(S)-Trolox

Names

[ Name ]:
(S)-Trolox

[Synonym ]:
UNII-O763YB84E3
MFCD00180756
(S)-(-)-3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carboxylic acid
(-)-(S)-6-hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid
(S)-(-)-Trolox
(S)-(-)-Trolox C
(S)-Trolox(TM)
(2S)-6-Hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid

Biological Activity

[Description]:

(S)-Trolox is a water-soluble analogue of vitamin E, in which the phytyl chain is replaced with a carboxyl group. (S)-Trolox is frequently used as a model compound for studies of structural features, as well as a standard for evaluation of antioxidant activity. (S)-Trolox has potent and specific neuroprotective and antioxidant effects[1][2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[In Vitro]

The neuroprotective efficacy of antioxidant molecules against iodoacetate (IAA) neurotoxicity in rat cerebellar granule cell (CGC) cultures is investigated. In the absence of MK-801, (S)-Trolox displays marginal neuroprotective effects. In the presence of MK-801 (10 μM), the neuroprotective efficacy of (S)-Trolox is greatly enhanced, giving rise to a recovery in MTT-reductase activity equivalent to 80–100% of control cultures. (S)-Trolox displays EC50 value of 78 μM. The fluorescence increase in IAA-stimulated DCFH-DA-loaded cultures is inhibited in a dose-dependent manner by the antioxidants (S)-Trolox with an IC50 value of 97 μM. The antioxidant (S)-Trolox demonstrate apotent and specific neuroprotective action in an in vitro model of neurodegeneration induced by inhibition of the glycolytic enzyme GAPDH[1].

[References]

[1]. Malcolm CS, et al. Characterization of iodoacetate-mediated neurotoxicity in vitro using primary cultures of rat cerebellar granule cells. Free Radic Biol Med. 2000 Jan 1;28(1):102-7.

[2]. Górecki M, et al. Chromane helicity rule--scope and challenges based on an ECD study of various trolox derivatives. Org Biomol Chem. 2014 Apr 14;12(14):2235-54.

Chemical & Physical Properties

[ Density]:
1.219g/cm3

[ Boiling Point ]:
450.3ºC at 760 mmHg

[ Melting Point ]:
160ºC (dec.)(lit.)

[ Molecular Formula ]:
C₁₄H₁₈O₄

[ Molecular Weight ]:
250.29000

[ Flash Point ]:
171ºC

[ Exact Mass ]:
250.12100

[ PSA ]:
66.76000

[ LogP ]:
2.48570

[ Index of Refraction ]:
1.567

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-37/39

[ RIDADR ]:
NONH for all modes of transport

[ 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%

Articles

Chem. Lett. , 465, (1989)

Related Compounds

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