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[ CAS No. 1257-08-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1257-08-5
Chemical Structure| 1257-08-5
Structure of 1257-08-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1257-08-5 ]

CAS No. :1257-08-5 MDL No. :MFCD00075936
Formula : C22H18O10 Boiling Point : -
Linear Structure Formula :- InChI Key :LSHVYAFMTMFKBA-TZIWHRDSSA-N
M.W : 442.37 Pubchem ID :107905
Synonyms :
ECG;(-)-Epicatechin 3-O-gallate;Epicatechin-3-O-gallate.;Epicatechin 3-gallate;(−)-Epicatechin-3-O-gallate;(−)-Epicatechin 3-gallate;(−)-ECG;Epicatechin gallate

Calculated chemistry of [ 1257-08-5 ]

Physicochemical Properties

Num. heavy atoms : 32
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.14
Num. rotatable bonds : 4
Num. H-bond acceptors : 10.0
Num. H-bond donors : 7.0
Molar Refractivity : 110.04
TPSA : 177.14 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : 2.2
Log Po/w (MLOGP) : 0.05
Log Po/w (SILICOS-IT) : 1.04
Consensus Log Po/w : 1.32

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.7
Solubility : 0.0885 mg/ml ; 0.0002 mol/l
Class : Soluble
Log S (Ali) : -4.86
Solubility : 0.00612 mg/ml ; 0.0000138 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.09
Solubility : 0.36 mg/ml ; 0.000815 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.16

Safety of [ 1257-08-5 ]

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 [ 1257-08-5 ]

* 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 [ 1257-08-5 ]

[ 1257-08-5 ] Synthesis Path-Downstream   1~34

  • 1
  • [ 485-80-3 ]
  • [ 863-03-6 ]
  • [ 108907-44-4 ]
  • 3
  • [ 18162-48-6 ]
  • [ 863-03-6 ]
  • [ 853687-37-3 ]
YieldReaction ConditionsOperation in experiment
91% With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20℃; Example 1A (-)-ECG-7TBSTBS; To a solution of <strong>[863-03-6](-)-epicatechin gallate</strong> 1 (2.0g, 4.4mmol), in DMF(10ml_) at 0C was added imidazole (3.0g, 0.044mol) followed by tert-butyldimethylsilyl chloride (6.6g, 0.044mol) and the mixture was allowed towarm to room temperature overnight. On completion of reaction the mixturewas diluted with water (20mL). The product was then partitioned betweenether (2x 20mL) and water (20ml_). The organics were then combined, driedwith MgS04, filtered and concentrated in vacua to yield a colourless oil whichwas purified by flash chromatography (eluting with 5% Et20: Pet Ether) togive the product 2 as a colourless oil, 5.0g, 91%; 6H (400MHz, CDCI3) 0.08-0.21 (m, 42H, 7x OSi(CH3)2C(CH3)3), 0.90- 0.98 (m, 63H, 7xOSi(CH3)2C(CH3)3), 2.97 (d, 2H, J3.1, ArCH2CHCHO), 5.05 (s, 1H,ArCH2CHCHO), 5.56 (m, 1H, ArCH2CHCHO), 5.96 (d, 1H, J2.3, ArH), 6.18(d, 1H, J 2.3, ArH), 6.74 (d, 1H, J 8.7, ArH), 6.89 (d, 1H, J 2.1, ArH) 6.95 (dd,1H, J8.3, 2.1, ArH), 7.09 (s, 2H, 2x ArH); 5C (100MHz, CDCI3)-4.4, -4.3, -4.2-4.1, -3.9, -3.7, 18.1, 18.2, 18.3, 18.4, 18.8, 25.7, 25.8, 25.9, 26.1, 26.7,68.0, 76.7, 101.7, 103.7, 103.9, 115.3, 119.3, 119.7, 120.8, 121.7, 131.1,142.9, 146.6, 148.2, 154.7, 154.9, 155.6, 165.0; MS (m/z) No mass ionobserved; [a]D -57.9 (c 1.0, CHCI3, at 25C).
