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Merck
CN

A9861

Auraptene

≥98% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C19H22O3
CAS Number:
495-02-3
Molecular Weight:
298.38
NACRES:
NA.77
PubChem Substance ID:
329771062
UNSPSC Code:
12352200
MDL number:
MFCD00075948

Key Documents

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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+

SMILES string

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

InChI key

RSDDHGSKLOSQFK-RVDMUPIBSA-N

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

−20°C

Quality Level

100

General description

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.

Biochem/physiol Actions

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.

Features and Benefits

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000157986
0000067166
0000064559
072M4754V

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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
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
Auraptene and Its Role in Chronic Diseases
Drug Discovery from Mother Nature, 399-407 (2016)
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