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R6256

Sigma-Aldrich

13-cis-Retinal

≥85% (HPLC)

Synonym(s):

13-cis-Vitamin A aldehyde, Vitamin A aldehyde

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About This Item

Empirical Formula (Hill Notation):
C20H28O
CAS Number:
472-86-6
Molecular Weight:
284.44
EC Number:
207-456-1
MDL number:
MFCD00074858
UNSPSC Code:
12352103
PubChem Substance ID:
24899385
NACRES:
NA.32

biological source

synthetic (organic)

Assay

≥85% (HPLC)

form

powder

color

yellow to yellow-orange

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H]C(=O)C(/[H])=C(C)\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-HWCYFHEPSA-N

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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

Certificates of Analysis (COA)

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F Gai et al.
Science (New York, N.Y.), 279(5358), 1886-1891 (1998-04-16)
Chemical dynamics in proteins are discussed, with bacteriorhodopsin serving as a model system. Ultrafast time-resolved methods used to probe the chemical dynamics of retinal photoisomerization in bacteriorhodopsin are discussed, along with future prospects for ultrafast time-resolved crystallography. The photoisomerization of
Amir Aharoni et al.
Biophysical journal, 82(5), 2617-2626 (2002-04-20)
Bacteriorhodopsin (bR) is characterized by a retinal-protein protonated Schiff base covalent bond, which is stable for light absorption. We have revealed a light-induced protonated Schiff base hydrolysis reaction in a 13-cis locked bR pigment (bR5.13; lambda(max) = 550 nm) in
A Filipowicz et al.
International journal of nanomedicine, 7, 4819-4828 (2012-09-14)
Bioconjugates of a polyamidoamine (PAMAM) G3 dendrimer and an aldehyde were synthesized as carriers for vitamins A and B₆, and the bioavailability of these vitamins for skin nutrition was investigated. Nuclear magnetic resonance (NMR) and ultraviolet-visible methods were used to
Valentyn I Prokhorenko et al.
Science (New York, N.Y.), 313(5791), 1257-1261 (2006-09-02)
Optical control of the primary step of photoisomerization of the retinal molecule in bacteriorhodopsin from the all-trans to the 13-cis state was demonstrated under weak field conditions (where only 1 of 300 retinal molecules absorbs a photon during the excitation
J K McBee et al.
Biochemistry, 39(37), 11370-11380 (2000-09-14)
In the retinal rod and cone photoreceptors, light photoactivates rhodopsin or cone visual pigments by converting 11-cis-retinal to all-trans-retinal, the process that ultimately results in phototransduction and visual sensation. The production of 11-cis-retinal in adjacent retinal pigment epithelial (RPE) cells
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