Umbelliferone, a white crystalline organic powder found in the Umbelliferae plant family, is used in sunscreen and pulsed dye laser therapy. It absorbs harmful UVB radiation and can also be used as a whitener.
Umbelliferone is the common name of 7-hydroxycoumarin lactone, a white crystalline organic powder, soluble in alcohol. More technically, the International Union of Pure and Applied Chemistry assigns it the name 7-hydroxychromen-2-one. This substance is found widely in nature, particularly in the Umbelliferae or Apiaceae plant family. It is an active ingredient in sunscreen preparations, although some studies indicate that it may be capable of inducing a genetic mutation. Umbelliferone is also used in pulsed dye laser therapy for the treatment of vascular lesions.
The name “umbelliferone”, indicative of its vegetable origin, derives from the same root as “umbrella”. This is because umbiliferous plants are characterized by their flowering canopy or “umbel,” which is exemplified by Queen Anne’s lace or wild carrot, Daucus carota. Related plants include the carrot, celery, fennel and hemlock. Laboratory extraction of lactone from plants was reported in the German chemical literature as early as the 1860s. Today, umbelliferone is most often prepared synthetically.
The structure of umbelliferone comprises two six-membered rings, one of which incorporates an oxygen atom. It is prepared in the laboratory by condensation. In this technique, a ring structure with a small side feature, perhaps a hydroxyl group, adds a molecular fragment to an adjacent carbon. These two lateral fragments then close by joining the other ends to form a second ring, the one with the oxygen atom. During this cyclization, called Pechmann condensation, a water molecule is released.
The applied sunscreen reduces the user’s exposure to harmful ultraviolet radiation. Although the full ultraviolet spectrum covers the 10 to 400 nanometer wavelength region, it is only a specific part of it, the part that reaches the lower atmosphere, that poses a hazard. That portion is divided into two regions: ultraviolet A (UVA) and ultraviolet B (UVB), which are approximately 320-400 nanometers and 290-320 nanometers, respectively. UVB rays can be particularly harmful and has been strongly linked to skin cancer. Umbelliferone absorbs ultraviolet energy at 300, 305 and 325 nanometers, effectively reducing the amount of UVB radiation that can be absorbed by the skin.
Another application of umbelliferone is as a whitener or optical brightener. Energy that is absorbed in the ultraviolet region triggers revitalization, or fluorescence, in the blue region of the optical spectrum. This fluorescence imparts an appearance of whiteness, just as a bluing agent imparts whiteness to laundered clothing. Indeed, in textile cleaning, the availability of optical brighteners such as umbelliferone has significantly reduced the demand for such brightening agents.
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