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Isopimpinellin

5,8-Dimethoxyfurano[3,2-g]benzopyran-7-one

5,8-Dimethoxypsoralen · 5,8-Dimethoxy-6,7-furanocoumarin

Furanocoumarin ether · C₁₃H₁₀O₅

Chemical structure of Isopimpinellin
2D structure PubChem / NCI CIR

Chemical info

CAS number CAS
482-27-9
Molecular formula
C₁₃H₁₀O₅
Molecular weight
246.22 g/mol
Aroma
No distinctive odor, a non-volatile solid.

Safety

Low concern · Not phototoxic

Isopimpinellin is a furanocoumarin occurring in lime, expressed lime and rue oils. Unlike bergapten and psoralen, isopimpinellin is not phototoxic.

Skin. When confirmed to contain only trace amounts of psoralen, bergapten and methoxsalen, isopimpinellin is not phototoxic in chick skin bioassay. Earlier phototoxicity reports are attributed to contamination with highly active psoralens.

Mutagenicity. Not photomutagenic in studies. Not genotoxic or photogenotoxic in micronucleus assays.

Cancer. Significant anticancer activity. An oral dose of 70 mg/kg inhibited B[a]P-DNA adduct formation in mouse skin by 37 percent. At 35, 70 and 150 mg/kg it reduced mean papilloma counts by 49, 73 and 78 percent.


Usage guidelines

Concern level
Low, not phototoxic
SCCP
Maximum 1 ppm in cosmetic products (includes isopimpinellin)
Oils with high content
Lime (expressed) 0.1 – 1.3 percent

Found in essential oils

Principal sources
Lime (expressed)0.1 – 1.3 %
Rue0.02 %
Lemon (expressed)0 – 0.011 %

Pharmacokinetics

Isopimpinellin is a potent inhibitor of CYP1A1, suggesting an anticancer mechanism via blocking bioactivation of procarcinogens.


Notes

Since isopimpinellin is neither phototoxic nor photogenotoxic, the SCCP guideline for this compound should be revised in light of modern data.