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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

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLBQ7110V
SLBC9413V
120M5021V
120M5021
039K5006

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Isabelle Gagnon et al.
Biochimica et biophysica acta, 1596(1), 156-162 (2002-05-02)
Retinal dehydrogenase (RALDH) isozymes catalyze the terminal oxidation of retinol into retinoic acid (RA) that is essential for embryogenesis and tissue differentiation. To understand the role of mouse type 2 RALDH in synthesizing the ligands (all-trans and 9-cis RA) needed
U C Fischer et al.
Biophysical journal, 31(1), 139-145 (1980-07-01)
Protonation changes of the protein occur during the reconstitution of bacteriorhodopsin from bacterio-opsin and all-trans retinal in the purple membrane of Halobacterium halobium. The protonation changes are conveniently determined from measures of the pH changes after photoisomerisation of 9-cis retinal
Isabelle Gagnon et al.
Biochemical pharmacology, 65(10), 1685-1690 (2003-05-20)
Retinal dehydrogenases (RALDHs) convert retinal into retinoic acids (RAs), which are important signaling molecules in embryogenesis and tissue differentiation. We expressed mouse RALDH type 1 (mRALDH1) in Escherichia coli and studied the kinetic properties of the recombinant enzyme for retinal
C C Huang
American journal of otolaryngology, 7(1), 55-57 (1986-01-01)
The in vivo effects of retinoids on head and neck tumors were studied using Fisher 344 rats with squamous cell carcinoma implanted in the palate. Retinoids were given orally to rats, starting 2 weeks after tumor implantation. The animals were
Akira Kawanabe et al.
Biochemistry, 45(14), 4362-4370 (2006-04-06)
Archaeal-type rhodopsins can accommodate either all-trans- or 13-cis,15-syn-retinal in their chromophore binding site in the dark, but only the former isomer is functionally important. In contrast, Anabaena sensory rhodopsin (ASR), an archaeal-type rhodopsin found in eubacteria, exhibits a photochromic interconversion
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