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CAS No. : | 7326-19-4 | MDL No. : | MFCD00078062 |
Formula : | C9H10O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VOXXWSYKYCBWHO-MRVPVSSYSA-N |
M.W : | 166.17 | Pubchem ID : | 643327 |
Synonyms : |
D-3-Phenyllactic acid
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 43.96 |
TPSA : | 57.53 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.51 cm/s |
Log Po/w (iLOGP) : | 1.01 |
Log Po/w (XLOGP3) : | 1.13 |
Log Po/w (WLOGP) : | 0.67 |
Log Po/w (MLOGP) : | 1.1 |
Log Po/w (SILICOS-IT) : | 1.1 |
Consensus Log Po/w : | 1.0 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.75 |
Solubility : | 2.93 mg/ml ; 0.0176 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.93 |
Solubility : | 1.94 mg/ml ; 0.0117 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.64 |
Solubility : | 3.8 mg/ml ; 0.0229 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.62 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
98.5% | With sulfuric acid; sodium nitrite at 0 - 20℃; for 18h; | |
98% | With sulfuric acid; sodium nitrite for 36h; | |
87% | Stage #1: D-(R)-phenylalanine With sulfuric acid; sodium nitrite In water at 0 - 10℃; for 3h; Stage #2: With water at 10 - 20℃; |
82% | With sulfuric acid; sodium nitrite at 0 - 20℃; for 4h; | |
82% | With sulfuric acid; sodium nitrite In water at 0℃; for 1.25h; | |
78% | Stage #1: D-(R)-phenylalanine With sulfuric acid; water; sodium nitrite at 0 - 10℃; for 3h; Stage #2: at 10 - 20℃; | |
77% | With sulfuric acid; sodium nitrite In water at 0℃; for 1.75h; | |
75% | With sulfuric acid; sodium nitrite In water 0 deg C, 3 h, RT, 2 h; | |
70% | With sulfuric acid; sodium nitrite In water for 24h; Ambient temperature; | |
68% | With sulfuric acid; sodium nitrite In water at 0 - 20℃; | (R)-2-Amino-3-phenylpropionic acid (5.3 g, 32 mmol) was placed into a three- necked flask, and water (24 mL) was added. The flask was fitted with two addition funnels. 2N H2SO4 (18 mL) was placed in one addition funnel and 2N aqueous NaNO2 (18 mL) was placed in the other one. The reaction vessel was cooled to 0°C, and the acid was added dropwise with stirring. After the initial amino acid was dissolved, dropwise addition of the NaNO2 solution started. Upon completion of the addition, the reaction was stirred at 0°C for 3 hours and then allowed to stir at room temperature for 2 days. Then the reaction mixture was extracted several times with ethyl acetate. The combined organic layers were dried, filtered and concentrated under reduced pressure to give E51 (3.6 g, 68% yield) as a white solid. |
62% | With sulfuric acid; sodium nitrite In water at 0 - 20℃; for 40h; | |
54% | With sodium nitrite In hexane; sulfuric acid; water | 89 (2R)-2-Hydroxy-3-phenylpropanoic acid (J. Med. Chem., 23, 666) EXAMPLE 89 (2R)-2-Hydroxy-3-phenylpropanoic acid (J. Med. Chem., 23, 666) Following the procedure of Johnson, 1980, D-phenylalanine (16.5 g, 100 mmol) was dissolved in 1N H2 SO4 (150 ml) and cooled to 0° C. A solution of NaNO2 (10.5 g, 150 mmol) in water (50 ml) was added dropwise. The mixture was stirred for 2 h at 0° C. and for 3 h at 25° C. The product was extracted into ether (5*100 ml) and the combined ether extracts were dried over Na2 SO4 and concentrated in vacuo to about 100 ml. Hexane (300 ml) was added and the product which crystallized out was collected by vacuum filtration to afford the title compound as a colorless solid (9 g, 54%); mp=124°-125° C. |
51% | With sulfuric acid; sodium nitrite In water Ambient temperature; | |
50% | With sulfuric acid; sodium nitrite In water at 0 - 20℃; | |
42% | With hydrogenchloride; sulfuric acid; sodium nitrite In chloroform at 0℃; for 6h; | |
With barium nitrite; sulfuric acid | ||
With hydrogenchloride; acetic acid; sodium nitrite | ||
With hydrogenchloride; silver(I) nitrite | ||
With sulfuric acid; potassium bromide; sodium nitrite | ||
With sulfuric acid; water; sodium nitrite In water Ambient temperature; | ||
Stage #1: D-(R)-phenylalanine With acetic acid; sodium nitrite In water Stage #2: With potassium carbonate In methanol; water | ||
With sulfuric acid; cis-nitrous acid at 0 - 20℃; for 24h; | ||
With sulfuric acid; sodium nitrite | ||
With sulfuric acid; sodium nitrite In water at 20℃; for 27h; Cooling with ice; | 1. 4.1 D-α-hydroxy acid 10(A-C, G) General procedure: A 60 ml of aqueous solution of sodium nitrite (20.7 g, 0.3 mol) was added into a stirred and ice-cooled solution of D-amino acids (9A-C, G, 50 mmol) in 1 M H2SO4 (100 ml, 0.1 mol) over 3 h, and the mixture was stirred for 24 h at room temperature until the completion of the reaction (monitored by ninhydrin). The mixture was adjusted to pH 6 with solid NaHCO3 and then to pH 3 with concentrated HCl followed by freeze-drying. The resulting residue was extracted with hot acetone (4×100 ml), and the extracts were concentrated and dried to offer colorless oil, to which ether (200 ml) was added and filtrated to remove insoluble solids, the filtrate was concentrated and re-crystallized in ether/hexanes mixture to afford 10(A-C, G) as white crystalline, yield 82%-92%. | |
With water; acetic acid; sodium nitrite at 0 - 20℃; for 24h; Inert atmosphere; | ||
74 % | With sulfuric acid; water; sodium nitrite at 0 - 20℃; |
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