Description
With a sweet, creamy, and herbal, fragrance, with a slightly burnt taste, dihydrocoumarin (DHC) is used as a flavoring agent in food, tobacco, soap, and perfume, etc. Its exotic flavor is well suited for caramel, nuts, dairy, vanilla, tropical fruit, and alcohol. It is a eukaryotic metabolite found in tonka beans grown in northern South America, from which it was isolated as early as the 1820s, as well as sweet clover. Other uses include as an organic solvent and pharmaceutical intermediary. It has been shown to influence the epigenetic process of human cells in vitro.
Sources
http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16151
http://www.bojensen.net/EssentialOilsEng/EssentialOils29/EssentialOils29.htm#Tonka
https://books.google.kg/books?id=pUEqBgAAQBAJ&pg=PA427&lpg=PA427&dq=dihydrocoumarin+uses&source=bl&ots=HTZrffvsXu&sig=GPGKqrMRXQaRJ-qgHk7aULeBmGw&hl=en&sa=X&redir_esc=y#v=onepage&q=dihydrocoumarin%20uses&f=false
https://products.symrise.com/aroma-molecules/product-search/dihydrocoumarin/action/pdf/
http://www.lookchem.com/3-4-Dihydrocoumarin/
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1315280/
Chemical Properties
Dihydrocoumarin has an odor similar to coumarin at room temperature or reminiscent of nitrobenzene at higher temperature. It has a burning taste.
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-Al
2O
3 catalysts . Hexahydrocoumarin is prepared by
cyanoethylation of cyclohexanone and hydrolysis of the nitrile group, followed
by ring closure to the lactone.
Occurrence
Reported found in Melilotus officinalis, from which it may be extracted by water distillation.
Uses
Hydrocoumarin can be used as a reagent to prepare splitomicin analogs as inhibitors of Sir2.
Uses
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.
Definition
ChEBI: A chromanone that is the 3,4-dihydro derivative of coumarin.
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.
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
