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R5754

Sigma-Aldrich

9-cis-Retinal

vitamin A analog

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Synonym(s):
Vitamin A aldehyde
Empirical Formula (Hill Notation):
C20H28O
CAS Number:
Molecular Weight:
284.44
EC Number:
MDL number:
PubChem Substance ID:

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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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

Premium Grade
form

powder

form

powder

form

crystalline

form

powder

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable

technique(s)

-

color

yellow to yellow-orange

color

yellow

color

yellow to very dark yellow, to Very Dark Orange

color

faint yellow to very dark yellow

mp

56-58 °C (lit.)

mp

62-64 °C

mp

61-63 °C (lit.)

mp

56-61 °C, 61-63 °C (lit.)

shipped in

dry ice

shipped in

dry ice

shipped in

dry ice

shipped in

dry ice

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

Signal Word

Warning

Hazard Statements

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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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
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