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| Targets |
3-Phenyllactic acid does not have a single well-defined molecular target but exhibits broad-spectrum antimicrobial activity. Its mechanism of action involves disruption of microbial cell membranes and interference with metabolic processes. The compound is a reagent involved in biological studies of enantioselectivity of lipase in transesterification and oxidation by glycolate oxidase and catalase. It can be used as a feed additive to replace antibiotics in livestock feeds.
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| ln Vitro |
One common organic acid found in honey and meals fermented by lactic acid bacteria is called DL-3-Phenyllactic Acid (PLA). Many different microorganisms, particularly lactic acid bacteria, are capable of producing it. With a wide range of effective antibacterial action against both bacteria and fungi, DL-3-phenyllactic acid has shown to be an excellent antimicrobial chemical. Furthermore, DL-3-phenyllactic acid has the potential to serve as a feed additive in substitution of antibiotics in animal feed [1].
- Antibacterial activity: PLA inhibits Listeria monocytogenes growth in culture medium, milk, and cheese. It reduced bacterial population by 4.5 log in ultra-high-temperature treatment whole milk after 5 days of culture. It also inhibits Gram-positive bacteria (Staphylococcus aureus, Enterococcus faecalis, Bacillus cereus) and Gram-negative bacteria (Salmonella enterica, Escherichia coli, Providencia stuartii, Klebsiella oxytoca). Higher inhibitory effect is observed at acidic pH. The mechanism is suggested to involve bacterial cell wall damage, as scanning electron microscopy showed damaged or broken cell wall, cell swelling and collapse. D-PLA showed slightly higher anti-Listeria activity than L-PLA. [1] - Antifungal activity: PLA inhibits yeasts (Candida pulcherrima, Candida parapsilosis, Rhodotorula mucilaginosa) and moulds (Aspergillus ochraceus, Penicillium roqueforti, Penicillium citrinu). MIC values for antiyeast activity are 50 to >500 mM at pH 4.0 to 6.0, and MIC against moulds at pH 4.0 is 45 mM. [1] In vitro, 3-phenyllactic acid is a broad-spectrum antimicrobial compound active against bacteria and fungi. Its antimicrobial activity has been characterized in susceptibility testing assays against various pathogens. The compound is a reagent involved in biological studies of enantioselectivity of lipase in transesterification and oxidation by glycolate oxidase and catalase. It is an ideal antimicrobial compound with broad and effective antimicrobial activity. |
| ln Vivo |
In vivo, 3-phenyllactic acid can be used as a feed additive to replace antibiotics in livestock feeds. Its broad-spectrum antimicrobial activity makes it a potential alternative to conventional antibiotics in animal husbandry. The compound is a common organic acid found in honey and fermented foods. However, specific in vivo efficacy data from animal models are limited in publicly available sources.
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| Enzyme Assay |
No detailed enzyme assay protocols are provided. However, the review mentions that lactate dehydrogenases (LDHs) from various strains can convert phenylpyruvic acid (PPA) to PLA. Kinetic parameters for some LDHs are given (see Table 3 and 4). For example, D-LDH from P. pentosaceus ATCC 25745: Km for phenylpyruvate = 1.73 mM, kcat = 173 s⁻¹, kcat/Km = 100 mM⁻¹s⁻¹. D-LDH from P. acidilactici DSM 20284: Km = 2.92 mM, kcat = 305 s⁻¹, kcat/Km = 105 mM⁻¹s⁻¹. Mutant L. pentosus D-LDH (Y52L): Km for phenylpyruvate = 0.067 mM, kcat/Km = not reported. Also D-HicDH from L. casei and D-ManDH from L. curvatus show Km for phenylpyruvate of 0.15 mM. No assay conditions described. [1]
In non-cell-based biochemical assays, 3-phenyllactic acid's antimicrobial activity is evaluated using standard susceptibility testing methods such as broth microdilution or agar diffusion assays. Minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) are determined against various bacterial and fungal pathogens. Its effects on enzyme activity (such as lipase, glycolate oxidase, and catalase) are assessed using enzyme assays. |
| Cell Assay |
In vitro cellular assays for 3-phenyllactic acid involve testing its effects on cultured microbial cells. Bacterial and fungal cultures are treated with varying concentrations of the compound, and growth inhibition is assessed by optical density measurements or colony counting. The compound's effects on microbial cell membrane integrity and metabolic activity may also be evaluated. However, specific cellular assay data are limited in publicly available sources.
