Name | 4-Hydroxycoumarin |
Synonyms | COUMARINOL 4-HYDROXYCUMARIN 4-Hydroxycoumarin 4-HYDROXYCOUMARIN 4-hydroxy coumarin HYDROXYCOUMARIN, 4- 4-coumarinyl alcohol 4-HYDROXY-CHROMEN-2-ONE 4-Hydroxy-chromen-2-one 4-hydroxy-2H-chromen-2-one 2-hydroxy-4H-chromen-4-one 4-hydroxy-1-benzopyran-2-one 4-hydroxy-2h-1-benzopyran-2-on 2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY- 4-[(1E)-3-hydroxyprop-1-en-1-yl]phenol sodium 2-oxo-3-(3-oxo-1-phenylbutyl)-2H-chromen-4-olate |
CAS | 1076-38-6 |
EINECS | 214-060-2 |
InChI | InChI:1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H |
InChIKey | VXIXUWQIVKSKSA-UHFFFAOYSA-N |
Molecular Formula | C9H6O3 |
Molar Mass | 162.14 |
Density | 1.1734 (rough estimate) |
Melting Point | 211-213 °C (lit.) |
Boling Point | 228.82°C (rough estimate) |
Water Solubility | PRACTICALLY INSOLUBLE |
Solubility | Easily soluble in ethanol, ether and hot water, hardly soluble in water. |
Vapor Presure | 0.02Pa at 25℃ |
Appearance | Pale yellow to brown crystalline powder |
Color | Clear colorless to slightly yellow |
BRN | 129768 |
pKa | 4.50±1.00(Predicted) |
Storage Condition | Store below +30°C. |
Refractive Index | 1.4500 (estimate) |
MDL | MFCD00006856 |
Physical and Chemical Properties | Melting Point 210-215°C water-soluble practically insoluble |
Use | Used for the manufacture of racumin fan and warfarin |
Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | 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 | DJ3100000 |
TSCA | Yes |
HS Code | 29322980 |
Hazard Note | Irritant |
Downstream Products | Bromoadiolone warfarin |
Reference Show more | 1. Gao Ruifang, Li Xiangsheng. Simultaneous Determination of Coumarin and Other 15 Compounds in Cosmetics by High Performance Liquid Chromatography [J]. Daily Chemical Industry, 2017, 47(12):719-722. 2. [IF = 4.411] Liang Yang et al."New Insights into the Antibacterial Activity of Hydroxycoumarins against Ralstonia solanacearum." Molecules. 2016 Apr;21(4):468 3. [IF = 3.963] Lin Cai et al."Plant-derived compounds: A potential source of drugs against Tobacco mosaic virus." Pestic Biochem Phys. 2020 Oct;169:104589 |
LogP | 1.6-2.31 at 21.2℃ |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
traits | yellowish or white-like crystalline powder |
Principle of Action | 4-hydroxycoumarin is a spice, and coumarins are widely distributed in the plant kingdom. The cattle and horses ate the spoiled alfalfa and bled to death due to loss of hemagglutination, which may be caused by the formation of dicoumarin in the plant. |
use | this product is an intermediate of medicine and pesticide. Used for the production of dicoumarin, new anticoagulant, warfarin and other anticoagulant drugs. These 4-hydroxycoumarin derivatives are a class of oral anticoagulant drugs. Diocoumarin has been replaced by warfarin due to irregular and incomplete absorption. The duration of dicoumarin was the longest (4-7d), warfarin was longer (3-5d), new anticoagulation was shorter (2-4d), and coumarin ethyl ester was the shortest (2-3d). 4-Hydroxycoumarin is also an intermediate of some rodenticide drugs, such as murmicide, chlorromicide, murmicide, murmicide naphthalene, biphenyl murmicide naphthalene, etc. Rodenticide is the first generation of anticoagulant rodenticide, which is widely used all over the world and has a good killing effect. The second generation of anticoagulant rodenticide is brominated biphenyl murine naphthalene, which can be poisoned to death by a single bait, accounting for 30% of the rodenticide market in the United States. 4-Hydroxycoumarin is also a spice, and coumarins are widely distributed in the plant kingdom. The cattle and horses ate the spoiled alfalfa and bled to death due to loss of hemagglutination, which may be caused by the formation of dicoumarin in the plant. Used to make rat-killing fans and rat-killing spirits |
Production method | It is obtained by cyclixing of methyl acetylsalicylate. Sodium carbonate and liquid paraffin are put into the reaction pot, heated and stirred in a closed manner, the temperature gradually rises to 240 ℃, and dissolved methyl acetylsalicylate is added. When the temperature drops for about 10min, it gradually rises and keeps at 240-260 ℃. After adding, return for 1h. Discharging, filtering, dissolving the filtrate and dissolving the solid in water, heating to about 70 ℃, separating a small amount of oil layer in the upper layer, adding hydrochloric acid to adjust the pH to 6, adding activated carbon to decolorization. Filter, acidify the filtrate with hydrochloric acid to pH 1, that is, 4-hydroxycoumarin is precipitated, add ice to make the precipitation complete, filter, wash with water until the lotion is neutral, and the filter cake is dried to obtain 4-hydroxycoumarin finished product. 15.21% yield. In production, acetylsalicyl chloride can be used as raw material to synthesize a-(2-hydroxybenzoyl) ethyl acetoacetate by shrinking with ethyl acetoacetate, and hydrolyzed with sodium hydroxide solution to obtain a-(2-Hydroxybenzoyl) sodium acetoacetate. Then in 92% sulfuric acid, cyclize at 110-115 ℃ to generate 3-acetyl-4-hydroxycoumarin, and then hydrolyze to obtain 4-hydroxycoumarin. The yield of this method is about 64%. |