A natural retinoid
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Product Type

Biochemicals
Natural Products

Research Area

Neuroscience
Ophthalmology

9-cis Retinal

Item No. 21692

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-cis-retinal
CAS Number
514-85-2
Synonyms
  • 9-cis Retinaldehyde
  • 9-cis Vitamin A aldehyde
Molecular Formula
C20H28O
Formula Weight
284.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: 10 mg/mlDMF: 25 mg/mlDMSO: 16 mg/mlEthanol: 25 mg/mlEthanol:PBS (pH 7.2)(1:2): 0.3 mg/ml
SMILES
CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C([H])=O)C(C)(C)CCC1
InChi Code
InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8-,17-13+
InChi Key
NCYCYZXNIZJOKI-MKOSUFFBSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    1 mg

    $54

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    5 mg

    $223

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    10 mg

    $290

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    Product Description

    9-cis Retinal is a natural retinoid that is produced by oxidation of 9-cis retinol by cis-retinol dehydrogenase (cRDH).1 It binds to cellular retinol-binding protein-I (CRBP-I) and CRBP-II (Kds = 8 and 5 nM, respectively) and to cellular retinaldehyde-binding protein (CRALBP; Kd = 53.3 nM).2,3 In vitro, 9-cis retinal inhibits differentiation of RCJ C5.18 chondrogenic cells into cartilage (IC50 = 8 nM).4 In vivo, it rescues cone electroretinogram (ERG) responses in Irbp-/- mice, which lack interphotoreceptor retinoid-binding protein and have diminished cone responses, when administered at a dose of 0.375 mg.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mertz, J.R., Shang, E., Piantedosi, R., et al. Identification and characterization of a stereospecific human enzyme that catalyzes 9-cis-retinol oxidation. A possible role in 9-cis-retinoic acid formation. The Journal of Biological Chemisty 272(18), 11744-11749 (1997).

    2. Kane, M.A., Bright, F.V., and Napoli, J.L. Binding affinities of CRBPI and CRBPII for 9-cis-retinoids. Biochim. Biophys. Acta 1810(5), 514-518 (2011).

    3. Golovleva, I., Bhattacharya, S., Wu, Z., et al. Disease-causing mutations in the cellular retinaldehyde binding protein tighten and abolish ligand interactions. The Journal of Biological Chemisty 278(14), 12397-12402 (2003).

    4. Von Schroeder, H.P., Hashimoto, Y., and Heerschie, J.N.M. The effects of natural and synthetic retinoids on the differentiation of RCJ C5.18 chondrogenic cells. Teratology 50(1), 54-62 (1994).

    5. Parker, R.O., Fan, J., Nickerson, J.M., et al. Normal cone function requires the interphotoreceptor retinoid binding protein. J. Neurosci. 29(14), 4616-4621 (2009).