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| Animal Protocol |
In vivo animal studies for 3-phenyllactic acid have been conducted in the context of its use as a feed additive. The compound is typically administered via feed or water, and its effects on animal growth, health, and microbial populations are assessed. Its potential to replace antibiotics in livestock feeds has been investigated. However, specific protocols and data are limited in publicly available sources.
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| ADME/Pharmacokinetics |
3-Phenyllactic acid has a molecular weight of 166.18 and a molecular formula of C9H10O3. It is an alpha-hydroxy analogue of phenylalanine. The compound is a broad-spectrum antimicrobial active against bacteria and fungi. It is produced by lactic acid bacteria and found in honey and fermented foods. The compound is typically stored as a powder at -20°C for long-term stability.
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| Toxicity/Toxicokinetics |
As a research compound and potential feed additive, 3-phenyllactic acid is not intended for human therapeutic use and should be handled with appropriate safety precautions. Comprehensive toxicology studies have not been extensively published, but the compound is generally considered safe for laboratory use. It should be stored and handled in accordance with standard laboratory safety guidelines.
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| References | |
| Additional Infomation |
3-Phenylonic acid is a 2-hydroxy monocarboxylic acid formed by replacing a methyl hydrogen atom in the lactic acid molecule with a phenyl group. It is a human metabolite, functionally related to racemic lactic acid, and is the conjugate acid of 3-phenyllactic acid. It has been reported that DL-3-phenyllactic acid is found in Rosa taiwanensis, rye (Secale cereale), and other organisms with relevant data.
PLA is naturally present in honey (especially thistle, heather, manuka) and in LAB-fermented foods. It is produced from phenylalanine via transamination to phenylpyruvic acid (PPA) and subsequent reduction by dehydrogenases. The metabolic pathway in LAB involves aromatic aminotransferase and α-ketoglutarate. PLA can be produced by various microorganisms including Lactobacillus, Enterococcus, Weissella, Leuconostoc, Propionibacterium, Bacillus coagulans, Geotrichum candidum, and Brevibacterium lactofermentum. High-level bioproduction has been achieved by fermentation with PPA feeding (e.g., Lactobacillus sp. SK007 produced 17.38 g/L PLA; B. coagulans SDM produced 37.3 g/L). Measurement methods include reverse-phase HPLC, GC/MS, capillary electrophoresis, and chiral HPLC for enantiomer separation. Potential applications include feed additives (improving growth performance, immune response, reducing E. coli in pigs and chickens), and pharmaceutical use for coronary disease and skin wrinkles. [1] 3-Phenyllactic acid (DL-3-Phenyllactic acid, PhLA) is an alpha-hydroxy analogue of phenylalanine and a broad-spectrum antimicrobial compound active against bacteria and fungi. It is produced by lactic acid bacteria and found in honey and fermented foods. The compound can be used as a feed additive to replace antibiotics in livestock feeds. 3-Phenyllactic acid is not an approved drug and is intended for research use only. |
| Molecular Formula |
C9H10O3
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| Molecular Weight |
166.17
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| Exact Mass |
166.062
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| CAS # |
828-01-3
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| Related CAS # |
57618-25-4 (mono-Na salt);57618-26-5 (Ca salt)
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| PubChem CID |
3848
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
331.6±22.0 °C at 760 mmHg
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| Melting Point |
95-98 °C
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| Flash Point |
168.5±18.8 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.577
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| LogP |
1.05
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
12
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| Complexity |
150
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
VOXXWSYKYCBWHO-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)
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| Chemical Name |
Benzenepropanoic acid, alpha-hydroxy-
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| Synonyms |
3Phenyllactic acid3 Phenyllactic acid 3-Phenyllactic acid NSC-2627 NSC2627NSC 2627Ba 2653 Ba-2653 Ba2653
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~125 mg/mL (~752.20 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (12.52 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (12.52 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (12.52 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.0179 mL | 30.0897 mL | 60.1793 mL | |
| 5 mM | 1.2036 mL | 6.0179 mL | 12.0359 mL | |
| 10 mM | 0.6018 mL | 3.0090 mL | 6.0179 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT05887544 | COMPLETED | Other: Exposure: Plant-based diet pattern Other: Intervention: Fermented dairy products Other: Exposure: individual foods and food groups |
Diabetes Mellitus, Type 2 | University of Copenhagen | 2023-06-01 | |
| NCT05067465 | COMPLETED | Dietary Supplement: Selected food groups | Healthy Lifestyle | University of Jena | 2021-10-14 | Not Applicable |
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