Skip to Content
Merck
All Photos(1)

Documents

SML2404

Sigma-Aldrich

EC23

≥98% (HPLC)

Synonym(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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C23H24O2
CAS Number:
104561-41-3
Molecular Weight:
332.44
MDL number:
MFCD18086921
UNSPSC Code:
12352200

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

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)

InChI key

OQVLOWLEEHYBJH-UHFFFAOYSA-N

Biochem/physiol Actions

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.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361d

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Hesham Haffez et al.
Molecular neurobiology, 55(3), 1942-1950 (2017-03-01)
All-trans retinoic acid (ATRA) plays key roles in neurogenesis mediated by retinoic acid receptors (RARs). RARs are important targets for the therapeutic regulation of neurogenesis but effective drug development depends on modelling-based strategies to design high-specificity ligands in combination with
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service