-Trolox Chemical Structure.png)
(R)-Trolox, a water soluble vitamin E analog, is a potent and competitive tyrosinase inhibitor with a Ki value of 0.83 mM and a ID50 value of 1.88 mM. The (R)-Trolox has stronger tyrosinase affinity than the (S) enantiomer (Ki value of 0.61 mM).
Physicochemical Properties
| Molecular Formula | C14H18O4 |
| Molecular Weight | 250.2903 |
| Exact Mass | 250.121 |
| CAS # | 53101-49-8 |
| Related CAS # | Trolox;53188-07-1;(S)-Trolox;53174-06-4 |
| PubChem CID | 6541354 |
| Appearance | White to off-white solid powder |
| Density | 1.219g/cm3 |
| Boiling Point | 450.3ºC at 760 mmHg |
| Melting Point | 162ºC (dec.)(lit.) |
| Flash Point | 171ºC |
| Index of Refraction | 1.567 |
| LogP | 2.485 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Heavy Atom Count | 18 |
| Complexity | 343 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | CC1=C(C2=C(CC[C@](O2)(C)C(=O)O)C(=C1O)C)C |
| InChi Key | GLEVLJDDWXEYCO-CQSZACIVSA-N |
| 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 |
| Chemical Name | (2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylic acid |
| HS Tariff Code | 2934.99.9001 |
| 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) |
Biological Activity
| 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]. |
| References |
[1]. Yu L. Inhibitory effects of (S)- and (R)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acids on tyrosinase activity. J Agric Food Chem. 2003 Apr 9;51(8):2344-7. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~200 mg/mL (~799.07 mM) |
| 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. 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. 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| 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 |