(2R)-2-hydroxy-3-phenylpropanoic acid

Base Information

• Chemical Name: (2R)-2-hydroxy-3-phenylpropanoic acid
• CAS No.: 7326-19-4
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.177
• Hs Code.: 29181990
• European Community (EC) Number: 230-803-3
• UNII: 68L11J0XBS
• DSSTox Substance ID: DTXSID70904708
• Nikkaji Number: J70.490C
• Wikidata: Q22574124
• Metabolomics Workbench ID: 37405
• Mol file: 7326-19-4.mol

Synonyms:7326-19-4;(R)-2-Hydroxy-3-phenylpropionic acid;(R)-2-hydroxy-3-phenylpropanoic acid;(2R)-2-hydroxy-3-phenylpropanoic acid;D-(+)-3-Phenyllactic acid;(R)-3-Phenyllactic acid;D-(+)-Phenyllactic acid;D-3-phenyllactic acid;(R)-(+)-3-Phenyllactic Acid;(R)-phenyllactate;3-Phenyl-D-lactic acid;L-Phenyl Lactate;L-3-Phenyllactate;MFCD00078062;(2R)-2-Hydroxy-3-phenyl-propanoic acid;3-Phenyllactic acid, (R)-;68L11J0XBS;D-?(+)?-?Phenyllactic acid;EINECS 230-803-3;l-2-hydroxy-3-phenyl-propionic acid;(2S)-2-Hydroxy-3-phenylpropionic acid;(R)-|A-Hydroxy-3-phenylpropionic acid;L-beta-Phenyllactic acid;(R)-3-(phenyl)lactate;(+)-2-Hydroxy-3-phenylpropionic acid;(s)-b-phenyllactic;(-)-b-phenyllactate;(s)-beta-phenyllactic;(2S)-2-Hydroxy-3-phenylpropionate;(-)-3-Phenyllactate;(-)-beta-phenyllactate;(S)-3-phenyl-Lactate;(-)-b-phenyllactic acid;D/L-3-phenyllactic acid;(-)-beta-phenyllactic acid;(S)-3-phenyl-Lactic acid;UNII-68L11J0XBS;SCHEMBL180366;(s)-a-hydroxy-benzenepropanoate;CHEBI:32978;DTXSID70904708;(-)-2-Hydroxy-3-phenylpropanoate;(-)-2-Hydroxy-3-phenylpropionate;(s)-a-hydroxy-benzenepropanoic acid;(s)-alpha-hydroxy-benzenepropanoate;(2R)-hydroxy-3-phenylpropanoic acid;(R)-2-hydroxy-3-phenylpropanoicacid;FD1250;s6326;D-(+)-3-Phenyllactic acid, 98%;AKOS005146076;AKOS016015834;(-)-2-Hydroxy-3-phenylpropanoic acid;(-)-2-Hydroxy-3-phenylpropionic acid;AC-5644;CS-W020670;(rac)-2-hydroxy-3-phenylpropionic acid;(s)-alpha-hydroxy-benzenepropanoic acid;AK-44083;DS-14380;HY-30219;(R)-(+)-2-Hydroxy-3-phenylpropionic Acid;AM20060716;P1981;C05607;EN300-116770;Q22574124;Z1255364914

Chemical Property of (2R)-2-hydroxy-3-phenylpropanoic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 6.17E-05mmHg at 25°C
• Melting Point: 122-124 °C(lit.)
• Refractive Index: 1.5500 (estimate)
• 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 (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)
• Water Solubility.: Soluble in water.
• 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:

99% ^*data from raw suppliers

D-(+)-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: D-(+)-3-Phenyllactic Acid is an 3-aryl analogue of D-Lactic acid with antimicrobial activity. D-(+)-3-Phenyllactic Acid is partiularly effective in inhibiting the growth of Listeria monocytogenes. D-(+)-3-Phenyllactic acid is a chiral building block that is used in preparation of statine. Starting material in preparation of the hypoglycemic agent enlitazone and of (15)N-labeled phenylalanine. Chiral building block employed in the preparation of statine. Starting material in the preparation of the hypoglycemic agent enlitazone and of 15N-labeled phenylalanine.

Technology Process of (2R)-2-hydroxy-3-phenylpropanoic acid

There total 73 articles about (2R)-2-hydroxy-3-phenylpropanoic 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:

D-(R)-phenylalanine

Phenylalanine

(-)-menthol

phenyllactic acid

Downstream raw materials:

methyl 2-hydroxy-3-phenylpropionate

D-α-hydroxyhydrocinnamic acid t-butyl ester

(2R)-2-(4-nitrophenyl)sulfonyloxy-3-cyclohexyl-propionic acid benzyl ester

(S)-2-[((5S,8R)-5-Isopropyl-3,6-dioxo-4,7-diaza-tricyclo[8.6.2.0^13,17]octadeca-1⁽¹⁶⁾,10⁽¹⁸⁾,11,13⁽¹⁷⁾,14-pentaen-8-yl)-methoxy-phosphinoyloxy]-3-phenyl-propionic acid methyl ester

Refernces

• 1、 Chen, Bo,Li, Min,Li, Yanwei,Ma, Ming,Tian, Shaixiao,Tong, Wei,Wang, Jian-Bo,Xu, Guangyu,Yue, Yue,Zhang, Hongxia. "Semirational Design of Fluoroacetate Dehalogenase RPA1163 for Kinetic Resolution of α-Fluorocarboxylic Acids on a Gram Scale". . p. 3143 - 3151. Retrieved 2020/03/23.
• 2、 Lee, Hoe-Suk,Park, Jisu,Yoo, Young Je,Yeon, Young Joo. "A novel D-2-hydroxy acid dehydrogenase with high substrate preference for phenylpyruvate originating from lactic acid bacteria: Structural analysis on the substrate specificity". . p. 37 - 44. Retrieved 2019/03/11.