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CAS No. : | 1131-94-8 | MDL No. : | MFCD00016829 |
Formula : | C9H10O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BWXLCOBSWMQCGP-UHFFFAOYSA-N |
M.W : | 182.17 | Pubchem ID : | 160562 |
Synonyms : |
3-Hydroxy-4-methoxyphenylacetic acid;iso-HVA;Homoisovanillic acid
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 46.5 |
TPSA : | 66.76 Ų |
GI absorption : | High |
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) : | -7.18 cm/s |
Log Po/w (iLOGP) : | 1.02 |
Log Po/w (XLOGP3) : | 0.33 |
Log Po/w (WLOGP) : | 1.03 |
Log Po/w (MLOGP) : | 0.79 |
Log Po/w (SILICOS-IT) : | 1.08 |
Consensus Log Po/w : | 0.85 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.32 |
Solubility : | 8.7 mg/ml ; 0.0478 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.3 |
Solubility : | 9.22 mg/ml ; 0.0506 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.73 |
Solubility : | 3.41 mg/ml ; 0.0187 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.43 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44.4% | With copper(ll) sulfate pentahydrate; sodium hydroxide In water at 150℃; for 20 h; Sealed tube | To a 125mL sealed tube was added sodium hydroxide (24.5g, 612mmol), copper sulfate pentahydrate (1.02g, 4.08mmol), water (60mL) was dissolved, let cool, 3-bromo-4-methoxyphenylacetic acid (10g , 40.8 mmol), sealed tube stoppered and stirred at 150 deg.C oil bath for 20h, cooled to room temperature, was added dropwise concentrated hydrochloric acid pH 3, suction filtered, the filter cake was washed with water, drained filter cake was collected and purified by column layer chromatography (dichloromethane: methanol 30: 1) gave an off-white solid (3.3g, yield 44.4percent). |
44.4% | With copper(ll) sulfate pentahydrate; sodium hydroxide In water at 150℃; for 20 h; Sealed tube | 125mL sealed tube was added sodium hydroxide (24.5g, 612mmol), copper sulfate pentahydrate (1.02g, 4.08mmol), water (60mL) was dissolved, let cool, 3-bromo-4-methoxyphenylacetic acid (10g , 40.8 mmol), sealed tube stoppered and stirred at 150 deg.C oil bath for 20h, cooled to room temperature, was added dropwise concentrated hydrochloric acid pH 3, suction filtered, the filter cake was washed with water, drained filter cake was collected and purified by column layer chromatography (dichloromethane: methanol 30: 1) gave an off-white solid (3.3g, yield 44.4percent). |
44.4% | With copper(ll) sulfate pentahydrate; sodium hydroxide In water at 150℃; for 20 h; Sealed tube | 125 ml sealed tube is added to sodium hydroxide (24.5g, 612mmol), five water copper sulfate (1.02g, 4 . 08mmol), water (60 ml) is dissolved, a cup, by adding 3-bromo-4-methoxy-acetic acid (10g, 40.8mmol), tightly sealing, in 150 °C stirring in oil bath 20h, cooling to room temperature, hydrochloric acid drop enriching adjusted to pH 3, filtered, the filter cake washed with water, drying, collecting filter cake, and using column chromatography (dichloromethane: methanol 30:1) purified getting white solid (3.3g, yield 44.4percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.6 mmol | Stage #1: at 85 - 90℃; Stage #2: at 10 - 55℃; for 1 h; |
The resorcinol 3 mmolAnd substituted phenylacetic acid3 mmolDissolved in fresh steam boron trifluoride ether solution 2mL,Heated to 85 ~ 90 ,Magnetic stirring 6 ~ 10h (TLC shows the basic disappearance of raw materials),Cooled to 10 ° C, and 5 mL of dimethylformamide was added dropwise to obtain a mixture I. Vilsmeyer-Haack Reagent:The dimethylformamide (8.1 mL) was cooled to 10 ° C,5 mmol of phosphorus pentachloride was added in portions and heated to 55 ° C,Magnetic stirring was carried out for 1 h to give a pale red or yellow mixture II. The mixture II was added to the mixture I in portions over 30 min,After stirring at room temperature for 3 h, the reaction solution was poured into 30 mL of methanolated hydrochloric acid (0.1 mol / L), heated to 70 ° C, kept at a constant temperature for 50 min, and allowed to stand still.After distillation under reduced pressure, it was washed with 150 mL of water and then extracted with 150 mL of ethyl acetate (150 mL x 3 times) and then washed with water (150 mL x 2 times) and spin-dried ethyl acetate (filtered in a large amount of ethyl acetate extract) And then spin dry,Has been removed some impurities), with a small amount of ethanol suspension precipitation part of the pigment, centrifugal filtration, take the precipitation under nitrogen protection with ethanol thermo-crystallization.At present, the silica gel column was separated with MeOH: CH2Cl2 = 1: 35 as the developing solvent to obtain 1.6 mmol of product, the yield was 50percent ~ 60percent. |
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