Auraptene

Modify Date: 2024-01-04 17:32:52

Auraptene Structure
Auraptene structure
Common Name Auraptene
CAS Number 495-02-3 Molecular Weight 298.376
Density 1.1±0.1 g/cm3 Boiling Point 455.5±45.0 °C at 760 mmHg
Molecular Formula C19H22O3 Melting Point 66 °C
MSDS Chinese USA Flash Point 195.4±23.3 °C

 Use of Auraptene


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].

 Names

Name auraptene
Synonym More Synonyms

 Auraptene 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
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

 Safety Information

Safety Phrases S24/25
RIDADR NONH for all modes of transport

 Articles23

More 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...

 Synonyms

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
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