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

Description

D-(+)-Phenyllactic acid, also known as the (S)-enantiomer of 3-phenyllactic acid, is a 3-aryl analogue of D-Lactic acid with antimicrobial properties. It is a white to light yellow crystal powder that has gained attention for its potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
D-(+)-Phenyllactic acid is used as a chiral building block for the preparation of statine, an important compound in the pharmaceutical sector. It is also utilized as a starting material in the preparation of the hypoglycemic agent enlitazone, which is beneficial for managing blood sugar levels in diabetic patients.
Used in Biotechnology Industry:
D-(+)-Phenyllactic acid serves as a starting material in the preparation of 15N-labeled phenylalanine, which is used in various biotechnological applications, including research and development of new drugs and therapies.
Used in Food Industry:
D-(+)-Phenyllactic acid is used as an antimicrobial agent, particularly effective in inhibiting the growth of Listeria monocytogenes, a harmful bacterium that can cause foodborne illnesses. Its application in the food industry helps maintain food safety and quality.

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

• 1257267-02-9 (R)-N-(benzyloxycarbonyl)-O-(2-hydroxy-3-phenylpropanoyl)hydroxylamine 
• 1257267-20-1 C₂₃H₃₁NO₅Si 
• 457-45-4 (±)-2-fluoro-3-phenylpropanoic acid 
• 50353-47-4 phenyl acetaldehyde cyanohydrin 
• 73086-98-3 (R)-2-Aminooxy-3-phenyl-propionic acid; hydrobromide 
• 114-76-1 sodium phenylphyruvate 
• 89426-78-8 (1S,2S,6R,7R)-4-(1-Methoxymethoxy-2-phenyl-ethyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 
• 111505-52-3 D-α-hydroxyhydrocinnamic acid t-butyl ester 
• 100-39-0 benzyl bromide 
• 89426-77-7 (1S,2S,6R,7R)-4-Methoxymethoxymethyl-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 
• 30836-32-9 (S)-2-Acetoxy-3-phenylpropionsaeure-methylester 
• 13674-16-3 methyl 2-hydroxy-3-phenylpropanoate 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 108033-82-5 (R)-2-hydroxy-3-phenylpropionitrile 

Downstream Products

• 15399-05-0 ethyl (R)-2-hydroxy-3-phenylpropanoate 
• 156469-00-0 (2R)-3-cyclohexyl-2-hydroxypropionic acid 
• 343566-38-1 (2'R,4S)-5-(tert-butyldimethylsilanyloxy)-4-(2'-hydroxy-3'-phenylpropionyl-amino)pentanoic acid tritylamide 
• 111505-52-3 D-α-hydroxyhydrocinnamic acid t-butyl ester 
• 161313-44-6 (2R)-2-(4-nitrophenyl)sulfonyloxy-3-cyclohexyl-propionic acid benzyl ester 
• 701261-77-0 (tert-butoxycarbonylimino-{3-[2-({6-methoxymethoxy-1-[2-(2-methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionyl]-octahydro-indole-2-carbonyl}-amino)-ethyl]-2,5-dihydro-pyrrol-1-yl}-methyl)-carbamic acid tert-butyl ester 
• 701261-96-3 2-tert-butoxycarbonylamino-5-[3-({6-methoxymethoxy-1-[2-(2-methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionyl]-octahydro-indole-2-carbonyl}-amino)-propylidene]-5,6-dihydro-4H-pyrimidine-1-carboxylic acid tert-butyl ester 
• 701261-92-9 (2S,3aS,6R,7aS)-6-Acetoxy-1-[(R)-2-((R)-2-methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionyl]-octahydro-indole-2-carboxylic acid methyl ester 
• 701261-94-1 (2S,3aS,6R,7aS)-6-Methoxymethoxy-1-[(R)-2-((R)-2-methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionyl]-octahydro-indole-2-carboxylic acid 
• 701261-75-8 (2S,3aS,6R,7aS)-6-Methoxymethoxy-1-[(R)-2-((R)-2-methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionyl]-octahydro-indole-2-carboxylic acid methyl ester 
• 701261-93-0 (2S,3aS,6R,7aS)-6-Hydroxy-1-[(R)-2-((R)-2-methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionyl]-octahydro-indole-2-carboxylic acid methyl ester 
• 701261-91-8 (R)-2-((R)-2-Methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionic acid benzyl ester 
• 701261-74-7 (R)-2-((R)-2-Methoxymethoxy-3-phenyl-propionylamino)-3-phenyl-propionic acid 
• 282551-84-2 MOM-D-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.