Dihydro Coumarin

Product Name:

Dihydro coumarin

CAS:

119-84-6

MF:

C9H8O2

MW:

148.16

EINECS:

204-354-9

Product Categories:

Coumarins

Mol File:

119-84-6.mol

Melting point 

24-25 °C(lit.)

Boiling point 

272 °C(lit.)

density 

1.169 g/mL at 25 °C(lit.)

FEMA 

2381 | DIHYDROCOUMARIN

refractive index 

n20/D 1.556(lit.)

Fp 

>230 °F

storage temp. 

Store below +30°C.

Specific Gravity

1.169

Water Solubility 

insoluble

JECFA Number

1171

BRN 

4584

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)

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)

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.

Chemical Properties

clear light yellow to brown liquid after melting

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 tem[1]perature. It has a burning taste

Uses

Perfumery.

Preparation

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.

General Description

White to pale yellow clear oily liquid with a sweet odor. Solidifies around room temperature.

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.

Raw materials

trans-Cinnamic acid-->Coumarin