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T3757

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
UNSPSC Code:
12352200
PubChem Substance ID:
24278733
NACRES:
NA.77
MDL number:
MFCD00673917
Quality level:
200
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Product Name

TTNPB,

Quality Level

200

solubility

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

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)

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.

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This Item
654085SML1198T3205
TTNPB

Sigma-Aldrich

T3757

TTNPB

TTNPB A synthetic stilbene analog of retinoic acid that acts as a potent retinoic acid receptor (RAR) agonist (EC50 = 21 nM, 4.0 nM, and 2.4 nM for RARα, RARβ, and RARγ, respectively).

Sigma-Aldrich

654085

TTNPB

Terutroban ≥95% (HPLC)

Sigma-Aldrich

SML1198

Terutroban

Tamibarotene ≥98% (HPLC)

Sigma-Aldrich

T3205

Tamibarotene

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

room temp

solubility

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

solubility

DMSO: 5 mg/mL

solubility

DMSO: 10 mg/mL, clear

solubility

DMSO: ≥10 mg/mL

Gene Information

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

Gene Information

-

Gene Information

-

Gene Information

-

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pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000469859
0000469859
0000403022
0000403022
0000347117

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Related Content

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
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
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
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Global Trade Item Number

SKUGTIN
T3757-10MG04061837344992

Questions

1–4 of 4 Questions  

  1. How should a solution of TTNPB in DMSO, be stored and for how long? thanks

    1 answer

    1. The solution stability has not been determined for this product. One paper reports storage of 1 mM stock solutions of TTNPB in 95 % ethanol at - 80 deg C, protected from light in opaque containers or foil wrap.

      Le, X.-F., et al., Regulation of AML2/CBFA3 in Hematopoietic Cells through the Retinoic Acid Receptor -Dependent Signaling Pathway. J. Biol. Chem., 274(31), 21651-21658 (1999).

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  2. What is the Department of Transportation shipping information for this product?

    1 answer

    1. 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.

      Helpful?

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

    1 answer

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

      Helpful?

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

    1 answer

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

      Helpful?

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