ChemicalBook > CAS DataBase List > AURAPTENE

AURAPTENE

Product Name: AURAPTENE
CAS No.: 495-02-3
Chemical Name: AURAPTENE
Synonyms: aurapten;AURAPTENE;Aurapten -RM;Aurapten【C19H22O3】;AURAPTENE(RG) 25mg;7-GERANYLOXYCOUMARIN;Auraptene, 10 mM in DMSO;Auraptene, Activates PPARalpha and PPARgamma;Auraptene, 98%, from Citrus maxima (Burm.) Merr.;(E)-7-((3,7-Dimethylocta-2,6-dien-1-yl)oxy)-2H-chromen-2-one
CBNumber: CB3269606
Molecular Formula: C19H22O3
Formula Weight: 298.38
MOL File: 495-02-3.mol

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AURAPTENE Property

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.
LogP: 5.690 (est)

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Safety

WGK Germany: 3
HS Code: 2932990090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: A9861
Product name: Auraptene
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $114.95
Updated: 2025/07/31

Sigma-Aldrich

Product number: A9861
Product name: Auraptene
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $363
Updated: 2025/07/31

TCI Chemical

Product number: A3147
Product name: Auraptene
Packaging: 25MG
Price: $101
Updated: 2025/07/31

TCI Chemical

Product number: A3147
Product name: Auraptene
Packaging: 100MG
Price: $275
Updated: 2025/07/31

Cayman Chemical

Product number: 14000
Product name: Auraptene
Purity: ≥98%
Packaging: 5mg
Price: $29
Updated: 2024/03/01

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AURAPTENE Chemical Properties,Usage,Production

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.

Animal Model:	Female C57BL/6 mice^[4].
Dosage:	100, 500 ppm
Administration:	Oral gavage (p.o.); mixed in the diet
Result:	Inhibited H. pylori–induced expression and/or production of CD74, macrophage migration inhibitory factor, interleukin-1b, and tumor necrosis factor-a in gastric mucosa, together with serum macrophage inhibitory protein-2.

Animal Model:	Sprague–Dawley rats with moderate myocardial infarction^[5].
Dosage:	5, 50 mg/kg
Administration:	Oral gavage (p.o.); 6 weeks
Result:	Suppresses PE-induced hypertrophic responses in cardiomyocytes. Prevented the development of cardiac hypertrophy and fibrosis in rats with myocardial infarction.

Animal Model:	Desoxycorticosterone acetate (DOCA) salt induced hypertensive rats^[8].
Dosage:	2, 4, 8, 16 mg/kg
Administration:	Oral gavage (p.o.); 5 weeks
Result:	Reduced the mean systolic blood pressure (MSBP) in DOCA salt treated rats.

IC 50

MMP-2

References

[1] BAHRAM BIBAK. A review of the pharmacological and therapeutic effects of auraptene[J]. BioFactors, 2019, 45 6: 867-879. DOI:10.1002/biof.1550
[2] YOSHIKO FURUKAWA. Neurotrophic effect of citrus auraptene: neuritogenic activity in PC12 cells.[J]. International Journal of Molecular Sciences, 2012, 13 5: 5338-5347. DOI:10.3390/ijms13055338
[3] YOSHIKO FURUKAWA. Citrus Auraptene Induces Expression of Brain-Derived Neurotrophic Factor in Neuro2a Cells.[J]. Molecules, 2020. DOI:10.3390/molecules25051117
[4] YUNSEON JANG. Auraptene Mitigates Parkinson’s Disease-Like Behavior by Protecting Inhibition of Mitochondrial Respiration and Scavenging Reactive Oxygen Species[J]. International Journal of Molecular Sciences, 2019. DOI:10.3390/ijms20143409
[5] WANG J, FU T, DONG R, et al. Hepatoprotection of auraptene from the peels of citrus fruits against 17α-ethinylestradiol-induced cholestasis in mice by activating farnesoid X receptor[J]. Food & Function, 2019, 7: 3839-3850. DOI:10.1039/c9fo00318e
[6] T TANAKA. Citrus auraptene exerts dose-dependent chemopreventive 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.[J]. Cancer research, 1998, 58 12: 2550-2556.

AURAPTENE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from AURAPTENE manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: Auraptene 495-02-3
Price: US $0.00-0.00/KG
Min. Order: 5mg
Purity: 99%HPLC
Supply Ability: 2000tons
Release date: 2020-01-06

Shanghai Standard Technology Co., Ltd.

Product: Auraptene 495-02-3
Price: US $0.00/mg
Min. Order: 20mg
Purity: ≥98%(HPLC)
Supply Ability: 100 g
Release date: 2020-08-21

Career Henan Chemical Co

Product: AURAPTENE 495-02-3
Price: US $2.00/KG
Min. Order: 1g
Purity: 98%min
Supply Ability: ask
Release date: 2020-01-08

495-02-3, AURAPTENERelated Search:

MERANZIN Celastrol Wogonin Harpagoside PEONIDIN CHLORIDE Nobiletin Lupeol BISINDOLYLMALEIMIDE I HYDROCHLORIDE Taxifolin Phenylbutazone Tranilast SINENSETIN(P) Geraniol AURAPTENE OXYPEUCEDANIN Acetoxyaurapten AURAPTENE(RG) 6-METHOXYAURAPTEN

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.

7-[[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]oxy]-2H-chromen-2-one

(E)-7-((3,7-Dimethylocta-2,6-dien-1-yl)oxy)-2H-chromen-2-one

Aurapten -RM

AURAPTENE(RG) 25mg

Auraptene, Activates PPARalpha and PPARgamma

Auraptene, 10 mM in DMSO

495-02-3

495-2-3