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SML2404

Sigma-Aldrich

EC23

≥98% (HPLC)

Synonyme(s) :

4-((5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethynyl)benzoic acid, 4-[2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)ethynyl]benzoic acid, AGN 190205, AGN-190205, AGN190205, BASF 46928, BASF-46928, BASF46928, EC 23, EC-23

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About This Item

Formule empirique (notation de Hill):
C23H24O2
Numéro CAS:
104561-41-3
Poids moléculaire :
332.44
Numéro MDL:
MFCD18086921
Code UNSPSC :
12352200

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

InChI

1S/C23H24O2/c1-22(2)13-14-23(3,4)20-15-17(9-12-19(20)22)6-5-16-7-10-18(11-8-16)21(24)25/h7-12,15H,13-14H2,1-4H3,(H,24,25)

Clé InChI

OQVLOWLEEHYBJH-UHFFFAOYSA-N

Actions biochimiques/physiologiques

EC23 is a synthetic, photostable all-trans retinoic acid (ATRA) analog/mimetic that targets RAR with greater affinity than ATRA (RARα/β/γ EC50 by cell-free TR-FRET binding assay = 3.7/3.3/16.8 with EC23 vs. 16.0/17.6/14.7 nM with ATRA) and does not bind retinoid x receptors (RXRs). EC23 induces differentiation of human pluripotent embryonic stem cells (0.1-10 μM) with a similar or better efficiency than ATRA.

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Warning

Mentions de danger

H361d

Classification des risques

Repr. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Graeme Clemens et al.
Molecular bioSystems, 9(4), 677-692 (2013-02-01)
All trans-retinoic acid (ATRA) is widely used to direct the differentiation of cultured stem cells. When exposed to the pluripotent human embryonal carcinoma (EC) stem cell line, TERA2.cl.SP12, ATRA induces ectoderm differentiation and the formation of neuronal cell types. We
S Murakami et al.
The Journal of pharmacy and pharmacology, 42(10), 723-726 (1990-10-01)
Two chalcone derivatives, xanthoangelol (1) and 4-hydroxyderricin (II) isolated from Angelica keiskei Koidzumi, inhibited pig gastric H+, K(+)-ATPase with IC50 values of 1.8 and 3.3 microM, respectively. The inhibition by I or II was competitive with respect to ATP and
Kirsty E Clarke et al.
Neurochemistry international, 106, 74-84 (2016-12-25)
The inability of neurites to grow and restore neural connections is common to many neurological disorders, including trauma to the central nervous system and neurodegenerative diseases. Therefore, there is need for a robust and reproducible model of neurite outgrowth, to
Haider M Hassan et al.
Cell reports, 19(8), 1685-1697 (2017-05-26)
Retinoic acid (RA) plays important roles in development, growth, and homeostasis through regulation of the nuclear receptors for RA (RARs). Herein, we identify Hypermethylated in Cancer 1 (Hic1) as an RA-inducible gene. HIC1 encodes a tumor suppressor, which is often
Victoria B Christie et al.
Organic & biomolecular chemistry, 6(19), 3497-3507 (2008-12-17)
All-trans-retinoic acid (ATRA) and its associated analogues are important mediators of cell differentiation and function during the development of the nervous system. It is well known that ATRA can induce the differentiation of neural tissues from human pluripotent stem cells.
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