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Merck
CN

R5754

Sigma-Aldrich

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
CAS Number:
分子量:
284.44
EC 号:
MDL编号:
UNSPSC代码:
12352205
PubChem化学物质编号:
NACRES:
NA.28
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质量水平

方案

≥95% (HPLC)

表单

powder

技术

HPLC: suitable

颜色

yellow to yellow-orange

mp

56-58 °C (lit.)

运输

dry ice

储存温度

−20°C

SMILES字符串

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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应用

9-顺式-视黄醛用于视色素再生。

生化/生理作用

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。

象形图

Exclamation mark

警示用语:

Warning

危险分类

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

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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访问文档库

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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