1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE
Acetovanillone
CAS: 498-02-2
Molecular Formula: C9H10O3
1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE - Names and Identifiers
| Name | Acetovanillone |
| Synonyms | Apocynin Acetovanillone 4-Hydroxy-3-methoxyacetophenone 4-Hydroxy-3-methoxybenzoic acid 3-Methoxy-4-Hydroxy Acetophenone 3'-Methoxy-4'-Hydroxyacetophenone 1-(4-hydroxy-3-methoxyphenyl)ethanone 1-(4-hydroxy-3-methoxyphenyl)-ethanon 1-(4-HYDROXY-3-METHOXYPHENYL) ETHANONE 1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE 1-(4-Hydroxy-3-methoxyphenyl)-ethanone (acetovanillone) 4'-Hydroxy-3'-Methoxyacetophenone 3-Methoxy-4-Hydroxyacetophenone |
| CAS | 498-02-2 |
| EINECS | 207-854-5 |
1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE - Physico-chemical Properties
| Molecular Formula | C9H10O3 |
| Molar Mass | 166.176 |
| Density | 1.158g/cm3 |
| Melting Point | 112-116℃ |
| Boling Point | 297.5°C at 760 mmHg |
| Flash Point | 125.5°C |
| Water Solubility | soluble in hot water |
| Solubility | DMSO : ≥ 100 mg/mL (601.79 mM);H2O : < 0.1 mg/mL (insoluble) |
| Vapor Presure | 0.000759mmHg at 25°C |
| Appearance | Morphological Solid |
| Color | Yellow to brown |
| Merck | 14,741 |
| BRN | 637373 |
| pKa | 8.18±0.18(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.537 |
| MDL | MFCD00008747 |
| Physical and Chemical Properties | White crystalline powder. |
| Use | Use in food additives. Use as an intermediate in organic synthesis |
1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 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 | 2 |
| RTECS | AM8800000 |
| TSCA | Yes |
| HS Code | 29145000 |
1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE - Upstream Downstream Industry
| Downstream Products | 乙酰丙酮 4-乙烯基-2-甲氧基苯酚 甲氧苯醌 4-氯 -6,7-二甲氧基喹啉 1-(2-羟基-3-甲氧苯基)乙酮 4-乙基间苯二酚 4-甲氧基-3-羟基苯乙酮 2,4-二甲氧基苯乙酮 |
1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE - Preparation
add anhydrous ethanol 25 mL, guaiacol 2. 0 mL( 18. 0 mmol), anhydrous potassium carbonate 5. 0g(36.2 mmol), sodium iodide 0.3g (2. 0 mmol) and bromon-propane 3.2 mL( 35, the liquid separation organic phase is washed with water (2 x 25 mL), anhydrous magnesium sulfate is dried, and the yellow liquid is dissolved by spin evaporation to obtain 12.86g, with a yield of 95.3%;
add 25 mL of dichloromethane and 11. 5g( 9. 0 mmol) to the reaction bottle, add 2.5g( 18.3mmol) of anhydrous zinc chloride to cool in an ice bath, add dropwise the mixed solution [dichloromethane (2.0mL) + acetic anhydride (1. 7 mL ,18. 0 mmol)], and slowly rise to room temperature for 4 h after dropping. Add 1 mol-L-1 of 40 mL hydrochloric acid, extract with dichloromethane (2 x 30 mL), combine the extract, wash with water (2 x 30 mL), dry and spin dissolving anhydrous magnesium sulfate to obtain 1.84g of yellow liquid mixture with a yield of 97.9% and a purity of 99. 1%;
16 mL of dichloromethane and 1.0g( 4. 8 mmol) of the mixture of isomers 3-methoxy 4-n-propoxyacetophenone and 3-propoxy4-methoxyacetophenone were sequentially added to the reaction bottle and stirred until completely dissolved (5min); Add 1.4g( 10. 5 mmol) of anhydrous aluminum trichloride and react at 35 ℃ for 4 h. Pour 1 mol-L-1 ammonium chloride solution (25mL) into the aqueous phase and extract it with dichloromethane (2 x 30 mL). The combined extract is spin-dissoluted and then separated and purified by silica gel column chromatography [eluent: V (petroleum ether):V (ethyl acetate) = 10: 1 to obtain rice white solid vanilla ethanone.
Last Update：2024-04-10 22:29:15
1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE - Nature
| melting point | 112-115°C (lit.) |
| boiling point | 263-265 °C/17 mmHg (lit.) |
| density | 1.1708 (rough estimate) |
| refractive index | 1.5101 (estimate) |
| flash point | >230 °F |
| storage conditions | Sealed in dry,Room Temperature |
| acidity coefficient (pKa) | 8.18±0.18(Predicted) |
| morphology | Solid |
| color | Yellow to brown |
| water solubility | soluble in hot water |
| Merck | 14,741 |
| BRN | 637373 |
| NIST chemical information | Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-(498-02-2) |
| EPA chemical information | Acetovanillone (498-02-2) |
Last Update：2024-04-09 20:52:54
1-(4-HYDROXY-3-METHOXYPHENYL)ETHAN-1-ONE - Introduction
overview
vanilla acetyl ketone is a synthetic raw material for a variety of psychotropic drugs and various new antimalarial drugs. It is often used as a cardiotonic and diuretic in medicine.
Vaniketone is currently recognized as a specific nicotinamide adenine dinucleotide oxidase inhibitor. Nicotinamide adenine dinucleotide phosphate (NADPH) oxidase and xanthine oxidase are the main sources of free radicals during myocardial reperfusion. Therefore, inhibiting its activity and reducing the generation of free radicals may reduce reperfusion injury. In this experiment, the use of NADPH oxidase inhibitor vaneethanone can protect the myocardium of reperfusion rats. This protection is related to its inhibition of NADPH oxidase activity and reduction of its mediated superoxide anion and peroxynitrite free radical production.
mechanism of action
vanetyl ketone can inhibit the activity of NADPH oxidase, reduce its mediated free radical generation, neutrophil infiltration and protect myocardium, protect cardiac function, reduce myocardial cell apoptosis and play an effective therapeutic effect on myocardial reperfusion injury.
application vanilla ethyl ketone, also known as vanilla ethyl ketone, acetyl vanilla ketone, has a weak vanilla smell. It is not only used in the perfume industry but also an important organic synthetic raw material. It can be used to synthesize psychotropic drugs Ipperidone and a variety of new antimalarial drugs. At the same time, it is also a commonly used antioxidant. It is currently recognized as a specific nicotinamide adenine dinucleotide oxidase inhibitor. It is also commonly used as a cardiotonic and diuretic in medicine.
application
Vanilla ethyl ketone can be used in the perfume industry and is also an important organic synthetic raw material. It can be used to synthesize the psychotropic drug Ipperidone and a variety of new antimalarial drugs. It is also a commonly used antioxidant. It is currently recognized as a specific nicotinamide adenine dinucleotide oxidase inhibitor. It is also commonly used as a cardiotonic and diuretic in medicine.
Last Update：2024-04-09 20:52:54
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