  • 4
  • [ 863-03-6 ]
  • (-)-(2R,3R,4R)-3,4,5,7,3',4'-hexahydroxyflavan [ No CAS ]
  • [ 490-46-0 ]
  • 5
  • [ 149-91-7 ]
  • [ 863-03-6 ]
  • theaflavate A [ No CAS ]
  • [ 34218-97-8 ]
  • [ 5146-12-3 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide;herseradish peroxidase; In acetone; for 0.75h;pH 5.0;Phosphate citrate buffer; Enzymatic reaction; ECG (0.5 g) and gallic acid (1 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1 :10, v/v, 50 mL), which contained 2 mg horseradish peroxidase. While being stirred, 2.0 mL of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 mL×3). After concentration, the residue was subjected to Sephadex LH 20 column eluted with acetone-water solvent system (45%). 20 mg epitheaflavic acid 3-gallate, 40 theaflavate A and 10 mg purpurogallin carboxylic acid were obtained. [0112] 1H NMR (CD3OD, 600 MHz): deltaH 8.64 1H s, 7.84 1H s, 7.83 1H s, 6.83 2H s, 6.02 1H d, J=2.4 Hz, 5.98 1H d, J=2.4, 5.61 1H s, 4.37 1H, m, 3.03 1H dd, J=4.8, 16.8 Hz, 2.87 d, J=16.8 Hz; 13C NMR (CD3OD, 150 MHz): deltaC 186.5, 170.1, 167.1, 158.0, 156.9, 155.1, 151.7, 148.9, 146.2, 139.8, 132.8, 131.6, 126.8, 122.6, 122.5, 120.8, 116.3, 110.0, 99.3, 96.9, 96.0, 75.7, 68.6, 27.2 ppm.
  • 6
  • [ 863-03-6 ]
  • [ 2596-50-1 ]
  • [ 30462-35-2 ]
YieldReaction ConditionsOperation in experiment
10% With polyphenol oxidase; In aq. phosphate buffer; for 2.0h;pH 6.0;Enzymatic reaction; Ina typical experiment, EC (290 mg) and EGC (306 mg) were added to a mixture of acetone and phosphate buffer (pH 6.0) (1:10 v/v,100 ml), C. sinensis cell culture (50 ml including 10.2 g cells), and 3% H2O2 (0.8 ml). The mixture was stirred for 4 min and thenextracted using CH3COOEt. Further, the organic layer was driedover anhydrous MgSO4 and concentrated in vacuo to provide TF(395 mg) with 70% yield and 100% conversion. In the HPLC analysis,12 peaks for EC and ECG were virtually absent, but a peak for TF was observed.
With dihydrogen peroxide;herseradish peroxidase; In acetone; for 0.75h;pH 5.0;Phosphate citrate buffer; Enzymatic reaction; ECG (1 g) and EGCG (1 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1:10, v/v, 50 mL), which contained 4 mg horseradish peroxidase. While being stirred, 2.0 ml of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 ml×3). After concentration, the residue was subjected to Sephadex LH 20 column eluted with acetone-water solvent system (45%). 100 mg theaflavin 3,3'-digallate was obtained. [0088] 1H NMR (CD3OD, 600 MHz): deltaH 7.79 1H s, 7.76 1H s, 7.47 1H s, 6.88 2H s, 6.80 2H s, 6.07 1H d, J=2.4 Hz, 6.03 2H d, J=2.4 Hz, 6.00 1H d, J=2.4 Hz, 5.86 1H brs, 5.76 1H m, 5.67 1H m, 5.21 1H s, 3.17 1H dd, J=4.8, 16.8 Hz, 3.09 1H dd, J=4.8, 17.4, 2.91 2H m.
polyphenol oxidase; at 20℃; for 6.0h;pH 5.0;Phosphate-citrate buffer; Enzymatic reaction; EC (1 g, 3.5 mmol) and EGC (1 g, 3.3 mmol) were dissolved into the 200 mL of phosphate-citrate buffer (50 mM, pH 5.0) along with 2 g of crude PPO enzyme. The enzymatic oxidation was carried out at room temperature for 6 hour with stirring. The reaction solution was then subjected to fractionation with the same volume of ethyl acetate with three times. Then, the organic layer was concentrated under reduced pressure. The resulting residues were subjected to Sephadex LH-20 column chromatography eluting with gradient of ethanol to 20% of acetone in ethanol. Among the collected 14 fractions (each c.a. 90 mL), 810 fractions were combined, and concentrated under reduced pressure. The resulting residue was subjected to further purification on a RP-18 silica gel column eluting with gradient of 40%50% of aqueous methanol. During elution, 38 fractions (each c.a. 13 mL) were received. Among them, 1017 fractions were combined, and concentrated under reduced pressure, and were subjected to freeze-drying. It yielded deep-reddish color of compound 1 (280 mg). Along with the same enzyme reaction and isolation procedure, compound 2 was obtained from EC and EGCG reaction. The enzymatic oxidation of EGC and ECG, ECG and EGCG reaction yielded compound 3 and compound 4, respectively.
