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Aurapten

Alias: 7-GeranyloxycoumarinAuraptenAuraptene
Cat No.:V7756 Purity: ≥98%
Auraptene is the most abundant natural geranoxycoumarin.
Aurapten
Aurapten Chemical Structure CAS No.: 495-02-3
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
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Product Description
Auraptene is the most abundant natural geranoxycoumarin. Auraptene reduces the secretion of matrix metalloproteinase 2 (MMP-2) as well as key inflammatory factors like IL-6, IL-8, and chemokine (CC motif) ligand-5 (CCL5).
Biological Activity I Assay Protocols (From Reference)
References

[1]. Anti-inflammatory and wound healing potential of citrus auraptene. J Med Food. 2013 Oct;16(10):961-4.

[2]. 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]. 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]. 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]. Auraptene, a citrus peel-derived natural product, prevents myocardial infarction-induced heart failure by activating PPARα in rats. Phytomedicine. 2022 Dec;107:154457.

[6]. Auraptene Has Antiviral Activity against Human Coronavirus OC43 in MRC-5 Cells. Nutrients. 2023 Jun 29;15(13):2960.

[7]. Protective Effects of Auraptene against Free Radical-Induced Erythrocytes Damage. J Pharmacopuncture. 2022 Dec 31;25(4):344-353.

[8]. 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.

Additional Infomation
Auraptene is a member of the class of coumarins that is umbelliferone in which the phenolic hydrogen has been replaced by a geranyl group.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.
Auraptene has been reported in Sinacalia tangutica, Polygala paniculata, and other organisms with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H22O3
Molecular Weight
298.38
Exact Mass
298.156
CAS #
495-02-3
PubChem CID
1550607
Appearance
Off-white to light yellow solid powder
Density
1.1±0.1 g/cm3
Boiling Point
455.5±45.0 °C at 760 mmHg
Melting Point
66 °C
Flash Point
195.4±23.3 °C
Vapour Pressure
0.0±1.1 mmHg at 25°C
Index of Refraction
1.549
LogP
5.69
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
6
Heavy Atom Count
22
Complexity
469
Defined Atom Stereocenter Count
0
SMILES
O(C1C([H])=C([H])C2C([H])=C([H])C(=O)OC=2C=1[H])C([H])([H])/C(/[H])=C(\C([H])([H])[H])/C([H])([H])C([H])([H])/C(/[H])=C(\C([H])([H])[H])/C([H])([H])[H]
InChi Key
RSDDHGSKLOSQFK-RVDMUPIBSA-N
InChi Code
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+
Chemical Name
7-[(2E)-3,7-dimethylocta-2,6-dienoxy]chromen-2-one
Synonyms
7-GeranyloxycoumarinAuraptenAuraptene
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~50 mg/mL (~167.57 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.97 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (6.97 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (6.97 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.3514 mL 16.7572 mL 33.5143 mL
5 mM 0.6703 mL 3.3514 mL 6.7029 mL
10 mM 0.3351 mL 1.6757 mL 3.3514 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT04744922 COMPLETED Dietary Supplement: Extracts of citrus peels standardized
in AUR and NAR (phytocomplex).
Subjective Cognitive Decline IRCCS Centro San Giovanni di Dio Fatebenefratelli 2021-04-07 Not Applicable
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