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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] |
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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]
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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] |
| 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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