Auraptene

Names

[ CAS No. ]:
495-02-3

[ Name ]:
Auraptene

[Synonym ]:
2H-1-Benzopyran-2-one, 7-((3,7-dimethyl-2,6-octadienyl)oxy)-, (E)-
Coumarin, 7-[(3,7-dimethyl-2,6-octadienyl)oxy]-, (E)-
Auraptene
2H-1-Benzopyran-2-one, 7-[(3,7-dimethyl-2,6-octadienyl)oxy]-, (E)-
7-{[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]oxy}-2H-chromen-2-one
7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-2H-1-benzopyran-2-one 7-Geranyloxycoumarin Aurapten
7-{[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]oxy}-2H-chromen-2-one
2H-1-Benzopyran-2-one, 7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-
7-Geranyloxycoumarin
7-{[(2E)-3,7-Diméthyl-2,6-octadièn-1-yl]oxy}-2H-chromén-2-one
aurapten

Biological Activity

[Description]:

Auraptene is the most abundant naturally occurring geranyloxycoumarin. Auraptene is primarily isolated from plants in the Rutaceae family, such as citrus fruits. Auraptene decreases the secretion of matrix metalloproteinase 2 (MMP-2) as well as key inflammatory mediators, including IL-6, IL-8, and chemokine (C-C motif) ligand-5(CCL5)[1].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Metabolic Enzyme/Protease >> MMP

[Target]

MMP-2

[References]

[1]. La VD, et al. Anti-inflammatory and wound healing potential of citrus auraptene. J Med Food. 2013 Oct;16(10):961-4.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
455.5±45.0 °C at 760 mmHg

[ Melting Point ]:
66 °C

[ Molecular Formula ]:
C₁₉H₂₂O₃

[ Molecular Weight ]:
298.376

[ Flash Point ]:
195.4±23.3 °C

[ Exact Mass ]:
298.156891

[ PSA ]:
39.44000

[ LogP ]:
5.69

[ Appearance of Characters ]:
white to off-white

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.549

[ Storage condition ]:
?20°C

[ Water Solubility ]:
DMSO: >20mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

Precursor & DownStream

Precursor

DownStream

Articles

Suppression of mitochondrial respiration with auraptene inhibits the progression of renal cell carcinoma: involvement of HIF-1α degradation.

Oncotarget 6 , 38127-38, (2015)

Renal cell carcinoma (RCC) progression resulting from the uncontrolled migration and enhanced angiogenesis is an obstacle to effective therapeutic intervention. Tumor metabolism has distinctive featur...

Novel prodrugs for the treatment of colonic diseases based on 5-aminosalicylic acid, 4'-geranyloxyferulic acid, and auraptene: biological activities and analytical assays.

Curr. Drug Deliv. 9(2) , 112-21, (2012)

A pro-drug is a substance administered in a pharmacologically inactive structure that, once administered, is metabolised in vivo into the corresponding active principle. The rationale for the design o...

Development of a quantitative bioassay to assess preventive compounds against inflammation-based carcinogenesis.

Nitric Oxide 25(2) , 183-94, (2011)

Reducing cancer incidence and mortality by use of cancer-chemopreventive agents is an important goal. We have established an in vitro bioassay that is able to screen large numbers of candidate chemica...