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SML0541

Sigma-Aldrich

7α,25-二羟基胆固醇

≥98% (HPLC), powder, GPR183 agonist

别名:

5-胆甾烯-3β,7α,25-三醇

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About This Item

经验公式（希尔记法）:
C27H46O3
CAS号:
64907-22-8
分子量:
418.65
MDL编号:
MFCD20488904
UNSPSC代码:
12352211
PubChem化学物质编号:
329825542
NACRES:
NA.77

产品名称

7α,25-二羟基胆固醇, ≥98% (HPLC)

质量水平

100

方案

≥98% (HPLC)

表单

powder

颜色

white to beige

溶解性

DMSO: 5 mg/mL (clear solution)

储存温度

2-8°C

SMILES字符串

C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

1S/C27H46O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-24,28-30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1

InChI key

BQMSKLCEWBSPPY-IKVTXIKFSA-N

应用

7α,25-二羟基胆固醇已被用作G蛋白偶联受体183（Gpr183）的配体。

生化/生理作用

7α,25-二羟基胆固醇 (7α,25-OHC)是孤儿GPCR受体EBI2 (GPR183)的一种有效选择性内源性配体，其EC50值在皮摩尔范围内。新发现的EBI2-氧甾醇信号通路已被证明在适应性免疫应答中具有重要作用，包括驱动免疫细胞迁移。 体外 和 体内 研究表明，7α,25-OHC可以作为趋化因子指导B细胞、T细胞和树突状细胞的迁移。
7α,25-二羟基胆固醇具有阻断T细胞活化早期步骤的能力。

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

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分析证书(COA)

Lot/Batch Number
0000374986
0000374987
0000374986
0000374987
0000258536

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Norman B Javitt
Current opinion in lipidology, 18(3), 283-288 (2007-05-15)
Recent findings extend the biologic activities of oxysterols as ligands for nuclear receptors to a role in morphogenesis during fetal development and to a role in the metabolism of photooxidation products of cholesterol in the retina. A 1000-fold increase of
C Moog et al.
Anticancer research, 13(4), 953-958 (1993-07-01)
New water soluble derivatives of oxysterols--the phosphodiesters of oxysterols and of nucleosides--have been synthesized. In vitro, these compounds share the biological properties of their parent oxysterols. Furthermore, they display anticancer activity when injected i.p. in mice bearing experimental tumors. The
C Moog et al.
International journal of immunopharmacology, 11(5), 559-565 (1989-01-01)
The effects of an oxysterol, 7,25-dihydroxycholesterol (7,25-OHC), cyclosporin A (CsA) and dexamethasone (Dex) on the blastogenic response of murine lymphocytes to various stimuli were investigated. 7,25-OHC markedly depressed the response to Con A, anti-T3 monoclonal antibodies and to the combination
J Zhang et al.
Biochimica et biophysica acta, 1344(3), 241-249 (1997-02-18)
The metabolism of 25-hydroxycholesterol in different cell types was studied and the role of 7 alpha-hydroxylation for the effect of 25-hydroxycholesterol on the activity of HMG-CoA reductase was determined. Human diploid fibroblasts (HDF) and the human melanoma cell line SK-MEL-2
C Moog et al.
Biochimie, 73(10), 1321-1326 (1991-10-01)
Oxysterols exhibit a wide variety of biological activities, including potent immunosuppressive effects. 7 beta,25-Dihydroxycholesterol (7,25-OHC), a synthetic oxysterol, has been shown to strongly inhibit the lymphocyte response to different stimuli. This compound has been chosen as a model compound to
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