Dibenzoylmethane
Encyclopedia
1,3-diphenylpropane-1,3-dione (dibenzoylmethane, DBM) is an aromatic 1,3-diketone
, acetylacetone
(acac) derivative, where both methyl groups have been substituted by phenyl groups. It is white solid melting 77-78°C. Similiary to acac, DBM exist as two tautomeric forms, however keto-enol equilibrium of DBM is strongly shifted to the enol form. It is result of formation of intra-molecular hydrogen bond, which is conjugated with phenyl rings . The resonance-assisted hydrogen bond is responsible for high photostability of such compounds, and therefore, some derivates of DBM (e.g. Avobenzone
) have found application as sunscreen
s.
Diketone
A diketone is a molecule containing two ketone groups. The simpliest diketone is diacetyl, also known as 2,3-butanedione. Diacetyl, acetylacetone, and hexane-2,5-dione are examples of 1,2-, 1,3-, and 1,4-diketones, respectively...
, acetylacetone
Acac
ACAC may refer to:* American Council for Accredited Certification, a private, non-profit certifying body* Atlanta Contemporary Art Center, a contemporary art museum in Atlanta* ACAC consortium, a subsidiary of China Aviation Industry Corporation...
(acac) derivative, where both methyl groups have been substituted by phenyl groups. It is white solid melting 77-78°C. Similiary to acac, DBM exist as two tautomeric forms, however keto-enol equilibrium of DBM is strongly shifted to the enol form. It is result of formation of intra-molecular hydrogen bond, which is conjugated with phenyl rings . The resonance-assisted hydrogen bond is responsible for high photostability of such compounds, and therefore, some derivates of DBM (e.g. Avobenzone
Avobenzone
Avobenzone is an oil soluble ingredient used in sunscreen products to absorb the full spectrum of UVA rays....
) have found application as sunscreen
Sunscreen
Sunblock is a lotion, spray, gel or other topical product that absorbs or reflects some of the sun's ultraviolet radiation on the skin exposed to sunlight and thus helps protect against sunburn...
s.