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 |
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. |
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 |
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. |