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Merck
CN

A9861

Sigma-Aldrich

Auraptene

≥98% (HPLC)

别名:

7-Geranyloxycoumarin, 7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-2H-1-benzopyran-2-one, Aurapten

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About This Item

经验公式(希尔记法):
C19H22O3
CAS号:
分子量:
298.38
MDL编号:
UNSPSC代码:
12352200
PubChem化学物质编号:
NACRES:
NA.77

质量水平

方案

≥98% (HPLC)

表单

powder

颜色

white to off-white

溶解性

DMSO: >20 mg/mL

储存温度

−20°C

SMILES字符串

C\C(C)=C\CC\C(C)=C\COc1ccc2C=CC(=O)Oc2c1

InChI

1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+

InChI key

RSDDHGSKLOSQFK-RVDMUPIBSA-N

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一般描述

Auraptene (7-geranyloxycoumarin) is a prenyloxycoumarin, that is abundantly present in nature. It is produced by several plant species, such as Rutaceae and Umbeliferae (Apiaceae) families.

生化/生理作用

Auraptene is an ACAT inhibitor and estrogen receptor modulator.
Auraptene is an estrogen receptor modulator that also acts as an ACAT inhibitor. It displays anti-tumor effects in several xenograft and chemically-induced murine tumor models. Auraptene induces apoptosis and is anti-proliferative in cancer cell lines. It has agonistic properties against PPARs, and interferes with lipid and cholesterol production by inhibiting ACAT (IC50 = 4 uM).
Auraptene (7-geranyloxycoumarin) possesses anti-oxidant, anti-bacterial, anti-inflammatory and anti-tumor activities.

特点和优势

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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Akira Murakami et al.
BioFactors (Oxford, England), 30(3), 179-192 (2008-06-06)
Bone resorption is known to accelerate during the onset of several disorders, including osteoporosis (OP) and rheumatoid arthritis (RA). Some epidemiological surveys have suggested that a high intake of vegetables and fruits has an inverse relation to such disease incidence
Fatemeh Soltani et al.
Phytotherapy research : PTR, 24(1), 85-89 (2009-05-16)
The antigenotoxicity effects of auraptene on DNA damage in human peripheral lymphocytes were studied using alkaline single cell gel electrophoresis. Auraptene at concentrations of 5, 10, 25, 50, 100, 200 and 400 microM was tested under simultaneous treatment with 25
Takuji Tanaka et al.
Nutrition and cancer, 60 Suppl 1, 70-80 (2008-11-15)
Dietary polyphenols are important potential chemopreventive natural agents. Other agents, such as citrus compounds, are also candidates for cancer chemopreventives. They act on multiple key elements in signal transduction pathways related to cellular proliferation, differentiation, apoptosis, inflammation, and obesity. This
Satoshi Okuyama et al.
European journal of pharmacology, 699(1-3), 118-123 (2012-12-12)
Cerebral ischemia causes delayed neuronal cell death in the hippocampus resulting in sequential cognitive impairments. Hyper-activated inflammation following ischemia is one of the etiologies for delayed neuronal cell death. In the present study, using a transient global ischemia mouse model
Akira Murakami
Forum of nutrition, 61, 193-203 (2009-04-16)
A regulated low level of nitric oxide (NO) production in the body is essential for maintaining homeostasis (neuroprotection, vasorelaxation, etc.), though certain pathophysiological conditions associated with inflammation involve de novo synthesis of inducible NO synthase (iNOS) in immune cells, including

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