Trolox

Names

[ Name ]:
Trolox

[Synonym ]:
6-Hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid
6-Hydroxy-2,5,7,8-tetramethyl-2-chromanecarboxylic acid
6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID
Trolox
6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carboxylic acid
2H-1-Benzopyran-2-carboxylic acid, 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-
MFCD00006846
EINECS 258-422-8
6-Hydroxy-2,5,7,8-tetramethyl-chroman-; 2-carboxylic acid

Biological Activity

[Description]:

Troloxa is a cell-permeable and water-soluble vitamin E analogue and is a powerful antioxidant.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

[In Vitro]

Troloxa has shown to protect mammalian cells from oxidative damage. Troloxa is effective in preventing myocyte necrosis in cell culture studies and in a canine model of two hours of left anterior descending coronary artery (LAD) occlusion followed by four hours of reperfusion[1]. Trolox could prevent oxidative stress-induced apoptosis in thymocytes. Pre- or posttreatment of cells with Trolox reduced H2O2-induced DNA fragmentation to control levels and below. [2]. Trolox is a hydrophilic analogue of alpha-tocopherol and reported to scavenge peroxyl radicals better than vitamin E in sodium dodecyl sulfate micelles and in liposomes. Trolox prolongs substantially the survival of human ventricular myocytes and hepatocyte against oxyradicals generated with xanthine oxidase plus hypoxanthine, and prevented lysis of red cells exposed to an azo-initiator[3].

[Cell Assay]

Thymocytes are treated with Trolox (10 mM) before, during, or after 10 min exposure to 10 μM H2O2. Trolox incubations that are conducted before or after H2O2 exposures are performed in TCM. Trolox treatments that are administered concurrently with H2O2 are performed in PBS with ferrous sulfate[1].

[References]

[1]. Mickle DA, et al. Myocardial salvage with trolox and ascorbic acid for an acute evolving infarction. Ann Thorac Surg. 1989 Apr;47(4):553-7.

[2]. Forrest VJ, et al. Oxidative stress-induced apoptosis prevented by Trolox. Free Radic Biol Med. 1994 Jun;16(6):675-84.

[3]. Wu TW, et al. The cytoprotective effect of Trolox demonstrated with three types of human cells. Biochem Cell Biol. 1990 Oct;68(10):1189-94.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
450.3±45.0 °C at 760 mmHg

[ Melting Point ]:
187-189ºC(lit.)

[ Molecular Formula ]:
C₁₄H₁₈O₄

[ Molecular Weight ]:
250.290

[ Flash Point ]:
171.0±22.2 °C

[ Exact Mass ]:
250.120514

[ PSA ]:
66.76000

[ LogP ]:
3.01

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.568

[ Storage condition ]:
0-6°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ2273000

CHEMICAL NAME :: 2H-1-Benzopyran-2-carboxylic acid, 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-

CAS REGISTRY NUMBER :: 53188-07-1

LAST UPDATED :: 199806

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C14-H18-O4

MOLECULAR WEIGHT :: 250.32

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAOCA7 Journal of the American Oil Chemists' Society. (Champaign, IL) V.24-56, 1947-79. Volume(issue)/page/year: 52,174,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAOCA7 Journal of the American Oil Chemists' Society. (Champaign, IL) V.24-56, 1947-79. Volume(issue)/page/year: 52,174,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1630 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAOCA7 Journal of the American Oil Chemists' Society. (Champaign, IL) V.24-56, 1947-79. Volume(issue)/page/year: 52,174,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1700 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAOCA7 Journal of the American Oil Chemists' Society. (Champaign, IL) V.24-56, 1947-79. Volume(issue)/page/year: 52,174,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1930 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAOCA7 Journal of the American Oil Chemists' Society. (Champaign, IL) V.24-56, 1947-79. Volume(issue)/page/year: 52,174,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAOCA7 Journal of the American Oil Chemists' Society. (Champaign, IL) V.24-56, 1947-79. Volume(issue)/page/year: 52,174,1975

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36

[ WGK Germany ]:
2

[ RTECS ]:
DJ2273000

[ HS Code ]:
2932999099

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%