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
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)
| 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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23385959
Curator's Comment: Trolox (6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid) is CNS active in animals. No human data available.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Trolox equivalent antioxidant capacity of different geometrical isomers of alpha-carotene, beta-carotene, lycopene, and zeaxanthin. | 2002-01-02 |
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| Plant phenolics as dietary antioxidants for herbivorous insects: a test with genetically modified tobacco. | 2001-12 |
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| Mechanism of azathioprine-induced injury to hepatocytes: roles of glutathione depletion and mitochondrial injury. | 2001-12 |
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| 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 |
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| Role of reactive oxygen intermediates in Japanese encephalitis virus infection in murine neuroblastoma cells. | 2001-11-23 |
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| Novel potent inhibitors of lipid peroxidation with protective effects against reperfusion arrhythmias. | 2001-11-22 |
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| Estimation of free radical-quenching activity of leaf pigment extracts. | 2001-11-14 |
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| Wine phenolic antioxidants inhibit AP-1 transcriptional activity. | 2001-11 |
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| 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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27895554
Mice: 10 mg/kg or 40 mg/kg Trolox
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25745867
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
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admin
on
Edited
Mon Mar 31 22:10:50 GMT 2025
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Mon Mar 31 22:10:50 GMT 2025
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| Record UNII |
S18UL9710X
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| Record Status |
Validated (UNII)
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| Record Version |
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Trolox
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258-422-8
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