2,5-dihydroxy acetophenone
2',5'-Dihydroxyacetophenone
CAS: 490-78-8
Molecular Formula: C8H8O3
2,5-dihydroxy acetophenone - Names and Identifiers
| Name | 2',5'-Dihydroxyacetophenone |
| Synonyms | QUINACETOPHENONE Acetylhydroquinone 2-Acetylhydroquinone 2-Acetyl hydroquinone 2,5-Dihydroxyacetophenone 2,5-dihydroxy acetophenone 2',5'-dihydroxy-acetophenon 2',5'-Dihydroxyacetophenone 2',5'-Dihydroxy acetophenone 1-Acetyl-2,5-dihydroxybenzene 2,5-Dihydroxy-1-acetylbenzene Acetophenone, 2',5'-dihydroxy- 1-(2,5-dihydroxyphenyl)ethanone 1-(2,5-dihydroxyphenyl)-ethanon 2-AcetylhydroquinoneQuinacetophenone |
| CAS | 490-78-8 |
| EINECS | 207-716-4 |
| InChI | InChI=1/C8H8O3/c1-5(9)7-4-6(10)2-3-8(7)11/h2-4,10-11H,1H3 |
| InChIKey | WLDWSGZHNBANIO-UHFFFAOYSA-N |
2,5-dihydroxy acetophenone - Physico-chemical Properties
| Molecular Formula | C8H8O3 |
| Molar Mass | 152.15 |
| Density | 1.2143 (rough estimate) |
| Melting Point | 204-206°C(lit.) |
| Boling Point | 234.6°C (rough estimate) |
| Flash Point | 167.1°C |
| Water Solubility | insoluble |
| Solubility | dioxane: 50mg/mL, clear |
| Vapor Presure | 9.41E-05mmHg at 25°C |
| Appearance | Crystallization |
| Color | Yellow to yellow-green |
| BRN | 637903 |
| pKa | 9.86±0.18(Predicted) |
| Storage Condition | Store below +30°C. |
| Refractive Index | 1.4447 (estimate) |
| MDL | MFCD00002343 |
| Physical and Chemical Properties | Yellowish green needle-like crystals. Melting Point 202-203 °c. Soluble in alcohol, insoluble in ether and benzene, almost insoluble in cold water. It is yellow in alkali solution and blue in iron trioxide. Can sublimate. |
| Use | for organic synthesis. |
| In vitro study | 2,5-Dihydroxyacetophenone significantly inhibits NO production via the suppression of iNOS expression and significantly decreases levels of the pro-inflammatory cytokines TNF-α and IL-6 via the down-regulation of their mRNA expression in LPS-stimulated RAW264.7 cells. 2,5-Dihydroxyacetophenone potently inhibits the phosphorylation of extracellular signal-related kinase (ERK) 1/2 and the nuclear translocation of nuclear factor-κB (NF-κB) p65 in LPS-stimulated cells. |
2,5-dihydroxy acetophenone - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - 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 | AM7700000 |
| TSCA | Yes |
| HS Code | 29145000 |
| Hazard Note | Irritant |
2,5-dihydroxy acetophenone - Introduction
Soluble in alcohol, hardly soluble in ether and benzene, almost insoluble in cold water. It is yellow in alkaline solution and blue in case of iron trioxide. Can sublimate.
Last Update：2022-10-16 17:25:26
2,5-dihydroxy acetophenone - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Biological activity | 2 ',5'-Dihydroxyacetophenone (DHAP, 2-Acetylhydroquinone, Quinacetophenone) is a mixture of dihydroxyacetophenone isomers, Used for food seasoning. 2 ',5'-Dihydroxyacetophenone significantly inhibited NO production by inhibiting the expression of iNOS. 2 ',5'-Dihydroxyacetophenone can significantly reduce the expression level of pro-inflammatory cytokines TNF-α and IL-6 by blocking ERK1/2 and NF-κB signaling pathways. |
| Target | Value |
| use | for organic synthesis. |
| Production method | It is obtained by reacting hydroquinone diacetate in the presence of aluminum trichloride. |
Last Update：2024-04-10 22:29:15
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