Trolox Chemical Properties

Melting point:

187-189 °C (lit.)

Boiling point:

313.42°C (rough estimate)

Density 

1.0616 (rough estimate)

refractive index 

1.4970 (estimate)

storage temp. 

2-8°C

solubility 

Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml). Also soluble in Water at alkalinepH.

form 

Crystalline Powder

pka

3.35±0.20(Predicted)

color 

White to faintly beige

Water Solubility 

water: 0.5mg/mL (slightly soluble)
ethanol: 150mg/mL
methanol: soluble

BRN 

1384051

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.

InChI

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)

InChIKey

GLEVLJDDWXEYCO-UHFFFAOYSA-N

SMILES

C1(C)(C(O)=O)OC2=C(C)C(C)=C(O)C(C)=C2CC1

CAS DataBase Reference

53188-07-1(CAS DataBase Reference)

EPA Substance Registry System

3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid (53188-07-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

DJ2273000

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Trolox Usage And Synthesis

Description

Trolox (53188-07-1) is a water soluble derivative of vitamin E. Displays antioxidant and radical scavenging activities.1 Prevents lipid peroxidation induced by CYP2E1 in Hep G2 cells.2 Trolox inhibits peroxynitrite-mediated oxidative stress and apoptosis in rat thymocytes.3

Chemical Properties

white to fainly beige crystalline powder

Uses

An antioxidant derived from water-soluble vitamin E

Uses

Trolox is a Vitamin E analog that also maintains the antioxidant capabilities which Vitamin E shows. Neuroprotective product.

Definition

ChEBI: A chromanol that is 6-hydroxychromane which is substituted by a carboxy group at position 2 and by methyl groups at positions 2, 5, 7, and 8. A cell-permeable, water-soluble analogue of vitamin E, it is used as a standard for measuring the antioxidant capa ity of complex mixtures.

Application

Trolox is a cell-permeable, water-soluble derivative of vitamin E with potent antioxidant properties. lt is commonly used as a standard or positive control in antioxidant assays.  In addition, trolox is used to assessthe role of oxidative injury in processes like neuronal cell death and aging.  It is effective as adjunctivetherapy in the treatment of certain cancers.

General Description

(±)-6-Hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid (Trolox) exhibits radical scavenging and antioxidant activities.

Mechanism of action

Trolox can protect against oxidative stress, genotoxicity and inflammation induced by CS through ROS scavenging mechanism, and serve as a potential antioxidant prevention strategy against oxidative injury of ATII cells in CS-related lung diseases.

Synthesis

Example 7: Synthesis of 6-hydroxy-2,5,7,8-tetramethylbenzodihydropyran-2-carboxylic acid The 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid ester (137.3 kg) obtained in Example 6 was dissolved in methanol (137.3 kg) in a 2000 L reactor equipped with a glass liner. Subsequently, a solution containing water (411 kg) and sodium hydroxide (27 kg) was slowly added dropwise to the reaction mixture over a period of 2 hours and the hydrolysis reaction was carried out at 80 °C for 2 hours. After completion of the reaction, the hydrolysis mixture was neutralized with a solution of potassium bisulfate (91.9 kg) dissolved in water (411.9 kg) at 80 °C for 2 hours. The reaction mixture was separated by centrifugation and the obtained crystals were collected and dried using a conical dryer to finally obtain 6-hydroxy-2,5,7,8-tetramethylbenzodihydropyran-2-carboxylic acid (130.2 kg) in white powder form. The reaction score based on 6-hydroxy-2,3,5-trimethylbenzene and the results of high performance liquid chromatography (HPLC) analysis were as follows: Conversion yield: 99.9% Separation yield: 99.3% Chemical purity: 99.6%

storage

Store at +4°C

References

[1] KENNETH D. MASSEY  Karen P B. Free radical damage in neonatal rat cardiac myocyte cultures: Effects of α-tocopherol, trolox, and phytol[J]. Free Radical Biology and Medicine, 1990, 8 5: Pages 449-458. DOI:10.1016/0891-5849(90)90058-q
[2] Q CHEN A I C. Cytotoxicity and apoptosis produced by cytochrome P450 2E1 in Hep G2 cells.[J]. Molecular Pharmacology, 1998, 53 4: 638-648. DOI:10.1124/mol.53.4.638
[3] MARIA G. SALGO  William A P. Trolox Inhibits Peroxynitrite-Mediated Oxidative Stress and Apoptosis in Rat Thymocytes[J]. Archives of biochemistry and biophysics, 1996, 333 2: Pages 482-488. DOI:10.1006/abbi.1996.0418

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