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[ CAS No. 529-44-2 ] {[proInfo.proName]}

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Chemical Structure| 529-44-2
Chemical Structure| 529-44-2
Structure of 529-44-2 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 529-44-2 ]

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Product Details of [ 529-44-2 ]

CAS No. :529-44-2 MDL No. :MFCD00006827
Formula : C15H10O8 Boiling Point : -
Linear Structure Formula :- InChI Key :IKMDFBPHZNJCSN-UHFFFAOYSA-N
M.W : 318.24 Pubchem ID :5281672
Synonyms :
Cannabiscetin;LDN-0014058;HSDB 7682;NSC 407290
Chemical Name :3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

Calculated chemistry of [ 529-44-2 ]

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 8.0
Num. H-bond donors : 6.0
Molar Refractivity : 80.06
TPSA : 151.59 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.08
Log Po/w (XLOGP3) : 1.18
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : -1.08
Log Po/w (SILICOS-IT) : 1.06
Consensus Log Po/w : 0.79

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.01
Solubility : 0.314 mg/ml ; 0.000988 mol/l
Class : Soluble
Log S (Ali) : -3.96
Solubility : 0.035 mg/ml ; 0.00011 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.66
Solubility : 0.698 mg/ml ; 0.00219 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.27

Safety of [ 529-44-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 529-44-2 ]

* 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 [ 529-44-2 ]

[ 529-44-2 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 64-17-5 ]
  • [ 529-44-2 ]
  • 3-ethoxy-6,8-dibromo-2-(2,6-dibromo-3,4,5-trihydroxy-phenyl)-5,7-dihydroxy-chromen-4-one [ No CAS ]
  • 2
  • [ 529-44-2 ]
  • [ 127-08-2 ]
  • 3,5,7-trihydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one; monopotassium-compound [ No CAS ]
  • 3
  • [ 529-44-2 ]
  • [ 127-09-3 ]
  • [ 14813-29-7 ]
  • 4
  • [ 529-44-2 ]
  • [ 108-24-7 ]
  • 3,7-diacetoxy-5-hydroxy-2-(3,4,5-triacetoxy-phenyl)-chromen-4-one [ No CAS ]
  • 5
  • [ 529-44-2 ]
  • [ 108-24-7 ]
  • [ 14813-29-7 ]
YieldReaction ConditionsOperation in experiment
85% With sodium acetate; at 80℃; for 6h; In a 250mL eggplant-shaped flask compound 3-1 <strong>[529-44-2]myricetin</strong> (5g, 15.7mmol), sodium acetate (10.3g, 125mmol), acetic anhydride (32g, 314mmol) were added and refluxed for 6h at 80 C. After stopping the reaction, water was added 100mL, ultrasound, suction filtered, the filter cake was recrystallized from ethyl acetate to the system, to give the compound as a white solid 7.65 g, yield 85% shown in Figure 3-6, the data confirmed the structure of compound 3-1 see FIG. 2 and FIG.
61% With pyridine; at 15℃; for 16h; To a solution of <strong>[529-44-2]3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one</strong> (1 g) in pyridine (10 mL) was added acetyl acetate (15.26 g), then the mixture was stirred at 15C for 16 h. The solvent wasremoved and the mixture was poured into ice water under stirring. The solid was filtered, washed with water and dried in vacuum to give [3,5-diacetoxy-4-oxo-2-(3,4,5-triacetoxyphenyl)chromen-7-yl] acetate (1.1 g, 61% yield) as a gray solid. LCMS 571.1 (M÷Hj 1H NMR (400 MHz, CDCI3): O 7.260 (s, 2H), 7.349 (d, 1 H), 6.886 (d, 1 H), 2.441 (s, 3H), 2.372 (s, 3H), 2.353 (s, 3H), 2.341 (s, 3H), 2.333 (s, 6H) ppm
61% With pyridine; at 15℃; for 16h; To a solution of <strong>[529-44-2]3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one</strong> (1 g) in pyridine (10 ml_) was added acetyl acetate (15.26 g), then the mixture was stirred at 15C for 16 h. The solvent was removed and the mixture was poured into ice water under stirring. The solid was filtered, washed with water and dried in vacuum to give compound 11 (1 .1 g, 61 % yield) as a gray solid. LCMS 571 .1 (M+H+) 1H NMR (400 MHz, CDC ) 7.260 (s, 2H), 7.349 (d, 1H), 6.886 (d, 1H), 2.441 (S,3H), 2.372 (S,3H), 2.353 (S,3H), 2.341 (S,3H), 2.333 (s, 6H)
61% With pyridine; at 15℃; for 12h; To a solution of <strong>[529-44-2]3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one</strong> (1 g) in pyridine (1 0 mL) was added acetyl acetate (15.26 g), then the mixture was stirred at 15C for 16 h. The solvent was removed and the mixture was poured into ice water under stirring. The solid was filtered, washed with water and dried in vacuum to give compound 1 1 (1 .1 g, 61 % yield) as a gray solid. LCMS 571 .1 (M+H+) 1 H NMR (400 MHz, CDCb) 7.260 (s, 2H), 7.349 (d, 1 H), 6.886 (d, 1 H), 2.441 (s, 3H), 2.372 (s, 3H), 2.353 (s, 3H), 2.341 (s, 3H), 2.333 (s, 6H)
61% at 15℃; for 16h; To a solution of <strong>[529-44-2]3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one</strong> (1 g) in pyridine (10 mL) was added acetyl acetate (15.26 g), then the mixture was stirred at 15C for 16 h. The solvent was removed and the mixture was poured into ice water under stirring. The solid was filtered, washed with water and dried in vacuum to give compound 23 (1 .1 g,61 % yield) as a gray solid. LCMS 571 .1 (M+H+) 1 H NMR (400 MHz, CDCb) d 7.260 (s, 2H), 7.349 (d,1 H),6.886 (d,1 H), 2.441 (s,3H), 2.372 (s,3H), 2.353 (S,3H), 2.341 (s,3H), 2.333 (s,6H)

  • 6
  • [ 529-44-2 ]
  • [ 75-03-6 ]
  • [ 861320-32-3 ]
  • 7
  • [ 529-44-2 ]
  • [ 93-97-0 ]
  • 3,5,7-tris-benzoyloxy-2-(3,4,5-tris-benzoyloxy-phenyl)-chromen-4-one [ No CAS ]
  • 8
  • [ 529-44-2 ]
  • [ 77-78-1 ]
  • [ 5084-19-5 ]
  • 10
  • [ 529-44-2 ]
  • [ 74-88-4 ]
  • [ 5084-19-5 ]
  • 13
  • [ 529-44-2 ]
  • 3,5,7-tris-benzoyloxy-2-(3,4,5-tris-benzoyloxy-phenyl)-chromen-4-one [ No CAS ]
  • 14
  • [ 529-44-2 ]
  • [ 77-78-1 ]
  • [ 15868-40-3 ]
  • [ 14290-57-4 ]
  • 17
  • [ 529-44-2 ]
  • 3,3',4',5,5',7-hexahydroxy-α-hydroxychalcone [ No CAS ]
  • 18
  • [ 529-44-2 ]
  • [ 256486-45-0 ]
YieldReaction ConditionsOperation in experiment
With 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl; In dimethyl sulfoxide; at 19.84℃;Inert atmosphere;Kinetics; Mechanism; General procedure: The reaction between PhOH and DPPH? was carriedout in the medium of DMSO from which oxygenwas preliminarily removed by bubbling with argon for15-20 min, which made it possible to exclude the possibilityof phenol interaction with the products of theirconversion with oxygen. The reaction kinetics wasstudied by UV spectroscopy using a Specord S300 UV-VIS instrument (Carl Zeiss Jena, GDR) at 293 ±2 K in a range of initial concentrations of reacting substancesof 10-4-10-5 mol/L [8-10]. The DPPH? concentrationwas calculated based on absorbance datausing the molar extinction coefficient epsilonDMSO = 1.2 ×104 L mol-1 cm-1.
