72107-05-2

Usage

Uses

Used in Rubber Industry:
2,2,4-Trimethyl-1,2-dihydro-quinolin-6-ol is used as an antioxidant for rubber products such as tires and conveyor belts. It provides protection against heat and oxygen ageing, delaying the onset of cracking and deterioration, and thus extending the lifespan and performance of these products.
Used in Polymer-based Materials:
2,2,4-Trimethyl-1,2-dihydro-quinolin-6-ol has potential applications as an antioxidant in other polymer-based materials. Its ability to capture and neutralize free radicals can help prevent the degradation of these materials, enhancing their durability and performance.
Used in Lubricants:
TMQ also shows promise as an antioxidant in lubricants. By neutralizing free radicals, it can help maintain the quality and performance of lubricants, reducing wear and tear on machinery and extending their service life.

InChI:InChI=1/C12H15NO/c1-8-7-12(2,3)13-11-5-4-9(14)6-10(8)11/h4-7,13-14H,1-3H3

Upstream product

• 91-53-2 Ethoxyquin 
• 16489-90-0 6-ethoxy-2,2,4-trimethyl-1,3-dihydroquinoline 
• 7732-18-5 water 
• 3763-77-7 2,2,4-trimethyl-6-ethoxy-1,2-dihydroquinoline 

Downstream Products

• 4071-18-5 2,2,4-trimethyl-6-oxo-2,6-dihydroquinoline 
• 74-31-7 N,N'-diphenyl-1,4-phenylenediamine 
• 79787-62-5 1,2-dihydro-2,2,4-trimethyl-6-quinolinyl retinoate 
• 1203564-77-5 1-(3-methylbenzyl)-1,2-dihydro-2,2,4-trimethylquinolin-6-ol 
• 1203564-59-3 6-(3,5-dimethoxybenzyloxy)-1,2-dihydro-2,2,4-trimethylquinoline 
• 1203564-69-5 1-(3,5-dimethoxybenzyl)-1,2-dihydro-2,2,4-trimethylquinolin-6-ol 
• 1203564-68-4 1-benzyl-1,2-dihydro-2,2,4-trimethylquinolin-6-ol 
• 1203564-60-6 6-(4-methoxybenzyloxy)-1,2-dihydro-2,2,4-trimethylquinoline 
• 1203564-79-7 1-(4-fluorobenzyl)-1,2-dihydro-2,2,4-trimethylquinolin-6-ol 
• 1203564-72-0 1-(3,4-dichlorobenzyl)-1,2-dihydro-2,2,4-trimethylquinolin-6-ol 
• 1203564-81-1 1-(4-tert-butylbenzyl)-1,2-dihydro-2,2,4-trimethylquinolin-6-ol 
• 1203564-61-7 6-(2-methoxybenzyloxy)-1,2-dihydro-2,2,4-trimethylquinoline 
• 1203564-73-1 1-(4-methylbenzyl)-1,2-dihydro-2,2,4-trimethylquinolin-6-ol 
• 1203564-58-2 1,2-dihydro-2,2,4-trimethyl-6-(phenethyloxy)quinoline 

Relevant academic research and scientific papers

Neuroprotective effect of 6-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline mediated via regulation of antioxidant system and inhibition of inflammation and apoptosis in a rat model of cerebral ischemia/reperfusion

The aim of the study was the assessment of the neuroprotective potential of 6-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline (DHQ) and its effect on inflammation, apoptosis, and transcriptional regulation of the antioxidant system in cerebral ischemia/reperfusion (CIR) in rats. The CIR rat model was constructed using the bilateral common carotid artery occlusion followed by reoxygenation. DHQ was administered at a dose of 50 mg/kg for three days. Histological staining was performed using hematoxylin and eosin. The level of S100B protein, 8-hydroxy-2-deoxyguanosine, and 8-isoprostane was assessed using an enzyme immunoassay. The intensity of apoptosis was assessed based on the activity of caspases and DNA fragmentation. The activity of enzymes was measured spectrophotometrically, the level of gene transcripts was assessed by real-time PCR. DHQ reduced the histopathological changes and normalized levels of S100B, lactate, pyruvate, and HIF-1 mRNA in the CIR rat model. In addition, DHQ decreased the oxidative stress markers in animals with a pathology. The tested compound also inhibited inflammation by decreasing the activity of myeloperoxidase, expression of interleukins and Nfkb2. DHQ-treated rats with CIR showed decreased caspase activity, DNA fragmentation, and AIF expression. DHQ changed activity of antioxidant enzymes to the control values, decreased the expression of Cat, Gsr, and Nfe2l2, which was overexpressed in CIR, and activated the expression of Sod1, Gpx1, Gsta2, and Foxo1. DHQ showed a neuroprotective effect on CIR in rats. The neuroprotective effect involve mechanisms such as the inhibition of oxidative stress, leading to a reduction in the inflammatory response and apoptosis and the modulation of the antioxidant defense components.

