AURAPTENE CAS 495-02-3

Introduction：Basic information about AURAPTENE CAS 495-02-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

AURAPTENE Basic information

• Product Name: AURAPTENE
• Synonyms: AURAPTENE;7-GERANYLOXYCOUMARIN;2H-1-Benzopyran-2-one,7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-;7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-2H-1-benzopyran-2-one;aurapten;7-[[(3E)-3,7-Dimethyl-2,6-octadienyl]oxy]-2H-1-benzopyran-2-one;Aurapten【C19H22O3】;Auraptene, 98%, from Citrus maxima (Burm.) Merr.
• CAS: 495-02-3
• MF: C19H22O3
• MW: 298.38
• Mol File: 495-02-3.mol

AURAPTENE Chemical Properties

• Melting point: 91 °C
• Boiling point: 455.5±45.0 °C(Predicted)
• density: 1.079±0.06 g/cm3(Predicted)
• storage temp.: Sealed in dry,Store in freezer, under -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.
• 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+
• InChIKey: RSDDHGSKLOSQFK-RVDMUPIBSA-N
• SMILES: C\C(C)=C\CC\C(C)=C\COc1ccc2C=CC(=O)Oc2c1
• LogP: 5.690 (est)

Safety Information

• WGK Germany: 3
• HS Code: 2932990090
• Storage Class: 11 - Combustible Solids

AURAPTENE Usage And Synthesis

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.

Chemical Properties

Soluble in methanol, ethanol, DMSO and other organic solvents, derived from the unripe or nearly ripe dried outer pericarp of Hualizhou pomelo or pomelo of the Brassicaceae family; Citrus red.

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ChEBI: Auraptene is a member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group.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.

Synthesis

93-35-6

6138-90-5

495-02-3

Synthesis procedure for Aurapten (5): propylene oxide (159 μL, 0.80 mmol) was added to a stirred mixture of 7-hydroxycoumarin (100 mg, 0.62 mmol) and anhydrous potassium carbonate (171 mg, 1.24 mmol) in anhydrous N,N-dimethylformamide (5 mL) under argon protection. The reaction mixture was stirred under reflux conditions for 3 hours. After completion of the reaction, the reaction mixture was neutralized with 1 M aqueous hydrochloric acid. The brown residue obtained was dissolved in dichloromethane (20 mL), washed sequentially with water (2 x 20 mL), saturated saline (30 mL) and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a brown oil, which was purified by fast column chromatography using diethyl ether-hexane (1:1) as eluent to give a white powdery product 5 (181 mg, 76% yield). The structure of the product was confirmed by 1H NMR, 13C NMR and high resolution fast atom bombardment mass spectrometry (HR-FABMS).

in vivo

Auraptene (200, 500 ppm, mixed in the diet, p.o.) delays the tumor progression of breast cancer rats by inhibiting cyclin D1 protein^[3].Auraptene (100, 500 ppm, mixed in the diet, p.o.) alleviates gastritis by reducing Helicobacter pylori colonization and pro-inflammatory mediator production in C57BL/6 mice^[4].Auraptene (5, 50 mg/kg, 6 weeks, p.o.) prevents heart failure caused by myocardial infarction by activating peroxisome proliferator activated receptor alpha (PPAR alpha) in rats ^[5].Auraptene (2, 4, 8, 16 mg/kg, 5 weeks, p.o.) exhibits anti hypertensive effects in hypertensive rats by reducing mean systolic blood pressure^[8].

• Animal Model: Mammary carcinogenesis model in female Sprague Dawley rats^[3].
• Dosage: 200, 500 ppm
• Administration: Oral gavage (p.o.); mixed in the diet
• Result: Delayed median time to tumor by 39 days and reduced Insulin like Growth Factor-1 (IGF-1, 10 ng/mL)-induced cyclin D1 expression by 40% in MCF-7 cells.