  • 20
  • [ 529-44-2 ]
  • C14H10O9 [ No CAS ]
  • 21
  • [ 529-44-2 ]
  • [ 57-50-1 ]
  • myricetin-3'-O-α-D-glucopyranoside [ No CAS ]
  • myricetin-4'-O-α-D-glucopyranoside [ No CAS ]
  • 22
  • [ 529-44-2 ]
  • AdoMet [ No CAS ]
  • [ 53472-37-0 ]
  • 23
  • [ 529-44-2 ]
  • 2-(3,4,5-trihydroxybenzyl)-3-(2,4,6-trihydroxyphenyl)quinoxaline [ No CAS ]
  • 24
  • [ 529-44-2 ]
  • hydrochloride of 2',6,6',8-tetramino-3,3',4',5,5',7-hexahydroxyflavone [ No CAS ]
  • 25
  • [ 529-44-2 ]
  • hydrobromide of 2',6,6',8-tetrahydrazino-3,3',4',5,5',7-hexahydroxyflavone [ No CAS ]
  • 26
  • [ 529-44-2 ]
  • hydrobromide of 2',6,6',8-tetrakis(diethylamino)-3,3',4',5,5',7-hexahydroxyflavone [ No CAS ]
  • 27
  • [ 529-44-2 ]
  • 3,3',5,5'-tetrabromo-4,4',7-tris(2,4-dinitrophenylhydrazono)-2',6,6',8-tetrahydroxyflavone [ No CAS ]
  • 28
  • [ 529-44-2 ]
  • 4,4',7-tris(2,4-dinitrophenylhydrazono)-3,3',5,5'-tetrahydroxy-2',6,6',8-tetranitroflavone [ No CAS ]
  • 29
  • [ 529-44-2 ]
  • aluminium(III) ion [ No CAS ]
  • Al(myricetin)(3+) [ No CAS ]
  • 30
  • [ 529-44-2 ]
  • aluminium(III) ion [ No CAS ]
  • Al(myricetin)2(3+) [ No CAS ]
  • 31
  • iron(III) chloride hexahydrate [ No CAS ]
  • [ 529-44-2 ]
  • Fe(myricetin)2(3+) [ No CAS ]
  • 32
  • iron(III) chloride hexahydrate [ No CAS ]
  • [ 529-44-2 ]
  • Fe(myricetin)(3+) [ No CAS ]
  • 33
  • [ 529-44-2 ]
  • copper(II) ion [ No CAS ]
  • Cu(myricetin)(2+) [ No CAS ]
  • 34
  • [ 529-44-2 ]
  • zinc(II) cation [ No CAS ]
  • Zn(myricetin)(2+) [ No CAS ]
  • 35
  • [ 529-44-2 ]
  • C15H9(2)HO8 [ No CAS ]
  • 36
  • [ 17912-87-7 ]
  • [ 3615-41-6 ]
  • [ 529-44-2 ]
  • 37
  • [ 1241909-29-4 ]
  • [ 2280-44-6 ]
  • [ 10257-28-0 ]
  • [ 529-44-2 ]
  • 38
  • [ 1241909-30-7 ]
  • [ 10257-28-0 ]
  • [ 529-44-2 ]
  • 40
  • [ 100-53-8 ]
  • proanthocyanidin [ No CAS ]
  • [ 220886-23-7 ]
  • [ 529-44-2 ]
  • [ 213007-61-5 ]
  • [ 220886-22-6 ]
  • [ 154-23-4 ]
  • [ 2596-50-1 ]
  • (epi)catechin-3-O-gallate benzylthioether [ No CAS ]
  • 42
  • [ 529-44-2 ]
  • [ 124233-31-4 ]
  • 43
  • [ 1357272-88-8 ]
  • [ 59-23-4 ]
  • [ 149-91-7 ]
  • [ 529-44-2 ]
  • 44
  • C16H24N2O18P2 [ No CAS ]
  • [ 529-44-2 ]
  • Myricetin 3-glucuronide [ No CAS ]
  • 45
  • [ 529-44-2 ]
  • [ 1245697-26-0 ]
  • myricetin 3-O-glucuronide [ No CAS ]
  • C21H18O14 [ No CAS ]
  • C21H18O14 [ No CAS ]
  • 46
  • [ 133-89-1 ]
  • [ 529-44-2 ]
  • [ 15648-86-9 ]
  • 47
  • [ 7491-74-9 ]
  • [ 529-44-2 ]
  • C15H10O8*C6H10N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% In isopropyl alcohol; at 20℃; for 312h; <strong>[529-44-2]Myricetin</strong> (25 mg, 0.077 mmol) and piracetam (11 mg, 0.077 mmol) were combined in 8 mL isopropyl alcohol with stirring. Resulting solution was filtered and allowed to slowly evaporate at ambient temperature. After 13 days, dark-yellow, block-like crystals (Fig. S1) precipitated (yield 54%). The solid phase was filtered, washed with ethyl acetate, allowed to dry at ambient conditions and used for single-crystal X-ray diffraction. Same procedure was employed to obtain samples for powder diffraction, Raman spectroscopy, thermal analysis (TG-DTA and DSC) and 1H NMR solution study.
  • 49
  • [ 16268-29-4 ]
  • [ 529-44-2 ]
  • myricetin 7-O-α-L-rhamnopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
With flavonol 7-O-rhamnosyltransferase from Arabidopsis thaliana; In dimethyl sulfoxide; at 20℃; for 48h;Microbiological reaction; Enzymatic reaction; General procedure: Cultures were made to a volume of 200 mL in LB medium supplemented with respective antibiotics. In case of recombinant strain harboring pET41b-AtUGT89C1 kanamycin 50 mug/mL was added inculture broth while in recombinant strain harboring pET32b-AtRHM1, ampicillin 100 mug/mL was added. After 3 hours, each culture was aseptically transferred into 50 mL falcon tube and centrifuged for 10 min at 1000 RCF. Supernatant was discarded and cell was re-suspended in autoclaved distilled water. Equal density (OD6001.5) of cells was inoculated into 100 mL LB medium in shake flask at 4 RCF and incubated at 37C until the final OD600 reached to 0.5-0.7. The cultures were then induced by 0.1 mM isopropyl-1-thio-beta-D-galactopyranoside (IPTG) and incubated at 20C for 15 h to allow protein expression. Flavonoids as substrates were added at a concentration of 0.2 mM by dissolving in dimethyl sulfoxide (DMSO) in each flask for whole-cell biocatalysis reaction. The biotransformation reaction was carried out for 48 h at 20C.
