| Identification | More | [Name]
Hydrocoumarin | [CAS]
119-84-6 | [Synonyms]
1,2-BENZODIHYDROPYRONE
3,4-Dihydro-1-benzopyran-2-one
3,4-DIHYDRO-2H-1-BENZOPYRAN-2-ONE
3,4-DIHYDROCOUMARIN
AKOS 222-08
BENZODIHYDROPYRONE
CHROMAN-2-ONE
DIHYDROBENZENOPYRONE
DIHYDROBENZOPYRONE
DIHYDROCOUMARIN
DIHYDROCOUMARIN,3,4-
FEMA 2381
HYDROCOUMARIN
MELILOTIN
MELILOTINE
MELILOTOL
2-Chromanone
2-oxo-chroma
3,4-dihydro-2h-1-benzopyran-2-on
3,4-dihydro-coumari | [EINECS(EC#)]
204-354-9 | [Molecular Formula]
C9H8O2 | [MDL Number]
MFCD00006881 | [Molecular Weight]
148.16 | [MOL File]
119-84-6.mol |
| Chemical Properties | Back Directory | [Appearance]
clear light yellow to brown liquid after melting | [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 | [refractive index ]
n20/D 1.556(lit.)
| [Fp ]
>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℃ | [Uses]
Perfumery. | [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]
119-84-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [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). |
| Hazard Information | Back Directory | [General Description]
White to pale yellow clear oily liquid with a sweet odor. Solidifies around room temperature. | [Reactivity Profile]
3,4-DIHYDROCOUMARIN(119-84-6) 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. This chemical may hydrolyze under alkaline or acidic conditions. | [Air & Water Reactions]
Solutions of the chemical in water are stable for less than two hours. Insoluble in water. | [Fire Hazard]
This chemical is combustible. | [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 temperature. It has a burning taste | [Occurrence]
Reported found in Melilotus officinalis, from which it may be extracted by water distillation. | [Definition]
ChEBI: A chromanone that is the 3,4-dihydro derivative of coumarin. | [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. | [Synthesis Reference(s)]
Tetrahedron Letters, 37, p. 4555, 1996 DOI: 10.1016/0040-4039(96)00902-1 | [Biochem/physiol Actions]
Taste at 10 ppm |
| Questions And Answer | Back Directory | [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/
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