U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C14H18O4
Molecular Weight 250.2903
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID

SMILES

CC1=C(O)C(C)=C2CCC(C)(OC2=C1C)C(O)=O

InChI

InChIKey=GLEVLJDDWXEYCO-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C14H18O4
Molecular Weight 250.2903
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Trolox (6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) is a synthetic Vitamin E analog exerting antioxidant properties. Trolox is widely used for estimation of antioxidant capacity in the assay based on electron transfer reaction. Trolox-equivalent antioxidant capacity (TEAC) assay is based on the suppression of the absorbance of radical cations of 2,2′-azinobis(3-ethylbenzothiazoline 6-sulfonate) (ABTS) by antioxidants in the test sample when ABTS incubates with a peroxidase (metmyoglobin) and hydrogen peroxide.

CNS Activity

Curator's Comment: Trolox (6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) is CNS active in animals. No human data available.

Originator

Curator's Comment: reference retrieved from http://www.sciencedirect.com/science/article/pii/S1319016417301755#b0180 | http://www.tcichemicals.com/en/in/product/tci-topics/ProductHighlights_20141110.html # Hoffmann-La Roche Inc.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Trolox equivalent antioxidant capacity of different geometrical isomers of alpha-carotene, beta-carotene, lycopene, and zeaxanthin.
2002-01-02
Plant phenolics as dietary antioxidants for herbivorous insects: a test with genetically modified tobacco.
2001-12
Mechanism of azathioprine-induced injury to hepatocytes: roles of glutathione depletion and mitochondrial injury.
2001-12
Comparison of the antioxidant effects of equine estrogens, red wine components, vitamin E, and probucol on low-density lipoprotein oxidation in postmenopausal women.
2001-11-28
Role of reactive oxygen intermediates in Japanese encephalitis virus infection in murine neuroblastoma cells.
2001-11-23
Novel potent inhibitors of lipid peroxidation with protective effects against reperfusion arrhythmias.
2001-11-22
Estimation of free radical-quenching activity of leaf pigment extracts.
2001-11-14
Wine phenolic antioxidants inhibit AP-1 transcriptional activity.
2001-11
Guava fruit (Psidium guajava L.) as a new source of antioxidant dietary fiber.
2001-11
Antioxidant activity and phenolic compounds in selected herbs.
2001-11
Studies on the constituents of Cyclanthera pedata fruits: isolation and structure elucidation of new flavonoid glycosides and their antioxidant activity.
2001-11
Glutamate induces oxidative stress not mediated by glutamate receptors or cystine transporters: protective effect of melatonin and other antioxidants.
2001-11
Antioxidative and antimutagenic activity of yeast cell wall mannans in vitro.
2001-10-18
The influence of pH on antioxidant properties and the mechanism of antioxidant action of hydroxyflavones.
2001-10-01
Development and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe.
2001-10
Attenuation of Zn2+ neurotoxicity by aspirin: role of N-type Ca2+ channel and the carboxyl acid group.
2001-10
Differential activation pattern of redox-sensitive transcription factors and stress-inducible dilator systems heme oxygenase-1 and inducible nitric oxide synthase in hemorrhagic and endotoxic shock.
2001-10
Dark and photoinduced interactions between Trolox, a polar-solvent-soluble model for vitamin E, and riboflavin.
2001-09-15
Effect of antioxidants on preservation of motility,viability and acrosomal integrity of equine spermatozoa during storage at 5 degrees C.
2001-09-01
Enhancement of hyperthermia-induced apoptosis by a free radical initiator, 2,2'-azobis (2-amidinopropane) dihydrochloride, in human histiocytic lymphoma U937 cells.
2001-09
Red wine antioxidants bind to human lipoproteins and protect them from metal ion-dependent and -independent oxidation.
2001-09
Reaction of melatonin with hemoglobin-derived oxoferryl radicals and inhibition of the hydroperoxide-induced hemoglobin denaturation in red blood cells.
2001-09
Endothelin-1 synthesis and endothelin B receptor expression in human coronary artery smooth muscle cells and monocyte-derived macrophages is up-regulated by low density lipoproteins.
2001-09
Plasma antioxidant capacity of HIV-seropositive and healthy subjects during long-term ingestion of fruit juices or a fruit-vegetable-concentrate containing antioxidant polyphenols.
2001-09
The antioxidant activity of aqueous spinach extract: chemical identification of active fractions.
2001-09
Total antioxidant status and coronary artery calcification in type 1 diabetes.
2001-09
Phototoxic process after rapid photosensitive membrane damage of 5,5"-bis(aminomethyl)-2,2':5',2"-terthiophene dihydrochloride.
2001-08-30
Oxidative stress modulates osteoblastic differentiation of vascular and bone cells.
2001-08-15
Kinetics of the chemiluminescence associated to the reaction between peroxyl radicals and proteins.
2001-08
Bioflavonoid rescue of ascorbate at a membrane interface.
2001-08
Iron overload, oxidative stress, and axonal dystrophy in brain disorders.
2001-08
Effect of processing and storage on the antioxidant ellagic acid derivatives and flavonoids of red raspberry (Rubus idaeus) jams.
2001-08
Neuroprotective and neurorescuing effects of isoform-specific nitric oxide synthase inhibitors, nitric oxide scavenger, and antioxidant against beta-amyloid toxicity.
2001-08
Oxidant stress in nephrotic syndrome: comparison of F(2)-isoprostanes and plasma antioxidant potential.
2001-08
Abnormalities of retinal metabolism in diabetes and experimental galactosemia. VII. Effect of long-term administration of antioxidants on the development of retinopathy.
2001-08
Masking of antioxidant capacity by the interaction of flavonoids with protein.
2001-08
The adenine nucleotide translocator: a target of nitric oxide, peroxynitrite, and 4-hydroxynonenal.
2001-07-19
Application of ABTS radical cation for selective on-line detection of radical scavengers in HPLC eluates.
2001-07-15
Serum proteins modified by neutrophil-derived oxidants as mediators of neutrophil stimulation.
2001-07-01
Synthesis of a triantioxidant compound: combination of beta-apo-8'-carotenoic acid, selenacapryloic acid and trolox in a triglyceride.
2001-07
Antioxidant principles from Bauhinia tarapotensis.
2001-07
1,2-bis(2-Aminophenoxy)ethane-N,N,N',N'-tetraacetic acid induces caspase-mediated apoptosis and reactive oxygen species-mediated necrosis in cultured cortical neurons.
2001-07
Role of auxin-induced reactive oxygen species in root gravitropism.
2001-07
Effects of a high-fat meal on resistance vessel reactivity and on indicators of oxidative stress in healthy volunteers.
2001-07
Hydrogen peroxide removal and glutathione mixed disulfide formation during metabolic inhibition in mesencephalic cultures.
2001-06
Ambient particulate matter induces relaxation of rat aortic rings in vitro.
2001-05
Antioxidants inhibit JNK and p38 MAPK activation but not ERK 1/2 activation by angiotensin II in rat aortic smooth muscle cells.
2001-05
H2O2-induced cell death in human glioma cells: role of lipid peroxidation and PARP activation.
2001-04
Reactive oxygen species generated by glia are responsible for neuron death induced by human immunodeficiency virus-glycoprotein 120 in vitro.
2001
The 'pivotal antioxidant' hypothesis for the role of flavonoids in their reduction of HO* radical-induced damage on DNA.
2001
Patents

