| Identification | More | [Name]
6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID | [CAS]
53188-07-1 | [Synonyms]
6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID
(+/-)-6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMANE-2-CARBOXYLIC ACID
TIMTEC-BB SBB005933
TROLOX
TROLOX(R)
TROLOXTM C
3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2h-1-benzopyran-2-carboxylicaci
troloxc
(+/-)-6-HYDROXY-2,5,7,8-TETRAMETHYL-CHRO M.-2-CARBOXYL.AC
trolox tm
3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid
rac-2,5,7,8-Tetramethyl-6-hydroxychroman-2α*-carboxylic acid | [EINECS(EC#)]
258-422-8 | [Molecular Formula]
C14H18O4 | [MDL Number]
MFCD00006846 | [Molecular Weight]
250.29 | [MOL File]
53188-07-1.mol |
| Chemical Properties | Back Directory | [Appearance]
white to fainly beige crystalline powder | [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. ]
0-6°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. | [Cosmetics Ingredients Functions]
SKIN CONDITIONING | [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) |
| Hazard Information | Back Directory | [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]
Trolox(53188-07-1) is a Vitamin E analog that also maintains the antioxidant capabilities which Vitamin E shows.
| [Uses]
An antioxidant derived from water-soluble vitamin E | [Application]
Trolox(53188-07-1) 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.
| [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. | [General Description]
(±)-6-Hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid (Trolox) exhibits radical scavenging and antioxidant activities. | [Mechanism of action]
Trolox(53188-07-1) 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) Massey et al. (1990), Free radical damage in neonatal rat cardiac myocyte cultures: effects of alpha-tocopherol, Trolox and phytol; Free Radic. Biol. Med., 8 449
2) Chen et al. (1998), Cytotoxicity and apoptosis produced by cytochrome P450 2E1 in Hep G2 cells; Mol. Pharmacol., 53 638
3) Brookes et al. (1996), Trolox inhibits peroxynitrite-mediated oxidative stress and apoptosis in rat thymocytes; Arch. Biochem. Biophys., 333 482 |
|
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