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A9861

Sigma-Aldrich

Auraptene

≥98% (HPLC)

Sinônimo(s):

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

Fórmula empírica (Notação de Hill):
C19H22O3
Número CAS:
495-02-3
Peso molecular:
298.38
Número MDL:
MFCD00075948
Código UNSPSC:
12352200
ID de substância PubChem:
329771062
NACRES:
NA.77

Nível de qualidade

100

Ensaio

≥98% (HPLC)

Formulário

powder

cor

white to off-white

solubilidade

DMSO: >20 mg/mL

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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+

chave InChI

RSDDHGSKLOSQFK-RVDMUPIBSA-N

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Descrição geral

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.

Ações bioquímicas/fisiológicas

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.

Características e benefícios

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
072M4754V
021M4706V

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Takuji Tanaka et al.
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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
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
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
Satoshi Okuyama et al.
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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
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Bioscience, biotechnology, and biochemistry, 74(5), 1018-1024 (2010-05-13)
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