  • 50
  • [ 6315-52-2 ]
  • [ 529-44-2 ]
  • 4'-O-(2-hydroxy)ethylmyricetin [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With potassium carbonate; In N,N-dimethyl-formamide; 4 was obtained from <strong>[529-44-2]myricetin</strong> (509 mg, 1.6 mmol), ethylene glycol ditosylate (296 mg, 0.8 mmol), K2CO3 (276 mg, 2.0 mmol) and DMF (30 mL), according to the general procedure, as a yellow amorphous powder (262 mg, yield: 45%); UV (MeOH) lambdamax(log epsilon) 364 (5.92), 253 (4.36) nm; IR (K Br)numax: 3540, 3446, 3334, 2933, 1657, 1617, 1596, 1506, 1102 cm-1. 1H NMR (DMSO-d6, 400 MHz): delta 12.42 (1H, br s, 5-OH), 7.33 (1H, s, H-2'), 7.24 (1H, s, H-6'), 6.43 (1H, s, H-8), 6.20 (1H, s, H-6), 4.31 (2H, m, H-1"), 4.29 (2H, m, H-2"); 13C NMR (DMSO-d6, 100 MHz): delta 176.0 (C-4), 164.2 (C-7), 160.8 (C-5), 156.2 (C-9), 146.3 (C-3'), 145.8 (C-5'), 143.9 (C-2), 136.5 (C-3), 134.2 (C-4'), 122.7 (C-1'), 108.0 (C-6), 107.8 (C-2'), 103.1 (C-10), 98.3 (C-6), 93.5 (C-8), 64.2 (C-1"), 64.1 (C-2"); HRESIMS m/z 345.0602 [M-H2O+H]+ (calcd for [C17H13O8]+, 345.0605).
262 mg With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; Will be followed by stirring<strong>[529-44-2]Myricetin</strong> (509 mg, 1.6 mmol),DMF (30mL), K2CO3 (276mg, 2.0mmol) was added to a 50ml three-necked flask,And heated to 110 C,Then 296 mg of ethylene glycol bis-p-toluenesulfonate are slowly added,The mixture was stirred at 110 C for 3-5 h (TLC followed by a PE: ethyl acetate (EA): formic acid (HCOOH) = 10: 10: 1 v / v) Ethyl acetate (30-60 mL)Suction filtration, concentrated under reduced pressure to give the crude product,The crude product was purified by silica gel column chromatography or HPLC semi-preparative method,Drying afforded the compound HEMY (262 mg).
  • 51
  • [ 529-44-2 ]
  • [ 7460-82-4 ]
  • 4'-O-[2-(2-hydroxyethyl)hydroxy]ethylmyricetin [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With potassium carbonate; In N,N-dimethyl-formamide; 5 was obtained from <strong>[529-44-2]myricetin</strong> (509 mg, 1.6 mmol), diethylene glycol ditosylate (332 mg, 0.8 mmol), K2CO3 (276 mg, 2.0 mmol) and DMF (30 mL), according to the general procedure, as a yellow amorphous powder (236 mg, yield: 36%); UV (MeOH) lambdamax(log epsilon) 364 (2.56), 253 (2.40) nm; IR (K Br)numax: 3397, 2948, 1654, 1021 cm-1; 1H NMR (DMSO-d6, 400 MHz): delta 12.39 (1H, br s, 5-OH), 7.42 (1H, s, H-2'), 7.31 (1H, s, H-6'), 6.43 (1H, s, H-8), 6.20 (1H, s, H-6), 4.38 (2H, br s, H-1"), 4.17 (2H, br s, H-2"), 3.84 (2H, br s, H-3"), 3.39 (2H, br s, H-4"); 13C NMR (DMSO-d6, 100 MHz): delta 176.1 (C-4), 164.4 (C-7), 160.7 (C-5), 156.3 (C-9), 152.4 (C-3'), 150.6 (C-5'), 145.4 (C-2), 141.0 (C-4'), 136.8 (C-3), 125.7 (C-1'), 112.2 (C-6'), 109.8 (C-2'), 103.0 (C-10), 98.4 (C-6), 93.5 (C-8), 73.1 (C-3"), 72.9 (C-2"), 72.4 (C-1"), 72.1 (C-4"); HRESIMS (positive) m/z 389.0865 [M-H2O+H]+ (calcd for [C19H17O9]+, 389.0867).
236 mg With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; The pure <strong>[529-44-2]myricetin</strong> (509 mg, 1.6 mmol),DMF (30mL), K2CO3 (276mg, 2.0mmol) was added to a 50ml three-necked flask,And heated to 110 C,Then 332 mg of diethylene glycol bis-p-toluenesulfonate is slowly added,The mixture was stirred at 110 C for 3-5 h (TLC followed by a PE: ethyl acetate (EA): formic acid (HCOOH) = 10: 10: 1 v / v) Ethyl acetate (30-60 mL)Suction filtration, concentrated under reduced pressure to give the crude product,The crude product was purified by silica gel column chromatography or HPLC semi-preparative method, dried,The compound HEEMY (236 mg) was obtained.
  • 52
  • [ 529-44-2 ]
  • [ 19249-03-7 ]
  • 4'-O-{2-[2-(2-hydroxyethyl)hydroxyethyl]hydroxy}ethylmyricetin [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With potassium carbonate; In N,N-dimethyl-formamide; 6 was obtained from <strong>[529-44-2]myricetin</strong> (509 mg, 1.6 mmol), triethylene glycol ditosylate (367 mg, 0.8 mmol), K2CO3 (276 mg, 2.0 mmol) and DMF (30 mL), according to the general procedure, as a brownish amorphous powder (156 mg, yield: 22%); UV (MeOH) lambdamax(log epsilon): 339 (2.53), 260 (2.41) nm; IR (K Br)numax: 3410, 2925, 1649, 1197, 1043 cm-1; 1H NMR (DMSO-d6, 400 MHz): delta 12.67 (1H, br s, 5-OH), 6.70 (2H, s, H-2', 6'), 6.35 (1H, s, H-8), 6.18 (1H, s, H-6), 4.28 (2H, br s, H-1"), 3.97 (2H, d, J = 4.4 Hz, H-2"), 3.65 (2H, br s, H-6"), 3.32 (2H, br s, H-3"), 3.22 (2H, br s, H-4"), 3.04 (2H, d, J = 4.4 Hz, H-5"); 13C NMR (DMSO-d6, 100 MHz): delta 177.8 (C-4), 165.3 (C-7), 161.4 (C-5), 159.1 (C-9), 156.7 (C-2), 150.3 (C-3', 5'), 136.7 (C-4'), 136.0 (C-3), 123.9 (C-1'), 108.3 (C-2', 6'), 104.1 (C-10), 98.9 (C-6), 93.8 (C-8), 72.2 (C-5"), 71.8 (C-2"), 69.7 (C-1"), 69.1 (C-3"), 69.0 (C-4"), 68.3 (C-6"); HRESIMS (positive) m/z 433.1127 [M-H2O+H]+ (calcd for [C21H21O10]+, 433.1129).
  • 53
  • [ 37860-51-8 ]
  • [ 529-44-2 ]
  • 4'-O-{{2-{2-[2-(2-hydroxyethyl)hydroxyethyl]hydroxyethyl}hydroxy}}ethylmyricetin [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With potassium carbonate; In N,N-dimethyl-formamide; 7 was obtained from <strong>[529-44-2]myricetin</strong> (509 mg, 1.6 mmol), tetraethylene glycol ditosylate (402 mg, 0.8 mmol), K2CO3 (276 mg, 2.0 mmol) and DMF (30 mL), according to the general procedure, as a yellow amorphous powder (200 mg, yield: 25%); UV (MeOH) lambdamax(log epsilon) 345 (2.54), 265 (2.42) nm; IR (K Br)numax: 3043, 2925, 1655, 1198, 1043 cm-1. 1H NMR (DMSO-d6, 400 MHz): delta 12.64 (1H, br s, 5-OH), 7.06 (2H, s, H-2', 6'), 6.32 (1H, s, H-8), 6.15 (1H, s, H-6), 4.27 (2H, br s, H-1"), 4.13 (2H, br s, H-2"), 3.69 (2H, t, J = 4.8 Hz, H-8"), 3.50 (2H, br s, H-3"), 3.45 (2H, t, J = 4.8 Hz, H-4"), 3.37 (4H, m, H-5", 6"), 3.29 (2H, m, H-7"); 13C NMR (DMSO-d6, 100 MHz): delta 177.8 (C-4), 165.7 (C-7), 161.3 (C-5), 156.5 (C-9), 156.0 (C-2), 150.1 (C-3', 5'), 137.0 (C-4'), 136.6 (C-3), 124.4 (C-1'), 108.3 (C-2', 6'), 103.7 (C-10), 99.0 (C-6), 93.6 (C-8), 71.5 (C-7"), 71.0 (C-2"), 70.4 (C-1"), 70.2 (C-3"), 70.1 (C-4"), 70.0 (C-5"), 69.5 (C-6"), 69.0 (C-8"); HRESIMS m/z 477.1389 [M-H2O+H]+ (calcd for [C23H25O11]+, 477.1391).
