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文件

R3255

Sigma-Aldrich

13-顺式-维甲酸

≥98% (HPLC)

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别名:
异维甲酸
经验公式（希尔记法）:
C20H28O2
CAS号:
4759-48-2
分子量:
300.44
EC 号:
225-296-0
MDL编号:
MFCD00079542
UNSPSC代码:
12352106
PubChem化学物质编号:
24278676
NACRES:
NA.77

质量水平

200

检测方案

≥98% (HPLC)

形式

powder

技术

HPLC: suitable

颜色

yellow to yellow-orange

mp

172-175 °C (lit.)

储存温度

−20°C

SMILES字符串

[H]\C(C(O)=O)=C(C)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C

InChI

1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14-

InChI key

SHGAZHPCJJPHSC-XFYACQKRSA-N

基因信息

human ... NOS2(4843) , RARA(5914) , RARB(5915) , RARG(5916)

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相关类别

应用

13-顺式-视黄酸已被用作：
  • LA-N-5分化用新鲜培养基的成分
  • 处理髓母细胞瘤细胞进行细胞分化
  • 处理椭球状体以生成延时视频
  • 考察非洲爪蟾在明亮和黑暗条件下的头部变形活动

生化/生理作用

13-顺式维甲酸(RA)具有抗炎、抗肿瘤作用。RA的作用通过RAR-β和RAR-α受体介导。RA可减弱细胞因子刺激小鼠系膜细胞iNOS的表达和活性。它诱导线粒体膜通透性转变，表现为肿胀和膜电位下降，并通过凋亡途径刺激细胞色素C的释放。这些活性被EGTA和环孢素A逆转。RA也通过增加转录部分增加MMP-1蛋白的表达。

特点和优势

这种化合物是基因调控研究的特色产品。点击此处发现更多特色基因调控产品。在sigma.com/discover-bsm可了解更多关于生物活性小分子的其他研究领域。

象形图

Health hazardExclamation mark
GHS08,GHS07

警示用语：

Danger

危险分类

Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

分析证书(COA)

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M P Rigobello et al.
Biochemical pharmacology, 58(4), 665-670 (1999-07-21)
Retinoic acids, structurally related to vitamin A, inhibit the in vitro proliferation of different types of normal and neoplastic cells. The effects of all-trans, 9-cis, and 13-cis retinoic acids were tested on mitochondria isolated from rat liver. All the compounds
Differential expression, distinct localization and opposite effect on Golgi structure and cell differentiation by a novel splice variant of human PRMT5
Sohail M , et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1853(10), 2444-2452 (2015)
Live multicellular tumor spheroid models for high-content imaging and screening in cancer drug discovery
Reid B G, et al.
Current Chemical Genomics and Translational Medicine, 8(Suppl-1), 27-27 (2014)
P K Datta et al.
Kidney international, 56(2), 486-493 (1999-08-05)
Nitric oxide (NO) release as a result of cytokine-mediated activation of inducible nitric oxide synthase (iNOS) in mesangial cells can be sustained and lead to oxidative injury in various forms of glomerular inflammation. Inhibition of iNOS expression and/or activity could
Induction of pronephric tubules by activin and retinoic acid in presumptive ectoderm of Xenopus laevis
Moriya N, et al.
Development, Growth & Differentiation, 35(2), 123-128 (1993)
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