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Oxypeucedanin

4-(2,3-Epoxy-3-methylbut-2-enoxy)-7H-furo[3,2-g][1]benzopyran-7-one

Prangolarin

Tetracyclic furanocoumarin ether epoxide · C₁₆H₁₄O₅

Chemical structure of Oxypeucedanin
2D structure PubChem / NCI CIR

Chemical info

CAS number CAS
3173-02-2
Molecular formula
C₁₆H₁₄O₅
Molecular weight
286.28 g/mol
Aroma
No characteristic aroma. A solid compound occurring as a furanocoumarin in lemon peel.

Safety

Phototoxic · Restricted

Oxypeucedanin is a furanocoumarin occurring at low levels in expressed lemon and lime oils. The compound is phototoxic but weaker than bergapten.

Skin. Oxypeucedanin elicited photopigmentation on colored guinea pig skin, with phototoxic potency about 25 percent of bergapten. Oral oxypeucedanin was photosensitizing to 2-week-old broiler chicks.

Liver. Rats given ip injection of 100 mg/kg/day oxypeucedanin for 8 weeks showed no hepatic lesions, no changes in hepatic enzyme activity, glutathione or DNA concentrations.

Mutagenicity. Non-mutagenic in the Ames test. However, may be photomutagenic (not specifically studied).

Cancer. Oxypeucedanin dose-dependently inhibited in vitro proliferation of human cell lines for cancers of colon, lung, ovary, CNS and skin (melanoma).

Usage guidelines

Concern level
Moderate, phototoxic
SCCNFP limit
Maximum 1 ppm total furanocoumarins for all cosmetic products
Phototoxic potency
Approximately 25 percent of bergapten

Found in essential oils

Principal sources
Lemon (expressed)0.09 – 0.82 %
Lime (expressed)0.02 – 0.3 %

Notes

Oxypeucedanin is one of several furanocoumarins in expressed lemon and lime oils. The combined furanocoumarins, not any single compound, determine the phototoxicity of Citrus essential oils.