4-Hydroxycoumarin
Synonym(s):4-Hydroxy-1-benzopyran-2-one
- CAS NO.:1076-38-6
- Empirical Formula: C9H6O3
- Molecular Weight: 162.14
- MDL number: MFCD00006856
- EINECS: 214-060-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2025-01-27 09:38:02
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What is 4-Hydroxycoumarin?
Chemical properties
Yellow powder or chunks or Slightly yellow needle-like crystals. freely soluble in ethanol, ether and hot water. brown in color with ferric chloride.
The Uses of 4-Hydroxycoumarin
4-Hydroxycoumarin is a plant derived antioxidant, protecting against lipid peroxidation, as well as a potential inhibitor of HIV-1 Integrase. 4-Hydroxycoumarins are a very important class of biologically active drugs which are widely used as anticoagulants-Warfarin and Acenocoumarol.
Definition
ChEBI: 4-hydroxycoumarin is a hydroxycoumarin that is coumarin in which the hydrogen at position 4 is replaced by a hydroxy group. It is a conjugate acid of a 4-hydroxycoumarin(1-).
Synthesis Reference(s)
The Journal of Organic Chemistry, 25, p. 677, 1960 DOI: 10.1021/jo01074a630
Synthesis
4-Hydroxycoumarin is prepared by the reaction of o-hydroxyacetophenone and Diethyl carbonate. The steps are as follows:
General procedure: To a stirred mixture (1.15 mmol) and sodium hydride (138 mg, 5.75 mmol) in 5 ml dry toluene, a solution of the diethyl carbonate (1.15 mmol) in dry toluene was dropped. The mixture was reacted at 0°C for 30 min, then heated to reflux and reacted for another 4 h. The reaction mixture was quenched with water (20 mL) at ice bath and neutralized to pH 7 with 2 N HCl. The precipitate was filtered, washed with cold water and dried to get 6a-f. 1.2.1.1. 4-Hydroxy-2H-chromen-2-one (6a) White solidyield: 95; 1H NMR (600 MHz, DMSO-d6) δ 12.53 (s, 1H), 7.83 (d, J = 7.2 Hz, 1H), 7.65 (d, J = 7.8 Hz, 1H), 7.38-7.34 (m, 2H), 5.60 (s, 1H).
Properties of 4-Hydroxycoumarin
Melting point: | 211-213 °C (lit.) |
Boiling point: | 228.82°C (rough estimate) |
Density | 1.1734 (rough estimate) |
vapor pressure | 0.02Pa at 25℃ |
refractive index | 1.4500 (estimate) |
storage temp. | Store below +30°C. |
solubility | DMSO (Slightly), Methanol (Slightly) |
pka | 4.50±1.00(Predicted) |
form | Liquid |
color | Clear colorless to slightly yellow |
Odor | Very faint woody-medicinal odor with a with Aluminum chloride. nut-like, hcrbaccous tone |
Water Solubility | PRACTICALLY INSOLUBLE |
BRN | 129768 |
CAS DataBase Reference | 1076-38-6(CAS DataBase Reference) |
NIST Chemistry Reference | 4-Hydroxycoumarin(1076-38-6) |
EPA Substance Registry System | 2H-1-Benzopyran-2-one, 4-hydroxy- (1076-38-6) |
Safety information for 4-Hydroxycoumarin
Signal word | Warning |
Pictogram(s) |
![]() Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral |
Precautionary Statement Codes |
P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P501:Dispose of contents/container to..… |
Computed Descriptors for 4-Hydroxycoumarin
InChIKey | VXIXUWQIVKSKSA-UHFFFAOYSA-N |
4-Hydroxycoumarin manufacturer
ALTRAKEM PHARMA LIFE SCIENCES PRIVATE LIMITED
Medilux Laboratories Pvt Ltd
S D Fine Chem Limited
Clickchem Research LLP
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