An agonist of RAR and RXR isoforms
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9-cis Retinoic Acid

Item No. 14587

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-cis-retinoic acid
CAS Number
5300-03-8
Synonyms
  • Alitretinoin
  • NSC 659772
  • Panretin
  • 9-cis RA
Molecular Formula
C20H28O2
Formula Weight
300.4
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 0.5 mg/ml
λmax
242, 348, 357 nm
SMILES
CC1(C)C(/C=C/C(C)=C\C=C\C(C)=C\C(O)=O)=C(C)CCC1
InChi Code
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+
InChi Key
SHGAZHPCJJPHSC-ZVCIMWCZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $54

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    5 mg

    $146

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    10 mg

    $262

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    25 mg

    $523

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    Product Description

    9-cis Retinoic acid is a natural metabolite of vitamin A, derived from the intermediate all-trans retinoic acid (Item No. 11017).1 It potently activates all isoforms of retinoic acid receptor (RAR) (Ki = 0.5-27 nM) as well as retinoid X receptor (RXR) isoforms (Ki = 3.8-12 nM).2,3 RAR heterodimerizes with RXR, while RXR can homodimerize as well as heterodimerize with numerous partners in addition to RAR, thus allowing 9-cis retinoic acid to evoke a wide range of effects.4,1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kane, M.A. Analysis, occurrence, and function of 9-cis-retinoic acid. Biochim. Biophys. Acta 1821(1), 10-20 (2012).

    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. Umemiya, H., Fukasawa, H., Ebisawa, M., et al. Regulation of retinoidal actions by diazepinylbenzoic acids. Retinoid synergists which activate the RXR-RAR heterodimers. J. Med. Chem. 40(26), 4222-4234 (1997).

    4. Dawson, M.I., and Xia, Z. The retinoid X receptors and their ligands. Biochim. Biophys. Acta 1821(1), 21-56 (2012).