R5754
9-顺式视黄醛
vitamin A analog
别名:
维生素 A 醛
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关于此项目
经验公式（希尔记法）:
C20H28O
化学文摘社编号:
分子量:
284.44
NACRES:
NA.28
PubChem Substance ID:
UNSPSC Code:
12352205
EC Number:
208-188-8
MDL number:
产品名称
9-顺式视黄醛, vitamin A analog
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
Quality Level
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Application
9-顺式-视黄醛用于视色素再生。
Biochem/physiol Actions
视黄醛、视黄醇和视黄酸是维生素 A 的醛、醇和酸形式。由于脂肪链中的不饱和键，维 A 酸的几何异构体较多。
9-顺式视黄醛是脊椎动物视杆细胞色素的天然配体（生色团）。9-顺式视黄醛用于研究视功能的机制。
9-顺式视黄醛是脊椎动物视杆细胞色素的天然配体（生色团）。9-顺式视黄醛用于研究视功能的机制。
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Skin Irrit. 2
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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 A, et al.
eLife, 4 (2015)
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
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
Vladimir J Kefalov et al.
Neuron, 46(6), 879-890 (2005-06-15)
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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