Isopimpinellin

Modify Date: 2025-08-20 15:44:09

Isopimpinellin Structure
Isopimpinellin structure
 Common Name Isopimpinellin
CAS Number 482-27-9 Molecular Weight 246.215
Density 1.4±0.1 g/cm3 Boiling Point 448.7±45.0 °C at 760 mmHg
Molecular Formula C13H10O5 Melting Point 150-151ºC
MSDS Chinese USA Flash Point 225.1±28.7 °C
Symbol GHS06
GHS06		 Signal Word Danger

 Use of Isopimpinellin


Isopimpinellin, an orally active compound isolated from the roots of Pimpinella saxifrage. Isopimpinellin blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene. Isopimpinellin possesses anti-leishmania effect[1].

 Names

Name isopimpinellin
Synonym More Synonyms

 Isopimpinellin Biological Activity

Description Isopimpinellin, an orally active compound isolated from the roots of Pimpinella saxifrage. Isopimpinellin blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene. Isopimpinellin possesses anti-leishmania effect[1].
Related Catalog
In Vivo Isopimpinellin (oral gavage, 35-150 mg/kg) inhibits B[a]P-DNA adduct formation and DMBA–DNA adduct formation in SENCAR mice with skin tumor[1]. Animal Model: Female SENCAR mice (7-9 weeks of age) were fed AIN-76A semi-purified diet (Dyets, Bethlehem, PA) for 2 weeks prior to and during the study[1]. Dosage: 35–150 mg/kg. Administration: Oral gavage, suspended in 0.1 mL corn oil at 24 h and 2 h prior to topical treatment with [3H]B[a]P (200 nmol, 1 Ci/mmol) or [3H]DMBA (10 nmol, 10 Ci/mmol) (each in 0.2 mL acetone). Result: Significantly inhibited B[a]P-DNA adduct formation by 37 and 26%, respectively. Isopimpinellin (35, 70 and 150 mg/kg) blocked DMBA–DNA adduct formation by 23, 56 and 69%, respectively
References

[1]. Kleiner HE, et al. Oral administration of the citrus coumarin, isopimpinellin, blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene in SENCAR mice. Carcinogenesis. 2002 Oct;23(10):1667-75.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 448.7±45.0 °C at 760 mmHg
Melting Point 150-151ºC
Molecular Formula C13H10O5
Molecular Weight 246.215
Flash Point 225.1±28.7 °C
Exact Mass 246.052826
PSA 61.81000
LogP 2.31
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.612
InChIKey DFMAXQKDIGCMTL-UHFFFAOYSA-N
SMILES COc1c2ccoc2c(OC)c2oc(=O)ccc12
Storage condition 2-8°C

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H300
Precautionary Statements P264-P301 + P310
Hazard Codes T+
Risk Phrases 20/21/22
Safety Phrases 22-36/37/39-45-36/37-28
RIDADR UN 2811 6.1 / PGII
RTECS LV1049200

 Synthetic Route

4,9-dihydroxyfuro[3,2-g]chromen-7-one structure

4,9-dihydroxyfu...

CAS#:14348-23-3

methyl iodide structure

methyl iodide

CAS#:74-88-4

~80%

Isopimpinellin Structure

Isopimpinellin

CAS#:482-27-9

Literature: Bioorganic and Medicinal Chemistry, , vol. 20, # 2 p. 784 - 788
Xanthotoxin structure

Xanthotoxin

CAS#:298-81-7

~%

Isopimpinellin Structure

Isopimpinellin

CAS#:482-27-9

Literature: Journal of Organic Chemistry, , vol. 24, p. 523,525
Psoralen quinone structure

Psoralen quinone

CAS#:483-36-3

~%

Isopimpinellin Structure

Isopimpinellin

CAS#:482-27-9

Literature: Journal of Organic Chemistry, , vol. 24, p. 523,525
diazomethane structure

diazomethane

CAS#:186581-53-3

8-Hydroxybergapten structure

8-Hydroxybergapten

CAS#:1603-47-0

~%

Isopimpinellin Structure

Isopimpinellin

CAS#:482-27-9

Literature: Journal of the Chemical Society, , p. 4163,4168 Chemische Berichte, , vol. 71, p. 344,351 Yakugaku Zasshi, , vol. 58, p. 370,377 Monatshefte fuer Chemie, , vol. 72, p. 179,187 Yakugaku Zasshi, , vol. 60, p. 57,61 Chem.Abstr., , p. 3717
4,9-dihydroxyfuro[3,2-g]chromen-7-one structure

4,9-dihydroxyfu...

