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495-02-3,MFCD00075948
Catalog No.:AA00D8N3

495-02-3 | Auraptene

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1mg
99%
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$8.00   $6.00
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10mg
≥98%
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$56.00   $39.00
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50mg
99%
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$58.00   $41.00
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250mg
99%
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$107.00   $75.00
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00D8N3
Chemical Name:
Auraptene
CAS Number:
495-02-3
Molecular Formula:
C19H22O3
Molecular Weight:
298.3762
MDL Number:
MFCD00075948
SMILES:
C/C(=C\COc1ccc2c(c1)oc(=O)cc2)/CCC=C(C)C
NSC Number:
711511
Properties
Computed Properties
 
Complexity:
469  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
22  
Hydrogen Bond Acceptor Count:
3  
Rotatable Bond Count:
6  
XLogP3:
5.3  

Upstream Synthesis Route

[1]Phytochemistry,1998,vol.47,#8,p.1521-1525

[2]ChemicalandPharmaceuticalBulletin,2004,vol.52,#10,p.1171-1174

[3]BioorganicandMedicinalChemistry,2012,vol.20,#2,p.784-788

[4]BulletindesSocietesChimiquesBelges,1994,vol.103,#7-8,p.405-424

[5]OrganicandBiomolecularChemistry,2006,vol.4,#8,p.1604-1610

[6]JournalofMedicinalChemistry,1992,vol.35,#10,p.1877-1882

[7]BioorganicandMedicinalChemistryLetters,2011,vol.21,#19,p.5770-5773

[8]EuropeanJournalofMedicinalChemistry,2012,vol.57,p.134-142

[9]BioorganicandMedicinalChemistryLetters,2014,vol.24,#19,p.4654-4658

[10]BioorganicandMedicinalChemistryLetters,2017,vol.27,#13,p.2920-2925

[11]JournalofNaturalProducts,2017,vol.80,#6,p.1939-1943

[12]PhytotherapyResearch,2017,vol.31,#9,p.1369-1375

[1]Phytochemistry,2004,vol.65,#22,p.3021-3027

[1]BioorganicandMedicinalChemistryLetters,2017,vol.27,#13,p.2920-2925

[1]Phytochemistry(Elsevier),1992,vol.31,#4,p.1363-1366

[2]Phytochemistry(Elsevier),1992,vol.31,#4,p.1363-1366

[1]JournalofNaturalProducts,2009,vol.72,#9,p.1702-1704

Downstream Synthesis Route

[1]Phytochemistry,1998,vol.47,p.1521-1525

[2]ChemicalandPharmaceuticalBulletin,2004,vol.52,p.1171-1174

[3]BioorganicandMedicinalChemistry,2012,vol.20,p.784-788

[4]BulletindesSocietesChimiquesBelges,1994,vol.103,p.405-424

[5],2020

[6]OrganicandBiomolecularChemistry,2006,vol.4,p.1604-1610

[7]JournalofMedicinalChemistry,1992,vol.35,p.1877-1882

[8]BioorganicandMedicinalChemistryLetters,2011,vol.21,p.5770-5773

[9]EuropeanJournalofMedicinalChemistry,2012,vol.57,p.134-142

[10]BioorganicandMedicinalChemistryLetters,2014,vol.24,p.4654-4658

[11]BioorganicandMedicinalChemistryLetters,2017,vol.27,p.2920-2925

[12]JournalofNaturalProducts,2017,vol.80,p.1939-1943

[13]PhytotherapyResearch,2017,vol.31,p.1369-1375

[14]EuropeanJournalofMedicinalChemistry,2018,vol.152,p.274-282

[1]ChemicalandPharmaceuticalBulletin,2004,vol.52,p.1171-1174

[2]JournalofMedicinalChemistry,1992,vol.35,p.1877-1882

[3]Tetrahedron,1988,vol.44,p.101-110

[4]IndianJournalofChemistry-SectionBOrganicandMedicinalChemistry,1982,vol.21,p.496-498

[5]Phytochemistry,2004,vol.65,p.3021-3027

[6]Tetrahedron,1988,vol.44,p.101-110

[1]TetrahedronLetters,1987,vol.28,p.2579-2582

[1]AgriculturalandBiologicalChemistry,1987,vol.51,p.419-423

[1]JournalofMedicinalChemistry,1992,vol.35,p.1877-1882

Literature

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Auraptene attenuates gastritis via reduction of Helicobacter pylori colonization and pro-inflammatory mediator production in C57BL/6 mice.

