2,5-Dihydroxyacetophenone

Names

[ CAS No. ]:
490-78-8

[ Name ]:
2,5-Dihydroxyacetophenone

[Synonym ]:
Ethanone, 1- (2,5-dihydroxyphenyl)-
2,5-Dihydroxyphenyl methyl ketone,2-Acetyl-1,4-dihydroxybenzene,2-Acetylhydroquinone
2’,5’-Dihydroxyacetophenone
1-(2,5-Dihydroxyphenyl)ethanone
2',5'-Dihydroxyacetophenone
2',5'-Dihydroxy acetophenone
Quinacetophenone
EINECS 207-716-4
2-Acetylhydroquinone
2‘,5‘-Dihydroxyacetophenone
Ethanone, 1-(2,5-dihydroxyphenyl)-
MFCD00002343

Biological Activity

[Description]:

2,5-Dihydroxyacetophenone, isolated from Rehmanniae Radix Preparata, inhibits the production of inflammatory mediators in activated macrophages by blocking the ERK1/2 and NF-κB signaling pathways[1].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> MAPK/ERK Pathway >> ERK

Signaling Pathways >> Stem Cell/Wnt >> ERK

[Target]

ERK1

ERK2

NF-κB

[In Vitro]

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[1].

[References]

[1]. Han Y, et al. 2,5-dihydroxyacetophenone isolated from Rehmanniae Radix Preparata inhibits inflammatoryresponses in lipopolysaccharide-stimulated RAW264.7 macrophages. J Med Food. 2012 Jun;15(6):505-10.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
329.2±27.0 °C at 760 mmHg

[ Melting Point ]:
204-206 °C(lit.)

[ Molecular Formula ]:
C₈H₈O₃

[ Molecular Weight ]:
152.147

[ Flash Point ]:
167.1±20.2 °C

[ Exact Mass ]:
152.047348

[ PSA ]:
57.53000

[ LogP ]:
1.59

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.595

[ Water Solubility ]:
insoluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AM7700000

CHEMICAL NAME :: Acetophenone, 2',5'-dihydroxy-

CAS REGISTRY NUMBER :: 490-78-8

BEILSTEIN REFERENCE NO. :: 0637903

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C8-H8-O3

MOLECULAR WEIGHT :: 152.16

WISWESSER LINE NOTATION :: QR CQ BV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CBCCT* "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. (National Academy of Science Library, 2101 Constitution Ave., NW, Washington, DC 20418) Volume(issue)/page/year: 5,140,1953

Safety Information

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
AM7700000

[ HS Code ]:
29145000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914501900

[ Summary ]:
2914501900 other ketone-phenols。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Articles

2,5-Dihydroxyacetophenone: a matrix for highly sensitive matrix-assisted laser desorption/ionization time-of-flight mass spectrometric analysis of proteins using manual and automated preparation techniques Wenzel, Thomas; Sparbier, Katrin; Mieruch, Thorsten; Kostrzewa, Markus

Rapid Commun. Mass Spectrom. 20 , 785-789, (2005)