| Identification | Back Directory | [Name]
AURAPTENE | [CAS]
495-02-3 | [Synonyms]
aurapten
AURAPTENE
Aurapten【C19H22O3】
7-GERANYLOXYCOUMARIN
Auraptene, 98%, from Citrus maxima (Burm.) Merr.
7-[[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]oxy]-2H-chromen-2-one
7-[[(3E)-3,7-Dimethyl-2,6-octadienyl]oxy]-2H-1-benzopyran-2-one
7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-2H-1-benzopyran-2-one
2H-1-Benzopyran-2-one,7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]- | [Molecular Formula]
C19H22O3 | [MDL Number]
MFCD00075948 | [MOL File]
495-02-3.mol | [Molecular Weight]
298.38 |
| Chemical Properties | Back Directory | [Melting point ]
91 °C | [Boiling point ]
455.5±45.0 °C(Predicted) | [density ]
1.079±0.06 g/cm3(Predicted) | [storage temp. ]
?20°C | [solubility ]
DMSO: >20mg/mL | [form ]
powder | [color ]
white to off-white | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | [LogP]
5.690 (est) |
| Hazard Information | Back Directory | [Description]
Auraptene (495-02-3) is a bioactive terpenoid occurring in a variety of citrus fruits and possessing therapeutic potential.1?? Displays neuritogenic activity2?and neuroprotective effects via suppression of inflammation and induction of GDNF and BDNF in neuronal cells3. Attenuates ROS production and enhances mitochondrial respiration which mitigates Parkinson’s disease-like behavior.4?Displays hepatoprotective5?and chemopreventive activity6. | [Uses]
antineoplastic, apoptosis inducer | [Uses]
Auraptene is a natural bioactive monoterpene coumarin ether. Auraptene has shown a remarkable effect in the prevention of degenerative diseases. | [Definition]
ChEBI: Auraptene is a member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group. Ii is isolated from several edible fruits and vegetables and exhibits a variety of therapeutic properties. It has a role as a plant metabolite, an antineoplastic agent, an apoptosis inducer, a dopaminergic agent, a neuroprotective agent, an antihypertensive agent, a gamma-secretase modulator, a vulnerary, an EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor, a PPARalpha agonist, a gastrointestinal drug, a matrix metalloproteinase inhibitor, an antioxidant and a hepatoprotective agent. It is a member of coumarins and a monoterpenoid. It is functionally related to an umbelliferone. | [Biological Activity]
Anti-inflammatory and chemopreventive compound. Exerts tumor preventive effects through apoptosis. Suppresses cell proliferation and lipid peroxidation. Acts as an agonist of PPARs. Induces phase II drug-metabolizing enzymes. | [storage]
4°C, protect from light | [References]
1) Bibak et al. (2019), A Review of the Pharmacological and Therapeutic Effects of Auraptene; Biofactors, 45 867
2) Furukawa et al. (2012), Neurotrophic Effects of Citrus Auraptene: Neuritogenic Activity in PC12 Cells; Int. J. Mol. Sci., 13 5338
3) Furukawa et al. (2020), Citrus Auraptene Induces Expression of Brain-Derived Neurotrophic Factor in Neuro2a Cells; Molecules, 25 1117
4) Jang et al. (2019), Auraptene Mitigates Parkinson’s Disease-Like Behavior by Protecting Inhibition of Mitochondrial Respiration and Scavenging Reactive Oxygen Species; Int. J. Mol. Sci., 20 3409
5) Wang et al. (2019), Hepatoprotection of Auraptene From the Peels of Citrus Fruits Against 17α-ethinylestradiol-induced Cholestasis in Mice by Activating Farnesoid X Receptor; Food Funct., 10 3839
6) Tanaka et al. (1998), Citrus Auraptene Exerts Dose-Dependent Chemopreventative Activity in Rat Large Bowel Tumorigenesis: The Inhibition Correlates With Suppression of Cell Proliferation and Lipid Peroxidation and With Induction of Phase II Drug-Metabolizing Enzymes; Cancer Res., 58 2550 |
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