With tyrosinase from mushroom Agaricus bisporus; In aq. phosphate buffer; ethanol; at 25℃; for 0.5h;pH 6.0;Enzymatic reaction;Kinetics; General procedure: Unless otherwise specified, enzymatic reactions were performed using tyrosinase at 0.05mg/mL (156mU/mL) with each catechin and 0.1mg/mL (313 mU/mL) for TF synthesis in 50mM Na-phosphate buffer, pH 6.0, at 25C without pH control. Respective catechin solutions (10mM) were prepared using 20% ethanol/40mM Na-phosphate buffer, pH 6.0. After certain incubation periods, an aliquot (100muL) of the reaction mixture was collected and added into 1mL of 25mM citric acid solution (pH 2.4) to stop the reaction. These samples were cooled in an autosampler (L-2200, Hitachi, Tokyo) at 5-8C and analyzed by RP-HPLC, which was carried out using a Hitachi HPLC system (L-2130 pump, L-2400 UV detector) equipped with a SUS line filter (GL Science, Tokyo, Japan) and a Phenomenex SynergiTM 4mum Polar-RP 80 (4.6mm×150mm) column (Shimadzu GLC, Tokyo, Japan). Catechins were eluted using an aqueous 20% MeCN solution containing 0.05% phosphoric acid at flow rate of 1mL/min, and detected at 280nm. For TF1, TF2A, TF2B, and TF3, aqueous 32% MeCN solutions containing 0.05% phosphoric acid were used as eluents, and each retention time (tR) was identified using the TF standards, which were obtained as described previously [31]. The analysis of chromatograms was performed with the data processing software Chromato-PRO (Run Time Corporation, Tokyo, Japan).

  • 7
  • [ 863-03-6 ]
  • [ 490-46-0 ]
  • theaflavate B [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide;herseradish peroxidase; In acetone; for 0.75h;pH 5.0;Phosphate citrate buffer; Enzymatic reaction; EC (0.5 g) and ECG (0.5 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1:10, v/v, 50 mL), which contained 2 mg horseradish peroxidase. While being stirred, 2.0 mL of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 mL×3). After concentration, the residue was subjected to Sephadex LH 20 column eluted with acetone-water solvent system (45%). 200 mg theaflavate B was obtained. [0100] 1H NMR (CD3OD, 600 MHz): deltaH 8.26 1H s, 7.88 1H s, 7.59 1H s, 6.87 1H dd, J=1.8, 7.8 Hz, 6.86 1H d, J=1.8 Hz, 6.55 1H d, J=7.8 Hz, 6.16 1H d, J=2.4 Hz, 6.08 1H d, J=2.4, 6.05 1H d, J=2.4 Hz, 5.98 1H, d, J=2.4 Hz, 5.66 1H brs, 5.46 1H brs, 5.08 1H s, 4.14 1H brs, 3.34 dd, J=4.8, 16.8 Hz, 3.21 dd, J=4.8, 16.8 Hz, 3.17 dd, J=3.6, 16.2 Hz, 2.88 d, J=16.8; 13C NMR (CD3OD, 150 MHz): deltaC 186.4, 167.8, 158.3, 158.0, 157.9, 157.7, 157.4, 157.1, 154.9, 151.8, 149.5, 146.3, 146.0, 134.8, 132.3, 131.3, 126.5, 124.4, 123.7, 122.4, 119.2, 116.3, 115.8, 114.4, 100.7, 99.5, 97.2, 97.1, 96.6, 96.5, 78.1, 77.0, 72.1, 66.7, 30.0, 26.7 ppm.
