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isoimperatorin
7H-furo[3,2-g][1]benzopyran-7-one, 4-[(3-methyl-2-butenyl)oxy]-

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Name:4-(3-methylbut-2-enoxy)furo[3,2-g]chromen-7-one
CAS Number: 482-45-1Picture of molecule3D/inchi
FDA UNII: 0ZMV066080
Nikkaji Web:J13.192J
Beilstein Number:1291723
MDL:MFCD00272155
XlogP3-AA:3.80 (est)
Molecular Weight:270.28438000
Formula:C16 H14 O4
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:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 109.00 °C. @ 760.00 mm Hg
Boiling Point: 448.00 to 449.00 °C. @ 760.00 mm Hg (est)
Flash Point: 437.00 °F. TCC ( 224.90 °C. ) (est)
logP (o/w): 3.495 (est)
Soluble in:
 alcohol
 water, 7.782 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Isoimperatorin 98%
BOC Sciences
For experimental / research use only.
Isoimperatorin >98%
Odor: characteristic
Use: Isoimperatorin ist eine chemische Verbindung aus der Gruppe der Furocumarine und isomer zu Imperatorin. Isoimperatorin shows antimycobacterial and antimycobacterial activities. antimycobacterial, antimycobacterial
Carbosynth
For experimental / research use only.
isoImperatorin
Coompo
For experimental / research use only.
isoImperatorin from Plants ≥98%
Odor: characteristic
Use: Isoimperatorin inhibits the cyclooxygenase-2 (COX-2) and COX-1-dependent phases of prostaglandin D2 (PGD2) generation in bone marrow-derived mast cells (BMMC) in a concentration-dependent manner, with IC50 values of 10.7 microM and 24 microM, respectively. this compound consistently inhibited the production of leukotriene C4 (LTC4), as well as the degranulation reaction in BMMC, with an IC50 value of 5.7 microM and 9 microM, respectively. isoimperatorin has a dual cyclooxygenase-2 selective/5- lipoxygenase inhibitory activity, and therefore may provide the basis for novel anti-inflammatory drugs. Isoimperatorin possesses a potent hepatoprotective effect against AFB1, presumably through the induction of GSTa and the direct inhibition of CYP1A, and suggest that isoimperatorin should be considered a potential chemopreventive.
Santa Cruz Biotechnology
For experimental / research use only.
isoImperatorin
Sigma-Aldrich
For experimental / research use only.
isoImperatorin
analytical standard
 
Safety Information:
 
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 isoimperatorin usage levels up to:
 not for fragrance use.
 
Recommendation for isoimperatorin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :68081
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-(3-methylbut-2-enoxy)furo[3,2-g]chromen-7-one
Chemidplus:0000482451
RTECS:LV1513000 for cas# 482-45-1
 
References:
 4-(3-methylbut-2-enoxy)furo[3,2-g]chromen-7-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):68081
Pubchem (sid):135023458
 
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
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C16976
HMDB (The Human Metabolome Database):Search
FooDB:FDB003953
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 celery seed
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 glehniae root
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 lemon fruit oil
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 lemon oil
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 lime fruit
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 masterwort root
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 parsley fruit
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 parsley leaf
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 parsley root
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 parsley seed
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 parsnip seed
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Synonyms:
7H-furo(3,2-g)(1)benzopyran-7-one, 4-((3-methyl-2-butenyl)oxy)-
7H-furo[3,2-g][1]benzopyran-7-one, 4-((3-methyl-2-butenyl)oxy)-
7H-furo[3,2-g][1]benzopyran-7-one, 4-[(3-methyl-2-buten-1-yl)oxy]-
7H-furo[3,2-g][1]benzopyran-7-one, 4-[(3-methyl-2-butenyl)oxy]-
4-((3-methyl-2-butenyl)oxy)-7H-furo(3,2-g)(1)benzopyran-7-one
4-[(3-methylbut-2-en-1-yl)oxy]-7H-furo[3,2-g]chromen-7-one
4-(3-methylbut-2-enoxy)furo[3,2-g]chromen-7-one
5-(3-methylbut-2-enyloxy)furano[3,2-g]chromen-2-one
 

Articles:

