Dihydrocoumarin

Chemical properties

Dihydrocoumarin forms colorless crystals (mp 24°C) with a sweet, herbal odor. Dihydrocoumarin is prepared by hydrogenation of coumarin, for example, in the presence of a Raney nickel catalyst. Another process employs the vapor-phase dehydrogenation of hexahydrocoumarin in the presence of Pd or Pt-Al₂O₃ catalysts . Hexahydrocoumarin is prepared by cyanoethylation of cyclohexanone and hydrolysis of the nitrile group, followed by ring closure to the lactone.

Chemical properties

Dihydrocoumarin has an odor similar to coumarin at room temperature or reminiscent of nitrobenzene at higher temperature. It has a burning taste.

Occurrence

Reported found in Melilotus officinalis, from which it may be extracted by water distillation.

The Uses of Dihydrocoumarin

Dihydrocoumarin may be used as an analytical reference standard for the determination of the analyte in guaco extracts and pharmaceutical preparations, and various plant extracts by chromatography-based techniques and capillary electrophoresis.

The Uses of Dihydrocoumarin

Hydrocoumarin can be used as a reagent to prepare splitomicin analogs as inhibitors of Sir2.

Definition

ChEBI: A chromanone that is the 3,4-dihydro derivative of coumarin.

What are the applications of Application

Dihydrocoumarin is a potential epigeenetic process disruptor and Sir2 inhibitor

Preparation

Dihydrocoumarin is synthesized by reduction of coumarin under pressure in the presence of nickel at 160 to 200°C or in the presence of Pd-BaSO4 in alcoholic solution.

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 4555, 1996 DOI: 10.1016/0040-4039(96)00902-1

General Description

Viscous, almost colorless liquid, solidifying in the cold, melting at 23° C. Sp. Gr. 1.19. B.P. 272° C. Slightly soluble in water, soluble in alcohol, miscible with oils.
Sweet-herbaceous, nutlike, haylike odor, usually described as "coumannic" or "tobacco-like".

Air & Water Reactions

Solutions of the chemical in water are stable for less than two hours. Insoluble in water.

Reactivity Profile

Hydrocoumarin is a lactone (behaves as an ester). Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Hydrocoumarin may hydrolyze under alkaline or acidic conditions.

Fire Hazard

Hydrocoumarin is combustible.

Biochem/physiol Actions

Taste at 10 ppm