Synthesis and antitrypanosomal evaluation of derivatives of N-benzyl-1,2-dihydroquinolin-6-ols: Effect of core substitutions and salt formation

Analogs of the trypanocidal lead compound 1-benzyl-1,2-dihydro-2,2,4- trimethylquinolin-6-yl acetate were prepared to extend the structure-activity relationship in this series of molecules, improve the in vivo antitrypanosomal activity of the lead, and de

Antitrypanosomal activity of 1,2-dihydroquinolin-6-ols and their ester derivatives

The current chemotherapy for second stage human African trypanosomiasis is unsatisfactory. A synthetic optimization study based on the lead antitrypanosomal compound 1,2-dihydro-2,2,4-trimethylquinolin-6-yl 3,5-dimethoxybenzoate (TDR20364, 1a) was undertaken in an attempt to discover new trypanocides with potent in vivo activity. While 6-ether derivatives were less active than the lead compound, several N1-substituted derivatives displayed nanomolar IC50 values against T. b. rhodesiense STIB900 in vitro, with selectivity indexes up to > 18000. 1-Benzyl-1,2-dihydro-2,2,4- trimethylquinolin-6-yl acetate (10a) displayed an IC50 value of 0.014 μM against these parasites and a selectivity index of 1700. Intraperitoneal administration of 10a at 50 (mg/kg)/day for 4 days caused a promising prolongation of lifespan in T. b. brucei STIB795-infected mice (>14 days vs 7.75 days for untreated controls). Reactive oxygen species were produced when T. b. brucei were exposed to 10a in vitro, implicating oxidative stress in the trypanocidal mode of action of these 1,2-dihydroquinoline derivatives.

GLUCOCORTICOID MIMETICS, METHODS OF MAKING THEM, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF

Compounds of Formula (I) wherein R1, R2, R3, R4, R5, R6, X, Y, and n are as defined herein, or a tautomer, prodrug, solvate, or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.

Cholesterol lowering/antioxidant nitroxides

The present invention relates to novel nitroxides which are useful for cholesterol lowering and as antioxidant agents. Also provided is a process for preparing the nitroxides of the present invention, pharmaceutical compositions, and a method of treating or inhibiting hypercholesterolemia, hyperlipidemia, atherosclerosis, and LDL oxidation which comprises administering to birds and mammals, in need of such treatment an effective amount of a compound of the present invention.

Antihyperlipidemic/antioxidant dihydroquinolines

The present invention relates to novel dihydroquinolines which are useful for cholesterol lowering and as antioxidant agents. Also provided is a process for preparing the dihydroquinolines of the present invention, pharmaceutical compositions, and a method of treating or inhibiting hypercholesterolemia, hyperlipidemia, atherosclerosis, and LDL oxidation which comprises administering to birds and mammals in need of such treatment an effective amount of a compound of the present invention.

X-RAY DIFFRACTION STRUCTURAL ANALYSIS OF 2,2,4-TRIMETHYL-SUBSTITUTED 6-HYDROXY-1,2-DIHYDRO- AND 6-OXO-2,6-DIHYDROQUINOLINES

An x-ray diffraction structural analysis was carried out on 6-hydroxy-1,2-dihydro- and 6-oxo-2,6-dihydro-2,2,4-trimethylquinolines on a diffractometer using λMo radiation.The structure was solved by the direct method and refined by the anisotropic method of least squares to give R = 0.044 and 0.040.The dihydrogenated ring in the 6-hydroxy derivative is nonplanar.The length of the C-C(=C) bond (1.470 Angstroem) and the nonplanarity of the ?-systems of the C=C double bond and of the benzene ring (dihedral angle 15.4 deg) indicate less conjugation in comparison with planar molecules.