2',5'-Dihydroxyacetophenone
Synonym(s):2′,5′-Dihydroxyacetophenone;2,5-Dihydroxyphenyl methyl ketone;2-Acetyl-1,4-dihydroxybenzene;2-Acetylhydroquinone;Acetylquinol
- CAS NO.:490-78-8
- Empirical Formula: C8H8O3
- Molecular Weight: 152.15
- MDL number: MFCD00002343
- EINECS: 207-716-4
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-20 11:41:24
What is 2',5'-Dihydroxyacetophenone?
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
The Uses of 2',5'-Dihydroxyacetophenone
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.
The Uses of 2',5'-Dihydroxyacetophenone
1-(2,5-Dihydroxyphenyl)ethanone 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.
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%).
What are the applications of 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.
Synthesis Reference(s)
The Journal of Organic Chemistry, 18, p. 1709, 1953 DOI: 10.1021/jo50018a014
Properties of 2',5'-Dihydroxyacetophenone
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 |
CAS DataBase Reference | 490-78-8(CAS DataBase Reference) |
NIST Chemistry Reference | Ethanone, 1-(2,5-dihydroxyphenyl)-(490-78-8) |
EPA Substance Registry System | Ethanone, 1-(2,5-dihydroxyphenyl)- (490-78-8) |
Safety information for 2',5'-Dihydroxyacetophenone
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. |
Computed Descriptors for 2',5'-Dihydroxyacetophenone
InChIKey | WLDWSGZHNBANIO-UHFFFAOYSA-N |
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