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R5754

Sigma-Aldrich

9-顺式视黄醛

vitamin A analog

同義詞:

维生素 A 醛

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About This Item

經驗公式（希爾表示法）:
C20H28O
CAS號碼:
514-85-2
分子量：:
284.44
EC號碼:
208-188-8
MDL號碼:
MFCD00135842
分類程式碼代碼:
12352205
PubChem物質ID:
24899382
NACRES:
NA.28

品質等級

200

化驗

≥95% (HPLC)

形狀

powder

技術

HPLC: suitable

顏色

yellow to yellow-orange

mp

56-58 °C (lit.)

運輸包裝

dry ice

儲存溫度

−20°C

SMILES 字串

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 密鑰

NCYCYZXNIZJOKI-MKOSUFFBSA-N

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相關類別

應用

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。

象形圖

Exclamation mark
GHS07

訊號詞

Warning

危險分類

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

儲存類別代碼

11 - Combustible Solids

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

個人防護裝備

dust mask type N95 (US), Eyeshields, Gloves

從最近期的版本中選擇一個：

分析證明 (COA)

Lot/Batch Number
SLCH6359
SLCG5990
SLCB8638
SLBZ1817
SLBT7264

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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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Retinoic Acid and Gene Expression

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.

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