Journal: Journal of medicinal food 20120701

Title: Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist.

Journal: Bioorganic & medicinal chemistry letters 20120501

Title: Novel prodrugs for the treatment of colonic diseases based on 5-aminosalicylic acid, 4'-geranyloxyferulic acid, and auraptene: biological activities and analytical assays.

Journal: Current drug delivery 20120301

Title: Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor.

Journal: Bioorganic & medicinal chemistry 20120115

Title: Neurotrophic effect of citrus auraptene: neuritogenic activity in PC12 cells.

Journal: International journal of molecular sciences 20120101

Title: Effects of Auraptene on IGF-1 Stimulated Cell Cycle Progression in the Human Breast Cancer Cell Line, MCF-7.

Journal: International journal of breast cancer 20120101

Title: Auraptene regulates gene expression involved in lipid metabolism through PPARα activation in diabetic obese mice.

Journal: Molecular nutrition & food research 20111201

Title: Pancreatic anticancer activity of a novel geranylgeranylated coumarin derivative.

Journal: Bioorganic & medicinal chemistry letters 20111001

Title: Identification, synthesis and quantification of process-related impurities in auraptene.

Journal: Journal of pharmaceutical and biomedical analysis 20110910

Title: Development of a quantitative bioassay to assess preventive compounds against inflammation-based carcinogenesis.

Journal: Nitric oxide : biology and chemistry 20110801

Title: Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.

Journal: Bioorganic & medicinal chemistry letters 20110715

Title: Potential benefits of supplementation with auraptene in cystic fibrosis.

Journal: Clinical nutrition (Edinburgh, Scotland) 20110401

Title: Auraptene: a natural biologically active compound with multiple targets.

Journal: Current drug targets 20110301

Title: Citrus auraptene: a potential multifunctional therapeutic agent for nonalcoholic fatty liver disease.

Journal: Annals of hepatology 20110101

Title: Effects of selected food phytochemicals in reducing the toxic actions of TCDD and p,p'-DDT in U937 macrophages.

Journal: Archives of toxicology 20101201

Title: Auraptene is an inhibitor of cholesterol esterification and a modulator of estrogen receptors.

Journal: Molecular pharmacology 20101101

Title: Anti-human immunodeficiency virus-1 constituents of the bark of Poncirus trifoliata.

Journal: Chemical & pharmaceutical bulletin 20100701

Title: A natural propenoic acid derivative activates peroxisome proliferator-activated receptor-beta/delta (PPARbeta/delta).

Journal: Life sciences 20100327

Title: Colorectal cancer chemoprevention by 2 beta-cyclodextrin inclusion compounds of auraptene and 4'-geranyloxyferulic acid.

Journal: International journal of cancer 20100215

Title: Auraptene from Ferula szowitsiana protects human peripheral lymphocytes against oxidative stress.

Journal: Phytotherapy research : PTR 20100101

Title: Suppression of CD74 expression and Helicobacter pylori adhesion by auraptene targeting serum starvation-activated ERK1/2 in NCI-N87 gastric carcinoma cells.

Journal: Bioscience, biotechnology, and biochemistry 20100101

Title: Effects of ATRA combined with citrus and ginger-derived compounds in human SCC xenografts.

Journal: BMC cancer 20100101

Title: Aggressive mammary carcinoma progression in Nrf2 knockout mice treated with 7,12-dimethylbenz[a]anthracene.

Journal: BMC cancer 20100101

Title: Prenyloxyphenylpropanoids as a novel class of anticonvulsive agents.

Journal: Bioorganic & medicinal chemistry letters 20090915

Title: Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4.

Journal: Journal of natural products 20090901

Title: Comparison of citrus coumarins on carcinogen-detoxifying enzymes in Nrf2 knockout mice.

Journal: Toxicology letters 20090328

Title: Identification and physiological evaluation of the components from citrus fruits as potential drugs for anti-corpulence and anticancer.

Journal: Bioorganic & medicinal chemistry 20090101

Title: Chemoprevention with phytochemicals targeting inducible nitric oxide synthase.

Journal: Forum of nutrition 20090101

Title: Citrus auraptene suppresses cyclin D1 and significantly delays N-methyl nitrosourea induced mammary carcinogenesis in female Sprague-Dawley rats.

Journal: BMC cancer 20090101

Title: Effects of chemopreventive citrus phytochemicals on human P-glycoprotein and multidrug resistance protein 1.

