Английская Википедия:Dibenzoylmethane

Материал из Онлайн справочника
Перейти к навигацииПерейти к поиску

Шаблон:Chembox

Dibenzoylmethane (DBM) is an organic compound with the formula (C6H5C(O))2CH2. DBM is the name for a 1,3-diketone, but the compound exists primarily as one of two equivalent enol tautomers.[1] DBM (actually its enol) is a white solid. Due to their high photostability and UV-absorbing properties, derivatives of DBM such as avobenzone, have found applications as sunscreen products.

Synthesis and reactions

DBM is prepared by condensation of ethyl benzoate with acetophenone.[2]

Like other 1,3-diketones (or their enols), DBM condenses with a variety of bifunctional reagents to give heterocycles. Hydrazine gives diphenylpyrazole. Urea and thiourea also condense to give six-membered rings. With metal salts, the conjugate base of DBM forms complexes akin to the metal acetylacetonates.

Occurrence and medicinal properties

Файл:Curcumin.svg
Curcumin, structurally related to DBM, is the bright yellow component of the spice turmeric.

Dibenzoylmethane (DBM) is a minor constituent in the root extract of Licorice (Glycyrrhiza glabra in the family Leguminosae).[3] It is also found in Curcumin. These occurrences have led to investigations into the medicinal properties of this class of compounds.[4][5]

DBM (and Trazodone) slow disease progression by preventing the cessation of protein synthesis in neurons.[6]

Related compounds

References