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CAS No. : | 22818-40-2 | MDL No. : | MFCD00004262 |
Formula : | C8H9NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LJCWONGJFPCTTL-SSDOTTSWSA-N |
M.W : | 167.16 | Pubchem ID : | 89853 |
Synonyms : |
4-Hydroxy-D-phenylglycine;D-(-)-4-Hydroxyphenylglycine
|
Chemical Name : | H-D-Phg(4-OH)-OH |
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 42.72 |
TPSA : | 83.55 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) : | -8.78 cm/s |
Log Po/w (iLOGP) : | 0.57 |
Log Po/w (XLOGP3) : | -2.06 |
Log Po/w (WLOGP) : | 0.15 |
Log Po/w (MLOGP) : | -2.01 |
Log Po/w (SILICOS-IT) : | 0.04 |
Consensus Log Po/w : | -0.66 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.18 |
Solubility : | 255.0 mg/ml ; 1.53 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 0.83 |
Solubility : | 1140.0 mg/ml ; 6.79 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.88 |
Solubility : | 22.1 mg/ml ; 0.132 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.54 |
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: |
* 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 |
---|---|---|
100% | at 20℃; for 10 h; | Step 1:To a solution of (R)-2-amino-2-(4-hydroxyphenyl)acetic acid 25a(D-4Hydroxyphenyl glycine, 10.0 g, 60.1 mmol) in methanol (200 mL) was added dropwise thionyl chloride (8 mL) and stirred at room temperature for 10 h. The reaction mixture was concentrated in vacuum and the residue was washed twice with ether to yield (Pv)-methyl 2-amino-2-(4-hydroxyphenyl)acetate (D-4-hydroxyphenylglycine methyl ester 25b (13.0 g, 60.0 mmol, 100percent) as a white solid. 1H NMR (300 MHz, DMSO- 6) ? 3.68 (s, 3 H), 5.07 (s, 1 H), 6.85 (d, J= 8.5 Hz, 2 H), 7.29 (d, J= 8.6 Hz, 2 H), 9.03 (s, 3 H), 10.02 (s, 1 H). Step 2:(R)-methyl 2-amino-2-(4-hydroxyphenyl)acetate 25b (©-4-hydroxyphenylglycine methyl ester, 0.302 g, 1.39 mmol) was dissolved in a freshly prepared aqueous solution of glyoxylic acid (1.27 g, 13.8 mmol) and copper(II) sulfate pentahydrate (0.35 g, 1.40 mmol) in a buffer containing 2.5 M pyridine and 0.5 M acetic acid. The mixture was stirred for 10 h at room temperature and then extracted with three portions of methylene chloride (10 mL). The organic layers were combined, washed three times with 0.5 M HC1 (20 mL), dried, filtered and concentrated in vacuum to dryness. The residue was purified by flash column chromatography (silica gel, eluting with chloroform) to yield methyl2- (4-hydroxyphenyl)-2-oxoacetate 25c (0.109 g, 6.06 mmol, 44percent) as a clear oil. 1H NMR (300 MHz, CDCls) ? 3.99 (s, 3 H), 5.41 (br s, 1 H), 6.95 (d, J= 8.8 Hz, 2 H), 8.00 (d, J = 8.8 Hz, 2 H). |
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