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Merck

R5754

9-cis-Retinal

vitamin A analog

Synonym(s):

Vitamin A aldehyde

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About This Item

Empirical Formula (Hill Notation):
C20H28O
CAS Number:
514-85-2
Molecular Weight:
284.44
NACRES:
NA.28
PubChem Substance ID:
24899382
UNSPSC Code:
12352205
EC Number:
208-188-8
MDL number:
MFCD00135842

Key Documents

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InChI key

NCYCYZXNIZJOKI-MKOSUFFBSA-N

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+

SMILES string

CC(=C\C=O)/C=C/C=C(C)\C=C\C1=C(C)CCCC1(C)C

assay

≥95% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

yellow to yellow-orange

mp

56-58 °C (lit.)

shipped in

dry ice

storage temp.

−20°C

Quality Level

200

Related Categories

Application

9-cis-Retinal has been used for visual pigment regeneration.

Biochem/physiol Actions

Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A. The retinoids exist as many geometric isomers due to the unsaturated bonds in the aliphatic chain.
9-cis retinal is a natural ligand (chromophore) of the vertebrate rod visual pigment. 9-cis retinal is used in studies on the mechanisms of visual function.

signalword

Warning

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

pictograms

Health hazardExclamation mark
GHS08,GHS07

Hazard Classifications

Repr. 2 - Skin Irrit. 2 - Skin Sens. 1

flash_point_f

No data available

flash_point_c

No data available

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Certificates of Analysis (COA)

Lot/Batch Number
0000518643
0000518643
0000496552
0000496552
0000476634

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A Cambrian origin for vertebrate rods
Sabrina A, et al.
eLife, 4 (2015)
Willem J deGrip et al.
Journal of natural products, 74(3), 383-390 (2011-02-12)
Retinal is the natural ligand (chromophore) of the vertebrate rod visual pigment. It occurs in either the 11-cis (rhodopsin) or the 9-cis (isorhodopsin) configuration. In its evolution to a G protein coupled photoreceptor, rhodopsin has acquired exceptional photochemical properties. Illumination
Wilfredo Credo Chung et al.
The journal of physical chemistry. A, 114(32), 8190-8201 (2010-07-30)
The dynamics of the photoisomerization of a model protonated Schiff base of 9-cis retinal in isorhodopsin is investigated using nonadiabatic molecular dynamics simulation combined with ab initio quantum chemical calculations on-the-fly. The quantum chemical part is treated at the complete-active
L Xu et al.
Current opinion in genetics & development, 9(2), 140-147 (1999-05-14)
The nuclear hormone receptors constitute a large family of transcription factors. The binding of the hormonal ligands induces nuclear receptors to assume a configuration that leads to transcriptional activation. Recent studies of retinoic acid and thyroid hormone receptors revealed that
Ching-Ju Tsai et al.
Science advances, 4(9), eaat7052-eaat7052 (2018-09-27)
Selective coupling of G protein (heterotrimeric guanine nucleotide-binding protein)-coupled receptors (GPCRs) to specific Gα-protein subtypes is critical to transform extracellular signals, carried by natural ligands and clinical drugs, into cellular responses. At the center of this transduction event lies the
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