CAS 495-02-3|Auraptene
| 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 | ChineseUSA | Flash Point | 195.4±23.3 °C |
Names
| Name | auraptene |
|---|---|
| Synonym | More Synonyms |
Auraptene BiologicalActivity
| 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/ImmunologySignaling 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 |
| InChIKey | RSDDHGSKLOSQFK-RVDMUPIBSA-N |
| SMILES | CC(C)=CCCC(C)=CCOc1ccc2ccc(=O)oc2c1 |
| 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 |