  • 8
  • [ 863-03-6 ]
  • [ 154-23-4 ]
  • neotheaflavate B [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide;herseradish peroxidase; In acetone; for 0.75h;pH 5.0;Phosphate citrate buffer; Enzymatic reaction; C (0.5 g) and ECG (0.5 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1:10, v/v, 50 mL), which contained 2 mg horseradish peroxidase. While being stirred, 2.0 ml of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 ml×3). After concentration, the residue was subjected to Sephadex LH 20 column eluted with acetone-water solvent system (45%). 90 mg neotheaflavate B was obtained. [0103] 1H NMR (CD3OD, 600 MHz): deltaH 8.77 1H s, 7.64 1H s, 7.61 1H s, 6.88 1H d, J=1.8 Hz, 6.82 1H dd, J=1.8, 8.4 Hz, 6.64 1H d, J=8.4 Hz, 6.03 1H d, J=2.4 Hz, 5.98 1H d, J=2.4, 5.96 2H brs, 5.58 1H brs, 5.38 1H brd, J=7.2 Hz, 5.04 1H s, 4.07 1H m, 3.03 dd, J=4.8, 16.8 Hz, 2.95 brd, J=16.8, 2.91 dd, J=4.8, 16.8 Hz, 2.66 dd, J=3.6, 16.2 Hz; 13C NMR (CD3OD, 150 MHz): deltaC 186.6, 167.7, 157.9, 157.7, 157.3, 157.0, 156.8, 154.7, 152.3, 149.8, 146.0, 145.8, 135.0, 134.3, 131.2, 128.8, 124.0, 122.5, 119.0, 116.2, 115.8, 114.4, 101.2, 99.2, 97.0, 96.8, 96.1, 95.9, 79.7, 78.0, 72.0, 69.6, 29.6, 26.6 ppm.
  • 9
  • [ 863-03-6 ]
  • [ 970-73-0 ]
  • [ 28543-07-9 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide;herseradish peroxidase; In acetone; for 0.75h;pH 5.0;Phosphate citrate buffer; Enzymatic reaction; ECG (1 g) and EGC (1 g) were dissolved in a mixture of acetone-pH 5.0 phosphate citrate buffer (1:10, v/v, 50 mL), which contained 4 mg horseradish peroxidase. While being stirred, 2.0 ml of 3.13% H2O2 was added four times during 45 minutes. The reaction mixture was extracted by ethyl acetate (50 ml×3). After concentration, the residue was subjected to Sephadex LH 20 column eluted with acetone-water solvent system (45%). 110 mg theaflavin 3'-gallate was obtained. [0085] 1H NMR (CD3OD, 600 MHz): deltaH 7.88 1H s, 7.87 1H s, 7.37 1H s, 6.84 2H s, 6.06 d, J=2.4 Hz, 6.00 1H d, J=2.4 Hz, 5.98 1H d, J=2.4 Hz, 5.97 d, J=2.4 Hz, 5.87 brs, 5.81 1H brd J=3.0 Hz, 4.94 1H brs, 4.33 1H brs, 3.09 1H dd, J=4.8, 17.4 Hz, 2.96 1H dd, J=4.8, 16.8, 2.88 1H brd, J=17.4 Hz, 2.86 dd, J=2.4, 16.8 Hz; 13C NMR (CD3OD, 150 MHz): deltaC 185.6, 167.2, 158.0, 157.9, 157.8, 157.7, 157.0, 156.6, 156.0, 155.5, 151.1, 146.2, 139.7, 134.8, 130.3, 128.8, 125.9, 123.0, 121.9, 120.9, 118.3, 99.8, 99.6, 96.8, 96.7, 95.8, 95.7, 81.2, 75.8, 68.3, 66.5, 29.3, 27.2 ppm.
