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Merck
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A9861

Sigma-Aldrich

Auraptene

≥98% (HPLC)

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C19H22O3
Numero CAS:
495-02-3
Peso molecolare:
298.38
Numero MDL:
MFCD00075948
Codice UNSPSC:
12352200
ID PubChem:
329771062
NACRES:
NA.77

Saggio

≥98% (HPLC)

Forma fisica

powder

Colore

white to off-white

Solubilità

DMSO: >20 mg/mL

Temperatura di conservazione

−20°C

Stringa SMILE

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+
RSDDHGSKLOSQFK-RVDMUPIBSA-N

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Descrizione generale

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.

Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

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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
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
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
Auraptene and Its Role in Chronic Diseases
Drug Discovery from Mother Nature, 399-407 (2016)
Salvatore Genovese et al.
Current drug targets, 12(3), 381-386 (2010-10-20)
Auraptene is the most abundant prenyloxycoumarin that occurs in nature. It has been isolated from plants belonging to many genus of the Rutaceae family, comprising several edible fruits and vegetables. Although known for a long time, only in the last
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