PubMed:Antiviral and cytotoxic evaluation of coumarins from Prangos ferulacea.
PubMed:Biotransformation of isoimperatorin by rat liver microsomes and its quantification by LC-MS/MS method.
PubMed:In vitro activity of isoimperatorin, alone and in combination, against Mycobacterium tuberculosis.
PubMed:Studies of the interaction between isoimperatorin and human serum albumin by multispectroscopic method: identification of possible binding site of the compound using esterase activity of the protein.
PubMed:High-expression β(1) adrenergic receptor/cell membrane chromatography method based on a target receptor to screen active ingredients from traditional Chinese medicines.
PubMed:Simultaneous determination of four components in Baige capsule by HPLC: application to pharmacokinetics and tissue distribution of normal and middle cerebral artery occlusion rats.
PubMed:[Effect of different plant growth regulators on yield and quality of Angelica dahurica var. formosana development].
PubMed:[Simultaneous determination of eight furocoumarines in cosmetics by high performance liquid chromatography and verification by liquid chromatography-tandem mass spectrometry].
PubMed:Simultaneous isolation of seven compounds from Glehnia littoralis roots by off-line overpressured layer chromatography guided by a TLC antioxidant autographic assay.
PubMed:[Inhibitory effect of imperatorin and isoimperatorin on activity of cytochrome P450 enzyme in human and rat liver microsomes].
PubMed:In vitro and in vivo antiproliferative effect of a combination of ultraviolet-A and alkoxy furocoumarins isolated from Umbelliferae medicinal plants, in melanoma cells.
PubMed:Identification of in vitro and in vivo metabolites of isoimperatorin using liquid chromatography/mass spectrometry.
PubMed:Simultaneous determination of scopoletin, psoralen, bergapten, xanthotoxin, columbianetin acetate, imperatorin, osthole and isoimperatorin in rat plasma by LC-MS/MS for pharmacokinetic studies following oral administration of Radix Angelicae Pubescentis extract.
PubMed:In vitro permeability analysis, pharmacokinetic and brain distribution study in mice of imperatorin, isoimperatorin and cnidilin in Radix Angelicae Dahuricae.
PubMed:[A new natural product from root of Angelica dahurica cv. Qibaizhi].
PubMed:Determination of cnidilin and its two metabolites in rat plasma by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry.
PubMed:Coumarins from Angelica archangelica Linn. and their effects on anxiety-like behavior.
PubMed:[Fingerprint analysis of Glehniae Radix by TLC].
PubMed:[Chemical constituents contained in seeds of Notopterygium franchetii].
PubMed:Comparison of two species of Notopterygium by high-performance liquid chromatography-photodiode array detection-electrospray ionization tandem mass spectrometry.
PubMed:[Fingerprint of Angelica polymorpha by HPLC].
PubMed:Simultaneous analysis of six major compounds in Osterici Radix and Notopterygii Rhizoma et Radix by HPLC and discrimination of their origins from chemical fingerprint analysis.
PubMed:Geographical variation of the furanocoumarin composition of the fruits of Icelandic Angelica archangelica.
PubMed:Pressurized liquid extraction of coumarins from fruits of Heracleum leskowii with application of solvents with different polarity under increasing temperature.
PubMed:Larvicidal activity of Cnidium monnieri fruit coumarins and structurally related compounds against insecticide-susceptible and insecticide-resistant Culex pipiens pallens and Aedes aegypti.
PubMed:Furocoumarins affect hepatic cytochrome P450 and renal organic ion transporters in mice.
PubMed:Study on pharmacokinetics and tissue distribution of pteryxin in mice by ultra-pressure liquid chromatography with tandem mass spectrometry.
PubMed:[Determination of supermolecular inclusion constants of hydroxylpropyl-beta-cylcodextrin with imperatorin and isoimperatorin by phase solubility method].
PubMed:[Determination of imperatorin and isoimperatorin in cosmetics by high performance liquid chromatography-tandem mass spectrometry].
PubMed:Antigenotoxic activity of naturally occurring furanocoumarins.
PubMed:Simultaneous quantification of 17 constituents from Yuanhu Zhitong tablet using rapid resolution liquid chromatography coupled with a triple quadrupole electrospray tandem mass spectrometry.
PubMed:Identification and quantification of coumarins in Peucedanum ostruthium (L.) Koch by HPLC-DAD and HPLC-DAD-MS.
PubMed:[Dynamic research of growth, N, P, K and active ingredients in Angelica dahurica var. formosana from Sichuan province].
