DL-3-Phenyllactic acid

Base Information

• Chemical Name: DL-3-Phenyllactic acid
• CAS No.: 828-01-3
• Deprecated CAS: 156-05-8
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 29181990
• European Community (EC) Number: 212-580-4
• NSC Number: 2627
• UNII: SC6T4O59BK
• DSSTox Substance ID: DTXSID30862436
• Nikkaji Number: J10.217B,J2.433.036B,J2.433.037K
• Wikidata: Q10395585
• Metabolomics Workbench ID: 124544
• ChEMBL ID: CHEMBL1778420
• Mol file: 828-01-3.mol

Synonyms:3-phenyllactate;3-phenyllactic acid;3-phenyllactic acid, (D)-isomer;3-phenyllactic acid, (DL)-isomer;3-phenyllactic acid, (L)-isomer;3-phenyllactic acid, calcium salt;3-phenyllactic acid, monosodium salt;beta-phenyllactic acid;phenyllactic acid

Chemical Property of DL-3-Phenyllactic acid

Chemical Property:

• Appearance/Colour: Off-white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 95-98 °C
• Refractive Index: 1.656
• Boiling Point: 327.2 °C at 760 mmHg
• PKA: 3.72±0.10(Predicted)
• Flash Point: 165.9 °C
• PSA: 57.53000
• Density: 1.261 g/cm³
• LogP: 0.67460
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly)
• 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:

96% 1H NMR ^*data from raw suppliers

DL-3-Phenyllactic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

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
• Uses: Reagent involved in biological studies of:Enantioselectivity of lipase in transesterificationOxidation by glycolate oxidase and catalase

Technology Process of DL-3-Phenyllactic acid

There total 155 articles about DL-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:

ethyl 3-phenylglycidate

2-bromo-3-phenylpropanoic acid

α-hydrazinobenzenepropanoic acid

2-oxo-3-(phenyl)propionic acid

Downstream raw materials:

L-3-phenyllactic acid

D-phenyllactic acid

methyl 2-hydroxy-3-phenylpropanoate

methyl 2-hydroxy-3-phenylpropionate

Refernces

• 1、 Bubl,Butts. "". . p. 4972. Retrieved 1951.
• 2、 La Mer,Greenspan. "". . p. 1492,1496. Retrieved 1934.
• 3、 Burgener, Simon,Cortina, Ni?a Socorro,Erb, Tobias J.. "Oxalyl-CoA Decarboxylase Enables Nucleophilic One-Carbon Extension of Aldehydes to Chiral α-Hydroxy Acids". supporting information. p. 5526 - 5530. Retrieved 2020/02/20.
• 4、 Ye, Ying,Ozaki, Taro,Umemura, Myco,Liu, Chengwei,Minami, Atsushi,Oikawa, Hideaki. "Heterologous production of asperipin-2a: Proposal for sequential oxidative macrocyclization by a fungi-specific DUF3328 oxidase". supporting information. p. 39 - 43. Retrieved 2019/01/04.