With tyrosinase from mushroom Agaricus bisporus; In aq. phosphate buffer; ethanol; at 25℃; for 0.5h;pH 6;Enzymatic reaction;Kinetics; General procedure: Unless otherwise specified, enzymatic reactions were performed using tyrosinase at 0.05mg/mL (156mU/mL) with each catechin and 0.1mg/mL (313 mU/mL) for TF synthesis in 50mM Na-phosphate buffer, pH 6.0, at 25C without pH control. Respective catechin solutions (10mM) were prepared using 20% ethanol/40mM Na-phosphate buffer, pH 6.0. After certain incubation periods, an aliquot (100muL) of the reaction mixture was collected and added into 1mL of 25mM citric acid solution (pH 2.4) to stop the reaction. These samples were cooled in an autosampler (L-2200, Hitachi, Tokyo) at 5-8C and analyzed by RP-HPLC, which was carried out using a Hitachi HPLC system (L-2130 pump, L-2400 UV detector) equipped with a SUS line filter (GL Science, Tokyo, Japan) and a Phenomenex SynergiTM 4mum Polar-RP 80 (4.6mm×150mm) column (Shimadzu GLC, Tokyo, Japan). Catechins were eluted using an aqueous 20% MeCN solution containing 0.05% phosphoric acid at flow rate of 1mL/min, and detected at 280nm. For TF1, TF2A, TF2B, and TF3, aqueous 32% MeCN solutions containing 0.05% phosphoric acid were used as eluents, and each retention time (tR) was identified using the TF standards, which were obtained as described previously [31]. The analysis of chromatograms was performed with the data processing software Chromato-PRO (Run Time Corporation, Tokyo, Japan).
  • 10
  • [ 863-03-6 ]
  • theaflavate A [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide;herseradish peroxidase; for 0.5h;pH 5.0;Enzymatic reaction; ECG (0.85 g) was dissolved in pH 5 buffer (1:10, v/v, 50 mL), which contained 2 mg horseradish peroxidase. While being stirred, 1.5 mL of 3.13% H2O2 was added three times during 30 minutes. The reaction mixture was extracted by ethyl acetate (50 mL×3). After concentration, the residue was subjected to Sephadex LH 20 column eluted with acetone-water solvent system (45%). 60 mg theaflavate A was obtained and 600 mg ECG was recovered. [0097] 1 H NMR (CD3OD, 600 MHz): deltaH 8.33 1H s, 7.81 1H s, 7.65 1H s, 6.87 1H dd, J=1.8, 7.8 Hz, 6.85 1H d, J=1.8 Hz, 6.80 2H, s,6.53 1H d, J=7.8 Hz, 6.15 1H d, J=2.4 Hz, 6.11 1H d, J=2.4, 6.09 1H d, J=2.4 Hz, 5.98 1H, d, J=2.4 Hz, 5.69 1H brs, 5.64 1H brs, 5.52 1H, brd, J=3.6Hz, 5.11 1H s,3.32 dd, J=4.8, 18.0Hz, 3.10 dd, J=4.8, 18.0Hz, 3.05 dd, J=1.8, 16.8 Hz, 2.91 d, J=16.8; 13C NMR (CD3OD, 150 MHz): deltaC 186.8, 167.8, 167.3, 158.2, 158.1, 158.0, 157.9, 157.2, 157.1, 155.3, 149.5, 146.4, 146.3, 146.0, 140.0, 133.5, 131.2, 126.6, 124.8, 122.9, 122.6, 121.0, 119.0, 116.4, 115.8, 114.2, 110.2, 100.0, 99.4, 97.3, 97.2, 96.5, 96.4, 78.0, 75.6, 72.1, 68.9, 27.3, 26.7 ppm.
