EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

auraptene
7-geranyloxycoumarin

Supplier Sponsors

Name:7-[(2E)-3,7-dimethylocta-2,6-dienoxy]chromen-2-one
CAS Number: 495-02-3Picture of molecule3D/inchi
FDA UNII: F79I1ZEL2E
Nikkaji Web:J108.361I
MDL:MFCD00075948
XlogP3:5.30 (est)
Molecular Weight:298.38194000
Formula:C19 H22 O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:colorless crystals (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 91.00 °C. @ 760.00 mm Hg
Boiling Point: 455.50 °C. @ 760.00 mm Hg (est)
Flash Point: 384.00 °F. TCC ( 195.40 °C. ) (est)
logP (o/w): 5.690 (est)
Soluble in:
 water, 0.1715 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Auraptene 98%
BOC Sciences
For experimental / research use only.
Auraptene 98.5%
Odor: characteristic
Use: Auraptene isolated from the peel of Poncirus trifoliata. It considerably reduces MSBP in hypertensive rats, but not in normotensive rats. antifungal; anti-tumor activity; anti-oxidant activity; anti-inflammatory effect
Coompo
For experimental / research use only.
Auraptene from Plants ≥95%
Santa Cruz Biotechnology
For experimental / research use only.
Auraptene ≥95%
Sigma-Aldrich: Sigma
For experimental / research use only.
Auraptene ≥98% (HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for auraptene usage levels up to:
 not for fragrance use.
 
Recommendation for auraptene flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :1550607
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
7-[(2E)-3,7-dimethylocta-2,6-dienoxy]chromen-2-one
Chemidplus:0000495023
 
References:
 7-[(2E)-3,7-dimethylocta-2,6-dienoxy]chromen-2-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):1550607
Pubchem (sid):135227194
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB34054
FooDB:FDB012300
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 apple wood apple fruit
Search Trop Picture
 lemon fruit oil
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 orange fruit
Search Trop Picture
 orange oil bitter
Search Trop Picture
 orange oil sweet
Search Trop Picture
 
Synonyms:
 aurapten
2H-1-benzopyran-2-one, 7-((3,7-dimethyl-2,6-octadienyl)oxy)-, (E)-
2H-1-benzopyran-2-one, 7-[(3,7-dimethyl-2,6-octadienyl)oxy]-, (E)-
2H-1-benzopyran-2-one, 7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-
 coumarin, 7-[(3,7-dimethyl-2,6-octadienyl)oxy]-, (E)-
7-[(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-{[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy}-2H-chromen-2-one
(E)-7-((3,7-dimethyl-2,6-octadienyl)oxy)-2H-1-benzopyran-2-one
7-[(3,7-dimethyl-2,6-octadienyl)oxy]-2H-chromen-2-one
7-((E)-3,7-dimethyl-octa-2,6-dienyloxy)-chromen-2-one
(E)-7-((3,7-dimethylocta-2,6-dien-1-yl)oxy)-2H-chromen-2-one
7-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}-2H-chromen-2-one
7-[(2E)-3,7-dimethylocta-2,6-dienoxy]chromen-2-one
7-((2E)-3,7-dimethylocta-2,6-dienyloxy)chromen-2-one
7-geranyl oxycoumarin
7-geranyloxycoumarin
(E)-meranzin
 

Articles:

PubMed:Auraptene has the inhibitory property on murine T lymphocyte activation.
PubMed:Auraptene increases the production of amyloid-β via c-Jun N-terminal kinase-dependent activation of γ-secretase.
PubMed:Antihypertensive effect of auraptene, a monoterpene coumarin from the genus Citrus, upon chronic administration.
PubMed:Suppression of mitochondrial respiration with auraptene inhibits the progression of renal cell carcinoma: involvement of HIF-1α degradation.
PubMed:Auraptene, a Major Compound of Supercritical Fluid Extract of Phalsak (Citrus Hassaku Hort ex Tanaka), Induces Apoptosis through the Suppression of mTOR Pathways in Human Gastric Cancer SNU-1 Cells.
PubMed:Anti-inflammatory effect of auraptene extracted from trifoliate orange (Poncirus trifoliate) on LPS-stimulated RAW 264.7 cells.
PubMed:Auraptene suppresses inflammatory responses in activated RAW264 macrophages by inhibiting p38 mitogen-activated protein kinase activation.
PubMed:Auraptene Acts as an Anti-Inflammatory Agent in the Mouse Brain.
PubMed:Anti-inflammatory and wound healing potential of citrus auraptene.
PubMed:Hypotensive activity of auraptene, a monoterpene coumarin from Citrus spp.
PubMed:Stimulation of phosphorylation of ERK and CREB by phellopterin and auraptene isolated from Citrusjunos.
PubMed:The plant coumarins auraptene and lacinartin as potential multifunctional therapeutic agents for treating periodontal disease.
PubMed:Quantitative evaluation of auraptene and umbelliferone, chemopreventive coumarins in citrus fruits, by HPLC-UV-FL-MS.
PubMed:Auraptene in the Peels of Citrus kawachiensis (Kawachi Bankan) Ameliorates Lipopolysaccharide-Induced Inflammation in the Mouse Brain.
PubMed:Auraptene attenuates gastritis via reduction of Helicobacter pylori colonization and pro-inflammatory mediator production in C57BL/6 mice.
PubMed:Effects of Auraptene on IGF-1 Stimulated Cell Cycle Progression in the Human Breast Cancer Cell Line, MCF-7.
PubMed:Auraptene regulates gene expression involved in lipid metabolism through PPARα activation in diabetic obese mice.
PubMed:Auraptene and its effects on the re-emergence of colon cancer stem cells.
PubMed:Anti-inflammatory and neuroprotective effects of auraptene, a citrus coumarin, following cerebral global ischemia in mice.
PubMed:Neurotrophic effect of citrus auraptene: neuritogenic activity in PC12 cells.
PubMed:Novel prodrugs for the treatment of colonic diseases based on 5-aminosalicylic acid, 4'-geranyloxyferulic acid, and auraptene: biological activities and analytical assays.
PubMed:Effects of citrus auraptene (7-geranyloxycoumarin) on hepatic lipid metabolism in vitro and in vivo.
PubMed:Auraptene is an inhibitor of cholesterol esterification and a modulator of estrogen receptors.
PubMed:Identification, synthesis and quantification of process-related impurities in auraptene.
PubMed:Auraptene: a natural biologically active compound with multiple targets.
PubMed:Auraptene from Ferula szowitsiana protects human peripheral lymphocytes against oxidative stress.
PubMed:Citrus auraptene: a potential multifunctional therapeutic agent for nonalcoholic fatty liver disease.
PubMed:Citrus auraptene suppresses cyclin D1 and significantly delays N-methyl nitrosourea induced mammary carcinogenesis in female Sprague-Dawley rats.
PubMed:Potential benefits of supplementation with auraptene in cystic fibrosis.
PubMed:Suppression of CD74 expression and Helicobacter pylori adhesion by auraptene targeting serum starvation-activated ERK1/2 in NCI-N87 gastric carcinoma cells.
PubMed:Evaluation of auraptene content in citrus fruits and their products.
PubMed:Immunomodulatory action of citrus auraptene on macrophage functions and cytokine production of lymphocytes in female BALB/c mice.
PubMed: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.
PubMed:Chemoprevention of 4-nitroquinoline 1-oxide-induced oral carcinogenesis by citrus auraptene in rats.
PubMed:Auraptene, a citrus coumarin, inhibits 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion in ICR mouse skin, possibly through suppression of superoxide generation in leukocytes.
PubMed:Colorectal cancer chemoprevention by 2 beta-cyclodextrin inclusion compounds of auraptene and 4'-geranyloxyferulic acid.
PubMed:Auraptene, a citrus fruit compound, regulates gene expression as a PPARalpha agonist in HepG2 hepatocytes.
PubMed:Citrus auraptene targets translation of MMP-7 (matrilysin) via ERK1/2-dependent and mTOR-independent mechanism.
PubMed:Suppressing effects of dietary supplementation of the organoselenium 1,4-phenylenebis(methylene)selenocyanate and the Citrus antioxidant auraptene on lung metastasis of melanoma cells in mice.
PubMed:Suppression of N-nitrosomethylbenzylamine-induced rat esophageal tumorigenesis by dietary feeding of auraptene.
PubMed:Citrus auraptene acts as an agonist for PPARs and enhances adiponectin production and MCP-1 reduction in 3T3-L1 adipocytes.
PubMed:Dietary administration with prenyloxycoumarins, auraptene and collinin, inhibits colitis-related colon carcinogenesis in mice.
PubMed:Protective effects of citrus nobiletin and auraptene in transgenic rats developing adenocarcinoma of the prostate (TRAP) and human prostate carcinoma cells.
PubMed:Citrus auraptene inhibits chemically induced colonic aberrant crypt foci in male F344 rats.
PubMed:Auraptene decreases the activity of matrix metalloproteinases in dextran sulfate sodium-induced ulcerative colitis in ICR mice.
PubMed:Zingiberaceous and citrus constituents, 1'-acetoxychavicol acetate, zerumbone, auraptene, and nobiletin, suppress lipopolysaccharide-induced cyclooxygenase-2 expression in RAW264.7 murine macrophages through different modes of action.