CAS#:14348-23-3

Dimethyl sulfate structure

Dimethyl sulfate

CAS#:77-78-1

~%

Isopimpinellin Structure

Isopimpinellin

CAS#:482-27-9

Literature: Journal of Organic Chemistry, , vol. 24, p. 523,525
diazomethane structure

diazomethane

CAS#:186581-53-3

4,9-dihydroxyfuro[3,2-g]chromen-7-one structure

4,9-dihydroxyfu...

CAS#:14348-23-3

~%

Isopimpinellin Structure

Isopimpinellin

CAS#:482-27-9

Literature: Monatshefte fuer Chemie, , vol. 59, p. 161,170
8-Hydroxybergapten structure

8-Hydroxybergapten

CAS#:1603-47-0

methyl iodide structure

methyl iodide

CAS#:74-88-4

~%

Isopimpinellin Structure

Isopimpinellin

CAS#:482-27-9

Literature: Journal of the Indian Chemical Society, , vol. 25, p. 139,141

 Articles1

More Articles
Application of the equivalency factor concept to the phototoxicity and –genotoxicity of furocoumarin mixtures

Food Chem. Toxicol. 68 , 257-66, (2014)

• The photo-cytotoxic, -mutagenic, and -clastogenic properties in V79 cells of thirteen furocoumarins (FCs), were analyzed. • Nine FC mixtures including one mixture ‘representing’ FCs in Angelica arch...

 IsopimpinellinBioassay

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Name: Primary cell-based high-throughput screening assay for identification of compounds th...
Source: Johns Hopkins Ion Channel Center
Target: regulator of G-protein signaling 4 isoform 2 [Homo sapiens]
External Id: JHICC_RGS_Act_HTS
Name: Luminescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: mu-type opioid receptor isoform MOR-1 [Homo sapiens]
External Id: OPRM1-OPRD1_AG_LUMI_1536_1X%ACT PRUN
Name: Photobinding to Poly(dA-dT)-Poly(dA-dT)-DNA after UV-A irradiation
Source: ChEMBL
Target: Nucleic Acid
External Id: CHEMBL762651
Name: QFRET-based biochemical primary high throughput screening assay to identify exosite i...
Source: The Scripps Research Institute Molecular Screening Center
Target: disintegrin and metalloproteinase domain-containing protein 17 preproprotein [Homo sapiens]
External Id: ADAM17_INH_QFRET_1536_1X%INH PRUN
Name: ERK5 transcriptional activity HTS
Source: 24565
Target: N/A
External Id: ERK5 transcriptional activity-HTS
Name: Fluorescence-based cell-based primary high throughput screening assay to identify ago...
Source: The Scripps Research Institute Molecular Screening Center
Target: muscarinic acetylcholine receptor M1 [Homo sapiens]
External Id: CHRM1_AG_FLUO8_1536_1X%ACT PRUN
Name: Photobinding to Poly(dA-dT)-Poly(dA-dT)-DNA in dark, determined by the shift of therm...
Source: ChEMBL
Target: Nucleic Acid
External Id: CHEMBL763193
Name: uHTS identification of small molecule activators of the adaptive arm of the Unfolded ...
Source: Burnham Center for Chemical Genomics
Target: N/A
External Id: BCCG-A405-UPR-XBP1-PrimaryAgonist-Assay
Name: High throughput fluorescence intensity-based biochemical assay to screen for small mo...
Source: University of Pittsburgh Molecular Library Screening Center
Target: furin (paired basic amino acid cleaving enzyme), isoform CRA_a [Homo sapiens]
External Id: MH080376 Biochemical HTS for Inhibitors of the Proprotein Convertase Furin.
Name: Fluorescence polarization to screen for inhibitor that competite the binding of FadD2...
Source: Broad Institute
Target: FATTY-ACID-CoA LIGASE FADD28 (FATTY-ACID-CoA SYNTHETASE)
External Id: 2147-01_Inhibitor_SinglePoint_HTS_Activity
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 Synonyms

5,8-Dimethoxypsoralen
4,9-Dimethoxy-furo[3,2-g]chromen-7-one
4,9-Dimethoxyfuro[3,2-g]benzopyran-7-one
4,9-Dimethoxy-7H-furo[3,2-g][1]benzopyran-7-one
4,9-dimethoxyfuro[3,2-g]chromen-7-one
4,9-Dimethoxy-7H-furo[3,2-g]chromen-7-one
MFCD00017407
Isopimpinellin
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