Sample Use Guides

Mice: 10 mg/kg or 40 mg/kg Trolox
Route of Administration: Intraperitoneal
Trolox (2 mM) and 1 mM ascorbic acid pre-treatment significantly reduced intracellular oxidative stress, increased wound healing capacity and reduced FD-4 permeability in oxidatively stressed IPEC-J2 cell monolayers.
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:10:50 GMT 2025
Edited
by admin
on Mon Mar 31 22:10:50 GMT 2025
Record UNII
S18UL9710X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TROLOX
Preferred Name English
6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID
Systematic Name English
2H-1-BENZOPYRAN-2-CARBOXYLIC ACID, 3,4-DIHYDRO-6-HYDROXY-2,5,7,8-TETRAMETHYL-
Systematic Name English
6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID, (±)-
Common Name English
3,4-DIHYDRO-6-HYDROXY-2,5,7,8-TETRAMETHYL-2H-1-BENZOPYRAN-2- CARBOXYLIC ACID
Systematic Name English
TROLOX C
Brand Name English
(±)-6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID
Systematic Name English
(R,S)-6-HYDROXY-2,5,7,8-TETRAMETHYL-2-CHROMANECARBOXYLIC ACID
Common Name English
2H-1-BENZOPYRAN-2-CARBOXYLIC ACID, 3,4-DIHYDRO-6-HYDROXY-2,5,7,8-TETRAMETHYL-, (±)-
Systematic Name English
(±)-TROLOX
Common Name English
TROLOX [MI]
Common Name English
6-HYDROXY-2,5,7,8-TETRAMETHYL-3,4-DIHYDRO-2H-CHROMENE-2-CARBOXYLIC ACID
Systematic Name English
Code System Code Type Description
CHEBI
82625
Created by admin on Mon Mar 31 22:10:50 GMT 2025 , Edited by admin on Mon Mar 31 22:10:50 GMT 2025
PRIMARY
WIKIPEDIA
Trolox
Created by admin on Mon Mar 31 22:10:50 GMT 2025 , Edited by admin on Mon Mar 31 22:10:50 GMT 2025
PRIMARY
SMS_ID
100000145786
Created by admin on Mon Mar 31 22:10:50 GMT 2025 , Edited by admin on Mon Mar 31 22:10:50 GMT 2025
PRIMARY
EPA CompTox
DTXSID60866306
Created by admin on Mon Mar 31 22:10:50 GMT 2025 , Edited by admin on Mon Mar 31 22:10:50 GMT 2025
PRIMARY
MERCK INDEX
m12040
Created by admin on Mon Mar 31 22:10:50 GMT 2025 , Edited by admin on Mon Mar 31 22:10:50 GMT 2025
PRIMARY
EVMPD
SUB124570
Created by admin on Mon Mar 31 22:10:50 GMT 2025 , Edited by admin on Mon Mar 31 22:10:50 GMT 2025
PRIMARY
PUBCHEM
40634
Created by admin on Mon Mar 31 22:10:50 GMT 2025 , Edited by admin on Mon Mar 31 22:10:50 GMT 2025
PRIMARY
CAS
53188-07-1
Created by admin on Mon Mar 31 22:10:50 GMT 2025 , Edited by admin on Mon Mar 31 22:10:50 GMT 2025
PRIMARY
FDA UNII
S18UL9710X
Created by admin on Mon Mar 31 22:10:50 GMT 2025 , Edited by admin on Mon Mar 31 22:10:50 GMT 2025
PRIMARY
ECHA (EC/EINECS)
258-422-8
Created by admin on Mon Mar 31 22:10:50 GMT 2025 , Edited by admin on Mon Mar 31 22:10:50 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> DERIVATIVE