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Auraptene

CAT: 0804-HY-N2388-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N2388-02Size:5 mg
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Description
Auraptene is an orally active geranyloxycoumarin that can be isolated from plants in the Brassicaceae family, antibacterial, anti-pathogen, antioxidant, anti-tumor, and neuroprotective effects. Auraptene plays an important role in the treatment of various chronic diseases such as hypertension and cystic fibrosis[1][2].
CAS Number
495-02-3
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Bacterial; MMP; PPAR
Type
Natural Products
Related Pathways
Anti-infection; Cell Cycle/DNA Damage; Metabolic Enzyme/Protease; Vitamin D Related/Nuclear Receptor
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Inflammation/Immunology; Neurological Disease; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/auraptene.html
Purity
99.97
Solubility
DMSO : 50 mg/mL (ultrasonic)
Smiles
O=C1C=CC2=CC=C(OC/C=C(C)/CC/C=C(C)/C)C=C2O1
Molecular Formula
C19H22O3
Molecular Weight
298.38
Precautions
H302, H315, H319, H335
References & Citations
[1]La VD, et al. Anti-inflammatory and wound healing potential of citrus auraptene. J Med Food. 2013 Oct;16 (10) :961-4. |[2]Krishnan P, et al. Effects of Auraptene on IGF-1 Stimulated Cell Cycle Progression in the Human Breast Cancer Cell Line, MCF-7. Int J Breast Cancer. 2012;2012:502092.|[3]Krishnan P, et al. Citrus auraptene suppresses cyclin D1 and significantly delays N-methyl nitrosourea induced mammary carcinogenesis in female Sprague-Dawley rats. BMC Cancer. 2009 Jul 29;9:259. |[4]Sekiguchi H, et al. Auraptene attenuates gastritis via reduction of Helicobacter pylori colonization and pro-inflammatory mediator production in C57BL/6 mice. J Med Food. 2012 Jul;15 (7) :658-63. |[5]Sunagawa Y, et al. Auraptene, a citrus peel-derived natural product, prevents myocardial infarction-induced heart failure by activating PPARα in rats. Phytomedicine. 2022 Dec;107:154457. |[6]Min JS, et al. Auraptene Has Antiviral Activity against Human Coronavirus OC43 in MRC-5 Cells. Nutrients. 2023 Jun 29;15 (13) :2960.|[7]Jamialahmadi K, et al. Protective Effects of Auraptene against Free Radical-Induced Erythrocytes Damage. J Pharmacopuncture. 2022 Dec 31;25 (4) :344-353. |[8]Razavi BM, et al. Antihypertensive effect of auraptene, a monoterpene coumarin from the genus Citrus, upon chronic administration. Iran J Basic Med Sci. 2015 Feb;18 (2) :153-8.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
MMP-2

Chemical Information

Auraptene

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 an antioxidant, an antineoplastic agent, an antihypertensive agent, a dopaminergic agent, a gamma-secretase modulator, a matrix metalloproteinase inhibitor, a gastrointestinal drug, a hepatoprotective agent, a neuroprotective agent, an apoptosis inducer, a PPARalpha agonist, a vulnerary, a plant metabolite and an EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor. It is a member of coumarins and a monoterpenoid. It is functionally related to an umbelliferone.

CAS Number495-02-3
PubChem CID1550607
IUPAC Name7-[(2E)-3,7-dimethylocta-2,6-dienoxy]chromen-2-one
Molecular FormulaC19H22O3
Molecular Weight298.4
XLogP5.3
Topological Polar Surface Area35.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count6
Heavy Atom Count22
Formal Charge0
Complexity469
SMILES
CC(=CCC/C(=C/COC1=CC2=C(C=C1)C=CC(=O)O2)/C)C
InChI
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
Chemical Structure
2D Structure
2D structure of Auraptene
CAS: 495-02-3
CID: 1550607
Formula: C19H22O3
MW: 298.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight298.4
XLogP35.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count6
Exact Mass298.15689456
Monoisotopic Mass298.15689456
Topological Polar Surface Area35.5 Ų
Heavy Atom Count22
Formal Charge0
Complexity469
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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