| Identification | More | [Name]
2',5'-Dihydroxyacetophenone | [CAS]
490-78-8 | [Synonyms]
1-(2,5-DIHYDROXYPHENYL)ETHAN-1-ONE
1-(2,5-DIHYDROXYPHENYL)ETHANONE
2',5'-DIHYDROXYACETOPHENONE
2,5-DIHYDROXYACETOPHENONE
2,5-DIHYDROXYPHENYL METHYL KETONE
2-ACETYL-1,4-DIHYDROXYBENZENE
2-ACETYLHYDROQUINONE
ACETYLQUINOL
QUINACETOPHENONE
1-(2,5-dihydroxyphenyl)-ethanon
1-Acetyl-2,5-dihydroxybenzene
2,5-Dihydroxy-1-acetylbenzene
2’,5’-dihydroxy-acetophenon
Acetophenone, 2',5'-dihydroxy-
Acetylhydroquinone
2',5'-Dihydroxyacetophenone 2-Acetylhydroquinone
2,5-Dihydroxyacetophenone, 98+%
2-Acethylhydroquinone
Ethanone, 1-(2,5-dihydroxyphenyl)-
2,5-DIHYDROXYACETOPHENONE extrapure | [EINECS(EC#)]
207-716-4 | [Molecular Formula]
C8H8O3 | [MDL Number]
MFCD00002343 | [Molecular Weight]
152.15 | [MOL File]
490-78-8.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow to yellow-green crystals or | [Melting point ]
204-206 °C(lit.)
| [Boiling point ]
234.6°C (rough estimate) | [density ]
1.2143 (rough estimate) | [refractive index ]
1.4447 (estimate) | [storage temp. ]
Store below +30°C. | [solubility ]
dioxane: 50 mg/mL, clear
| [form ]
Crystals or Crystalline Powder | [pka]
9.86±0.18(Predicted) | [color ]
Yellow to yellow-green | [Water Solubility ]
insoluble | [BRN ]
637903 | [Cosmetics Ingredients Functions]
SKIN CONDITIONING
BLEACHING
ANTIOXIDANT | [InChI]
1S/C8H8O3/c1-5(9)7-4-6(10)2-3-8(7)11/h2-4,10-11H,1H3 | [InChIKey]
WLDWSGZHNBANIO-UHFFFAOYSA-N | [SMILES]
CC(=O)c1cc(O)ccc1O | [LogP]
1.274 (est) | [CAS DataBase Reference]
490-78-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Ethanone, 1-(2,5-dihydroxyphenyl)-(490-78-8) | [EPA Substance Registry System]
490-78-8(EPA Substance) |
| Hazard Information | Back Directory | [Description]
2',5'-Dihydroxyacetophenone is a natural phenolic compound that is found in many plants. It has been shown to have anti-inflammatory properties through its ability to inhibit the production of pro-inflammatory cytokines, such as tumor necrosis factor alpha and interleukin 1 beta. | [Chemical Properties]
yellow to yellow-green crystals or | [Uses]
2',5'-Dihydroxyacetophenone is an intermediate used in various synthetic preparations of pharmaceutical goods, 1-(2,5-Dihydroxyphenyl)ethanone was untilized in the synthesis of new flavonoid fatty acid esters with anti-adipogenic and glucose consumption enhancing activities.
| [Application]
2',5'-Dihydroxyacetophenone inhibits the formation of reactive oxygen species and nitric oxide in rat neutrophils. It also has the ability to reduce oxidative stress by scavenging free radicals and inhibiting lipid peroxidation. The underlying mechanism for these effects is not fully understood but may be due to its ability to act as a substrate for matrix-assisted laser desorption ionization (MALDI). This means that it can react with protocatechuic acid molecules that are present in the sample preparation chamber, leading to polymerase chain reaction (PCR) amplification. | [Definition]
ChEBI: 2',5'-Dihydroxyacetophenone is an aromatic ketone. | [Preparation]
Preparation by Fries rearrangement of hydroquinone diacetate,
with aluminium chloride(91%) (76%)(63–77%) (55–60%)
with zinc chloride in refluxing acetic acid (quantitative yield)
with boron trifluoride etherate in benzene at reflux (65%). | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 18, p. 1709, 1953 DOI: 10.1021/jo50018a014 |
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