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Merck
CN

R5754

Sigma-Aldrich

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
EC Number:
208-188-8
MDL number:
MFCD00135842
UNSPSC Code:
12352205
PubChem Substance ID:
24899382
NACRES:
NA.28

Key Documents

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Quality Level

200

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

SMILES string

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

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

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332,H315

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000476634
0000476639
0000476634
0000476639
0000399695

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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
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
Vladimir J Kefalov et al.
Neuron, 46(6), 879-890 (2005-06-15)
Retinal rod and cone pigments consist of an apoprotein, opsin, covalently linked to a chromophore, 11-cis retinal. Here we demonstrate that the formation of the covalent bond between opsin and 11-cis retinal is reversible in darkness in amphibian red cones
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
Darwin Toledo et al.
The Journal of biological chemistry, 286(46), 39993-40001 (2011-09-24)
Two different mutations at Gly-90 in the second transmembrane helix of the photoreceptor protein rhodopsin have been proposed to lead to different phenotypes. G90D has been classically associated with congenital night blindness, whereas the newly reported G90V substitution was linked
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