L-beta-Phenyllactic acid is a naturally occurring alpha-hydroxy carboxylic acid (2-hydroxypropanoic acid derivative) bearing a β-hydroxyl group and a benzyl-like phenyl substituent on the carbon skeleton, with the "L-" prefix indicating a specific stereochemical form. The molecule contains a carboxylic acid functional group and a secondary alcohol, enabling it to exist as a hydrogen-bonding donor/acceptor pair and to form salts or esters under standard organic chemistry conditions. In biochemical and synthetic research, it is used as a chiral building block and as a precursor for preparing more complex hydroxy-acid derivatives, including labeled or conjugatable analogues for structure-activity studies and analytical method development.
CAT No: CP26745
CAS No:20312-36-1
Synonyms/Alias:20312-36-1;L-(-)-3-Phenyllacticacid;(S)-2-Hydroxy-3-phenylpropionicacid;(S)-2-Hydroxy-3-phenylpropanoicacid;L(-)-3-Phenyllacticacid;(S)-(-)-3-Phenyllacticacid;D-3-phenyllacticacid;(S)-(-)-2-Hydroxy-3-phenylpropionicAcid;MFCD00004244;L-3-phenyllacticacid;(S)-3-phenyllacticacid;(2S)-2-hydroxy-3-phenylpropanoicacid;(R)-3-Phenyllacticacid;ALPHA-HYDROXY-BETA-PHENYL-PROPIONICACID;(R)-3-phenyllactate;D-Phenyllactate;2ctc;D-b-Phenyllactate;delta-Phenyllactate;D-3-Phenyllactate;b-Phenyl-D-lactate;(R)-b-Phenyllactate;delta-3-Phenyllactate;PubChem6413;(+)-b-Phenyllactate
L-beta-Phenyllactic acid is an L-configured alpha-hydroxy carboxylic acid bearing a benzylic stereocenter, with the formula characterized by a secondary alcohol adjacent to a carboxylic acid. The molecule's chiral center and the juxtaposition of hydroxyl and carboxyl functional groups enable stereoselective derivatization, including formation of esters, amides, and protected intermediates for downstream coupling chemistry. The benzylic aryl substituent influences acidity, hydrogen-bonding behavior, and reactivity in esterification, oxidation/reduction, and metal-mediated transformations. As a chiral amino-acid-adjacent building block and process-relevant intermediate, L-beta-Phenyllactic acid can be converted into more elaborated chiral fragments used in fine chemical synthesis and stereocontrolled molecular construction.
1. Chiral Building Block Synthesis
L-beta-Phenyllactic acid is applied in chiral synthesis workflows where an L-configured hydroxy acid provides a stereodefined handle for constructing substituted carbon frameworks. The secondary alcohol and carboxylic acid can be selectively functionalized through esterification, amidation, or temporary protection strategies that control chemoselectivity during subsequent transformations. Benzylic substitution allows incorporation into chiral auxiliaries or chiral fragments that can be carried forward into larger scaffolds via activation of the carboxyl group. Downstream use commonly includes preparing stereochemically defined intermediates for asymmetric synthesis and structure elaboration in synthetic organic chemistry.
2. Polymer And Material Precursors
L-beta-Phenyllactic acid is suitable for industrial chemical manufacturing routes that require functionalized hydroxy acid monomers or reactive intermediates for polymer modification. The hydroxyl group can participate in ester-forming reactions or be converted into activated derivatives that enable incorporation into polymer backbones, side chains, or crosslinkable networks. The carboxylic acid functionality supports salt formation and controlled reactivity in formulation-adjacent processes, while the chiral benzylic motif can influence material surface properties and compatibility with other functional monomers. Industrially oriented use can include preparing chiral additives or reactive intermediates that feed into specialty chemical production and functional material synthesis.
3. Flavor, Fragrance, And Specialty Chemicals
L-beta-Phenyllactic acid is used in fine chemical and specialty ingredient development where hydroxy acid functionality supports conversion into odor- and taste-relevant derivatives or process intermediates. The presence of both hydroxyl and carboxyl groups enables derivatization into esters or lactate-related analogs that can be tuned for volatility, solubility, and compatibility with formulation matrices. Benzylic chirality can be carried through into downstream products when stereochemical integrity is required for consistent sensory or physicochemical profiles. This chemistry aligns with industrial fine chemical synthesis and specialty chemical production that relies on controlled functional group transformation rather than peptide-specific coupling.
4. Chiral Intermediate For Pharmaceutical R&D
L-beta-Phenyllactic acid is applied in pharmaceutical research settings as a chiral intermediate for generating stereodefined fragments used in medicinal chemistry and process chemistry development. The carboxylic acid can be activated for coupling chemistry, while the adjacent hydroxyl group can undergo protection/deprotection cycles to orchestrate regioselective transformations on the benzylic center. The aryl-substituted hydroxy acid motif can serve as a precursor to chiral esters, amides, or oxidized/reduced derivatives that support scaffold diversification. Downstream formation of substituted chiral intermediates supports iterative synthesis of analog series and stereochemical control in route design.
5. Analytical Reference And Stereochemical Studies
L-beta-Phenyllactic acid is employed in analytical research as a stereochemically defined standard or reference material for method development and chiral separation studies. The L-configuration and well-defined hydroxy acid functional groups enable reproducible derivatization for chromatographic detection, including transformations that accentuate differences between enantiomers or diastereomeric derivatives. The benzylic hydroxyl and carboxyl groups facilitate formation of detectable derivatives under common analytical derivatization conditions. Broader relevance includes supporting quality-by-design investigations for chiral intermediate characterization and enabling stereochemical verification in applied synthetic workflows.
6. Biochemical And Chemical Biology Substrates
L-beta-Phenyllactic acid is applicable to chemical biology research where hydroxy acid substrates can be used to probe enzyme selectivity, metabolic transformations, or stereochemical recognition. The molecule's secondary alcohol and carboxylate arrangement supports interactions with enzymes that accommodate hydroxy acids, enabling studies of stereochemical preference and functional group tolerance. Derivatization into labeled or immobilizable analogs may be used to track uptake, conversion, or binding events in biochemical assays. Downstream utility can include generating chemically characterized probes and intermediates that connect amino-acid-adjacent stereochemistry to biochemical investigation and applied research intermediate preparation.
1. The spatiotemporal control of signalling and trafficking of the GLP-1R
5. Peptides as Active Ingredients: A Challenge for Cosmeceutical Industry
If you have any peptide synthesis requirement in mind, please do not hesitate to contact us at . We will endeavor to provide highly satisfying products and services.
Creative Peptides is a trusted CDMO partner specializing in high-quality peptide synthesis, conjugation, and manufacturing under strict cGMP compliance. With advanced technology platforms and a team of experienced scientists, we deliver tailored peptide solutions to support drug discovery, clinical development, and cosmetic innovation worldwide.
From custom peptide synthesis to complex peptide-drug conjugates, we provide flexible, end-to-end services designed to accelerate timelines and ensure regulatory excellence. Our commitment to quality, reliability, and innovation has made us a preferred partner across the pharmaceutical, biotechnology, and personal care industries.
Read More