A potent, selective RAR agonist
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TTNPB

Item No. 16144

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[(1E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propen-1-yl]-benzoic acid
CAS Number
71441-28-6
Synonyms
  • AGN 191183
  • Arotinoid Acid
  • Ro 13-7410
Molecular Formula
C24H28O2
Formula Weight
348.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMF:PBS (pH 7.2) (1:5): 0.16 mg/mlDMSO: 2 mg/mlEthanol: 0.1 mg/ml
λmax
229, 303 nm
SMILES
CC1(C)C2=C(C=CC(/C(C)=C/C3=CC=C(C(O)=O)C=C3)=C2)C(C)(C)CC1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $49

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    5 mg

    $120

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    10 mg

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    Product Description

    TTNPB is an analog of retinoic acid (Item No. 11017) that potently and selectively activates retinoic acid receptors (EC50s = 21, 4, and 2.4 nM for RARα, RARβ, and RARγ, respectively).1,2 It does not act on retinoid X receptors and weakly agonizes farnesoid X receptor (EC50 > 1 µM).2,3 TTNPB is used to study RAR action in diverse processes, including epidermal cell proliferation, embryogenesis, and stem cell differentiation.4,5,6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Beard, R.L., Chandraratna, R.A., Colon, D.F., et al. Synthesis and structure-activity relationships of stilbene retinoid analogs substituted with heteroaromatic carboxylic acids. J. Med. Chem. 38(15), 2820-2829 (1995).

    2. Wong, M.F., Repa, J.J., Clagett-Dame, M., et al. Synthesis and receptor binding affinity of conformationally restricted retinoic acid analogues. Bioorg. Med. Chem. Lett. 7(17), 2313-2318 (1997).

    3. Maloney, P.R., Parks, D.J., Haffner, C.D., et al. Identification of a chemical tool for the orphan nuclear receptor FXR. J. Med. Chem. 43(16), 2971-2974 (2000).

    4. Thacher, S.M., Standeven, A.M., Athanikar, J., et al. Receptor specificity of retinoid-induced epidermal hyperplasia: Effect of RXR-selective agonists and correlation with topical irritation. J. Pharmacol. Exp. Ther. 282(2), 528-534 (1997).

    5. Minucci, S., Saint-Jeannet, J.P., Toyama, R., et al. Retinoid X receptor-selective ligands produce malformations in Xenopus embryos. Proc. Natl. Acad. Sci. USA 93(5), 1803-1807 (1996).

    6. Araoka, T., Mae, S., Kurose, Y., et al. Efficient and rapid induction of human iPSCs/ESCs into nephrogenic intermediate mesoderm using small molecule-based differentiation methods. PLoS One 9(1), e84881 (2014).

    7. Hou, P., Li, Y., Zhang, X., et al. Pluripotent stem cells induced from mouse somatic cells by small-molecule compounds. Science 341(6146), 651-654 (2013).