  • 54
  • [ 3590-12-3 ]
  • [ 529-44-2 ]
  • 4'-O-(2-N,N-hydroxy ethyl-phenyl)-ethyl myricetin [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With potassium carbonate; In N,N-dimethyl-formamide; 8 was obtained from <strong>[529-44-2]myricetin</strong> (509 mg, 1.6 mmol), K2CO3 (276 mg, 2.0 mmol), N,N-bis[2-(p-toluenesulfonyloxy) ethyl]-N-phenylamine (468 mg, 0.8 mmol) and DMF (30 mL), according to the general procedure, as a yellow amorphous powder (398 mg, yield: 52%); UV (MeOH) lambdamax(log epsilon) 363 (2.56), 260.4 (2.42) nm; IR (K Br)numax: 3378, 2925, 2372, 1655, 1594, 1118 cm-1. 1H NMR (DMSO-d6, 400 MHz): delta 12.39 (1H, br s, 5-OH), 7.23 (2H, s, H-2', 6'), 7.13 (2H, t, J = 7.8 Hz, H-7", 9"), 6.74 (2H, d, J = 8.3 Hz, H-6", 10"), 6.36 (1H, s, H-8), 6.18 (1H, s, H-6), 4.09 (2H, t, J = 6.8 Hz, H-2"), 3.72 (2H, t, J = 6.8 Hz, H-1"), 3.56 (2H, t, J = 6.8 Hz, H-3"), 3.44 (2H, t, J = 6.8 Hz, H-4"); 13C NMR (DMSO-d6, 100 MHz): delta 176.0 (C-4), 164.9 (C-7), 160.7 (C-5), 156.3 (C-9), 150.5 (C-3', 5'), 147.9 (C-5"), 145.7 (C-2), 136.7 (C-4'), 136.0 (C-3), 129.1 (C-1'), 125.9 (C-7", 9"), 115.4 (C-8"), 111.5 (C-6", 10"), 107.2 (C-2', 6'), 102.8 (C-10), 98.4 (C-6), 93.3 (C-8), 68.7 (C-1"), 58.1 (C-4"), 53.0 (C-3"), 50.3 (C-2"); HRESIMS m/z 482.1456 [M-H2O+H]+ (calcd for [C25H24NO9]+, 482.1446).
  • 55
  • [ 16695-22-0 ]
  • [ 529-44-2 ]
  • 4'-O-(2-N,N-hydroxy ethyl-toluene-4-sulfonyl)-ethyl myricetin [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With potassium carbonate; In N,N-dimethyl-formamide; 9 was obtained from <strong>[529-44-2]myricetin</strong> (509 mg, 1.6 mmol), K2CO3 (276 mg, 2.0 mmol), N,O,O'-Tri(toluene-4-sulfonyl)diethanolamine (454 mg, 0.8 mmol) and DMF (30 mL), according to the general procedure, as a light yellow amorphous powder (402 mg, yield: 45%); UV (MeOH) lambdamax(log epsilon) 364 (2.56) nm; IR (K Br)numax: 3397, 2923, 1656, 1160, 1048 cm-1. 1H NMR (DMSO-d6, 400 MHz): delta 12.39 (1H, br s, 5-OH), 7.63 (2H, d, J = 8.0 Hz, H-6", 10"), 7.47 (1H, s, H-2'), 7.38 (2H, d, J = 8.0 Hz, H-7", 9"), 7.31 (1H, s, H-6'), 6.43 (1H, s, H-8), 6.20 (1H, s, H-6), 4.41 (2H, br s, H-1"), 4.23 (2H, br s, H-2"), 3.44 (4H, br s, H-3", 4"), 2.36 (3H, s, H-11"); 13C NMR (DMSO-d6, 100 MHz): delta 176.1 (C-4), 164.5 (C-7), 160.7 (C-5), 156.2 (C-9), 152.5 (C-3'), 150.6 (C-5'), 145.2 (C-2), 143.3 (C-8"), 140.9 (C-5"), 136.9 (C-4'), 135.1 (C-3), 129.9 (C-7", 9"), 126.9 (C-6", 10"), 126.1 (C-1'), 111.9 (C-6'), 110.2 (C-2'), 103.0 (C-10), 98.4 (C-6), 93.5 (C-8), 73.2 (C-1"), 72.7 (C-4"), 52.2 (C-3"), 51.9 (C-2"), 20.9 (C-11"); HRESIMS m/z 542.1113 [M-H2O+H]+ (calcd for [C26H24NO10S]+, 542.1115).
402 g With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; In a 50 ml three-neck bottle are sequentially added myricitrin in (509 mg, 1 . 6mmol), DMF (15 ml), K2CO3(276 mg, 2 . 0mmol), heating to 110 C, and then is slowly dripped N, N-bis [2 - (P-sulfonyloxy) ethyl]-P-toluene sulfonamide (454 mg, 0 . 8mmol) solution of DMF (15 ml), constant temperature 110 C reaction 3-5h (TLC tracking of the reaction, developing agent is petroleum ether (PE): ethyl acetate (EA): formic acid (HCOOH) =10:10:1, v/v), the reaction solution is poured into the acetic acid ethyl ester (30-60mL) in, filtered, concentrated under reduced pressure to get the crude product, the crude product by silica gel chromatography purification column or half preparation HPLC method, drying, HTEMY obtained compound (402 mg). The preparation method of this invention has the synthetic steps are simple, low cost, mild condition, and the like.
  • 56
  • [ 529-44-2 ]
  • [ 147-85-3 ]
  • C15H10O8*2C5H9NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; for 0.25h;Sonication; <strong>[529-44-2]Myricetin</strong>-proline cocrystals were prepared by adding <strong>[529-44-2]myricetin</strong>(210.0 mg, 3.699% (w/w)) to nearly saturated solutions of proline(42.0 mg, 0.740% (w/w)) in ethanol (7 mL, 95.561% (w/w)),and the mixture was sonicated for 15 min and equilibrated overnightat 37C. The precipitate was obtained by suction filtrationafter it precipitated completely and was dried totally in a fumehood. A physical mixture was also prepared by simply mixing <strong>[529-44-2]myricetin</strong>and proline at the same ratio with <strong>[529-44-2]myricetin</strong>-prolinecocrystals.
