L-(-)-3-Phenyllactic acid

Base Information

• Chemical Name: L-(-)-3-Phenyllactic acid
• CAS No.: 20312-36-1
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 29181980
• European Community (EC) Number: 243-726-5
• UNII: KW7SNV9X8B
• DSSTox Substance ID: DTXSID801342710
• Nikkaji Number: J9.307F
• Wikidata: Q27093482
• Metabolomics Workbench ID: 52332
• Mol file: 20312-36-1.mol

Synonyms:20312-36-1;L-(-)-3-Phenyllactic acid;(S)-2-Hydroxy-3-phenylpropanoic acid;(S)-2-Hydroxy-3-phenylpropionic acid;L-3-phenyllactic acid;L(-)-3-Phenyllactic acid;(2S)-2-hydroxy-3-phenylpropanoic acid;(S)-(-)-3-Phenyllactic acid;(S)-3-phenyllactic acid;(S)-(-)-2-Hydroxy-3-phenylpropionic Acid;D-3-Phenyllactate;D-Phenyllactic acid;ALPHA-HYDROXY-BETA-PHENYL-PROPIONIC ACID;L-beta-Phenyllactic acid;KW7SNV9X8B;(-)-3-Phenyllactic acid;(S)-phenyllactic acid;3-Phenyllactic acid, (S)-;Lactic acid, 3-phenyl-, (S)-;EINECS 243-726-5;Benzenepropanoic acid, .alpha.-hydroxy-, (.alpha.S)-;MFCD00004244;L-Phenyllactic acid;(r)-phenyllactic acid;D-Phenyllactate;(+)-2-Hydroxy-3-phenylpropionic acid;2ctc;D-b-Phenyllactate;(S)-2-Hydroxy-3-phenyl-propionic acid;delta-Phenyllactate;b-Phenyl-D-lactate;L-3-phenyllacticacid;(R)-b-Phenyllactate;delta-3-Phenyllactate;(+)-b-Phenyllactate;D-b-Phenyllactic acid;delta-Phenyllactic acid;(+)-3-Phenyllactate;Benzenepropanoic acid, .alpha.-hydroxy-, (S)-;(R)-beta-Phenyllactate;b-Phenyl-D-lactic acid;delta-beta-Phenyllactate;D-PLA;(+)-beta-Phenyllactate;(R)-3-phenyl-Lactate;beta-Phenyl-delta-lactate;UNII-KW7SNV9X8B;(R)-b-Phenyllactic acid;(+)-b-Phenyllactic acid;delta-3-Phenyllactic acid;L(-)-3-Phenyllacticacid;(+)-3-Phenyllactic acid;(R)-3-phenyl-Lactic acid;(R)-beta-Phenyllactic acid;delta-beta-Phenyllactic acid;(+)-beta-Phenyllactic acid;beta-Phenyl-delta-lactic acid;L-(?)-3-Phenyllactic acid;SCHEMBL197252;D-2-Hydroxy-3-phenylpropionate;(R)-a-hydroxy-Benzenepropanoate;CHEBI:43065;GTPL12418;(R)-a-Hydroxy-3-phenylpropionate;DTXSID801342710;(+)-2-Hydroxy-3-phenylpropionate;(R)-2-Hydroxy-2-phenylpropionate;(R)-2-Phenyl-2-hydroxypropanoate;delta-2-Hydroxy-3-phenylpropionate;(R)-alpha-hydroxy-Benzenepropanoate;(2R)-2-hydroxy-2-phenylpropanoate;(2R)-2-Hydroxy-2-phenylpropionate;(R)-a-hydroxy-Benzenepropanoic acid;D-2-Hydroxy-3-phenylpropionic acid;FD1244;s6271;(R)-alpha-Hydroxy-3-phenylpropionate;L-(-)-3-Phenyllactic acid, 98%;(R)-a-Hydroxy-3-phenylpropionic acid;(S)-alpha-Hydroxybenzenepropanoic acid;AKOS016842323;alpha(S)-Hydroxybenzene propanoic acid;(2S)-2-hydroxy-3-pheylpropionic acid;(R)-2-Hydroxy-2-phenylpropionic acid;(R)-2-Phenyl-2-hydroxypropanoic acid;AC-5645;CS-W020023;DB02494;delta-2-Hydroxy-3-phenylpropionic acid;(2R)-2-Hydroxy-2-phenylpropionic acid;(R)-alpha-hydroxy-Benzenepropanoic acid;(2S) -2-hydroxy-3-phenylpropionic acid;(R)-alpha-Hydroxy-3-phenylpropionic acid;AS-14701;BP-12963;HY-30220;AM20060541;P1168;EN300-192762;A814431;J-013207;J-521622;Q27093482;Z1255386695

