An isomer of vitamin A
Related Products
Isomer(s)
413459-cis Retinol 20241Vitamin A
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11-cis Retinol

Item No. 33207

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
22737-96-8
Synonyms
  • 11-cis Vitamin A Alcohol
Molecular Formula
C20H30O
Formula Weight
286.5
Purity
≥85%
Formulation
An oil
Solubility(Learn about Variance in Solubility)
Chloroform: slightly solubleMethanol: slightly soluble
SMILES
OC/C=C(C)/C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C
InChi Code
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6-,12-11+,16-8+,17-13+
InChi Key
FPIPGXGPPPQFEQ-IOUUIBBYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    1 mg

    $334

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    Product Description

    11-cis Retinol is an isomer of vitamin A (Item No. 20241). It is formed from vitamin A, via a trans-retinyl ester intermediate, by the enzyme RPE65 in the retinal pigment epithelium and then converted to 11-cis retinal as part of the visual cycle.1,2 11-cis Retinol is an agonist of salamander and human red rod opsins expressed in COS cells and an inverse agonist of salamander red cone opsin, as well as human red and green cone opsins expressed in COS cells.3 It promotes pigment formation in cone, but not rod, photoreceptors.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rando, R.R. The biochemistry of the visual cycle. Chem. Rev. 101(7), 1881-1896 (2001).

    2. Guignard, T.J.P., Jin, M., Pequignot, M.O., et al. FATP1 inhibits 11-cis retinol formation via interaction with the visual cycle retinoid isomerase RPE65 and lecithin: Retinol acyltransferase. The Journal of Biological Chemisty 285(24), 18759-18768 (2010).

    3. Ala-Laurila, P., Cornwall, M.C., Crouch, R.K., et al. The action of 11-cis-retinol on cone opsins and intact cone photoreceptors. The Journal of Biological Chemisty 284(24), 16492-16500 (2009).