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C5865

Sigma-Aldrich

CD437

≥98% (HPLC), solid

Synonym(s):

6-[3-(1-Adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid, AHPN

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About This Item

Empirical Formula (Hill Notation):
C27H26O3
CAS Number:
125316-60-1
Molecular Weight:
398.49
MDL number:
MFCD03106506
UNSPSC Code:
12352200
PubChem Substance ID:
24724445
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

impurities

~0.5 mol/mol water

color

yellow

mp

271.6-276 °C

solubility

DMSO: >10 mg/mL
H2O: insoluble

storage temp.

−20°C

SMILES string

OC(=O)c1ccc2cc(ccc2c1)-c3ccc(O)c(c3)C45CC6CC(CC(C6)C4)C5

InChI

1S/C27H26O3/c28-25-6-5-22(20-1-2-21-11-23(26(29)30)4-3-19(21)10-20)12-24(25)27-13-16-7-17(14-27)9-18(8-16)15-27/h1-6,10-12,16-18,28H,7-9,13-15H2,(H,29,30)

InChI key

LDGIHZJOIQSHPB-UHFFFAOYSA-N

Gene Information

human ... RARA(5914) , RARB(5915) , RARG(5916)

Biochem/physiol Actions

CD437 is a retinoic acid receptor (RAR)γ-selective agonist, γ-selective retinoid; potent inducer of apoptosis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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Hideyuki Shirasawa et al.
The American journal of sports medicine, 49(2), 332-339 (2021-01-12)
The infiltration of fat tissue into skeletal muscle, a condition referred to as muscle fatty infiltration or fatty degeneration, is regarded as an irreversible event that significantly compromises the motor function of skeletal muscle. To investigate the effect of retinoic
Fang Tan et al.
Frontiers in microbiology, 10, 2301-2301 (2019-10-28)
Enterococcus faecalis (E. faecalis), a biofilm-forming pathogen, causes nosocomial infections. In recent years, drug resistance by enterococci has become increasingly severe due to widespread antibiotic abuse. Therefore, novel antibacterial agents are urgently needed. In this study, the synthetic retinoid compound
Almudena Bosch et al.
Breast cancer research : BCR, 14(4), R121-R121 (2012-08-28)
Retinoic acid signaling plays key roles in embryonic development and in maintaining the differentiated status of adult tissues. Recently, the nuclear retinoic acid receptor (RAR) isotypes α, β and γ were found to play specific functions in the expansion and
Leeanna El-Houjeiri et al.
Molecular cancer therapeutics, 16(10), 2047-2057 (2017-06-18)
Acute myeloid leukemia (AML) is one of the most frequent types of blood malignancies. It is a complex disorder of undifferentiated hematopoietic progenitor cells. The majority of patients generally respond to intensive therapy. Nevertheless, relapse is the major cause of
Liyue Zhang et al.
Journal of molecular signaling, 5, 12-12 (2010-08-14)
A variety of pathways target CDKI p21WAF1/CIP1 expression at transcriptional, post-transcriptional as well as translational levels. We previously found that cell growth suppressing retinoid CD437 enhanced expression of p21WAF1/CIP1 and DNA damage inducible GADD45 proteins in part by elevating their
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Articles

Retinoic Acid and Gene Expression

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.

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