  • 11
  • [ 63604-98-8 ]
  • [ 863-03-6 ]
  • 12
  • [ 1486-48-2 ]
  • [ 863-03-6 ]
  • 13
  • [ 1486-47-1 ]
  • [ 863-03-6 ]
  • 14
  • [ 20728-73-8 ]
  • [ 863-03-6 ]
  • 15
  • [ 87292-49-7 ]
  • [ 863-03-6 ]
  • 16
  • [ 87292-54-4 ]
  • [ 863-03-6 ]
  • 17
  • [ 732298-08-7 ]
  • [ 863-03-6 ]
  • 18
  • [ 732298-11-2 ]
  • [ 863-03-6 ]
  • 19
  • [ 918157-97-8 ]
  • [ 863-03-6 ]
  • 20
  • [ 918158-03-9 ]
  • [ 863-03-6 ]
  • 21
  • [ 149-91-7 ]
  • [ 863-03-6 ]
  • [ 34218-97-8 ]
YieldReaction ConditionsOperation in experiment
polyphenol oxidase; at 20℃; for 5.0h;pH 5.0;Phosphate-citrate buffer; Enzymatic reaction; EC (1.160 g, 4.0 mmole) and gallic acid (0.520 g, 4.0 mmole) were dissolved in the 100 mL of phosphate-citrate buffer (50 mM, pH 5.0), and 1.2 g of crude PPO enzyme was added into the reaction solution with stirring. The enzymatic oxidation was carried out at room temperature for 3.5 hour. After the reaction, the solution extracted with the same volume of ethyl acetate with three times. Then, the ethyl acetate extracts was concentrated in vacuo. The resulting residues were then subjected to Sephadex LH-20, eluting with gradient of ethanol to 20% of acetone in ethanol. Among the collected 168 (each c.a. 15 mL) fractions, 4752 fractions were combined, and it was concentrated under reduced pressure. The resulting residue was applied on a RP-18 silica gel column eluting with gradient of 20%50% of aqueous methanol, and it was afforded compound 5. Then, 7285 fractions, isolated from Sephadex LH-20, were combined, and it was subjected to RP-18 column chromatography eluting with gradient of 10%50% of aqueous methanol, and compound 6 was isolated. [0137] ECG (0.66 g) and gallic acid (0.26 g) were dissolved in the 50 mL of phosphate-citrate buffer (50 mM, pH 5.0), and 1.2 g of crude PPO enzyme was dissolved in the reaction solution. The enzymatic oxidation was performed at room temperature for 5 hour. The reaction solution was then extracted with ethyl acetate with three times. Then, the organic layer was concentrated under reduced pressure. The resulting residues were subjected to Sephadex LH-20 column chromatography eluting with gradient of ethanol to 20% of acetone in ethanol. Among the collected 128 fractions (each c.a. 15 mL), 1820 fractions were combined, and concentrated under reduced pressure. The resulting residue was subjected for further purification on a RP-18 silica gel column eluting with gradient of 20%50% of aqueous methanol, and afforded compound 7. The 3748 fractions were combined and subjected to RP-18 column chromatography for further purification eluting with gradient of 10%30% of aqueous methanol, and afforded compound 8. The 90108 fractions were combined and subjected to RP-18 column chromatography eluting with gradient of 40%50% of aqueous methanol, and it was then afforded compound 9.
  • 22
  • [ 863-03-6 ]
  • [ 970-73-0 ]
  • [ 30462-34-1 ]
YieldReaction ConditionsOperation in experiment
polyphenol oxidase; at 20℃; for 6h;pH 5;Phosphate-citrate buffer; Enzymatic reaction; EC (1 g, 3.5 mmol) and EGC (1 g, 3.3 mmol) were dissolved into the 200 mL of phosphate-citrate buffer (50 mM, pH 5.0) along with 2 g of crude PPO enzyme. The enzymatic oxidation was carried out at room temperature for 6 hour with stirring. The reaction solution was then subjected to fractionation with the same volume of ethyl acetate with three times. Then, the organic layer was concentrated under reduced pressure. The resulting residues were subjected to Sephadex LH-20 column chromatography eluting with gradient of ethanol to 20% of acetone in ethanol. Among the collected 14 fractions (each c.a. 90 mL), 810 fractions were combined, and concentrated under reduced pressure. The resulting residue was subjected to further purification on a RP-18 silica gel column eluting with gradient of 40%50% of aqueous methanol. During elution, 38 fractions (each c.a. 13 mL) were received. Among them, 1017 fractions were combined, and concentrated under reduced pressure, and were subjected to freeze-drying. It yielded deep-reddish color of compound 1 (280 mg). Along with the same enzyme reaction and isolation procedure, compound 2 was obtained from EC and EGCG reaction. The enzymatic oxidation of EGC and ECG, ECG and EGCG reaction yielded compound 3 and compound 4, respectively.
