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
More
Less

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)
More
Less

Safety

WGK Germany 
3
HS Code 
2932990090
More
Less

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.

More
Less

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
More
Less

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

More
Less

AURAPTENE Suppliers

Americas 1 Canada 1 China 155 Europe 1 Germany 1 India 3 Japan 1 United Kingdom 4 United States 17 USA 1 Global 185
ALB Technology Limited
Tel
702-983-3769
Fax
702-983-3769
Email
sales@albtechnology.com
Country
United States
ProdList
2993
Advantage
55
EMMX Biotechnology LLC
Tel
888-539-0666
Fax
888-539-0666
Email
info@emmx.com
Country
United States
ProdList
8447
Advantage
60
TargetMol Chemicals Inc.
Tel
+1-781-999-5354; +17819995354
Email
marketing@targetmol.com
Country
United States
ProdList
32435
Advantage
58
Aladdin Scientific
Tel
Email
tp@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
TargetMol Chemicals Inc.
Tel
+1-781-999-5354;
Email
support@targetmol.com
Country
United States
ProdList
39035
Advantage
58
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6718
Advantage
47
Focus Biomolecules
Tel
--
Fax
--
Email
sales@focusbiomolecules.com
Country
United States
ProdList
1284
Advantage
58
Abcam Limited
Tel
--
Fax
--
Email
us.orders@abcam.com
Country
United States
ProdList
6001
Advantage
50
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
United States Biological
Tel
--
Fax
--
Email
chemicals@usbio.net
Country
United States
ProdList
6214
Advantage
80
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
Combi-Blocks Inc.
Tel
--
Fax
--
Email
sales@combi-blocks.com
Country
United States
ProdList
6618
Advantage
69
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
FortopChem Technology Limited
Tel
--
Fax
--
Email
sales@fortopchem.com
Country
United States
ProdList
1099
Advantage
50
Santa Cruz Biotechnology, Inc.
Tel
--
Fax
--
Email
scbt@scbt.com
Country
United States
ProdList
3597
Advantage
60
ChromaDex
Tel
--
Fax
--
Email
sales@chromadex.com
Country
United States
ProdList
2501
Advantage
76
LKT Laboratories, Inc.
Tel
--
Fax
--
Email
info@lktlabs.com
Country
United States
ProdList
2164
Advantage
64
More
Less

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