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R5754

9-cis-Retinal

Name: 9-<I>cis</I>-Retinal
Brand: SIGMA

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

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Properties

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

Description

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

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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A Cambrian origin for vertebrate rods

Sabrina A, et al.

eLife, 4 (2015)

Cyclopropyl and isopropyl derivatives of 11-cis and 9-cis retinals at C-9 and C-13: subtle steric differences with major effects on ligand efficacy in rhodopsin.

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

A Cambrian origin for vertebrate rods.

Sabrina Asteriti et al.

eLife, 4 (2015-06-23)

Vertebrates acquired dim-light vision when an ancestral cone evolved into the rod photoreceptor at an unknown stage preceding the last common ancestor of extant jawed vertebrates (~420 million years ago Ma). The jawless lampreys provide a unique opportunity to constrain

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Global Trade Item Number

SKU	GTIN
R5754-25MG	04061836695712
R5754-100MG	04061833275993