol whilst hot, and the solution is filtered. The filtrate is cooled and ether is added until the mixture begins to turn cloudy. The reaction product which hereupon precipitates in a crystalline form is filtered off and washed with ether. This gives 4-(2,3-epoxy-propoxy)-phenyl-beta-D-glucopyranoside as a diastereomer mixture, melting point 154-156C, [alpha]D20 = - 52.4 in methanol.
  • 48
  • 1-O-benzyl-2S-anhydro-D-glycerol [ No CAS ]
  • [ 497-76-7 ]
  • [ 57506-12-4 ]
YieldReaction ConditionsOperation in experiment
In sodium hydroxide; water; acetonitrile; c. A solution of 100 g of 4-hydroxyphenyl-beta-D-glucopyranoside and 60.5 g of 1-O-benzyl-2S-anhydro-D-glycerol in 366 ml of 0.1 N sodium hydroxide solution and 740 ml of acetonitrile is boiled under reflux in a nitrogen atmosphere for 50 hours. The solvent is then distilled off in a waterpump vacuum and the residue is taken up in 1 liter of water. The product which has crystallized out is filtered off, recrystallized from 1 liter of water and dried, whereupon 4-(3-benzyloxy-2S-hydroxy-propoxy)-phenyl-beta-D-glucopyranoside is obtained, melting point 146-147C; Rf value 0.45 on silica gel thin layer plates in the system methylene chloride-methanol, 3:1; [alpha]D20 = - 34 +- 1 (methanol, c = 1.027).
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  • [ 75-36-5 ]
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  • [ 221688-06-8 ]
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  • [ 1277161-49-5 ]
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  • [ 1186473-08-4 ]
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  • [ 1277161-39-3 ]
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  • [ 934767-95-0 ]
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  • [ 769-78-8 ]
  • [ 497-76-7 ]
  • [ 71202-99-8 ]
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  • [ 17719-70-9 ]
  • [ 497-76-7 ]
  • [ 221688-07-9 ]
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  • [ 18120-64-4 ]
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  • [ 1277161-53-1 ]
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  • [ 10604-64-5 ]
  • [ 497-76-7 ]
  • [ 1277161-71-3 ]
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  • [ 54519-07-2 ]
  • [ 497-76-7 ]
  • [ 1277161-57-5 ]
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  • [ 95063-02-8 ]
  • [ 497-76-7 ]
  • [ 1277161-61-1 ]
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  • [ 497-76-7 ]
  • [ 50-99-7 ]
  • [ 123-31-9 ]
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  • [ 56401-20-8 ]
  • [ 123-31-9 ]
  • [ 497-76-7 ]
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  • [ 59-56-3 ]
  • [ 497-76-7 ]
  • 1-O-β-D-cellotriopyranosyl hydroquinone [ No CAS ]
  • [ 7013-26-5 ]
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  • [ 123-31-9 ]
  • [ 59-56-3 ]
  • [ 497-76-7 ]
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  • [ 50-00-0 ]
  • [ 617-89-0 ]
  • [ 497-76-7 ]
  • A-Fa [ No CAS ]
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  • [ 1240244-47-6 ]
  • [ 497-76-7 ]
  • [ 63555-01-1 ]
YieldReaction ConditionsOperation in experiment
75% With Lipozyme TL IM; In tert-butyl alcohol; at 40℃; for 288h;Molecular sieve; Enzymatic reaction; General procedure: The preparative reaction was performed in 10 mL DURAN flasks with a sealing lid on a vibrating shaker set up to 300 rpm in thermostat at constant temperature 40 C. The reaction mixture comprised 1 mmol of either methyl beta-D-glucopyranoside (194 mg) or <strong>[497-76-7]arbutin</strong> (272 mg) or salidroside (300 mg) together with 1.5 mmol (309 mg) of vinyl caffeate, 0.4 g of activated molecular sieves 4A and 0.4 g of Lipozyme TL IM in 5 mL of tert-butanol. After the conversion became constant (monitored by HPLC), which means 17, 12 and 16 days for caffeoylation of 1, 5 and 6, respectively, the reaction mixture was filtered and solid parts including the enzyme were washed with acetonitrile. Activated charcoal was added and the suspension was briefly boiled. The mixture was filtered again and solvents were removed by evaporation. The residue was purified by chromatography on the column of silica-gel eluted with ethyl acetate. Fractions comprising the pure product were collected and the solvent was removed by evaporation. The honey-like residues was precipitated from toluene and separated by filtration under argon.