  • 57
  • [ 480-18-2 ]
  • [ 99-50-3 ]
  • [ 83-30-7 ]
  • C15H10O7 [ No CAS ]
  • [ 30048-34-1 ]
  • 2'-hydroxytaxifolin [ No CAS ]
  • [ 69098-01-7 ]
  • [ 529-44-2 ]
  • [ 139-85-5 ]
  • 58
  • [ 553-26-4 ]
  • [ 529-44-2 ]
  • C15H10O8*2C10H8N2*H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With water; In ethanol; acetone; at 25℃; for 3h; <strong>[529-44-2]Myricetin</strong> (15.9 mg, 0.05 mmol) and 4,40-bipyridine dehydrate (9.6 mg, 0.05 mmol) were taken in a 1:1 M ratio and dissolved in an ethanol-acetone solution (v/v 4:110 mL); the solution was stirred at 25 C. After 3 h, the filtrate was allowed to stand at room temperature for slow evaporation. The yellow bulk crystals were obtained 10 days later (Fig. S1a). IR data (KBr cm1):3718w, 3341s, 3290s, 3099 m, 3057 m, 2704w, 2573w, 1940w,1655s, 1597s, 1503s, 1321s, 1205s, 1168s, 1110s, 1053s, 1026s, 999s,933m, 839 m, 808s, 767m, 729 m, 646s, 619s, 573 m, 524 m, 484m(Fig. S4) [34,35].
  • 59
  • [ 529-44-2 ]
  • C15H8O8 [ No CAS ]
  • 60
  • [ 529-44-2 ]
  • [ 74-88-4 ]
  • [ 190323-49-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 60h; Myricitrin was added in a round bottom flask 2.32g (5mmol) was dissolved in 60mLDMF 11.06g (16mmol) K2CO3After stirring for 10min, slowly added 10mL (32mmol) of methyl iodide, stirred for 60h at room temperature, the precipitate was filtered, washed with ethyl acetate and the combined filtrate, and the filtrate was poured into 100mL water and extracted three times with ethyl acetate, the combined organic phases under reduced pressure. concentrated and the concentrate was dissolved in 30mL of absolute ethanol, warmed to reflux, after the solution is clear, 8mL of concentrated hydrochloric acid was added under reflux, yellow solids precipitated slowly, the reaction was continued 2h, cooled, placed the refrigerator overnight, filtered to give the crude product a, a crude product without purification, was used directly in the next reaction.
4.64 g of <strong>[529-44-2]myricetin</strong> (10 mmol) was sequentially added to a 250 mL round bottom flask.22.09 g of crystalline K2CO3 (16 mmol) and 120 mL of DMF,After stirring at room temperature for 0.5 to 1 hour, 7.50 mL of methyl iodide (120 mmol) was slowly added dropwise.After stirring at room temperature for 48 h, the reaction was followed by TLC (methanol: ethyl acetate = 1: 4, V/V).After the reaction was stopped, the precipitate was filtered, and the residue was washed with dichloromethane to remove the residue.The combined filtrates were diluted with 100 mL of water and extracted three times with dichloromethane.The organic layers were combined, concentrated under reduced pressure, and then concentrated in 30 mL of anhydrous ethanol and warmed to reflux.10 mL of concentrated hydrochloric acid was added under reflux, followed by precipitation of a yellow solid.Continue the reaction for 2 h, cool, filter,Obtain crude product3-hydroxy-3',4',5',5,7-pentamethoxy-parmicin (intermediate a),Yield: 54.4%.
4.64 g of <strong>[529-44-2]myricetin</strong> (10 mmol), 22.09 g of K2CO3·1/2H2O (16 mmol) and 120 mL of DMF were sequentially added to a 250 mL round bottom flask.After stirring at room temperature for 0.5-1 h,7.50 mL of methyl iodide (120 mmol) was slowly added dropwise.Stir at room temperature for 48 h,The reaction was followed by TLC (methanol: ethyl acetate = 1: 4, V/V). After the reaction was stopped, the precipitate was filtered, and the residue was washed with dichloromethane, and the filtrate was combined and diluted with 100 mL of water.Extracted three times with dichloromethane, the combined organic layersThe concentrate was then dissolved in 30 mL of absolute ethanol.The temperature was raised to reflux, and after the solution was clarified, 16 mL of concentrated hydrochloric acid was added under reflux.Then a yellow solid precipitated and the reaction continued for 2 h.Cool, filter,The crude product 3-hydroxy-3',4',5',5,7-pentamethoxy<strong>[529-44-2]myricetin</strong> (intermediate a) was obtained in a yield: 54.4%.
  • 62
  • myricetin 3-O-β-4C1-galactopyranouronoide [ No CAS ]
  • [ 529-44-2 ]
YieldReaction ConditionsOperation in experiment
With acetic acid; In water; at 100℃; for 0.5h; Controlled acid hydrolysis (8 mg, 10%aq. AcOH, 30 min, 100 C) yielded only myricetin at the end;
  • 63
  • myricetin 3-O-β-4C1-galactopyranouronoide [ No CAS ]
  • [ 685-73-4 ]
  • [ 529-44-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; at 100℃; for 2h; Complete acid hydrolysis of 14 (11 mg in 5 ml, 2 N aq. HCl, at 100 Cfor 2 h) yielded myricetin and galacturonic acid;
  • 64
  • myricetin 3-O-(2'',4''-di-O-acetyl)-α-L-rhamnopyranoside [ No CAS ]
  • [ 3615-41-6 ]
  • [ 529-44-2 ]
  • 65
  • [ 529-44-2 ]
  • [ 100-63-0 ]
  • C21H16N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Weigh 0.318g (1mmol) <strong>[529-44-2]myricetin</strong> into a round bottom flask,Join 20mL absolute ethanol,Stirring at room temperature for 10 minutes to dissolve all <strong>[529-44-2]myricetin</strong>,The 0.121 g (1.1 mmol) phenylhydrazine was slowly added dropwise to the flask with stirring for 10 minutes, mixed well,Add 0.3 mL of glacial acetic acid and heat to reflux at 60 C with TCL monitoring[Developing solvent V (ethyl acetate): V (petroleum ether) = 3: 2, add 0.05mL glacial acetic acid]Until the point of the raw material disappears in the mixture, stop the reaction to give a yellowish brown liquid, after decompression rotary evaporation,Ethanol wash, dry thoroughly in a vacuum oven at 60 C. Then, silica gel column chromatography was performed.Weigh 35g silica gel (200-300 mesh), pour 100mL petroleum ether and stir,After the wet column packing, loading, gradient elution. Eluent selection petroleum ether,-V (ethyl acetate): V (petroleum ether) = 1: 20,1: 10,1: 5,1: 2,1: 1, ethyl acetate methanol. Collect all the flow lines TLC,The fractions containing the same fractions were combined, evaporated under reduced pressure,Concentrated and put in a vacuum oven thoroughly dried at 60 C, after the tan solid.Experimental results: silica gel column chromatography eluent - ethyl acetate: petroleum ether (volume ratio) using 1: 20,1: 10,1: 5,1: 2,1: 1, the results of each fraction Of the separation of the phase separation is not clear enough to collect the flow of mixed, collecting some difficulties, analysis of the reasons may need to collect the polarity of the target larger, so further increase the polarity of the eluent to improve V (ethyl acetate) : V (petroleum ether) ratio.
  • 66
  • [ 529-44-2 ]
  • [ 114915-20-7 ]
  • docetaxel myricetin [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; at 20 - 55℃; 0.50gDocetaxelAnd 0.20g<strong>[529-44-2]Myricetin</strong>Add 60 mL of methanol,Stir to a clear solution at room temperature, spin down the solution under reduced pressure at 55C, and vacuum dry at 25C.The resulting product isDocetaxel <strong>[529-44-2]Myricetin</strong> Amorphous.
