Dihydrocoumarin Chemical Properties

Melting point:

24-25 °C (lit.)

Boiling point:

272 °C (lit.)

Density 

1.169 g/mL at 25 °C (lit.)

vapor pressure 

13.6kPa at 20℃

FEMA 

2381 | DIHYDROCOUMARIN

refractive index 

n20/D 1.556(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform, Methanol (Sparingly)

form 

Solid

color 

Colourless to Off-White

Specific Gravity

1.169

Odor

at 10.00 % in dipropylene glycol. sweet tonka coumarinic coconut herbal cinnamon balsamic

Odor Type

tonka

Water Solubility 

insoluble

JECFA Number

1171

BRN 

4584

LogP

1.82 at 25℃

CAS DataBase Reference

119-84-6(CAS DataBase Reference)

NIST Chemistry Reference

2H-1-Benzopyran-2-one, 3,4-dihydro-(119-84-6)

EPA Substance Registry System

3,4-Dihydrocoumarin (119-84-6)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

MW5775000

TSCA 

Yes

HS Code 

29322980

Hazardous Substances Data

119-84-6(Hazardous Substances Data)

Toxicity

The acute oral LD₅₀ value in rats was reported as 1.65 g/kg (1.47-1.83 g/ kg) (Moreno, 1972a). The acute dermal LD₅₀ value in rabbits was reported as > 5 g/kg (Moreno, 1972b).

MSDS

• Language:English Provider:Hydrocoumarin
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Dihydrocoumarin Usage And Synthesis

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 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.

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.

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.

Definition

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

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

Dihydrocoumarin(119-84-6)Related Product Information

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• Ethanol
• Sodium bicarbonate
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• Dihydrocoumarin
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• 6,7-DIMETHOXY-4-METHYL-CHROMAN-2-ONE
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• 3-[(Z)-(3-CHLOROANILINO)METHYLIDENE]-2H-CHROMENE-2,4-DIONE
• 3-(2,6-DICHLOROPHENYL)-3A,9B-DIHYDRO-4H-CHROMENO[3,4-D]ISOXAZOL-4-ONE
• 4-(4-CHLOROPHENYL)-5,7-DIHYDROXY-2-CHROMANONE
• 3-((Z)-[4-(TRIFLUOROMETHYL)ANILINO]METHYLIDENE)-2H-CHROMENE-2,4-DIONE
• Hydrocoumarin, 6-acetamido-3-(1-pyrrolidinylcarbonyl)-