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R3255

Sigma-Aldrich

13-顺式-维甲酸

≥98% (HPLC)

同義詞:

异维甲酸

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About This Item

經驗公式（希爾表示法）:
C20H28O2
CAS號碼:
4759-48-2
分子量：:
300.44
EC號碼:
225-296-0
MDL號碼:
MFCD00079542
分類程式碼代碼:
12352106
PubChem物質ID:
24278676
NACRES:
NA.77

化驗

≥98% (HPLC)

形狀

powder

技術

HPLC: suitable

顏色

yellow to yellow-orange

mp

172-175 °C (lit.)

儲存溫度

−20°C

SMILES 字串

[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 密鑰

SHGAZHPCJJPHSC-XFYACQKRSA-N

基因資訊

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

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相關類別

應用

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。

特點和優勢

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。

象形圖

Health hazardExclamation mark
GHS08,GHS07

訊號詞

Danger

危險分類

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

標靶器官

Respiratory system

儲存類別代碼

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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

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

分析證明 (COA)

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存取文件庫

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)
UAB30, a novel RXR agonist, decreases tumorigenesis and leptomeningeal disease in group 3 medulloblastoma patient-derived xenografts
Garner E F, et al.
Journal of Neuro-Oncology, 140(2), 209-224 (2018)
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
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)
Raoud Marayati et al.
Translational oncology, 14(1), 100893-100893 (2020-10-04)
Retinoic acid (RA) therapy has been utilized as maintenance therapy for high-risk neuroblastoma, but over half of patients treated with RA relapse. Neuroblastoma stem cell-like cancer cells (SCLCCs) are a subpopulation of cells characterized by the expression of the cell
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文章

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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