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Dihydrocoumarin

Description Sources
Product Name
Dihydrocoumarin
CAS No.
119-84-6
Chemical Name
Dihydrocoumarin
Synonyms
3,4-DIHYDROCOUMARIN;CHROMAN-2-ONE;HYDROCOUMARIN;3,4-DIHYDRO-2H-1-BENZOPYRAN-2-ONE;2H-1-Benzopyran-2-one, 3,4-dihydro-;MELILOTIN;3,4-Dihydro-1-benzopyran-2-one;Tonkamel;FEMA 2381;MELILOTOL
CBNumber
CB4413174
Molecular Formula
C9H8O2
Formula Weight
148.16
MOL File
119-84-6.mol
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Dihydrocoumarin Property

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)
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Safety

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).
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H317May cause an allergic skin reaction

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W238104
Product name
Dihydrocoumarin
Purity
≥99%, FCC, FG
Packaging
1kg
Price
$80.9
Updated
2024/03/01
Sigma-Aldrich
Product number
W238104
Product name
Dihydrocoumarin
Purity
≥99%, FCC, FG
Packaging
5kg
Price
$217
Updated
2024/03/01
Sigma-Aldrich
Product number
W238104
Product name
Dihydrocoumarin
Purity
≥99%, FCC, FG
Packaging
10Kg
Price
$360
Updated
2024/03/01
Sigma-Aldrich
Product number
D104809
Product name
Dihydrocoumarin
Purity
99%
Packaging
5g
Price
$36.3
Updated
2024/03/01
Sigma-Aldrich
Product number
07552
Product name
Dihydrocoumarin
Purity
analytical standard
Packaging
1ml
Price
$69.5
Updated
2022/05/15
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Dihydrocoumarin Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Coumarin trans-Cinnamic acid

Preparation Products

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View Lastest Price from Dihydrocoumarin manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Dihydrocoumarin 119-84-6
Price
US $100.00-45.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-06
Hebei Weibang Biotechnology Co., Ltd
Product
Cinnamic acid 119-84-6
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5tons
Release date
2024-12-03
Shandong Deshang Chemical Co., Ltd.
Product
Dihydrocoumarin 119-84-6
Price
US $10.00-7.00/kg
Min. Order
1kg
Purity
99.99%
Supply Ability
10 tons
Release date
2024-06-07

119-84-6, DihydrocoumarinRelated Search:

Nickel Potassium cinnamate Ethanol Sodium bicarbonate URANIUM Barium hydroxide Metronidazole Dihydrocoumarin 4-HYDROXY MEPHENYTOIN 3-Phenylpropionic acid Vanillin 6,7-DIMETHOXY-4-METHYL-CHROMAN-2-ONE 3-[(Z)-ANILINOMETHYLIDENE]-2H-CHROMENE-2,4-DIONE 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)-

  • AKOS 222-08
  • 3,4-Dihydro-1-benzopyran-2-one
  • 3,4-DIHYDRO-2H-1-BENZOPYRAN-2-ONE
  • 3,4-DIHYDROCOUMARIN
  • Hydrocoumarin,6-methyl-4phenyl-3,4dihydro-6-methyl-4-phenyl-2h-benzopyran-2-one
  • Dihydrocoumarin 1g [119-84-6]
  • Dihydrocoumarin,3,4-Dihydro-1-benzopyran-2-one, Benzodihydropyrone, Hydrocoumarin
  • DIHYDROCOUMARIN,3,4-(RG)
  • 3,4-dihydrobenzopyran-2-one
  • DIHYDROCOUMARIN FOR SYNTHESIS
  • DihydrocouMarin 99%
  • Two hydrogen
  • 2-Chromanone
  • 2-oxo-chroma
  • 3,4-dihydro-2h-1-benzopyran-2-on
  • 3,4-dihydro-coumari
  • 3,4-Dihydroxycoumarin
  • Benzopyranone, dihydro-
  • Chroman, 2-oxo-
  • Coumarin, 3,4-dihydro-
  • Hydrocinnamic acid, o-hydroxy-, delta-lactone
  • 1,2-BENZODIHYDROPYRONE
  • BENZODIHYDROPYRONE
  • DIHYDROBENZENOPYRONE
  • DIHYDROBENZOPYRONE
  • DIHYDROCOUMARIN
  • DIHYDROCOUMARIN,3,4-
  • CHROMAN-2-ONE
  • HYDROCOUMARIN
  • FEMA 2381
  • MELILOTIN
  • MELILOTINE
  • MELILOTOL
  • meliloticlactone
  • NCI-C55890
  • o-hydroxy-hydrocinnamicacidelta-lactone
  • oxochroman
  • USAF do-12
  • usafdo-12
  • 2H-1-Benzopyran-2-one, 3,4-dihydro-
  • 3,4-Dihydroqoumarin
  • 2H-1-BENZOPYRAN-2-ONE,3,4-D
  • 8-Azabicyclo[3.2.1]octan-3-one, 8-(phenylmethyl)-
  • 4H-1-Benzopyran-2(3H)-one
  • Dihydrocoumarin,99%
  • 3,4-Dihydro-1-benzopyran-2-one, Benzodihydropyrone, Hydrocoumarin
  • Tonkamel
  • DIHYDROCOUMARIN 99+% FCC
  • 3,4-Dihydrocoumarin &gt
  • Dihydrocoumarin@1000 μg/mL in Acetone
  • Cinnamic acid USP/EP/BP
  • Meliotine Coumarin, 3, 4-Dihydro- 3, 4-Dyhydrocoumarin CAS 119-84-6
  • 3,4-dihydrochromen-2-one
  • ihydrocoumarin
  • 119-84-6
  • Heterocyclic Building Blocks
  • Coumarins
  • Building Blocks