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| Targets |
(R)-Mandelic acid is a chiral alpha-hydroxy acid that interacts with various biological targets. It has been reported to have the health functions of killing sperm, reducing Yin (a traditional concept), inhibiting bacteria, and possessing anti-inflammatory activity. The compound exhibits antioxidant and anti-inflammatory activities by reducing the liberation of auto-antigens, oxygen free radicals, and pro-inflammatory mediators, resulting in inhibition of protein denaturation. Its stereochemistry plays a critical role in its biological activity. As a human xenobiotic metabolite, it is a conjugate acid of (R)-mandelate.
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| ln Vitro |
In vitro, (R)-mandelic acid demonstrates antimicrobial and anti-inflammatory properties. It has been shown to inhibit bacterial growth and reduce inflammation in various cell-based models. The compound's antioxidant activity is attributed to its ability to scavenge free radicals and reduce oxidative stress. (R)-Mandelic acid reduces the liberation of auto-antigens and pro-inflammatory mediators, resulting in the inhibition of protein denaturation, which is favorable for dismissing pain associated with arthritis. The compound's gentle exfoliating effects are due to its ability to break down the bonds between dead skin cells, promoting cell turnover.
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| ln Vivo |
In vivo, (R)-mandelic acid has been studied for its antimicrobial and anti-inflammatory effects. It has the health function of inhibiting bacteria and reducing inflammation. The compound's antioxidant and anti-inflammatory activities contribute to its potential in dismissing pain related to arthritis. Due to its antimicrobial properties and gentle exfoliating effects, it is used in skincare formulations to treat acne, hyperpigmentation, and signs of aging. For in vivo formulation, (R)-mandelic acid can be prepared in 10% DMSO + 40% PEG300 + 5% Tween 80 + 45% saline at 2 mg/mL.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for (R)-mandelic acid are not extensively documented, as the compound is primarily studied for its antimicrobial and anti-inflammatory properties rather than specific receptor binding. However, its antioxidant activity can be assessed using assays that measure the scavenging of free radicals, such as DPPH or ABTS assays. The compound's inhibition of protein denaturation can be evaluated using standard protein denaturation assays, where the compound's ability to prevent heat-induced denaturation of proteins such as bovine serum albumin is measured. These assays provide insights into the compound's anti-inflammatory mechanisms.
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| Cell Assay |
In vitro cell-based assays for (R)-mandelic acid evaluate its antimicrobial and anti-inflammatory activities. For antimicrobial studies, bacterial cultures are treated with serial dilutions of the compound, and the minimum inhibitory concentration (MIC) is determined. For anti-inflammatory studies, cells such as macrophages are treated with (R)-mandelic acid and stimulated with lipopolysaccharide (LPS) to induce inflammation. The production of pro-inflammatory cytokines (e.g., TNF-α, IL-6) is measured by ELISA. The compound's effects on cell viability are assessed using MTT or LDH release assays. The compound's gentle exfoliating effects can be evaluated using skin cell models.
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| Animal Protocol |
In vivo animal experiments for (R)-mandelic acid have not been extensively reported, as the compound is primarily used in cosmetic and topical applications rather than systemic therapeutic studies. For potential in vivo studies, the compound can be formulated in 10% DMSO + 40% PEG300 + 5% Tween 80 + 45% saline at 2 mg/mL for administration. The compound's anti-inflammatory effects could be evaluated in animal models of inflammation, such as carrageenan-induced paw edema. Its antimicrobial effects could be assessed in models of bacterial infection. Comprehensive in vivo studies are needed to fully characterize the compound's pharmacological effects.
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| ADME/Pharmacokinetics |
Pharmacokinetic (PK) data for (R)-mandelic acid are limited. The compound has a molecular weight of 152.15 g/mol and is highly soluble in water (50 mg/mL) and DMSO (60 mg/mL). As a small, hydrophilic molecule, it is expected to be rapidly absorbed and eliminated. The compound is a human xenobiotic metabolite, suggesting that it is processed by normal metabolic pathways. For topical applications, (R)-mandelic acid is absorbed through the skin and exerts local effects. Comprehensive ADME studies are needed to fully characterize its systemic pharmacokinetics.
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| Toxicity/Toxicokinetics |
The toxicity profile of (R)-mandelic acid is generally considered favorable, as it is used in cosmetic and skincare products at safe concentrations. The compound has been shown to have low toxicity in cell culture. However, like other alpha-hydroxy acids, it can cause skin irritation at high concentrations or with prolonged use. It should be used with appropriate safety precautions in laboratory settings. For research use only, not for human or veterinary therapeutic use. Comprehensive toxicological studies are needed to fully characterize the safety profile of (R)-mandelic acid.
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| References |
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| Additional Infomation |
(R)-Mandrine is the (R)-enantiomer of mandelic acid. It is a human heterologous metabolite. It is the conjugate acid of (R)-mandelic acid ester and the enantiomer of (S)-mandelic acid. (R)-Mandrine has been reported in Pisolithus tinctorius, Pisolithus arhizus, and other organisms with relevant data. See also: (R)-Mandrine ester (note moved here).
(R)-Mandelic acid (D-(-)-Mandelic acid) is the (R)-enantiomer of mandelic acid, an aromatic alpha-hydroxy acid with antimicrobial, anti-inflammatory, and antioxidant properties. It has a molecular formula of C₈H₈O₃ and a molecular weight of 152.15 g/mol. The compound is used in skincare formulations to treat acne, hyperpigmentation, and signs of aging due to its gentle exfoliating effects. It also has a role as a human xenobiotic metabolite. (R)-Mandelic acid is soluble in water (50 mg/mL) and DMSO (60 mg/mL). It is for research use only and is not intended for human consumption. |
| Molecular Formula |
C8H8O3
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| Molecular Weight |
152.1473
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| Exact Mass |
152.047
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| CAS # |
611-71-2
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| PubChem CID |
11914
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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 |
321.8±22.0 °C at 760 mmHg
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| Melting Point |
130-134ºC
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| Flash Point |
162.6±18.8 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.591
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| LogP |
0.92
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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 |
2
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| Heavy Atom Count |
11
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| Complexity |
138
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C1=CC=C(C=C1)[C@H](C(=O)O)O
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| InChi Key |
IWYDHOAUDWTVEP-SSDOTTSWSA-N
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| InChi Code |
InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1
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| Chemical Name |
(2R)-2-hydroxy-2-phenylacetic acid
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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 : ~100 mg/mL (~657.25 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.43 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 25.0 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: ≥ 2.5 mg/mL (16.43 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 25.0 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: ≥ 2.5 mg/mL (16.43 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 | 6.5725 mL | 32.8623 mL | 65.7246 mL | |
| 5 mM | 1.3145 mL | 6.5725 mL | 13.1449 mL | |
| 10 mM | 0.6572 mL | 3.2862 mL | 6.5725 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.
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