Isopimpinellin

Names

[ CAS No. ]:
482-27-9

[ Name ]:
Isopimpinellin

[Synonym ]:
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
7H-Furo[3,2-g][1]benzopyran-7-one, 4,9-dimethoxy-
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]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

Research Areas >> Inflammation/Immunology

[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

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

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

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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...