CAS 53188-07-1 Trolox (HCID 40634)

Overview

Trolox is 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 capacity of complex mixtures. It has a role as a ferroptosis inhibitor, an antioxidant, a radical scavenger, a neuroprotective agent and a Wnt signalling inhibitor. It is a chromanol, a monocarboxylic acid and a member of phenols.

Names & identifiers

Preferred name: Trolox
IUPAC: 6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylic acid
English name: Trolox
Molecular formula: C14H18O4
Molecular weight: 250.29

Names & synonyms

trolox53188-07-16-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acidTROLOX C3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acidS18UL9710X6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carboxylic acid6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acidCHEBI:82625DTXSID60866306(+--)-troloxRefChem:543360

Show more names

(+/-)-6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMANE-2-CARBOXYLIC ACIDtroloxcTROLOX(R)trolox tm238813-1GTROLOXTM CTrolox(R),97%Trolox, 97% 1GRTrolox, 97% 5GR

DTXCID60220823(+--)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid2h-1-benzopyran-2-carboxylic acid, 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-, (+--)-258-422-86-Hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acidMFCD0000684656305-04-52H-1-Benzopyran-2-carboxylic acid, 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-

Database identifiers

CAS: 53188-07-1、56305-04-5
PubChem CID: 40634
DTXSID: DTXSID60866306
ChEMBL: CHEMBL153
ChEBI: CHEBI:82625
UNII: S18UL9710X
EC Number: 258-422-8
Nikkaji: J236.392E

Properties

Computed structural properties

XLogP: 2.8
Topological polar surface area: 66.8 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 1
Heavy atoms: 18
Formal charge: 0
Complexity: 343

Experimental & physicochemical properties

Chemical ClassesAntioxidant

LogP2.61

Collision Cross Section149.97 Å² [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point: 187 · 187-189 °C (lit.)
Boiling point: 313.42 °C · 313.42°C (rough estimate)
Density: 1.0616 · 1.0616 (rough estimate)
refractive index: 1.497 · 1.4970 (estimate)
storage temp.: 2 · 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 · 3.35±0.20(Predicted)
color: White to faintly beige
Water Solubility: 0.5 mg/mL · water: 0.5mg/mL (slightly soluble)ethanol: 150mg/mLmethanol: soluble
BRN: 1384051 · 1384051
Stability: 1 year · 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 · 53188-07-1(CAS DataBase Reference)
FDA UNII: 18 UL9710X · S18UL9710X
EPA Substance Registry System: 3 · 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid (53188-07-1)
UNSPSC Code: 12352205 · 12352205
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 2 · 2
RTECS: 2273000 · DJ2273000
TSCA: TSCA listed
HS Code: 29339900 · 29339900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (98.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 90 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (98.9%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 2
tsca: TSCA listed
rtecs: DJ2273000
hs_code: 29339900
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2
Precautionary statements: P261-P305+P351+P338-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationNaturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.

Cellular LocationsMembrane

Uses & manufacturing

General Manufacturing Information2H-1-Benzopyran-2-carboxylic acid, 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-: ACTIVE

Applications · 4 items

DescriptionTrolox (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

UsesAn antioxidant derived from water-soluble vitamin E

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

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

Upstream & downstream products

Upstream raw materials

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

衢州润东化工有限公司0570-8789886 18892685668 · [email protected]

湖北永阔科技有限公司027-59223108 15972152991 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Additional notes · 1 item

DefinitionChEBI: 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.