isopimpinellin
7H-furo(3,2-g)(1)benzopyran-7-one, 4,9-dimethoxy- (8CI)(9CI)
Identification
| Name | isopimpinellin |
| IUPAC | 4,9-dimethoxyfuro[3,2-g]chromen-7-one |
| CAS Number | 482-27-9 |
| FDA UNII | 20GCF755G6 |
| Molecular Formula | C13 H10 O5 |
| Molecular Weight | 246.21870000 |
| MDL Number | MFCD00017407 |
| Nikkaji Number | J5.787H |
| Beilstein | 262337 |
| XlogP3 | 1.90 (est) |
Regulatory
Physical Properties
| Appearance | yellow crystals (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 147.00 to 148.00 °C. @ 760.00 mm Hg |
| Boiling Point | 448.00 to 449.00 °C. @ 760.00 mm Hg (est) |
| Flash Point | 437.00 °F. TCC ( 225.10 °C. ) (est) |
| logP (o/w) | 1.407 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
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 isopimpinellin usage levels up to | not for fragrance use. |
| Recommendation for isopimpinellin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
4,9-
dimethoxy-7H-furo(3,2-g) (1)benzopyran-7-one
4,9-
dimethoxy-7H-furo[3,2-g][1]benzopyran-7-one
4,9-
dimethoxy-7H-furo[3,2-g]chromen-7-one
4,9-
dimethoxy-furo[3,2-g]chromen-7-one
5,8-
dimethoxyfurano-2,3,6,7-coumarin
5,9-
dimethoxyfurano[3,2-g]chromen-2-one
4,9-
dimethoxyfuro[3,2-g]chromen-7-one
4,9-
dimethoxypsoralen
5,8-
dimethoxypsoralen
5,8-
dimethoxypsoralene
7H-
furo(3,2-g)(1)benzopyran-7-one, 4,9-dimethoxy- (8CI)(9CI)
7H-
furo[3,2-g][1]benzopyran-7-one, 4,9-dimethoxy-
PubMed:
[Chemical constituents of Angelica nitida roots].
PubMed:
Furocoumarins and coumarins photoinactivate Colletotrichum acutatum and Aspergillus nidulans fungi under solar radiation.
PubMed:
Optimal extraction and fingerprint analysis of Cnidii fructus by accelerated solvent extraction and high performance liquid chromatographic analysis with photodiode array and mass spectrometry detections.
PubMed:
The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins.
PubMed:
5-Geranyloxy-7-methoxycoumarin inhibits colon cancer (SW480) cells growth by inducing apoptosis.
PubMed:
Coumarins from the Herb Cnidium monnieri and Chemically Modified Derivatives as Antifoulants against Balanus albicostatus and Bugula neritina Larvae.
PubMed:
Essential oil composition and larvicidal activity of Toddalia asiatica roots against the mosquito Aedes albopictus (Diptera: Culicidae).
PubMed:
Chemical composition of hexane extract of Citrus aurantifolia and anti-Mycobacterium tuberculosis activity of some of its constituents.
PubMed:
Separation and purification of furanocoumarins from Toddalia asiatica (L.) Lam. using microwave-assisted extraction coupled with high-speed counter-current chromatography.
PubMed:
Pressurized liquid extraction of coumarins from fruits of Heracleum leskowii with application of solvents with different polarity under increasing temperature.
PubMed:
Simultaneous determination of pimpinellin, isopimpinellin and phellopterin in rat plasma by a validated UPLC-MS/MS and its application to a pharmacokinetic study after administration of Toddalia asiatica extract.
PubMed:
Furanocoumarins in celeriac from different farming systems: a 3-year study.
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:
Biological activities of Indian celery, Seseli diffusum (Roxb. ex Sm.) Sant. & Wagh.
PubMed:
Microbial transformation of Isopimpinellin by Glomerella cingulata.
PubMed:
Effects of furanocoumarins from apiaceous vegetables on the catalytic activity of recombinant human cytochrome P-450 1A2.
PubMed:
Furanocoumarins from Dorsteniafoetida.
PubMed:
Vasorelaxation by extracts of Casimiroa spp. in rat resistance vessels and pharmacological study of cellular mechanisms.
PubMed:
Antifibrotic activity of coumarins from Cnidium monnieri fruits in HSC-T6 hepatic stellate cells.
PubMed:
Simultaneous and sensitive determination of xanthotoxin, psoralen, isoimpinellin and bergapten in rat plasma by liquid chromatography-electrospray ionization mass spectrometry.
