auraptene
7-geranyloxycoumarin
Identification
| Name | auraptene |
| IUPAC | 7-[(2E)-3,7-dimethylocta-2,6-dienoxy]chromen-2-one |
| CAS Number | 495-02-3 |
| FDA UNII | F79I1ZEL2E |
| Molecular Formula | C19 H22 O3 |
| Molecular Weight | 298.38194000 |
| MDL Number | MFCD00075948 |
| Nikkaji Number | J108.361I |
| XlogP3 | 5.30 (est) |
Regulatory
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) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
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Potential Uses
Natural Occurrence
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
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(â ).
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.