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Merck

R5754

9-cis-Retinal

vitamin A analog

Synonym(s):

Vitamin A aldehyde

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R5754-25MG

CZK 9,110.00

R5754-100MG

CZK 22,200.00

CZK 9,110.00

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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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1 of 4

This Item
R2500R763295144
9-cis-Retinal vitamin A analog

Sigma-Aldrich

R5754

9-cis-Retinal

all trans-Retinal powder, ≥98%

Sigma-Aldrich

R2500

all trans-Retinal

Retinol synthetic, ≥95% (HPLC), (Powder or Powder with Lumps)

Sigma-Aldrich

R7632

Retinol

Retinol BioXtra, ≥97.5% (HPLC), ~3100 U/mg

Sigma-Aldrich

95144

Retinol

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable

technique(s)

-

assay

≥95% (HPLC)

assay

≥98%

assay

≥95% (HPLC)

assay

≥97.5% (HPLC)

form

powder

form

powder

form

(Powder or Powder with Lumps)

form

(Powder or Powder with Lumps)

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

shipped in

dry ice

shipped in

dry ice

shipped in

dry ice

shipped in

dry ice

mp

56-58 °C (lit.)

mp

62-64 °C

mp

61-63 °C (lit.)

mp

56-61 °C, 61-63 °C (lit.)

Application

9-cis-Retinal has been used for visual pigment regeneration.[1]

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
0000496552
0000496552
0000476634
0000476639
0000476639

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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
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
View All Related Papers

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