Basic information
- Standard SMILES
O=c1ccc2ccccc2o1- InChIKey
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N- Molecular formula
- C9H6O2
- Average molar mass
- 146.14 g/mol
- Monoisotopic mass
- 146.03677943
Names & identifiers
- Preferred name
- Coumarin
- IUPAC
- chromen-2-one
- English name
- Coumarin
- Molecular formula
- C9H6O2
- Molecular weight
- 146.14
Names & synonyms
Show more names
Database identifiers
- CAS
91-64-5- PubChem CID
- 323
- DTXSID
DTXSID7020348- ChEMBL
CHEMBL6466- ChEBI
CHEBI:28794- UNII
- A4VZ22K1WT
- EC Number
- 202-086-7
- Nikkaji
- J3.218B
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 196
Physicochemical properties
- Melting point
- 68 · 68-73 °C (lit.)
- Boiling point
- 298 °C · 298 °C (lit.)
- Density
- 0.935 · 0.935
- vapor pressure
- 0.01 mm · 0.01 mm Hg ( 47 °C)
- refractive index
- 1.51 · 1.5100 (estimate)
- Flash point
- 162 °C · 162 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 1.7 g/l · 1.7g/l
- form
- Crystals or Crystalline Powder
- color
- White
- PH Range
- Non' uorescence (9.5) to light green ' uorescence (10.5)
- Odor
- 10 % · at 10.00 % in dipropylene glycol. sweet hay tonka new mown hay
- Odor Type
- tonka
- biological source
- synthetic
- Water Solubility
- 1.7 g/L · 1.7 g/L (20 ºC)
- λmax
- 275 nm · 275nm
- Merck
- 14 · 14,2562
- BRN
- 383644 · 383644
- Henry's Law Constant
- 9.9 · 9.9×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Major Application
- color filter, organic electroluminescent devices, liquid crystal displays, field emission displays, inks, nickel plating, detergents, deodorant for shoes, petroleum products, cigarettes, personal care products, cosmetics, sunscreen cream, perfumes, nucleic acid sequencing, antiinflammatory agent, treatment of cancer, neurotransmission disorders, bleeding disorders, cerebrovascular disease, thrombosis, hemorrhoids, rheumatic disease, arthritic disease, epilepsy, vaginitis, painkiller, teeth whitening agent, skin whitening agent, wound healing promoter
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
- InChIKey
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
- SMILES
- O=C1Oc2ccccc2C=C1
- LogP
- 1.39 at · 1.39 at 25℃
- Toxicology and Carcinogenesis
- Toxicology and Carcinogenesis Studies of Coumarin (CASRN 91-64-5) in F344/N Rats and B6C3F1 Mice (Gavage Studies)
- Substances Added to Food (formerly EAFUS)
- COUMARIN--PROHIBITED
- FDA 21 CFR
- 189.13 · 189.130
- CAS DataBase Reference
- 91 · 91-64-5(CAS DataBase Reference)
- EWG's Food Scores
- 4 · 4-7
- NCI Dictionary of Cancer Terms
- coumarin
- FDA UNII
- 4 VZ22K1WT · A4VZ22K1WT
- NCI Drug Dictionary
- coumarin
- IARC
- 3 · 3 (Vol. Sup 7, 77) 2000
- NIST Chemistry Reference
- Coumarin(91-64-5)
- EPA Substance Registry System
- Coumarin (91-64-5)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 25 · NA.25
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301+H311-H317
- Precautionary statements
- 261 · P261-P264-P270-P280-P301+P310-P302+P352+P312
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22-40-36/37/38-20/21/22-43
- Safety Statements
- 36 · 36-36/37-26
- RIDADR
- 2811 · UN 2811 6.1/PG 3
- WGK Germany
- 1 · 1
- RTECS
- 4200000 · GN4200000
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29322010 · 29322010
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 OralSkin Sens. 1
- Hazardous Substances Data
- 91 · 91-64-5(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in rats, guinea pigs: 680, 202 mg/kg (Jenner)
- REACH Registrations
- Active
- Limited Quantities
- 5 kg · 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- GN4200000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29322010
- Toxicity
- LD50 orally in rats, guinea pigs: 680, 202 mg/kg (Jenner)
- risk_code
- 22-40-36/37/38-20/21/22-43
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xn
- safety_code
- 36-36/37-26
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301+H311-H317
- Limited Quantities
- 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 OralSkin Sens. 1
- Precautionary statements
- P261-P264-P270-P280-P301+P310-P302+P352+P312
- Hazardous Substances Data
- 91-64-5(Hazardous Substances Data)
Chemistry & industry
Applications
Usesused as a spice for the preparation of floral fragrances such as lavender, rosemary and rosemary, used in perfumes, cosmetics, soaps and detergents; used as flavoring agents for blending fragrances to make the aroma be lasting and unchanged; used as an electroplating additive to prevent the occurrence of pores in coating and can increase the brightness; as the flavor enhancer of printing ink and plastic; formerly used as spices and cigarettes spices, banned from 197; Since then, China had also prohibited it application in food; used as pharmaceutical raw materials.Coumarin, as a laser dye, has an output laser range be within the blue-green region (420 ~ 570nm), has high fluorescence quantum efficiency, such as 7-ethylamino-6-methyl-4-trifluoromethyl coumarin Lactone 307), the structure is as follows:
DescriptionCoumarin is a naturally occurring Benzopyrone compound. It is found in a large number of plants belonging to many different families including tonka beans, woodruff, lavender oil, cassia, melilot (sweet clover), and other plants. It is found in edible plants such as strawberries, cinnamon, peppermint, green tea, carrots, and celery, as well as in partially fermented tea, red wine, beer, and other foodstuffs. Concentrations range from 87 000 ppm in cassia and 40 000 ppm in cinnamon to 20 ppm in peppermint and 5 ppb in tangerines.
OccurrenceFound in many plants and essential oils such as cassia, melilot, orchid, lavender and balsam of Peru (Spth, 1937; Gildemeister & Hoffman, 1966).
Usescoumarin is considered a blood thinner, it can also increase blood flow. Some sources cite anti-oxidant capacities, as well. It is a specific plant constituent and is what creates the fragrance of freshly mowed hay. Coumarin is found in such plants as cherries, lavender, licorice, and sweet clover.
UsesPharmaceutic aid (flavor). Found in tonka beans, levender oil, woodruff, sweet clover.
Usesantineoplastic, antiinflammatory, antihyperglycaemic
General DescriptionColorless crystals, flakes or colorless to white powder with a pleasant fragrant vanilla odor and a bitter aromatic burning taste.
Preparation methods
PreparationCoumarin is currently produced by Perkin synthesis from salicylaldehyde. In the presence of sodium acetate, salicylaldehyde reacts with acetic anhydride to produce coumarin and acetic acid. The reaction is carried out in the liquid phase at elevated temperature.A process for the production of coumarin from hexahydrocoumarin by dehydrogenation has also been elaborated.Since the odor of coumarin is relatively weak, strong-smelling by-products (e.g., vinylphenol) must be removed. Many purification methods have been reported and patented.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A chromenone having the keto group located at the 2-position.
DefinitionA colorless crystalline compound with a pleasant odor, used in making perfumes. On hydrolysis with sodium hydroxide it forms coumarinic acid.
Related reactions
Linked notes
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