An inverse agonist of opsin
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11-cis Retinal

Item No. 21377

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E,4Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal
CAS Number
564-87-4
Synonyms
  • 11-cis Retinaldehyde
  • 11-cis Vitamin A aldehyde
Molecular Formula
C20H28O
Formula Weight
284.4
Purity
≥65%
Formulation
An oil
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly solubleMethanol: Slightly soluble
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-IOUUIBBYSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    2 mg

    $3,025

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    Product Description

    11-cis Retinal is a chromophore that binds to opsin in the mammalian visual system as an inverse agonist forming the inactive conformation of rhodopsin.1 When 11-cis retinal absorbs a photon of light, it isomerizes to form all-trans retinal (Item No. 18449) beginning the phototransduction cycle, which is the basis for mammalian vision. A G121L mutation in opsin allows 11-cis retinal to bind as a partial agonist and activate rhodopsin in the absence of light.2 In a moth model of carotenoid deficiency-induced low visual sensitivity, 11-cis retinal application to compound eyes restored visual sensitivity almost completely.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tradtrantip, L., Sonawane, N.D., Namkung, W., et al. Nanomolar potency pyrimido-pyrrolo-quinoxalinedione CFTR inhibitor reduces cyst size in a polycystic kidney disease model. J. Med. Chem. 52(20), 6447-6455 (2009).

    2. Han, M., Lou, J., Nakanishi, K., et al. Partial agonist activity of 11-cis-retinal in rhodopsin mutants. The Journal of Biological Chemisty 272(37), 23081-23085 (1997).

    3. Bennett, R.R., and White, R.H. 11-cis retinal restores visual function in vitamin A-deficient Manduca. Vis. Neurosci. 6(5), 473-479 (1991).