| Size | Price | Stock | Qty |
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| 100mg |
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| 250mg |
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| 500mg |
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| 1g |
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| Other Sizes |
| Targets |
tyrosinase (mushroom tyrosinase): competitive inhibition, Ki = 0.83 mM, ID50 = 1.88 mM [1]
Tyrosinase - competitive inhibitor. |
|---|---|
| ln Vitro |
In comparison to controls without inhibitors, DMSO reduced tyrosinase activity at test levels (100 and 200 µL) in a total volume of 3.0 mL. Mushroom tyrosinase is inhibited by DMSO in a dose-dependent way. Tyrosinase activity was further reduced by adding two amounts of DMSO to tyrosinase digests containing (R)-Trolox ((R)-HTCCA). Additionally, DMSO has a dose-dependent effect on the inhibition of (R)-Trolox tyrosinase [1].
(R)-HTCCA inhibited mushroom tyrosinase activity in a dose-dependent manner. The ID50 value (concentration required to reduce tyrosinase activity to 50% of the control) was 1.88 mM. Kinetic analysis revealed that (R)-HTCCA acts as a competitive inhibitor of tyrosinase with respect to the substrate L-DOPA, with an inhibition constant (Ki) of 0.83 mM. The apparent Km and Vm of the L-DOPA oxidation reaction catalyzed by tyrosinase were 0.34 mM and 0.21 ΔA475nm/min, respectively. The presence of DMSO (dimethyl sulfoxide) further enhanced the inhibitory effect of (R)-HTCCA in a dose-dependent manner. [1] In vitro enzymatic assays demonstrate that (R)-Trolox is a competitive inhibitor of tyrosinase, the key enzyme in melanin biosynthesis. The compound exhibits a Ki of 0.83 mM and an ID50 of 1.88 mM, showing stronger affinity for tyrosinase than its (S)-enantiomer (Ki = 0.61 mM). By inhibiting tyrosinase, (R)-Trolox reduces melanin production, making it useful for studying melanogenesis regulation. The compound also functions as an antioxidant, scavenging free radicals and protecting against oxidative stress. The stereoselective interaction of (R)-Trolox with tyrosinase makes it valuable for studying enzyme-inhibitor interactions. |
| ln Vivo |
In vivo studies on (R)-Trolox are limited, as the compound is primarily used as a research tool for in vitro investigations of tyrosinase inhibition and antioxidant activity. The compound's antioxidant properties suggest potential applications in skin-whitening and anti-aging products, where it may reduce melanin production and protect against oxidative damage. However, detailed pharmacokinetic and efficacy data in animal models are limited. The compound is widely used in cosmetic and pharmaceutical research for its tyrosinase inhibitory and antioxidant activities.
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| Enzyme Assay |
For kinetic analysis: The tyrosinase reaction mixtures contained 0.5-2.0 mM L-DOPA, 0.1 M phosphate buffer (pH 6.8), and a final concentration of (R)-HTCCA (0.45 or 0.90 mM) in a total volume of 3.0 mL. The reaction was initiated by adding 125 U of mushroom tyrosinase and carried out at 25°C. The increase in absorbance at 475 nm (due to L-DOPA oxidation) was measured at 0.5, 1.0, 1.5, and 2.0 min. The initial velocity (vi) for each reaction was determined by linear least squares analysis of the plot of absorbance at 475 nm vs. time. Kinetic parameters were obtained using Hanes-Woolf plots ([S]/vi vs [S]), and the Ki value for (R)-HTCCA was derived from a secondary plot of apparent Km against inhibitor concentrations. [1]
For ID50 determination: Eight concentrations of (R)-HTCCA (0, 0.19, 0.39, 0.58, 0.88, 1.22, 1.70, and 2.19 mM) were tested. The reaction mixture contained 0.8 mM L-DOPA, 0.1 M phosphate buffer (pH 6.8), 67 U/mL mushroom tyrosinase, and the specified concentration of (R)-HTCCA in a final volume of 1.85 mL. Absorbance at 475 nm was measured against a pure water blank at 0.5 and 1 min of the reaction. The percent tyrosinase activity remaining was plotted against the inhibitor concentration to obtain the ID50 value. Triplicate reactions were performed for each concentration. [1] Tyrosinase inhibition assays are performed using mushroom tyrosinase enzyme and L-DOPA or L-tyrosine as substrates. The enzyme is incubated with the substrate and varying concentrations of (R)-Trolox, and the production of melanin or dopachrome is measured spectrophotometrically. Ki and ID50 values are calculated from dose-response curves. The stereoselectivity of inhibition is assessed by comparing the activity of (R)-Trolox with its (S)-enantiomer. Antioxidant activity is assessed using DPPH, ABTS, or FRAP assays, where the compound's ability to scavenge free radicals is measured. |
| Cell Assay |
Cellular assays for (R)-Trolox typically involve culturing melanocytes or melanoma cell lines and treating them with the compound at various concentrations. Melanin production is measured by spectrophotometric determination of melanin content in cell pellets or culture supernatants. Tyrosinase activity in cell lysates is measured using L-DOPA as a substrate. Cell viability is assessed using MTT or CellTiter-Glo assays to evaluate cytotoxicity. Antioxidant activity is assessed by measuring intracellular reactive oxygen species (ROS) levels using fluorescent probes such as DCFH-DA. Cytotoxicity against normal cells is assessed in parallel to evaluate selectivity.