  • 67
  • [ 529-44-2 ]
  • [ 56-40-6 ]
  • C17H12NO9(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In ethanol; at 56℃; for 0.5h;Microwave irradiation; Take <strong>[529-44-2]myricetin</strong> 1mmol (0.318g) dissolved in 50mL absolute ethanol, add 2mmol (0.08g) alcohol solution of NaOH 1mL, radiation in a microwave, while magnetic stirring, the temperature is set to 56 C, power 400W, then add Glycine 1mmol (0.075g) alcohol solution 10mL, reaction 0.5h, the formation of ethanol-insoluble precipitate, follow-up detection reaction by TLC, when the quercetin raw material point completely disappeared to prove the reaction is complete, alcohol washed 2 times, filtered brown Compound IV.
  • 68
  • [ 529-44-2 ]
  • [ 57-10-3 ]
  • C111H190O14 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; oxalyl dichloride; for 16h; As in Reaction Scheme below, <strong>[529-44-2]myricetin</strong> derivatives were prepared by subjecting <strong>[529-44-2]myricetin</strong> to acylation usinga fatty acid by using a base and oxalyl chloride. [0072] In particular, each of a plurality of types of acyl donors (2844.8 mg of stearic acid, 2564.2 mg of palmitic acid,and 2003.1 mg of lauric acid) was first allowed to react with oxalyl chloride to prepare a highly reactive fatty acid.Subsequently, 318.24 mg of <strong>[529-44-2]myricetin</strong> was mixed with a reaction product obtained from the reaction and 50 ml of pyridinebase. The resulting mixed solution was slowly heated to a temperature equal to room temperature or higher (40 C) toallow a reaction to occur and last for 16 hours.[0073] Next, the reaction solution was developed in thin layer chromatography to identify a spot corresponding to thecompound. Thereafter, column chromatography (Product Name: "M.S.GEL", AGC Si-Tech CO., INC.) was performedto remove unreacted <strong>[529-44-2]myricetin</strong>. Thereafter, the corresponding compound was dissolved in water and then extracted withchloroform, and this process was repeated several times to obtain a compound with high purity.[0074] As described above, organic compounds, i.e., <strong>[529-44-2]myricetin</strong> derivatives, prepared by acylation using a fatty acidand oxalyl chloride in the presence of a base catalyst were obtained. 1H NMR analysis results of a <strong>[529-44-2]myricetin</strong> derivativeobtained using palmitic acid as a fatty acid are illustrated in FIG. 4. In addition, 1H NMR analysis results of <strong>[529-44-2]myricetin</strong>derivatives obtained using acetic acid, stearic acid, and lauric acid as fatty acids instead of palmitic acid are illustratedin FIGS. 5, 6, and 7, respectively
  • 69
  • [ 529-44-2 ]
  • [ 123-62-6 ]
  • [4-oxo-3,5-di(propanoyloxy)-2-[3,4,5-tri(propanoyloxy)phenyl]chromen-7-yl] propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With pyridine; at 0 - 20℃;Inert atmosphere; Propionic anhydride (2 mL, 15.6 mmol) was added dropwise to a stirred solution of <strong>[529-44-2]myricetin</strong> (0.5g, 1 .56 mmol) in anhydrous pyridine (2.78 mL, 47.1 mmol) at 0C under N2 atmosphere. The resulting stirred solution was allowed to come to room temperature and reaction was monitored to completion by LCMS. The solution was diluted with 30 mL ethyl acetate and washed with H20 (30 mL), 1 M HCI (30 mL), H20 (30 mL), and saturated NaHCO3 (30 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated by rotary evaporation. The crude residue was purified by flash chromatography (silica, 10-100% ethyl acetate in hexanes) and fractions were concentrated by rotary evaporation to yieldCompound 195 (0.31 g, 30% yield) as a white solid. 1H NMR (DMSO-d6, 400 MHz): O 7.77 (s, 2H), 7.64(d, 1H), 7.16 (d, 1H), 2.60-2.70 (m, 12H), 1.07-1.17(m, 18H) ppm
30% With pyridine; at 0 - 20℃;Inert atmosphere; Propionic anhydride (2 ml_, 15.6 mmol) was added dropwise to a stirred solution of <strong>[529-44-2]myricetin</strong> (0.5 g, 1 .56 mmol) in anhydrous pyridine (2.78 ml_, 47.1 mmol) at 0C under N2 atmosphere. The resulting stirred solution was allowed to come to room temperature and reaction was monitored to completion by LCMS. The solution was diluted with 30 mL ethyl acetate and washed with H2O (30 mL), 1 M HCI (30 mL), H2O (30 mL), and saturated NaHCC>3 (30 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated by rotary evaporation. The crude residue was purified by flash chromatography (silica, 10-100% ethyl acetate in hexanes) and fractions were concentrated by rotary evaporation to yield Compound 13 (0.31 g, 30% yield) as a white solid. 1H-NMR (DMSO-d6, 400 MHz): d 7.77 (s, 2H), 7.64 (d, 1H), 7.16 (d, 1H), 2.60-2.70 (m, 12H), 1 .07-1 .17 (m, 18H)
30% With pyridine; at 0 - 20℃;Inert atmosphere; Propionic anhydride (2 ml_, 15.6 mmol) was added dropwise to a stirred solution of <strong>[529-44-2]myricetin</strong> (0.5 g, 1 .56 mmol) in anhydrous pyridine (2.78 ml_, 47.1 mmol) at 0 C under N2 atmosphere. The stirred solution was allowed to come to room temperature and reaction was monitored to completion by LCMS. The solution was diluted with 30 mL ethyl acetate and washed with H2O (30 mL), 1 M HCI (30 mL), H2O (30 mL), and saturated NaHCO3 (30 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated by rotary evaporation. The crude residue was purified by flash chromatography (silica, 10- 100% ethyl acetate in hexanes) and fractions were concentrated by rotary evaporation to yield Compound 13 (0.31 g, 30%) as a white solid. 1 H-NMR (DMSO-de, 400 MHz): d 7.77 (s, 2H), 7.64 (d, 1 H), 7.16 (d, (0488) 1 H), 2.60-2.70 (m, 12H), 1 .07-1 .17 (m, 18H)
30% With pyridine; at 0℃;Inert atmosphere; Propionic anhydride (2 mL,15.6 mmol) was added dropwise to a stirred solution of <strong>[529-44-2]myricetin</strong> (0.5 g,1 .56 mmol) in anhydrous pyridine (2.78 mL,47.1 mmol) at 0 cC under N atmosphere. The resulting stirred solution was allowed to come to room temperature and reaction was monitored to completion by LCMS. The solution was diluted with 30 mL ethyl acetate and washed with H O (30 mL),1 M HCI (30 mL), H O (30 mL), and saturated NaHCC>3 (30 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated by rotary evaporation. The crude residue was purified by flash chromatography (silica,10-100% ethyl acetate in hexanes) and fractions were concentrated by rotary evaporation to yield Compound 27 (0.31 g,30% yield) as a white solid. 1H-NMR (DMSO-d6,400 MHz): d 7.77 (s, 2H), 7.64 (d,1 H), 7.16 (d,1 H), 2.60-2.70 (m,12H),1 .07-1 .1 7 (m,18H)

  • 70
  • [ 108-73-6 ]
  • [ 529-44-2 ]
  • 71
  • [ 14585-04-7 ]
  • [ 529-44-2 ]
YieldReaction ConditionsOperation in experiment
95.2% With boron tribromide; In dichloromethane; at 10 - 15℃; for 10h; Flavonol 1-5 (500 mg, 1.3 mmol) was placed in a 100 mL eggplant-shaped flask.Dichloromethane (10 mL) was added, and a 1 M solution of BBr3 in dichloromethane (10.5 mL) was slowly added dropwise thereto at 10 to 15 C, and the reaction was kept for 10 hours.Stop the reaction, add a lot of ice water to quench,The dichloromethane in the system was dried and extracted with ethyl acetate three times.Dry over anhydrous sodium sulfate,Spin dry to a yellow solid 3-1 compound Yangmeisu 393.5mg,The yield was 95.2%. The compound structure confirmation data is shown in Figure 3 and Figure 4.