PubMed:
Application of the concept of relative photomutagenic potencies to selected furocoumarins in V79 cells.
PubMed:
Botanical origin of Indian celery seed (fruit).
PubMed:
Comparison of citrus coumarins on carcinogen-detoxifying enzymes in Nrf2 knockout mice.
PubMed:
Osthol and isopimpinellin from Fructus cnidii for the control of Dactylogyrus intermedius in Carassius auratus.
PubMed:
Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice.
PubMed:
In vitro antiplasmodial activity of extract and constituents from Esenbeckia febrifuga, a plant traditionally used to treat malaria in the Brazilian Amazon.
PubMed:
Identification of Ruta graveolens L. metabolites accumulated in the presence of abiotic elicitors.
PubMed:
[Simultaneous determination of 5 active components in Fructus Cnidii by HPLC].
PubMed:
[Studies on the chemical constituents of the aerial parts of Seseli mairei].
PubMed:
[Studies on chemical constituents from fruits of Paliurus ramosissimus].
PubMed:
[Inhibitory effects of 11 coumarin compounds against growth of human bladder carcinoma cell line E-J in vitro].
PubMed:
Simultaneous determination of urinary metabolites of methoxypsoralens in human and Umbelliferae medicines by high-performance liquid chromatography.
PubMed:
[Studies on chemical constituents in roots of Heracleum rapula].
PubMed:
Cytochrome P450-mediated metabolism of xanthotoxin by Papilio multicaudatus.
PubMed:
Naturally occurring coumarins inhibit 7,12-dimethylbenz[a]anthracene DNA adduct formation in mouse mammary gland.
PubMed:
Accumulation of biologically active furanocoumarins in agitated cultures of Ruta graveolens L. and Ruta graveolens ssp. divaricata (Tenore) Gams.
PubMed:
Melanogenesis stimulation in murine b16 melanoma cells by umberiferae plant extracts and their coumarin constituents.
PubMed:
Coumarins are competitive inhibitors of cytochrome P450 1B1, with equal potency for allelic variants.
PubMed:
Accumulation of biologically active furanocoumarins in Ruta graveolens ssp. divaricata (Tenore) Gams in vitro culture.
PubMed:
Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes.
PubMed:
Preparative isolation and purification of coumarins from Cnidium monnieri (L.) Cusson by high-speed counter-current chromatography.
PubMed:
[Quantification of isopimpinellin in root of Toddalia asiatica by HPLC].
PubMed:
Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against Drosophila melanogaster.
PubMed:
Computer-assisted, high-performance liquid chromatography with mass spectrometric detection for the analysis of coumarins in Peucedanum palustre and Angelica archangelica.
PubMed:
[Studies on the coumarins in the root of Zanthoxylum dimorphophyllum].
PubMed:
The furanocoumarins in the roots of Heracleum sibiricum L.
PubMed:
Cytotoxic activity of coumarins from the fruits of Cnidium monnieri on leukemia cell lines.
PubMed:
LC determination of impurities in methoxsalen drug substance: isolation and identification of isopimpinellin as a major impurity by atmospheric pressure chemical ionization LC/MS and NMR.
PubMed:
Constituents of Peucedanum zenkeri seeds and their antimicrobial effects.
PubMed:
Naturally occurring coumarins inhibit human cytochromes P450 and block benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene DNA adduct formation in MCF-7 cells.
PubMed:
A new dicoumarinyl ether and two rare furocoumarins from Ruta montana.
PubMed:
HPLC-NMR/HPLC-MS analysis of the bark extract of Stauranthus perforatus.
PubMed:
[Isolation and identification of active constituent of Toddalia asiatica in cardiovascular system].
PubMed:
Constituents of the fruits and leaves of Euodia daniellii.
PubMed:
Oral administration of the citrus coumarin, isopimpinellin, blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene in SENCAR mice.
PubMed:
Amino acids in SRS1 and SRS6 are critical for furanocoumarin metabolism by CYP6B1v1, a cytochrome P450 monooxygenase.
PubMed:
Effects of storage conditions on furocoumarin levels in intact, chopped, or homogenized parsnips.
PubMed:
Bullous phytophotodermatitis associated with high natural concentrations of furanocoumarins in limes.
PubMed:
Simultaneous determination of furanocoumarins in infusions and decoctions from "Carapiá" (dorstenia species) by high-performance liquid chromatography.
