All Photos(1)
2-[4-[[4-Hydroxy-3-(1-methylethyl)phenyl]methyl]-3,5-dimethylphenoxy]acetic acid, 3,5-Dimethyl-4-(4′-hydroxy-3′-isopropylbenzyl)phenoxyacetic acid, GC 1, GC-1
C20H24O4
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Quality Level
Assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 10 mg/mL, clear
storage temp.
−20°C
InChI
1S/C20H24O4/c1-12(2)17-9-15(5-6-19(17)21)10-18-13(3)7-16(8-14(18)4)24-11-20(22)23/h5-9,12,21H,10-11H2,1-4H3,(H,22,23)
InChI key
QNAZTOHXCZPOSA-UHFFFAOYSA-N
Biochem/physiol Actions
Sobetirome is also termed as 2-(4-(4-(benzyloxy)-3-isopropylbenzyl)-3,5-dimethylphenoxy)acetic acid/ GC-1. It has an inner-ring and negatively charged carboxylate groups at physiological pH. Sobetirome is considered as a cholesterol lowering agent in humans.
Sobetirome is an orally active and potent agonist at thyroid hormone receptor (TR) β and TRα that displays selective tissue action. Sobetirome is devoid of thyrotoxic adverse effects on the heart, bone, and skeletal muscle.
WGK
WGK 3
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Expert opinion on therapeutic targets, 20(2), 145-149 (2015-11-14)
Sobetirome binds selectively to the main hepatic form of thyroid hormone (TH) receptor, TRβ1, compared to TRα1, which is principally responsible for thyrotoxic effects on heart, muscle and bone. Sobetirome also preferentially accumulates in liver. It was originally envisaged that
Sobetirome prodrug esters with enhanced blood?brain barrier permeability.
Bioorganic & Medicinal Chemistry, 24(22), 5842-5854 (2016)
Bioorganic & medicinal chemistry, 24(22), 5842-5854 (2016-10-26)
There is currently great interest in developing drugs that stimulate myelin repair for use in demyelinating diseases such as multiple sclerosis. Thyroid hormone plays a key role in stimulating myelination during development and also controls the expression of important genes
Ester-to-amide rearrangement of ethanolamine-derived prodrugs of sobetirome with increased blood-brain barrier penetration.
Bioorganic & Medicinal Chemistry, 25(10), 2743-2753 (2017)
Atherosclerosis, 237(2), 544-554 (2014-12-03)
Thyroid hormone reduces plasma cholesterol and increases expression of low-density lipoprotein receptor (LDL-R) in liver, an effect mediated by thyroid receptor β (TRβ). The selective TRβ modulator GC-1 also enhances several steps in reverse cholesterol transport and can decrease serum
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