  • 72
  • [ 529-44-2 ]
  • [ 100-39-0 ]
  • C43H34O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% To a suspension of <strong>[529-44-2]myricetin</strong> (5.0 g, 10.8 mmol) in N, N-dimethylformamide(50 mL), potassium carbonate (15 g, 108 mmol) wasadded at room temperature under nitrogen atmosphere. Afterstirring for 1 h, benzyl bromide (13.2 mL, 108 mmol) was added tothe mixture. The mixture was reacted at 70 C for 12 h. Uponcooling to room temperature, the reaction mixture was poured intothe distilled water (100 mL), and then extracted with dichloromethane(20 mL x 4). Combined organic phase was washed withbrine (50 mL), dried with anhydrous sodium sulfate and concentratedin vacuo. The residue was dissolved in a mixture of tetrahydrofuran(50 mL) and 3M hydrochloric acid (50 mL). After stirringfor 8 h at 80 C, the resultant solution was filtered, and theyellow solid product was purified with silica gel (petroleum ether/ethyl acetate/dichloromethane, 2 : 1: 1) to afford Compound M1(amorphous pale yellow solid, 3.35 g, yield 46%). 1H NMR (500 MHz,DMSO-d6) delta 12.35 (s, 1H), 9.85 (s, 1H), 7.67 (s, 2H), 7.50 (t, J 6.7 Hz,6H), 7.39 (m, 12H), 7.29 (d, J 1.5 Hz, 2H), 6.90 (d, J 2.2 Hz, 1H), 6.48 (d, J 2.2 Hz, 1H), 5.26 (s, 2H), 5.20 (s, 4H), 5.05 (s, 2H). MS(ESI, m/z): 677.72 [M H]-.
  • 73
  • [ 529-44-2 ]
  • C71H54O12 [ No CAS ]
  • 74
  • [ 529-44-2 ]
  • C29H18O12 [ No CAS ]
  • 75
  • [ 4349-62-6 ]
  • [ 529-44-2 ]
  • C99H70O20 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63.4% To a suspension of commercially available M2 (1.22 g, 5.0 mmol)in acetonitrile (20 mL), <strong>[529-44-2]myricetin</strong> (159 mg, 0.5 mmol) was added.The mixture was stirred at room temperature for 30 min, then 4-dimethylaminopyridine (672 mg, 5.5 mmol) was added. Themixture was stirred at room temperature for 12 h. The organicphase was separated, washed with brine, dried with anhydroussodium sulfate, concentrated, and purified with silica gel(dichloromethane/ethyl acetate, 200 : 1 to 4 : 1) to afford CompoundM5 (amorphous white solid, 500 mg, yield 63.4%). 1H NMR(500 MHz, CDCl3) delta 8.29 (dd, J 8.0, 1.6, 1H), 8.07 (dd, J 7.8, 1.6,1H), 8.03 (dd, J 7.7, 1.6, 1H), 7.84 (dd, J 7.8, 1.6, 2H), 7.80 (dd,J 7.8, 1.6, 1H), 7.59e7.46 (m, 5H), 7.45e7.38 (m, 4H), 7.31 (ddd,J 21.5, 14.0, 6.9, 16H), 7.26e7.06 (m, 16H), 7.02 (dd, J 16.0, 5.0,3H), 6.85 (dd, J 24.0, 10.9, 4H), 6.76 (dd, J 8.4, 6.1, 3H), 6.67 (t,J 7.6, 1H), 5.21 (s, 2H), 5.19 (s, 2H), 5.04 (s, 2H), 5.00 (s, 4H), 4.88 (s,2H).
  • 76
  • [ 36535-79-2 ]
  • [ 529-44-2 ]
  • C41H36O23 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With polyphenol oxidase; In aq. phosphate buffer; at 25℃; for 2h;pH 4.5; Weigh 150g of <strong>[529-44-2]myricetin</strong> and rutin separately, dissolve in 15L of citrate-dibasic phosphate buffer solution with a pH of 4.5 (substrate concentration 2g/100mL), add a certain amount of apple polyphenol oxidase (add The amount was 2.5 g/L), the aeration amount was 15 L/min, and the reaction was carried out at 25 C for 2 hours, and the temperature was rapidly increased to 100 C by heating to inactivate the polyphenol oxidase for 5 minutes.The obtained reaction liquid was subjected to column chromatography on a polyamide resin, the column torus diameter ratio was 1:10, the volume ratio of the sample to the bed was 1:4, the loading flow rate was 2 BV/h, and the water was used successively, and the 5% ethanol aqueous solution was successively used. The mixture was eluted with a 95% aqueous solution of ethanol, and the 95% ethanol eluted fraction was collected, and concentrated under reduced pressure at 40 C to obtain a crude extract, which was further separated and purified using BUCHI medium pressure preparation, and column chromatography was carried out.Specification: 15mm*310mm, packing C18, flow rate 3mL/min, the crude extract was dissolved in 30% ethanol aqueous solution (concentration of 80mg/mL) as the sample solution, and the elution gradient was 15%-30% ethanol aqueous solution for 3h. , 30% ethanol aqueous solution for 2h, 30% -After elution with 60% ethanol aqueous solution for 3 h, 60%-95% ethanol aqueous solution for 2 h, 30% ethanol water elution solution was collected, concentrated under reduced pressure at 45 C to an alcohol-free taste, and lyophilized to obtain compound 1 (HPLC purity ? 98%) ).
  • 77
  • [ 482-35-9 ]
  • [ 529-44-2 ]
  • C35H26O19 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With polyphenol oxidase; In aq. phosphate buffer; at 35℃; for 0.75h; Weigh 200g of each of <strong>[529-44-2]myricetin</strong> and isoquercitrin, and dissolve in 15L of citrate-dibasic phosphate buffer solution with a pH of 3.5.Add a certain amount of tea polyphenol oxidase (addition amount is 2.0g / L),The ventilation was 25L/min and the reaction was carried out at 35 C for 45 minutes.Heating rapidly increased the temperature to 100 C to inactivate the polyphenol oxidase for 5 minutes.The obtained reaction liquid was subjected to column chromatography on a polyamide resin, and the column torus diameter ratio was 1:8.The volume ratio of the sample to the bed is 1:5, the loading rate is 2BV/h, and the water is used successively.The mixture was eluted with 5% aqueous ethanol solution and 95% aqueous ethanol solution, and the 95% ethanol eluted fraction was collected, and concentrated under reduced pressure at 40 C to obtain a crude extract, which was further separated and purified by using BUCHI medium pressure preparation. Column chromatography specification: 15 mm * 310 mm , filler C18, flow rate 3mL / min, the crude extract dissolved in 35% ethanol aqueous solution (concentration of 80mg / mL) as a sample solution, elution gradient of 15% -35% ethanol aqueous solution for 3h, 35% ethanol aqueous solution Elution 2h, 35%-60%Ethanol aqueous solution was eluted for 3 h, 60%-95% ethanol aqueous solution for 2 h, 35% ethanol water elution solution was collected, concentrated under reduced pressure at 45 C to an alcohol-free taste, and lyophilized to obtain compound 2 (HPLC purity ? 98%).
