7326-19-4

Basic information

• Product Name: D-(+)-Phenyllactic acid
• Synonyms: (R)-3-Phenyl-2-hydroxypropanoic acid;a-Hydroxybenzenepropanoic acid, (R)-;b-Phenyl-D-lactic acid;D-2-Hydroxy-3-phenylpropionic acid;(+)-3-Phenyl-D-lactic acid;(2R)-2-Hydroxy-3-phenylpropanoic acid;(2R)-2-Hydroxy-3-phenylpropionic acid;3-Phenyl-D-lactic acid
• CAS NO: 7326-19-4
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 230-803-3
• Product Categories: chiral
• Mol File: 7326-19-4.mol
• Article Data: 64

Chemical Properties

• Melting Point: 122-124 °C(lit.)
• Boiling Point: 254.38°C (rough estimate)
• Flash Point: 168.5 °C
• Appearance: White/Crystalline Powder
• Density: 1.1708 (rough estimate)
• Vapor Pressure: 6.17E-05mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: 3.72±0.10(Predicted)
• Water Solubility: Soluble in water.
• BRN: 2209793
• CAS DataBase Reference: D-(+)-Phenyllactic acid(CAS DataBase Reference)
• NIST Chemistry Reference: D-(+)-Phenyllactic acid(7326-19-4)
• EPA Substance Registry System: D-(+)-Phenyllactic acid(7326-19-4)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 22-24/25-45-36/37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 7326-19-4(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 7326-19-4 differently. You can refer to the following data:
1. 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.
2. 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.
3. Chiral building block employed in the preparation of statine. Starting material in the preparation of the hypoglycemic agent enlitazone and of 15N-labeled phenylalanine.

Definition

ChEBI: The (S)-enantiomer of 3-phenyllactic acid.

InChI:InChI=1/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)/p-1/t8-/m1/s1

Upstream product

• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 828-01-3 phenyllactic acid 
• 108-05-4 vinyl acetate 
• 50353-47-4 phenyl acetaldehyde cyanohydrin 
• 69056-25-3 (RS)-2-acetyloxy-3-phenyl propanoic acid 
• 457-45-4 (±)-2-fluoro-3-phenylpropanoic acid 
• 182937-63-9 (R)-2-(benzyloxy)-3-phenylpropanoic acid 
• 54917-78-1 trimethyl 3-phenylorthopropionate 
• 146235-25-8 (2R)-2-acetoxy-3-phenylpropanoic acid 
• 20312-36-1 L-3-phenyllactic acid 
• 64-17-5 ethanol 
• 421545-77-9 5-benzyl-1,3-dioxolane-2,4-dione 
• 73086-98-3 (R)-2-Aminooxy-3-phenyl-propionic acid; hydrobromide 
• 114-76-1 sodium phenylphyruvate 

Downstream Products

• 27000-00-6 methyl 2-hydroxy-3-phenylpropionate 
• 13674-16-3 methyl 2-hydroxy-3-phenylpropanoate 
• 146235-25-8 (2R)-2-acetoxy-3-phenylpropanoic acid 
• 15399-05-0 ethyl (R)-2-hydroxy-3-phenylpropanoate 
• 221662-81-3 C₂₁H₃₈O₃Si₂ 
• 156469-00-0 (2R)-3-cyclohexyl-2-hydroxypropionic acid 
• 301180-83-6 (2R,5R)-5-Benzyl-2-tert-butyl-[1,3]dioxolan-4-one 
• 7622-21-1 (R)-benzyl mandelate 
• 434949-13-0 benzyl (R)-4,6-O-benzylidene-2-deoxy-2-[(R)-2-hydroxy-3-phenylpropanamido]-β-D-allopyranoside 
• 408516-36-9 phenylmethyl (2S,5R)-2-(1-methylethyl)-4-oxo-5-(phenylmethyl)-1,3-dioxolane-2-carboxylate 
• 343566-38-1 (2'R,4S)-5-(tert-butyldimethylsilanyloxy)-4-(2'-hydroxy-3'-phenylpropionyl-amino)pentanoic acid tritylamide 
• 859723-92-5 (R)-2-Hydroxy-3-phenyl-propionic acid 8-bromo-octyl ester 
• 20312-36-1 L-3-phenyllactic acid 
• 828-01-3 phenyllactic acid 

Relevant articles and documents

Trikoveramides A-C, cyclic depsipeptides from the marine cyanobacterium Symploca hydnoides

Trikoveramides A – C, members of the kulolide superfamily of cyclic depsipeptides, were isolated from the marine cyanobacterium, Symploca hydnoides, collected from Bintan Island, Indonesia. Their planar structures were elucidated by a combination of NMR spectroscopy and HRMS spectral data. The absolute configurations of the amino acid and phenyllactic acid units were confirmed by Marfey's and chiral HPLC analyses, respectively, while the relative stereochemistry of the 3-hydroxy-2-methyl-7-octynoic acid (Hmoya) unit in trikoveramide A was elucidated by the application of the J-based configuration analysis and NOE correlations. The cytotoxic activity of the trikoveramides were evaluated against MOLT-4 human leukemia cells and gave IC50 values of 9.3 μM, 35.6 μM and 48.8 μM for trikoveramide B, trikoveramide C and trikoveramide A, respectively. In addition, trikoveramides A – C showed weak to moderate inhibition in the quorum sensing inhibitory assay based on the Pseudomonas aeruginosa lasB-gfp and rhlA-gfp bioreporter strains.

Glycerol conversion to high-value chemicals: The implication of unnatural α-amino acid syntheses using natural resources

Glycerol derivatives are an important class of compounds, which have great applications as basic structural building blocks in organic synthesis. O-Benzylglycerol was oxidised to produce a high-value compound in high yield using a NaOtBu-O2 system. Furthermore, the synthetic utility of the resulting product was demonstrated by its transformation into unnatural α-amino acids, thus showing the valorisation of glycerol biomass.

A novel D-2-hydroxy acid dehydrogenase with high substrate preference for phenylpyruvate originating from lactic acid bacteria: Structural analysis on the substrate specificity

2-Hydroxy acid dehydrogenases (2-HADHs) have been implicated in the synthesis of 2-hydroxy acids from 2-oxo acids that are used in wide areas of industry. D-lactate dehydrogenases (D-LDHs), a subfamily of 2-HADH, have been utilized to this purpose, yet they exhibited relatively low catalytic activity to the 2-oxo acids with large functional groups at C3. In this report, four putative 2-HADHs from Oenococcus oeni, Weissella confusa, Weissella koreensis and Pediococcus claussenii were examined for activity on phenylpyruvate (PPA), a substrate to 3-phenyllactic acid (PLA) with a C3 phenyl group. The 2-HADH from P. claussenii was found to have the highest kcat/Km on PPA with 1,348.03 s?1 mM?1 among the four enzymes with higher substrate preference for PPA than pyruvate. Sequential, structural and mutational analysis of the enzyme revealed that it belonged to the D-LDH family, and phenylalanine at the position 51 was the key residue for the PPA binding to the active site via hydrophobic interaction, whereas in the 2-HADHs from O. oeni and W. confusa the hydrophilic tyrosine undermined the interaction. Because phenyllactate is a potential precursor for pharmaceutical compounds, antibiotics and biopolymers, the enzyme could increase the efficiency of bio-production of valuable chemicals. This study suggests a structural basis for the high substrate preference of the 2-HADH, and further engineering possibilities to synthesize versatile 2-hydroxy acids.