  • 23
  • [ 863-03-6 ]
  • theaflavate A [ No CAS ]
  • [ 1013313-02-4 ]
  • [ 1013313-04-6 ]
  • 25
  • [ 863-03-6 ]
  • [ 87-66-1 ]
  • [ 1256244-33-3 ]
  • [ 1256244-36-6 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide; acetic acid;horseradish peroxidase; In water; acetone; at 30℃; for 1.0h;Enzymatic reaction; EXAMPLE 7; (1) Preparations of CompoundsSyntheses of Compounds 12 and 14 (theaflavanin 3-O-gallate) with Peroxidase; Used were horseradish peroxidase from Zymed Laboratories, Inc. as a peroxidase, epicatechin 3-O-gallate (ECG) of 90% purity or higher, which was purified by reversed-phase HPLC from tea extract, and pyrogallol from Nacalai Tesque, Inc. (99.0% purity).(2) ReactionsIn 10 ml of a 0.058 M acetic acid buffer, 4.3 mg of the horseradish peroxidase was dissolved, and to this solution, 250 mg of ECG (0.566 mmol) dissolved in 500 mul of acetone and 192.8 mg of pyrogallol (1.53 mmol) dissolved in 500 mul of acetone were added followed by stirring. Under 30 C. condition, 450 mul of a 3% (w/v) hydrogen peroxide solution was added to initiate a reaction. For improvement of reaction efficiency, 450 mul of a 3% (w/v) hydrogen peroxide solution was added twice, i.e., after 10 and 20 minutes of the reaction initiation. Added were 192.8 mg of pyrogallol (1.53 mmol) and 450 mul of a 3% hydrogen peroxide solution after 30 minutes of the reaction initiation, and then reacted for another 30 minutes.After 60 minutes of the reaction initiation, the reaction solution was loaded on a reversed-phase stationary phase (Waters Corp., Sep-Pak, C18-Vac 20 cc (5 g)) followed by washing with 40 ml of distilled water. Consecutive elutions were then performed with 20 ml of a 20% (v/v) aqueous acetonitrile solution and then with 40 ml of a 70% (v/v) aqueous acetonitrile solution. The 70% acetonitrile eluate was concentrated and lyophilized to obtain 68.0 mg of a fraction containing Compounds 12 and 14 (theaflavanin 3-O-gallate).The mixture containing Compounds 12 and 14 (theaflavanin 3-O-gallate) was purified by HPLC under the conditions below.The mixture was loaded on YMC-Pak Polymer C-18 (20×300 mm, YMC Co., Ltd.), and in the presence of 0.1% formic acid, a 30-minute isocratic elution with 30% acetonitrile and then an elution with a linear gradient of 30-45% acetonitrile (6 ml/min, 150 minutes) were performed. The component eluted at between 144 and 148 minutes and that eluted at between 158 and 162 minutes were lyophilized to obtain 3.9 mg of the compound identical to Compound 12 shown in Example 2 and 3.0 mg of Compound 14 (theaflavanin 3-O-gallate). Further, the component eluted at between 108 and 113 minutes in this chromatogram was lyophilized to obtain 36 mg of a brown solid (Compound 1 in Example 2: purprogallin).
  • 26
  • [ 863-03-6 ]
  • iodoEGCG [ No CAS ]
  • 27
  • [ 863-03-6 ]
  • (131)I-EGCG [ No CAS ]
  • 29
  • [ 863-03-6 ]
  • [ 2596-50-1 ]
  • [ 28543-07-9 ]
YieldReaction ConditionsOperation in experiment
14% With dihydrogen peroxide; horseradish peroxidase; In aq. phosphate buffer; acetone; for 2.0h;pH 6.0;Enzymatic reaction; Ina typical experiment, EC (290 mg) and EGC (306 mg) were added to a mixture of acetone and phosphate buffer (pH 6.0) (1:10 v/v,100 ml), C. sinensis cell culture (50 ml including 10.2 g cells), and 3% H2O2 (0.8 ml). The mixture was stirred for 4 min and thenextracted using CH3COOEt. Further, the organic layer was driedover anhydrous MgSO4 and concentrated in vacuo to provide TF(395 mg) with 70% yield and 100% conversion. In the HPLC analysis,12 peaks for EC and ECG were virtually absent, but a peak for TF was observed.
