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Merck
모든 사진(1)

문서

A9861

Sigma-Aldrich

Auraptene

≥98% (HPLC)

동의어(들):

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

실험식(Hill 표기법):
C19H22O3
CAS Number:
Molecular Weight:
298.38
MDL number:
UNSPSC 코드:
12352200
PubChem Substance ID:
NACRES:
NA.77

분석

≥98% (HPLC)

형태

powder

색상

white to off-white

solubility

DMSO: >20 mg/mL

저장 온도

−20°C

SMILES string

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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일반 설명

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.

생화학적/생리학적 작용

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.

특징 및 장점

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable


시험 성적서(COA)

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문서 라이브러리 방문

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 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
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
Annie Marquis et al.
BMC complementary and alternative medicine, 12, 80-80 (2012-06-30)
Periodontal diseases are bacterial infections leading to chronic inflammation disorders that are frequently observed in adults. In the present study, we evaluated the effect of auraptene and lacinartin, two natural oxyprenylated coumarins, on the growth, adherence properties, and collagenase activity

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