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| Animal Protocol |
In vivo efficacy of (R)-Trolox is evaluated in animal models of hyperpigmentation or oxidative stress. For skin-whitening studies, guinea pig or mouse models of UV-induced pigmentation are used, and the compound is applied topically. Skin pigmentation is assessed by visual scoring, colorimetry, or histological examination of melanin content. For antioxidant studies, animal models of oxidative stress such as ischemia-reperfusion injury or chemically induced oxidative damage are used, and endpoints include measurement of oxidative stress markers (malondialdehyde, glutathione) and histopathological examination of affected tissues. The compound's topical application and antioxidant properties support its use in dermatological research.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of (R)-Trolox have been characterized in the context of its use as a vitamin E analogue and antioxidant. The compound has a molecular weight of 250.29 and is soluble in organic solvents. As a lipophilic compound, (R)-Trolox is expected to be absorbed and distributed in biological systems. Key PK parameters including half-life, clearance, and bioavailability are determined using HPLC or LC-MS analysis of plasma and tissue samples following administration. The compound's ability to penetrate the skin is important for its topical applications in skin-whitening and antioxidant products.
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| Toxicity/Toxicokinetics |
Toxicological evaluation of (R)-Trolox has been conducted in the context of its use as a vitamin E analogue and antioxidant in food, cosmetic, and pharmaceutical products. The compound is generally considered safe for use at appropriate concentrations. Standard toxicology assessments include acute and repeated-dose toxicity studies, skin irritation and sensitization tests, and evaluation of effects on liver and kidney function. The compound's safety profile supports its use in cosmetic and pharmaceutical research applications. However, comprehensive toxicology data for pharmaceutical applications may be limited, and caution is advised for research use.
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| References | |
| Additional Infomation |
(R)-HTCCA is a water-soluble analogue of vitamin E (Trolox) and has been used as a water-soluble antioxidant standard. The compound showed potential for use as a tyrosinase inhibitor in food, cosmetic, and medicinal products due to its water solubility and presumed lower safety concerns. The study noted that the ID50 measurements were not performed at reaction equilibrium because melanin pigments are water-insoluble and precipitate. Additionally, the research used mushroom tyrosinase, and it was mentioned that tyrosinases from different sources may differ in structure and properties. The inhibitory activity reported is specifically against the diphenolase activity of mushroom tyrosinase. DMSO, a common solvent, was found to dose-dependently inhibit tyrosinase activity and to further enhance the inhibition by (R)-HTCCA, indicating a need for improved solvent systems in future tyrosinase inhibition studies. [1]
(R)-Trolox is a vitamin E analogue and a competitive tyrosinase inhibitor used in skin-whitening, antioxidant, and enzymology research. The compound is widely used to study melanogenesis regulation, oxidative stress modulation, and stereoselective enzyme-inhibitor interactions. (R)-Trolox demonstrates stronger affinity for tyrosinase than its (S)-enantiomer, making it valuable for studying stereoselectivity in enzyme inhibition. The compound is also used as an antioxidant in food, cosmetic, and pharmaceutical products. (R)-Trolox is not approved as a drug but is used as a research chemical and as an active ingredient in some cosmetic products. Its primary applications are in dermatological and antioxidant research. |
| Molecular Formula |
C14H18O4
|
|---|---|
| Molecular Weight |
250.2903
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| Exact Mass |
250.121
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| CAS # |
53101-49-8
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| Related CAS # |
Trolox;53188-07-1;(S)-Trolox;53174-06-4
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| PubChem CID |
6541354
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| Appearance |
White to off-white solid powder
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| Density |
1.219g/cm3
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| Boiling Point |
450.3ºC at 760 mmHg
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| Melting Point |
162ºC (dec.)(lit.)
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| Flash Point |
171ºC
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| Index of Refraction |
1.567
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| LogP |
2.485
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
18
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| Complexity |
343
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| Defined Atom Stereocenter Count |
1
|
| SMILES |
CC1=C(C2=C(CC[C@](O2)(C)C(=O)O)C(=C1O)C)C
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| InChi Key |
GLEVLJDDWXEYCO-CQSZACIVSA-N
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| InChi Code |
InChI=1S/C14H18O4/c1-7-8(2)12-10(9(3)11(7)15)5-6-14(4,18-12)13(16)17/h15H,5-6H2,1-4H3,(H,16,17)/t14-/m1/s1
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| Chemical Name |
(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylic 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 : ~200 mg/mL (~799.07 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.25 mg/mL (8.99 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 22.5 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. Solubility in Formulation 2: ≥ 2.25 mg/mL (8.99 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 22.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (8.31 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. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9954 mL | 19.9768 mL | 39.9537 mL | |
| 5 mM | 0.7991 mL | 3.9954 mL | 7.9907 mL | |
| 10 mM | 0.3995 mL | 1.9977 mL | 3.9954 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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