Journal: European journal of pharmacology 20081214

Title: Citrus auraptene acts as an agonist for PPARs and enhances adiponectin production and MCP-1 reduction in 3T3-L1 adipocytes.

Journal: Biochemical and biophysical research communications 20080201

Title: Umbelliprenin from Ferula szowitsiana inhibits the growth of human M4Beu metastatic pigmented malignant melanoma cells through cell-cycle arrest in G1 and induction of caspase-dependent apoptosis.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20080101

Title: Metabolism and absorption of auraptene (7-geranyloxylcoumarin) in male SD rats: comparison with 7-ethoxycoumarin.

Journal: Nutrition and cancer 20080101

Title: Citrus compounds inhibit inflammation- and obesity-related colon carcinogenesis in mice.

Journal: Nutrition and cancer 20080101

Title: Auraptene, a citrus fruit compound, regulates gene expression as a PPARalpha agonist in HepG2 hepatocytes.

Journal: BioFactors (Oxford, England) 20080101

Title: Apoptogenic activity of auraptene of Zanthoxylum schinifolium toward human acute leukemia Jurkat T cells is associated with ER stress-mediated caspase-8 activation that stimulates mitochondria-dependent or -independent caspase cascade.

Journal: Carcinogenesis 20070601

Title: Protective effects of citrus nobiletin and auraptene in transgenic rats developing adenocarcinoma of the prostate (TRAP) and human prostate carcinoma cells.

Journal: Cancer science 20070401

Title: Citrus auraptene suppresses azoxymethane-induced colonic preneoplastic lesions in C57BL/KsJ-db/db mice.

Journal: Nutrition and cancer 20070101

Title: Citrus auraptene reduces Helicobacter pylori colonization of glandular stomach lesions in Mongolian gerbils.

Journal: Journal of oleo science 20070101

Title: Citrus nobiletin suppresses bone loss in ovariectomized ddY mice and collagen-induced arthritis in DBA/1J mice: possible involvement of receptor activator of NF-kappaB ligand (RANKL)-induced osteoclastogenesis regulation.

Journal: BioFactors (Oxford, England) 20070101

Title: Auraptene decreases the activity of matrix metalloproteinases in dextran sulfate sodium-induced ulcerative colitis in ICR mice.

Journal: Bioscience, biotechnology, and biochemistry 20061201

Title: In vitro inhibitory activity of boropinic acid against Helicobacter pylori.

Journal: Bioorganic & medicinal chemistry letters 20061101

Title: Citrus auraptene targets translation of MMP-7 (matrilysin) via ERK1/2-dependent and mTOR-independent mechanism.

Journal: FEBS letters 20061002

Title: Dietary administration with prenyloxycoumarins, auraptene and collinin, inhibits colitis-related colon carcinogenesis in mice.

Journal: International journal of cancer 20060615

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Suppression of beta-catenin mutation by dietary exposure of auraptene, a citrus antioxidant, in N,N-diethylnitrosamine-induced hepatocellular carcinomas in rats.

Journal: Oncology reports 20050801

Title: [Chemical study of citrus plants in the search for cancer chemopreventive agents].

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20050301

Title: Aurapten, a coumarin with growth inhibition against Leishmania major promastigotes.

Journal: Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas 20041201

Title: Synthesis and anti-inflammatory activity of natural and semisynthetic geranyloxycoumarins.

Journal: Bioorganic & medicinal chemistry letters 20040503

Title: Dietary supplementation of the citrus antioxidant auraptene inhibits N,N-diethylnitrosamine-induced rat hepatocarcinogenesis.

Journal: Oncology 20040101

Title: Effects of selected food factors with chemopreventive properties on combined lipopolysaccharide- and interferon-gamma-induced IkappaB degradation in RAW264.7 macrophages.

Journal: Cancer letters 20030530

Title: Identification of epoxybergamottin as a CYP3A4 inhibitor in grapefruit peel.

Journal: European journal of clinical pharmacology 20030201

Title: Rapid and convenient method for preparing aurapten-enriched product from hassaku peel oil: implications for cancer-preventive food additives.

Journal: Journal of agricultural and food chemistry 20020522

Title: Inhibition of acetylcholinesterase activity by essential oil from Citrus paradisi.

Journal: Natural product letters 20010101

Title: La VD, et al. Anti-inflammatory and wound healing potential of citrus auraptene. J Med Food. 2013 Oct;16(10):961-4.

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