D-beta-Phenyllactic acid is a D-stereochemical, beta-hydroxy carboxylic acid bearing a phenyl-substituted side chain, structurally related to amino-acid-like hydroxy acid motifs used in peptide and stereochemical studies. The molecule contains a carboxyl functional group and a secondary alcohol (beta-hydroxyl) that can participate in esterification, ether formation, or derivatization for analytical detection and for incorporation into larger synthetic intermediates. In chemical research, it is employed as a stereodefined building block for preparing substituted hydroxy-acid derivatives, for structure-activity and chiral recognition experiments, and as a reference compound in analytical method development where the D-configuration and beta-hydroxy functionality are relevant.
CAT No: CP27407
CAS No:7326-19-4
Synonyms/Alias:7326-19-4;(R)-2-Hydroxy-3-phenylpropionicacid;(R)-2-hydroxy-3-phenylpropanoicacid;(2R)-2-hydroxy-3-phenylpropanoicacid;D-(+)-Phenyllacticacid;D-(+)-3-Phenyllacticacid;(R)-phenyllactate;(R)-(+)-3-PhenyllacticAcid;L-PhenylLactate;L-3-Phenyllactate;(s)-b-phenyllactic;(-)-b-phenyllactate;(s)-beta-phenyllactic;(-)-3-Phenyllactate;(-)-beta-phenyllactate;(S)-3-phenyl-Lactate;(-)-b-phenyllacticacid;(-)-3-Phenyllacticacid;(-)-beta-phenyllacticacid;(S)-3-phenyl-Lacticacid;(s)-a-hydroxy-benzenepropanoate;(-)-2-Hydroxy-3-phenylpropanoate;(-)-2-Hydroxy-3-phenylpropionate;(s)-a-hydroxy-benzenepropanoicacid;(s)-alpha-hydroxy-benzenepropanoate
D-beta-Phenyllactic acid is a chiral alpha-hydroxy carboxylic acid bearing a β-hydroxy stereocenter adjacent to the carboxyl group and a benzyl-substituted phenyl ring that increases hydrophobicity and conformational bias. The molecule contains a primary carboxylic acid functionality and a secondary alcohol, enabling acid-base chemistry, esterification, and oxidation to β-keto derivatives under standard organic conditions. The D-configuration provides stereochemical control for downstream transformations that preserve or translate chirality into higher-complexity intermediates. As a compact chiral building block, D-beta-Phenyllactic acid can serve as a chemically defined intermediate for amino acid derivative synthesis, chiral auxiliary or ligand preparation, and stereospecific route design in fine chemical and process chemistry.
1. Chiral Building Block
D-beta-Phenyllactic acid is used in chiral synthesis planning for constructing stereochemically defined intermediates where an alpha-hydroxy acid motif is required. The carboxylic acid and β-alcohol functional groups can be selectively protected or converted into activated derivatives for subsequent carbon-carbon bond formation, while the D-stereocenter supports stereospecific downstream elaboration. The benzyl phenyl substituent can influence reactivity and diastereoselectivity during transformations that proceed through acyl derivatives or oxidized intermediates. D-beta-Phenyllactic acid can therefore function as a chiral amino-acid-adjacent feedstock for asymmetric synthesis workflows and stereochemical library generation.
2. Pharmaceutical Intermediate
D-beta-Phenyllactic acid is applied as a process chemistry intermediate in routes that require a chiral hydroxy acid for making lactate-derived fragments and for preparing oxidized or esterified analogs used in medicinal chemistry. The acid group enables formation of esters, amides, or acid chlorides for coupling into larger scaffolds, while the β-hydroxy group can be transformed into carbonyl-containing intermediates that participate in heterocycle construction or side-chain tailoring. The D-configuration can be carried through as a stereochemical element that impacts conformational properties of downstream intermediates. D-beta-Phenyllactic acid thus supports pharmaceutical intermediate preparation where chirality preservation and functional-group interconversion are central to manufacturing route development.
3. Biocatalysis Substrate
D-beta-Phenyllactic acid is suitable for industrial biocatalysis and enzyme screening where hydroxy acid substrates are converted into higher-value chiral products. The presence of both a carboxylic acid and a β-hydroxyl group provides handles for enzyme-recognized transformations such as oxidation to β-keto acids, reduction to other hydroxy stereoisomers, or esterification to modulate substrate uptake. The D stereochemistry can be used to probe stereoselective enzyme behavior and to generate enantiopure derivatives that feed into downstream synthetic steps. D-beta-Phenyllactic acid can be employed in applied enzyme studies and specialty chemical production that rely on controlled stereochemical outcomes.
4. Chemical Derivatization Chemistry
D-beta-Phenyllactic acid is utilized in synthetic organic chemistry for derivatization strategies that convert the hydroxy acid into protected or activated intermediates. The carboxylic acid can be esterified to form amino acid ester analogs in coupling chemistry contexts, while the β-alcohol can be protected as an ether or ester to enable selective functional group manipulation. Oxidation of the β-hydroxy group can generate β-keto derivatives that participate in aldol-type chemistry, cyclization, or further functionalization to build carbonyl-rich motifs. D-beta-Phenyllactic acid thereby serves as a practical platform for stereochemically controlled intermediate formation and downstream scaffold elaboration.
5. Analytical Standards And Chiral QA
D-beta-Phenyllactic acid is applied in analytical research and quality assurance workflows that require chiral hydroxy acid standards and stereochemical reference materials. The defined D-configuration and well-characterized functional groups support method development for chiral chromatography, derivatization-based detection, and mass spectrometric identification of lactate-related species. The acid and alcohol functionalities enable reproducible derivatization to improve detectability and to distinguish stereoisomers when monitoring synthetic intermediates. D-beta-Phenyllactic acid can therefore be used to support analytical method validation and stereochemical tracking in amino acid derivative synthesis and related industrial chemical manufacturing.
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