  • 78
  • [ 117-39-5 ]
  • [ 529-44-2 ]
  • C29H16O14 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With polyphenol oxidase; In aq. phosphate buffer; at 30℃; for 1.2h; Weigh 75g of <strong>[529-44-2]myricetin</strong> and quercetin, respectively, dissolved in 15L of citric acid-dibasic sodium phosphate buffer with a pH of 4.0, and add a certain amount of pear polyphenol oxidase (addition amount is 1.5g/L).The aeration rate was 30 L/min, and the reaction was carried out at 30 C for 1.2 hours.Heating rapidly increased the temperature to 100 C to inactivate the polyphenol oxidase for 5 minutes.The obtained reaction liquid was subjected to column chromatography on a polyamide resin, and the column torus diameter ratio was 1:10, the volume ratio of the sample to the bed was 1:4, and the loading flow rate was 2 BV/h, followed by water,Elution with 5% aqueous ethanol solution and 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 specification: 15mm * 310mm, filler C18, flow rate 3mL / min, the crude extract was dissolved in 35% ethanol aqueous solution (concentration of 80mg /mL) as a sample solution, the elution gradient was eluted with 15%-35% ethanol aqueous solution for 3h, 35% ethanol aqueous solution for 2h, 35%-60% ethanol aqueous solution eluted for 3h, 60%-95% ethanol aqueous solution for 2h, collected 35% ethanol water elution solution, 45 C minusThe mixture was concentrated to a non-alcoholic taste and lyophilized to give Compound 3 (HPLC purity ? 98%).
  • 79
  • [ 2956-16-3 ]
  • [ 529-44-2 ]
  • [ 15648-86-9 ]
  • 80
  • [ 529-44-2 ]
  • [ 528-04-1 ]
  • C23H23NO13 [ No CAS ]
  • 81
  • [ 3616-06-6 ]
  • [ 529-44-2 ]
  • myricetin-3-O-xylopyranoside [ No CAS ]
  • 82
  • [ 529-44-2 ]
  • C14H22N2O16P2 [ No CAS ]
  • [ 56190-04-6 ]
  • 83
  • [ 529-44-2 ]
  • myricetin [ No CAS ]
  • 84
  • [ 106-31-0 ]
  • [ 529-44-2 ]
  • 3,5-bis(butanoyloxy)-4-oxo-2-[3,4,5-tris(butanoyloxy)phenyl]-4H-chromen-7-yl butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.79% With pyridine; at 20℃; for 12h;Inert atmosphere; A mixture of <strong>[529-44-2]3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one</strong> (0.2 g, 628.47 umol, 1 eq) , butanoyl butanoate (795.36 mg, 5.03 mmol, 822.50 uL, 8 eq) in Pyridine (5 ml_) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 20 C for 12 hr under N2 atmosphere. TLC indicated the reaction was completed and one new spot formed. The reaction mixture was washed with H2O (5 ml_), filtered and the filter cake was concentrated under reduced pressure to give a residue. Compound [3,5-di(butanoyloxy)-4-oxo-2-[3,4,5-tri(butanoyloxy)phenyl]chromen-7-yl]butanoate (0.378 g, 501.43 umol, 79.79% yield, 98% purity) was obtained as off-white solid. LCMS: (M+H+) 739.2 at 3.587 min. 1H NMR (400 MHz, Chloroform-d) d 7.62 (s, 2H), 7.35 (d, J= 2.2 Hz, 1H), 6.88 (d, J= 2.2 Hz, 1H), 2.74 (t, J=7.5Hz, 2H), 2.69 -2.52 (m, 10H), 1.91-1.70 (m, 12H), 1.12-0.98 (m, 18H).
  • 85
  • [ 529-44-2 ]
  • [ 141-75-3 ]
  • 3,5-bis(butanoyloxy)-4-oxo-2-[3,4,5-tris(butanoyloxy)phenyl]-4H-chromen-7-yl butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.79% With pyridine; for 12h;Inert atmosphere; A mixture of <strong>[529-44-2]3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one</strong> (0.2 g,628.47 umol,1 eq) , butanoyl butanoate (795.36 mg, 5.03 mmol, 822.50 uL, 8 eq) in Pyridine (5 ml_) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 20 C for 12 hr under N2 atmosphere. TLC indicated the reaction was completed and one new spot formed. The reaction mixture was washed with H2O (5 ml_), filtered and the filter cake was concentrated under reduced pressure to give a residue. Compound [3,5-di(butanoyloxy)-4-oxo-2-[3,4,5- tri(butanoyloxy)phenyl]chromen-7-yl] butanoate (0.378 g, 501 .43 mitioI, 79.79% yield,98% purity) was obtained as off-white solid. LCMS: (M+H+) 739.2 3.587 min. 1H NMR (400 MHz, Chloroform-d) d 7.62 (s, 2H), 7.35 (d, J = 2.2 Hz,1 H),6.88 (d, J = 2.2 Hz,1 H), 2.74 (t, J = 7.5 Hz, 2H), 2.69 - 2.52 (m,10H),1 .91 - 1 .70 (m,12H),1 .12 - 0.98 (m,18H).
  • 86
  • [ 529-44-2 ]
  • [ 633-65-8 ]
  • C20H18NO4(1+)*Cl(1-)*C15H10O8 [ No CAS ]
  • 87
  • [ 27200-12-0 ]
  • [ 529-44-2 ]
YieldReaction ConditionsOperation in experiment
42% (1) Dihydromyricetin (45 g) is dissolved in 300 ml of deionized water, and then heated to reflux to dissolve. Sodium hydroxide (10 g) aqueous solution (40 ml) is slowly added. After the addition, the solution is in a reflux state. Heat for 15 minutes.(2) Slowly add selenium dioxide (15 g) aqueous solution (60 ml). After the addition, stir at reflux temperature for 90 minutes. After the reaction is completed, the reaction is slowly cooled to 20-30 C.(3) 5M hydrochloric acid was added to adjust the pH to 4-5, and stirred for 30 minutes. Rotary steamed to 3-5 times the volume of dihydromyricetin, stirred at 10-20 C for 2 to 3 hours, and filtered.(4) The filter cake is added with an aqueous ethanol solution (80%, 200 ml) and beaten for 1 to 2 hours, filtered, and the filter cake is washed with the aqueous ethanol solution. The filter cake is collected and dried to obtain a red selenium elementary solid with a yield of 95% and a purity greater than 99%.(5) Combine the organic phases, spin dry until there is no ethanol taste, a large amount of solids precipitate, filter, and rinse the filter cake with an aqueous ethanol solution (10%) to obtain 19 g of yellow solid, which is myricetin. Yield: 42%. The purity is greater than 95%.
  • 88
  • [ 529-44-2 ]
  • [ 485-80-3 ]
  • [ 4423-37-4 ]
YieldReaction ConditionsOperation in experiment
With Citrus reticulata O-methyltransferase gene-pET32a recombinant; In aq. buffer; at 37℃; for 2h;pH 8;Enzymatic reaction;Kinetics; General procedure: A wide range of flavonoids along with caeic acid were incubated with recombinantCrOMT2-pET32a to explore the substrate specificity. A final volume of 200 L was used with 1mM SAM as methyl donor, 200 M phenolic substrates, and 25 muL purified enzyme in 50 mM Tris-HClbuer, pH 8.0. Assays were conducted for 2 h at 37 C and quenched with 200 muL methanol. The reactionproducts were filtered through a 0.22 mum filter and were analyzed by HPLC and mass spectrometry asdescribed below.
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