PubMed:
Antipruritic effect of Cnidii Monnieri Fructus (fruits of Cnidium monnieri CUSSON).
PubMed:
Role of cytochrome P450 1a1 and 1b1 in the metabolic activation of 7,12-dimethylbenz[a]anthracene and the effects of naturally occurring furanocoumarins on skin tumor initiation.
PubMed:
Inhibition of itch-scratch response by fruits of Cnidium monnieri in mice.
PubMed:
Vasorelaxing effect of coumarins from Cnidium monnieri on rabbit corpus cavernosum.
PubMed:
Oral administration of naturally occurring coumarins leads to altered phase I and II enzyme activities and reduced DNA adduct formation by polycyclic aromatic hydrocarbons in various tissues of SENCAR mice.
PubMed:
Coumarin compounds in Ammi majus L. callus cultures.
PubMed:
Furanocoumarins in Pastinaca sativa L. in vitro culture.
PubMed:
Cytotoxic components from the bark of Stauranthus perforatus from Monteverde, Costa Rica.
PubMed:
Rapid determination of furanocoumarins in creams and pomades using SPE and GC.
PubMed:
Isolation And Structure Elucidation Of 5,7-disubstituted Simple Coumarins In The Fruits Of Heracleum Mantegazzianum.
PubMed:
Effect of naturally occurring coumarins on the formation of epidermal DNA adducts and skin tumors induced by benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene in SENCAR mice.
PubMed:
Isolation and characterization of CYP6B4, a furanocoumarin-inducible cytochrome P450 from a polyphagous caterpillar (Lepidoptera:papilionidae).
PubMed:
Inhibition of the mutagenicity of 2-nitrofluorene, 3-nitrofluoranthene and 1-nitropyrene by flavonoids, coumarins, quinones and other phenolic compounds.
PubMed:
Isolation and identification of antimicrobial furocoumarins from parsley.
PubMed:
Development of an immunoassay to measure the absorption of dietary furanocoumarins in humans.
PubMed:
Isopimpinellin is not phototoxic in a chick skin assay.
PubMed:
Analysis, isolation and insecticidal activity of linear furanocoumarins and other coumarin derivatives fromPeucedanum (Apiaceae: Apioideae).
PubMed:
Inhibition and inactivation of murine hepatic ethoxy- and pentoxyresorufin O-dealkylase by naturally occurring coumarins.
PubMed:
Phototoxic coumarins in limes.
PubMed:
Differential inhibition of coumarin 7-hydroxylase activity in mouse and human liver microsomes.
PubMed:
[Studies on the chemical constituents of Rutaceae++ plants. LXVI. The chemical constituents of Toddalia asiatica (L.) Lam. (T. aculeata Pers.). (1). Chemical constituents of the root bark].
PubMed:
Phototoxicity due to Cachrys libanotis.
PubMed:
Host plant resistance and linear furanocoumarin content of Apium accessions.
PubMed:
Impact of atmospheric pollution on linear furanocoumarin content in celery.
PubMed:
Heracleum mantegazzianum growth phases and furocoumarin content.
PubMed:
Artificial defloration and furanocoumarin induction inPastinaca sativa (Umbelliferae).
PubMed:
Isopimpinellin is not phototoxic to viruses and cells.
PubMed:
Oxypeucedanin, a Major Furocoumarin in Parsley, Petroselinum crispum.
PubMed:
[Isopimpinellin--a furocoumarin from Heracleum sphondylium with chromosome damaging activity].
PubMed:
Biologically active principles of crude drugs. Anti-allergic principles in "Cnidii monnieri".
PubMed:
Identification of psoralen, 8-methoxypsoralen, isopimpinellin, and 5,7-dimethoxycoumarin in Pelea anisata H. Mann.
PubMed:
Furocoumarins of Heracleum laciniatum: isolation, phototoxicity, absorption and action spectra studies.
PubMed:
The furocoumarin composition of Pituranthos triradiatus.
PubMed:
HPLC analysis of linear furocoumarins (psoralens) in healthy celery (Apium graveolens).
PubMed:
Differential response of cultured parsley cells to elicitors from two non-pathogenic strains of fungi. 1. Identification of induced products as coumarin derivatives.
PubMed:
The biosynthesis of isopimpinellin.
PubMed:
Isolation of isopimpinellin from the fruits of Ammi majus L. natural coumarins. IV.