Chemical Property of L-(-)-3-Phenyllactic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 6.17E-05mmHg at 25°C
• Melting Point: 123-125 °C
• Refractive Index: -21 ° (C=2, H2O)
• Boiling Point: 331.6 °C at 760 mmHg
• PKA: 3.72±0.10(Predicted)
• Flash Point: 168.5 °C
• PSA: 57.53000
• Density: 1.265 g/cm³
• LogP: 0.67460
• Storage Temp.: 2-8°C
• Solubility.: Acetone (Sparingly), Chloroform (Slightly, Heated), DMSO, Methanol (Slightly)
• Water Solubility.: soluble
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 166.062994177
• Heavy Atom Count: 12
• Complexity: 150

Purity/Quality:

98%min ^*data from raw suppliers

L-(?)-3-Phenyllactic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 22-24/25-45-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)O)O
• Uses: L-(-)-3-Phenyllactic Acid is used in the synthetic preparation of peptidomimetics as neuropeptide S receptor agonists as well as many other useful compounds.

Technology Process of L-(-)-3-Phenyllactic acid

There total 144 articles about L-(-)-3-Phenyllactic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.5%

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → D-phenyllactic acid (828-01-3,7326-19-4,20312-36-1,156-05-8)

Guidance literature:

With sulfuric acid; sodium nitrite; at 0 - 20 ℃; for 18h;

DOI:10.3390/10010259

Reference yield: 93.0%

(R)-2-Hydroxy-3-phenyl-propionic acid (1R,2S,3R)-1,7,7-trimethyl-3-(methyl-phenyl-carbamoyloxy)-bicyclo[2.2.1]hept-2-yl ester → D-phenyllactic acid (828-01-3,7326-19-4,20312-36-1,156-05-8)

Guidance literature:

With potassium hydroxide; In methanol; water; for 5h;

DOI:10.1002/hlca.19860690310

Reference yield: 92.0%

(S)-2-Acetoxy-3-phenylpropionsaeure-methylester (30836-32-9) → D-phenyllactic acid (828-01-3,7326-19-4,20312-36-1,156-05-8)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 3h;

upstream raw materials:

L-phenylalanine

Phenylalanine

(-)-menthol

phenyllactic acid

Downstream raw materials:

(S)-methyl 2-hydroxy-3-phenylpropanoate

(S)-5-benzyl-2,2-dimethyl-4-oxo-1,3-dioxolane

piperidine amide of L-phenyllactic acid

4-methoxypiperidine amide of L-phenyllactic acid

Refernces

Two-carbon-elongated HIV-1 protease inhibitors with a tertiary-alcohol- containing transition-state mimic

10.1021/jm070680h

The research focuses on the development of a new generation of HIV-1 protease inhibitors featuring a tertiary-alcohol-based transition-state mimic. The study involves the elongation of the core structure of existing inhibitors by two carbon atoms and variation of the P1′ group to enhance inhibitory potency. The main experiments include the synthesis of two-carbon-elongated analogues using (S)-2-hydroxy-3-phenylpropionic acid as a starting material, followed by a series of chemical reactions to introduce different P1′ substituents. The synthesized inhibitors were then biologically evaluated for their antiviral activities, with measurements of Ki and EC50 values. X-ray crystallography was also employed to determine the binding modes of the inhibitors with the HIV-1 protease. The analyses revealed that the new inhibitors exhibited improved enzyme inhibition activities and cellular anti-HIV activities, with some compounds showing high permeability and metabolic stability. Reactants used in the synthesis include (S)-2-hydroxy-3-phenylpropionic acid, various hydrazides, and protecting groups like TBSOTf, among others. The study also investigated the effects of different P1′ groups on the inhibitors' activities, leading to the identification of new terminal P1′ substituents that improved antiviral activity.