  • 30
  • [ 143-07-7 ]
  • [ 863-03-6 ]
  • 3',3'',5''-tri-O-lauroyl epicatechin gallate [ No CAS ]
  • 31
  • [ 27200-12-0 ]
  • [ 863-03-6 ]
  • C36H26O17 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tea polyphenol oxidase; In aq. phosphate buffer; at 30℃; for 0.75h;pH 3.5;Enzymatic reaction; Weigh 75g of dihydromyricetin and epicatechin gallate, respectively.Dissolved in 15L of citrate-dibasic phosphate buffer at pH 3.5,Add a certain amount of tea polyphenol oxidase (addition amount is 2g/L),The ventilation was 30L/min and the reaction was carried out at 30 C for 45 minutes.Reheating quickly raises the temperature to 100 C to inactivate the polyphenol oxidase for 5 minutes.Stop the reaction. The obtained reaction liquid was subjected to column chromatography on a polyamide resin.The column torus diameter ratio is 1:8, the ratio of sample to column volume is 1:5, and the loading rate is 2BV/h.Elution with water, 5% aqueous ethanol solution, 95% aqueous ethanol solution,The 95% ethanol eluting site was collected, concentrated and dried under reduced pressure at 40 C to obtain a crude extract.Further separation and purification using BUCHI medium pressure preparation, column chromatography specifications:15mm*310mm, packing C18, flow rate 3mL/min,The crude extract was dissolved in 25% aqueous ethanol (concentration of 80 mg/mL)As a sample solution, the elution gradient was eluted with 15%-25% aqueous ethanol solution for 3 h.25% ethanol aqueous solution was eluted for 2 h, 25%-60% ethanol aqueous solution was eluted for 3 h,The solution was eluted with 60%-95% aqueous ethanol for 2 h, and a 25% ethanol water elution solution was collected.Concentrate under reduced pressure at 45 C to an alcohol-free taste, and freeze-dry to give Compound 2 (HPLC purity ? 98%).
  • 32
  • C25H24O10S [ No CAS ]
  • [ 863-03-6 ]
  • [ 79907-44-1 ]
  • 33
  • [ 1257-08-5 ]
  • [ 490-83-5 ]
  • [ 1643155-71-8 ]
  • [ 1643155-75-2 ]
YieldReaction ConditionsOperation in experiment
In aq. phosphate buffer at 4 - 37℃; for 9h; 4.2.3. Formation of Ascorbyl Adducts of Four Catechins General procedure: The citric acid-phosphate buer was prepared as described above. EGCG, EGC, ECG, and EC weredissolved in 10 mL of a citric acid-phosphate buer and stored at 4 °C in a refrigerator, determining theconcentration by UPLC. In total, 1200 mg of DHAA was dissolved in 20 mL of a citric acid-phosphatebuer, and 5 mL of DHAA solution was incubated with EGCG, EGC, ECG, or EC in buer solution.Four incubation systems were prepared; the total volume was 150 mL. The concentration of DHAA was2000 μg/mL. The concentrations of EGCG, EGG, ECG, and EC were 458 μg/mL, 442 μg/mL, 306 μg/mL,and 290 μg/mL, respectively. The concentrations of four catechins were all 1 mmol/L. The beaker wasincubated at 37 °C in a water bath kettle for 60, 120, 180, 240, 300, 360, 420, 480, and 540 min. The beaker was covered with film, preventing water loss, after which 2 mL of the reaction mixture was taken andthen filtered through a 0.22-μm filter for UPLC detection.
  • 34
  • [ 1257-08-5 ]
  • [ 480-18-2 ]
  • [ 89064-33-5 ]
YieldReaction ConditionsOperation in experiment
96 mg Stage #1: taxifolin With sodium tetrahydroborate; ethanol at 20℃; for 0.75h; Stage #2: (-)-epicatechin gallate With hydrogenchloride In water for 1h; 1 C-ECG and C-C-ECG: 350 mg (1.15 mmol) of (+)-taxifolin was dissolved in 20 ml of ethanol, 70 mg of NaBH4 was added, and the resulting mixture was stirred at room temperature for 45 minutes. In the resulting solution, 420 mg (0.95 mmol) of (-)-epicatechin-3-O-gallate (ECG) (manufactured by FUJIFILM Wako Pure Chemical Corporation) was dissolved, 40 ml of HCl (0.1 N) was then added, and the resulting mixture was stirred for 1 hour. The reaction product was purified by reverse-phase HPLC to give 96 mg of C-ECG and 34 mg of C-C-ECG.
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