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Merck
CN

T3757

Sigma-Aldrich

TTNPB

retinoic acid analog

Synonym(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

Empirical Formula (Hill Notation):
C24H28O2
CAS Number:
71441-28-6
Molecular Weight:
348.48
MDL number:
MFCD00673917
UNSPSC Code:
12352200
PubChem Substance ID:
24278733
NACRES:
NA.77

Key Documents

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Product Name

TTNPB,

solubility

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

Quality Level

200

storage temp.

−20°C

SMILES string

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+

InChI key

FOIVPCKZDPCJJY-JQIJEIRASA-N

Gene Information

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

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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.

Biochem/physiol Actions

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.

Features and Benefits

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.

Preparation Note

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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H319,H335,H360

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000469859
0000469859
0000403022
0000403022
0000347117

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

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    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What other solvent is TTNPB, product T3757, soluble in besides the solvents given in the product listing - chloroform, ethanol and DMSO?

    TTNPB, product T3757, is also soluble in dimethylformamide purged with an inert gas.

  6. How should a solution of TTNPB, product T3757, be stored?

    Following reconstitution a solution of TTNPB, T3757,  should be stored at 4° C.

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    Ask a Scientist here.

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
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
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
John S Bertram et al.
Biochimica et biophysica acta, 1740(2), 170-178 (2005-06-14)
Virtually all human tumors are deficient in gap junctional communication (GJC) and the restoration of GJC by forced expression of connexins reduces indices of neoplasia. The expression of connexin 43 (Cx43) is upregulated by cancer-preventive retinoids and carotenoids which correlates
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