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Auraptene

$113

  • Brand : BIOFRON

  • Catalogue Number : BF-A3017

  • Specification : 98%

  • CAS number : 495-02-3

  • Formula : C19H22O3

  • Molecular Weight : 298.38

  • PUBCHEM ID : 1550607

  • Volume : 25mg

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Catalogue Number

BF-A3017

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

298.38

Appearance

White powder

Botanical Source

peel of Poncirus trifoliata

Structure Type

Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

CC(=CCCC(=CCOC1=CC2=C(C=C1)C=CC(=O)O2)C)C

Synonyms

2H-1-Benzopyran-2-one, 7-((3,7-dimethyl-2,6-octadienyl)oxy)-, (E)-/Coumarin, 7-[(3,7-dimethyl-2,6-octadienyl)oxy]-, (E)-/Auraptene/2H-1-Benzopyran-2-one, 7-[(3,7-dimethyl-2,6-octadienyl)oxy]-, (E)-/7-{[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]oxy}-2H-chromen-2-one/7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-2H-1-benzopyran-2-one 7-Geranyloxycoumarin Aurapten/7-{[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]oxy}-2H-chromen-2-one/2H-1-Benzopyran-2-one, 7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-/7-Geranyloxycoumarin/7-{[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]oxy}-2H-chromen-2-one/aurapten

IUPAC Name

7-[(2E)-3,7-dimethylocta-2,6-dienoxy]chromen-2-one

Density

1.1±0.1 g/cm3

Solubility

Methanol; Ethyl Acetate

Flash Point

195.4±23.3 °C

Boiling Point

455.5±45.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:495-02-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31424600

Abstract

There is a growing awareness in herbal medications as they are usually safe and devoid of significant adverse effects. Auraptene is a natural bioactive monoterpene coumarin ether and is consumed all over the world. There is growing evidence of the therapeutic benefits of auraptene. Auraptene, also known as auraptene and 7-geranyloxycoumarin, is a bioactive monoterpene coumarin from Rutaceae family, which is isolated from Citrus aurantium (Seville orange) and Aegle marmelos (bael fruit). Auraptene is a highly pleiotropic molecule, which can modulate intracellular signaling pathways that control inflammation, cell growth, and apoptosis. It has a potential therapeutic role in the prevention and treatment of various diseases due to its anti-inflammatory and antioxidant activities as well as its excellent safety profile. In the present article, various pharmacological and therapeutic effects of auraptene were reviewed. Different online databases using keywords such as auraptene, therapeutic effects and pharmacological effects were searched until the end of September 2018, for this purpose. Auraptene has been suggested to be effective in the treatment of a broad range of disorders including inflammatory disorders, dysentery, wounds, scars, keloids, and pain. In addition, different studies have demonstrated that auraptene possesses numerous pharmacological properties including anti-inflammatory, anti-oxidative, anti-diabetic, anti-hypertensive and anti-cancer as well as neuroprotective effects. The present review provides a detailed survey of scientific researches regarding pharmacological properties and therapeutic effects of auraptene.

© 2019 International Union of Biochemistry and Molecular Biology.

KEYWORDS

auraptene; chemopreventive; pharmacological properties

Title

A review of the pharmacological and therapeutic effects of auraptene.

Author

Bibak B1,2, Shakeri F1, Barreto GE3, Keshavarzi Z1,2, Sathyapalan T4, Sahebkar A5,6,7.

Publish date

2019 Nov

PMID

27207438

Abstract

The high incidence of esophageal squamous cell carcinoma has been reported in selected ethnic populations including North of Iran. Low survival rate of esophageal carcinoma is partially due to the presence of stem-like cancer cells with chemotherapy resistance. In the current study, we aimed to determine the effects of auraptene, an interesting dietary coumarin with various biological activities, on malignant properties of stem-like esophageal squamous cell carcinoma, in terms of sensitivity to anticancer drugs and expression of specific markers. To do so, the half maximal inhibitory concentration values of auraptene, cisplatin, paclitaxel, and 5-fluorouracil were determined on esophageal carcinoma cells (KYSE30 cell line). After administrating combinatorial treatments, including nontoxic concentrations of auraptene + cisplatin, paclitaxel, or 5-fluorouracil, sensitivity of cells to chemical drugs and also induced apoptosis were assessed. In addition, quantitative real-time polymerase chain reaction was used to study changes in the expression of tumor suppressor proteins 53 and 21 ( P53 and P21), cluster of differentiation 44 ( CD44), and B cell-specific Moloney murine leukemia virus integration site 1 ( BMI-1) upon treatments. Results of thiazolyl blue assay revealed that auraptene significantly ( P < .05) increased toxicity of cisplatin, paclitaxel, and 5-fluorouracil in KYSE30 cells, specifically 72 hours after treatment. Conducting an apoptosis assay using flow cytometry also confirmed the synergic effects of auraptene. Results of quantitative real-time polymerase chain reaction revealed significant ( P < .05) upregulation of P53 and P21 upon combinatorial treatments and also downregulation of CD44 and BMI-1 after auraptene administration. Current study provided evidence, for the first time, that auraptene attenuates the properties of esophageal stem-like cancer cells through enhancing sensitivity to chemical agents and reducing the expression of CD44 and BMI-1 markers.

KEYWORDS

auraptene; esophageal cancer; stem-like cancer cells; synergic effects

Title

Auraptene Attenuates Malignant Properties of Esophageal Stem-Like Cancer Cells.

Author

Saboor-Maleki S1, Rassouli FB1,2, Matin MM1,2, Iranshahi M3.

Publish date

2017 Aug

PMID

27771936

Abstract

Auraptene (7-geranyloxycoumarin) is the best known and most abundant prenyloxycoumarin present in nature. It is synthesized by various plant species, mainly those of the Rutaceae and Umbeliferae (Apiaceae) families, comprising many edible fruits and vegetables such as lemons, grapefruit and orange. Auraptene has shown a remarkable effect in the prevention of degenerative diseases, in particular it has been reported to be one the most promising known natural chemopreventive agents against several types of cancer. The aim of this chapter is to review the effects of auraptene in the prevention and treatment of different chronic diseases.

KEYWORDS

Auraptene; Chemoprevention; Degenerative diseases; Hypertension; Lipid profile

Title

Auraptene and Its Role in Chronic Diseases.

Author

Derosa G1,2,3,4, Maffioli P5,6,7, Sahebkar A8,9,10.

Publish date

2016


Description :

Auraptene is the most abundant naturally occurring geranyloxycoumarin. Auraptene is primarily isolated from plants in the Rutaceae family, such as citrus fruits. Auraptene decreases the secretion of matrix metalloproteinase 2 (MMP-2) as well as key inflammatory mediators, including IL-6, IL-8, and chemokine (C-C motif) ligand-5(CCL5)[1].