PubMed:Effects of selected food phytochemicals in reducing the toxic actions of TCDD and p,p'-DDT in U937 macrophages.
PubMed:Metabolism and absorption of auraptene (7-geranyloxylcoumarin) in male SD rats: comparison with 7-ethoxycoumarin.
PubMed:Citrus auraptene reduces Helicobacter pylori colonization of glandular stomach lesions in Mongolian gerbils.
PubMed:Citrus auraptene suppresses azoxymethane-induced colonic preneoplastic lesions in C57BL/KsJ-db/db mice.
PubMed:Suppression of beta-catenin mutation by dietary exposure of auraptene, a citrus antioxidant, in N,N-diethylnitrosamine-induced hepatocellular carcinomas in rats.
PubMed:Dietary supplementation of the citrus antioxidant auraptene inhibits N,N-diethylnitrosamine-induced rat hepatocarcinogenesis.
PubMed:Suppression by citrus auraptene of phorbol ester-and endotoxin-induced inflammatory responses: role of attenuation of leukocyte activation.
PubMed: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.
PubMed:In vitro absorption and metabolism of a citrus chemopreventive agent, auraptene, and its modifying effects on xenobiotic enzyme activities in mouse livers.
PubMed:Studies on the constituents of orange oil. I. On the structure of auraptene.
PubMed:Potent and selective inhibitors of class A β-lactamase: 7-prenyloxy coumarins.
PubMed:Combination of bioautography with HPTLC-MS/NMR: a fast identification of acetylcholinesterase inhibitors from galbanum(†).
PubMed:Effects of Bioactive Substances from Citrus on the Central Nervous System and Utilization as Food Material.
PubMed:Biological properties and molecular targets of umbelliprenin--a mini-review.
PubMed:Semisynthetic studies identify mitochondria poisons from botanical dietary supplements--geranyloxycoumarins from Aegle marmelos.
PubMed:[Determination of the active constituents in aurantii fructus from Jiangxi province at different harvest time by HPLC].
PubMed:Comparison of citrus coumarins on carcinogen-detoxifying enzymes in Nrf2 knockout mice.
PubMed:Nelumal A, the active principle from Ligularia nelumbifolia, is a novel farnesoid X receptor agonist.
PubMed:Simultaneous quantification of polymethoxylated flavones and coumarins in Fructus aurantii and Fructus aurantii immaturus using HPLC-ESI-MS/MS.
PubMed:Aggressive mammary carcinoma progression in Nrf2 knockout mice treated with 7,12-dimethylbenz[a]anthracene.
PubMed:Development of a quantitative bioassay to assess preventive compounds against inflammation-based carcinogenesis.
PubMed:A new cytotoxic coumarin, 7-[(E)-3',7'-dimethyl-6'-oxo-2',7'-octadienyl] oxy coumarin, from the leaves of Zanthoxylum schinifolium.
PubMed:Effects of ATRA combined with citrus and ginger-derived compounds in human SCC xenografts.
PubMed:Effects of chemopreventive citrus phytochemicals on human P-glycoprotein and multidrug resistance protein 1.
PubMed:Sesquiterpene coumarins from Ferula szowitsiana and in vitro antileishmanial activity of 7-prenyloxycoumarins against promastigotes.
PubMed:Citrus compounds inhibit inflammation- and obesity-related colon carcinogenesis in mice.
PubMed:Cancer-preventive anti-oxidants that attenuate free radical generation by inflammatory cells.
PubMed:[Chemical study of citrus plants in the search for cancer chemopreventive agents].
PubMed:Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice.
PubMed:Neuroprotective effect of prenyloxycoumarins from edible vegetables.
PubMed: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.
PubMed:Cancer chemopreventive activity of terpenoid coumarins from Ferula species.
PubMed: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.
PubMed:Rapid analysis of gene expression changes caused by liver carcinogens and chemopreventive agents using a newly developed three-dimensional microarray system.
PubMed:Inhibition of acetylcholinesterase activity by essential oil from Citrus paradisi.
PubMed:Cell proliferation in cancer prevention; effects of preventive agents on estrogen-related endometrial carcinogenesis model and on an in vitro model in human colorectal cells.
PubMed:[Studies on the bioactive constituents of Aurantii Fructus Immaturus].
PubMed:Potential anti-allergic acridone alkaloids from the roots of Atalantia monophylla.
PubMed:Monoamine oxidase inhibitory coumarins from the aerial parts of Dictamnus albus.
PubMed:Inhibition of cell proliferation by nobiletin, a dietary phytochemical, associated with apoptosis and characteristic gene expression, but lack of effect on early rat hepatocarcinogenesis in vivo.
PubMed:Phytochemical analysis of anti-atherogenic constituents of Xue-Fu-Zhu-Yu-Tang using HPLC-DAD-ESI-MS.
PubMed:Synthesis and anti-inflammatory activity of natural and semisynthetic geranyloxycoumarins.
PubMed:Effects of selected food factors with chemopreventive properties on combined lipopolysaccharide- and interferon-gamma-induced IkappaB degradation in RAW264.7 macrophages.
PubMed:Further investigation of the modifying effect of various chemopreventive agents on apoptosis and cell proliferation in human colon cancer cells.
 
Notes:
Isol. from Citrus aurantium (Seville orange) and bael fruit (Aegle marmelos) Auraptene is a natural bioactive monoterpene coumarin ether. It was first isolated from members of the genus Citrus. Auraptene has shown a remarkable effect in the prevention of degenerative diseases. Many studies have reported the effect of auraptene as a chemopreventative agent against cancers of liver, skin, tongue, esophagus, and colon in rodent models. The effect in humans is not yet known.
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