PubMed:[Quantitative analysis of five components in the rhizome of Angelica polymorpha by RP-HPLC under different UV wavelengths].
PubMed:Isoimperatorin, cimiside E and 23-O-acetylshengmanol-3-xyloside from Cimicifugae rhizome inhibit TNF-α-induced VCAM-1 expression in human endothelial cells: involvement of PPAR-γ upregulation and PI3K, ERK1/2, and PKC signal pathways.
PubMed:Quantitative analysis of nine coumarins in rat urine and bile after oral administration of Radix Glehniae extract by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry.
PubMed:[Fast determination of active components in Angelica dahurica extract using capillary electrochromatography with methacrylate ester-based monolithic columns].
PubMed:Rapid identification of furanocoumarins in Angelica dahurica using the online LC-MMR-MS and their nitric oxide inhibitory activity in RAW 264.7 cells.
PubMed:Differentiation of four pairs of furocoumarin isomers by electrospray ionization tandem mass spectrometry.
PubMed:Imperatorin is responsible for the vasodilatation activity of Angelica Dahurica var. Formosana regulated by nitric oxide in an endothelium-dependent manner.
PubMed:beta-secretase inhibitory effects of furanocoumarins from the root of Angelica dahurica.
PubMed:Biotransformation of isoimperatorin and imperatorin by Glomerella cingulata and beta-secretase inhibitory activity.
PubMed:On-line concentration by field-enhanced sample injection with reverse migrating micelles in micellar electrokinetic capillary chromatography for the analysis of coumarins from traditional Chinese medicine and human serum.
PubMed:Coumarins from Angelica lucida L.--antibacterial activities.
PubMed:Notopterygium forbesii Boiss extract and its active constituent phenethyl ferulate attenuate pro-inflammatory responses to lipopolysaccharide in RAW 264.7 macrophages. A "protective" role for oxidative stress?
PubMed:[Studies on chemical constituents from roots of Angelica polymorpha].
PubMed:Notopterygium forbesii boiss extract and its active constituents increase reactive species and heme oxygenase-1 in human fetal hepatocytes: mechanisms of action.
PubMed:Rapid separation and identification of furocoumarins in Angelica dahurica by high-performance liquid chromatography with diode-array detection, time-of-flight mass spectrometry and quadrupole ion trap mass spectrometry.
PubMed:Simultaneous determination of five coumarins in Angelicae dahuricae Radix by HPLC/UV and LC-ESI-MS/MS.
PubMed:[Studies on chemical constituents in roots and rhizomes of Notopterygium incisum].
PubMed:[Chemical constituents of antibacterial activity fraction of Angelica polymorpha].
PubMed:Identification and determination of active components in Angelica dahurica Benth and its medicinal preparation by capillary electrophoresis.
PubMed:Supercritical fluid extraction for identification and determination of volatile metabolites from Angelica dahurica by GC-MS.
PubMed:The effects of isoimperatorin isolated from Angelicae dahuricae on cyclooxygenase-2 and 5-lipoxygenase in mouse bone marrow-derived mast cells.
PubMed:Simultaneous determination of 10 active components in traditional Chinese medicine "YIGONG" capsule by RP-HPLC-DAD.
PubMed:The simultaneous determination of coumarins in Angelica gigas root by high performance liquid chromatography-diode array detector coupled with electrospray ionization/mass spectrometry.
PubMed:[Studies on chemical constituents in fruit of Gardenia jasminoides].
PubMed:[Quantitative analysis of volatile oils and isoimperatorin in rhizoma et Radix notopterygii].
PubMed:Constituents, biological activities and quality control parameters of the crude extract and essential oil from Arracacia tolucensis var. multifida.
PubMed:Coumarins from Peucedanum luxurians.
PubMed:Quality assessment of Rhizoma et Radix Notopterygii by HPTLC and HPLC fingerprinting and HPLC quantitative analysis.
PubMed:Development and validation of a gas chromatography-mass spectrometry method for the determination of isoimperatorin in rat plasma and tissue: application to the pharmacokinetic and tissue distribution study.
PubMed:Ethyl acetate extract from Angelica Dahuricae Radix inhibits lipopolysaccharide-induced production of nitric oxide, prostaglandin E2 and tumor necrosis factor-alphavia mitogen-activated protein kinases and nuclear factor-kappaB in macrophages.
PubMed:Antiproliferative effect of furanocoumarins from the root of Angelica dahurica on cultured human tumor cell lines.
PubMed:Determination of liquiritin, naringin, hesperidin, thymol, imperatorin, honokiol, isoimperatorin, and magnolol in the traditional Chinese medicinal preparation Huoxiang-zhengqi liquid using high-performance liquid chromatography.