  • 66
  • [ 492-62-6 ]
  • [ 497-76-7 ]
  • 67
  • pentaacetate arbutin [ No CAS ]
  • [ 497-76-7 ]
YieldReaction ConditionsOperation in experiment
95.2% With methanol; sodium methylate; at 50℃; for 2h;Large scale; 3) sodium methoxide 1.8 kg,Methanol 193kg to 2000L reactor,80 kg of beta-pentaacetyl arbutin was put into a reaction kettle,Reaction at 50 C for 2 h,In 45 ~ 50 / -0.080Mpa vacuum distillation,When the methanol is distilled off,Add 36kg of water,Plus sodium sulfite and activated carbon for decolorization treatment 1h,filter,The filtrate was adjusted to pH = 6.5, 5 ~ 10 and crystallized for 12 h. The filtrate was dried for 5 h, and the yield of beta-arbutin was 94.2%.4) beta-arbutin crude 25kg into the 500L reactor,After washing with petroleum ether and drying,Adding 133 kg of ethanol,162kg of water,Ethanol / water ratio of 9:11, plus sodium sulfite and activated carbon,80 ~ 85 insulation 3h for decolorization,filter,Filtrate adjusted PH = 6.5,5 ~ 10 recrystallization 12h, centrifugal filtration, filter cake drying 12h, was finished beta-arbutin, yield 95.2%Mother liquor into the ethanol recovery tank, in 60 / -0.050Mpa vacuum distillation of ethanol recovery.
  • 68
  • [ 1125-88-8 ]
  • [ 497-76-7 ]
  • [ 19896-00-5 ]
YieldReaction ConditionsOperation in experiment
84% With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 70℃; for 14h; To a stirred solution of <strong>[497-76-7]arbutin</strong> (10 mmol, 2.7 g) in DMF (10 mL) was added benzaldehyde dimethyl acetal (12 mmol, 1.8 mL) and a catalytic amount of p-TsOH at room temperature. The reaction is heated up to 70 C and stirred for 14 h. H2O (30 mL) was then added, the white precipitate was filtrated and dried under vacuum to afford the title product as a white solid (3.0, 84 % yield). MP: 247-248 C Rf: 0.6 (50% Acetone/hexane), [alpha]21D -40.3 (c 0.60, acetone); MP: 247.1-248.5 C; IR (ATR) 3336, 1509, 1376, 1215, 1081, 1016, 748, 695 cm-1; 1H NMR (500 MHz, (CD3)2CO) delta 8.15 (s, 1H), 7.64-7.46 (m, 2H), 7.47-7.33 (m, 3H), 7.09-6.90 (m, 2H), 6.92-6.68 (m, 2H), 5.67 (s, 1H), 5.00 (d, J = 7.7 Hz, 1H), 4.80 (d, J = 4.3 Hz, 1H), 4.70 (d, J = 3.9 Hz, 1H), 4.32 (dd, J = 10.3, 4.7 Hz, 1H), 3.99-3.71 (m, 2H), 3.71-3.54 (m, 3H).13C NMR (125 MHz, (CD3)2CO) delta 153.3, 151.4, 138.7, 129.1, 128.4, 126.9, 118.7, 116.0, 103.2, 101.8, 81.4, 75.3, 74.0, 68.8, 66.8. HRMS (ESI) m/z:[M+Na]+ cacld for C19H20O7383.1101; Found 383.1191.
  • 69
  • [ 497-76-7 ]
  • C42H52O7Si [ No CAS ]
  • 70
  • [ 497-76-7 ]
  • C39H48O7Si [ No CAS ]
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  • [ 497-76-7 ]
  • C46H52O8Si [ No CAS ]
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  • [ 497-76-7 ]
  • C40H38O8 [ No CAS ]
  • 73
  • [ 497-76-7 ]
  • C25H26O10 [ No CAS ]
  • 74
  • [ 497-76-7 ]
  • C25H28O10 [ No CAS ]
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  • [ 497-76-7 ]
  • C22H24O7 [ No CAS ]
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  • [ 497-76-7 ]
  • C26H26O7 [ No CAS ]
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  • [ 497-76-7 ]
  • C40H34O9 [ No CAS ]
  • 78
  • [ 497-76-7 ]
  • C40H36O9 [ No CAS ]
  • 79
  • [ 497-76-7 ]
  • C21H34O7Si [ No CAS ]
  • 80
  • C21H22O10 [ No CAS ]
  • [ 22805-46-5 ]
  • [ 497-76-7 ]
  • 81
  • [ 497-76-7 ]
  • [ 492-61-5 ]
  • [ 123-31-9 ]
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  • [ 50-99-7 ]
  • [ 71-43-2 ]
  • [ 123-31-9 ]
  • [ 497-76-7 ]
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  • [ 123-31-9 ]
  • [ 5391-18-4 ]
  • [ 497-76-7 ]
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  • [ 492-61-5 ]
  • [ 497-76-7 ]
  • 85
  • [ 108-05-4 ]
  • [ 497-76-7 ]
  • [ 10338-88-2 ]
YieldReaction ConditionsOperation in experiment
92.5% With CSL lipase; In tetrahydrofuran; at 60℃; for 2.5h;Microwave irradiation; 0.73 mmol of <strong>[497-76-7]arbutin</strong>, 30 mmol of vinyl acetate,100 mg of CSL lipase was added to a reactor containing 20 mL of tetrahydrofuran.400W microwave heating to 60 C, 100r / min stirring reaction,The water activity of the reaction was 0.41, the reaction time was 2.5 h, and the reaction was terminated.The enzyme was filtered through a 0.22 mum microporous membrane, and the solvent was evaporated to dryness.The yield was 92.5%.
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