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T3757

Sigma-Aldrich

TTNPB

Synonyme(s) :

4-[(E)-2-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl]benzoic acid, Arotinoid acid

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About This Item

Formule empirique (notation de Hill):
C24H28O2
Numéro CAS:
71441-28-6
Poids moléculaire :
348.48
Numéro MDL:
MFCD00673917
Code UNSPSC :
12352200
ID de substance PubChem :
24278733
Nomenclature NACRES :
NA.77

Solubilité

ethanol: soluble 10 mM
DMSO: soluble 25 mM
chloroform/methanol: soluble 9.80-10.20 mg/mL, clear, colorless to light yellow

Niveau de qualité

200

Température de stockage

−20°C

Chaîne SMILES 

C\C(=C/c1ccc(cc1)C(O)=O)c2ccc3c(c2)C(C)(C)CCC3(C)C

InChI

1S/C24H28O2/c1-16(14-17-6-8-18(9-7-17)22(25)26)19-10-11-20-21(15-19)24(4,5)13-12-23(20,2)3/h6-11,14-15H,12-13H2,1-5H3,(H,25,26)/b16-14+

Clé InChI

FOIVPCKZDPCJJY-JQIJEIRASA-N

Informations sur le gène

human ... RARA(5914) , RARB(5915) , RARG(5916) , RXRA(6256) , RXRB(6257) , RXRG(6258)

Application

TTNPB has been used for transcriptional assays in 293T cells4. It has also been used as a RAR-agonist in cultured human cord blood CD34+CD38-lin- cells5.

Actions biochimiques/physiologiques

Selective and highly potent retinoic acid analog with affinity for retinoic acid receptors (RAR) α, β, and γ, which are nuclear transcription factors. Produces ligand-activated transcription of genes that possess retinoic acid responsive elements.

Caractéristiques et avantages

This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Notes préparatoires

TTNPB dissolves in CHCL3/MeOH (1/1) at 9.80 - 10.20 mg/ml to yield a clear, colorless to light yellow solution. It is also soluble at 10 mM in ethanol and at 25 mM in DMSO.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H315,H319,H335,H360

Classification des risques

Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Matthias W Büttner et al.
Chembiochem : a European journal of chemical biology, 8(14), 1688-1699 (2007-09-05)
Twofold sila-substitution (C/Si exchange) in the saturated ring of the tetrahydronaphthalene skeleton of the retinoid agonists TTNPB (1 a) and 3-methyl-TTNPB (2 a) leads to disila-TTNPB (1 b) and disila-3-methyl-TTNPB (2 b), respectively. The silicon compounds 1 b and 2
Bryan R Haugen et al.
The Journal of clinical endocrinology and metabolism, 89(1), 272-280 (2004-01-13)
Therapy for patients with advanced thyroid carcinoma is limited. Clinical and in vitro studies suggest that some patients with advanced thyroid cancer may respond to therapy with retinoic acid. mRNA expression of the six retinoic acid (RAR) and retinoid X
Olivier M Niemoeller et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 21(1-3), 193-202 (2008-01-23)
Vitamin A and retinoic acid have previously been shown to confer some protection against a severe course of malaria by fostering the phagocytosis of parasitized erythrocytes. Phagocytosis of erythrocytes is stimulated by phosphatidylserine exposure at the cell surface. The present
M S Sheikh et al.
The Journal of biological chemistry, 269(34), 21440-21447 (1994-08-26)
Retinoids mediate their actions via RARs (retinoic acid receptors) and RXRs (retinoid X receptors). Each class of these nuclear retinoid receptors is further subdivided into three species, namely alpha, beta, and gamma. Recent studies demonstrate that estrogen receptor (ER)-positive human
Masakazu Sato et al.
Oncotarget, 8(25), 40935-40945 (2017-04-14)
Cervical reserve cells are epithelial progenitor cells that are pathologically evident as the origin of cervical cancer. Thus, investigating the characteristics of cervical reserve cells could yield insight into the features of cervical cancer stem cells (CSCs). In this study
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