PubMed:Potent protective effect of isoimperatorin against aflatoxin B1-inducible cytotoxicity in H4IIE cells: bifunctional effects on glutathione S-transferase and CYP1A.
PubMed:[Studies on chemical constituents in roots of Heracleum rapula].
PubMed:New cosmetic agents for skin whitening from Angelica dahurica.
PubMed:Preparative isolation of imperatorin, oxypeucedanin and isoimperatorin from traditional Chinese herb "bai zhi"Angelica dahurica (Fisch. ex Hoffm) Benth. et Hook using multidimensional high-speed counter-current chromatography.
PubMed:In vitro GABA-transaminase inhibitory compounds from the root of Angelica dahurica.
PubMed:Coumarins are competitive inhibitors of cytochrome P450 1B1, with equal potency for allelic variants.
PubMed:[Determination of coumarins content in Radix Angelicae dahuricae by HPLC and UV].
PubMed:[Extraction of coumarins from Angelica dahurica by supercritical extraction and GC-MS analysis].
PubMed:Agents protecting against sepsis from the roots of Angelica dahurica.
PubMed:[Study on coumarin compounds from Exocarpium Citri Grandis].
PubMed:2D NMR spectroscopic analyses of archangelicin from the seeds of Angelica archangelica.
PubMed:[Determination of isoimperatorin and osthol in ganmao yixiaoshi capsule by RP-HPLC].
PubMed:Preparative isolation and purification of coumarins from Angelica dahurica (Fisch. ex Hoffn) Benth, et Hook. f (Chinese traditional medicinal herb) by high-speed counter-current chromatography.
PubMed:[Studies on quality standards of radix Angelicae dahuricae].
PubMed:HPLC micro-fractionation coupled to a cell-based assay for automated on-line primary screening of calcium antagonistic components in plant extracts.
PubMed:Antioxidative activity of furanocoumarins isolated from Angelicae dahuricae.
PubMed:Platelet anti-aggregatory effects of coumarins from the roots of Angelica genuflexa and A. gigas.
PubMed:Inhibitory effects of furanocoumarins isolated from the roots of Angelica dahurica on prostaglandin E2 production.
PubMed:[Studies on chemical constituents of Peucedanum medium Dunn var. garcile Dunn ex Shan at Sheh].
PubMed:Acetylcholinesterase inhibitors from the roots of Angelica dahurica.
PubMed:Furocoumarins from Angelica dahurica with hepatoprotective activity on tacrine-induced cytotoxicity in Hep G2 cells.
PubMed:Inhibitors of 5alpha -reductase type I in LNCaP cells from the roots of Angelica koreana.
PubMed:Indolopyridoquinazoline alkaloid from Leptothyrsa sprucei.
PubMed:Effects of furocoumarins from Cachrys trifida on some macrophage functions.
PubMed:Furanocoumarins from the root of Angelica dahurica.
PubMed:Preparative isolation and purification of notopterol and isoimperatorin from Notopterygium forbessi Boiss (Chinese traditional medicinal herb) by high-speed counter-current chromatography.
PubMed:Antiproliferative constituents from umbelliferae plants. V. A new furanocoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonica.
PubMed:Inhibitory effects of naturally occurring coumarins on the metabolic activation of benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene in cultured mouse keratinocytes.
PubMed:[Chemical constituents of Notopterygium forbesii Boiss].
PubMed:Coumarins and antiplatelet aggregation constituents from Formosan Peucedanum japonicum.
PubMed:Anti-inflammatory and analgesic activities from roots of Angelica pubescens.
PubMed:Analysis, isolation and insecticidal activity of linear furanocoumarins and other coumarin derivatives fromPeucedanum (Apiaceae: Apioideae).
PubMed:[Drug antagonism of TNF induced proliferation of bovine cerebromicrovascular smooth muscle cells].
PubMed:Inhibition and inactivation of murine hepatic ethoxy- and pentoxyresorufin O-dealkylase by naturally occurring coumarins.
PubMed:[Determination of coumarins in radix Angelicae Dahuricae before and after processing].
PubMed:[Reverse-phase HPLC determination of coumarins in the traditional Chinese drug bai-zhi (Angelica dahurica forma bai-zhi)].
PubMed:HPLC Analysis of the Main Furanocoumarins from Peucedanum palustre.
PubMed:[Studies of the active constituents of the Chinese drug "duhuo" Angelica pubescents].
PubMed:[TLC-UV spectrophotometric determination of imperatorin and isoimperatorin in Glehniae root].
PubMed:Furocoumarins in shoots ofPituranthos triradiatus (Umbelliferae) as protectants against grazing by hyrax (Procaviidea:Procavia capensis syriaca).
PubMed:The furocoumarin composition of Pituranthos triradiatus.
 
Notes:
tumor necrosis factor antagonist isolated from glehniae root.
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