R5754
9-cis-Retinal
vitamin A analog
동의어(들):
Vitamin A aldehyde
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크기 선택
제품정보 (DICE 배송 시 비용 별도)
실험식(Hill 표기법):
C20H28O
CAS 번호:
Molecular Weight:
284.44
NACRES:
NA.28
PubChem Substance ID:
UNSPSC Code:
12352205
EC Number:
208-188-8
MDL number:
Quality Level
InChI key
NCYCYZXNIZJOKI-MKOSUFFBSA-N
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+
SMILES string
CC(=C\C=O)/C=C/C=C(C)\C=C\C1=C(C)CCCC1(C)C
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
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.
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
저장 등급
11 - Combustible Solids
wgk
WGK 3
ppe
dust mask type N95 (US), Eyeshields, Gloves
hcodes
Hazard Classifications
Repr. 2 - Skin Irrit. 2 - Skin Sens. 1
flash_point_f
No data available
flash_point_c
No data available
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
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
Wilfredo Credo Chung et al.
The journal of physical chemistry. A, 114(32), 8190-8201 (2010-07-30)
The dynamics of the photoisomerization of a model protonated Schiff base of 9-cis retinal in isorhodopsin is investigated using nonadiabatic molecular dynamics simulation combined with ab initio quantum chemical calculations on-the-fly. The quantum chemical part is treated at the complete-active
S A Ross et al.
Physiological reviews, 80(3), 1021-1054 (2000-07-14)
The key role of vitamin A in embryonal development is reviewed. Special emphasis is given to the physiological action of retinoids, as evident from the retinoid ligand knockout models. Retinoid metabolism in embryonic tissues and teratogenic consequences of retinoid administration
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