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Details

Stereochemistry ACHIRAL
Molecular Formula C9H10O3
Molecular Weight 166.1742
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PAEONOL

SMILES

CC(=O)c1ccc(cc1O)OC

InChI

InChIKey=UILPJVPSNHJFIK-UHFFFAOYSA-N
InChI=1S/C9H10O3/c1-6(10)8-4-3-7(12-2)5-9(8)11/h3-5,11H,1-2H3

HIDE SMILES / InChI

Molecular Formula C9H10O3
Molecular Weight 166.1742
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26902832 | https://www.ncbi.nlm.nih.gov/pubmed/22680310 | https://www.ncbi.nlm.nih.gov/pubmed/22680310 | https://www.ncbi.nlm.nih.gov/pubmed/20096551

Paeonol (2-hydroxy-4-methoxyacetophenone) is a major phenolic component of the dried root bark of Paeonia suffruticosa Andrews (Paeoniaceae). Paeonol exhibits a wide variety of bioactivities including anti-inflammatory, antioxidative, immunoregulatory, antihypertensive, anti-hyperglycemic, antibacterial, anti-thrombotic, and antitumor effects. Paeonol inhibits anaphylactic reaction by regulating histamine and TNF-α. Paeonol tablets have been used for the treatment of rheumatic arthritis, fever, headache and neuralgia in Chinese clinics.

Originator

Sources: Journal de Pharmacie et de Chimie (1911), 3, 234-41.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
561.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Insecticides in Chinese medicinal plants: survey leading to jacaranone, a neurotoxicant and glutathione-reactive quinol.
2003 Apr 23
Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones.
2004 Apr
Paeonol suppresses intercellular adhesion molecule-1 expression in tumor necrosis factor-alpha-stimulated human umbilical vein endothelial cells by blocking p38, ERK and nuclear factor-kappaB signaling pathways.
2007 Mar
(E)-3-(2,3-Dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one.
2008 Aug 30
Paeonol exerts anti-angiogenic and anti-metastatic activities through downmodulation of Akt activation and inactivation of matrix metalloproteinases.
2009 Jul
Paeonol from Paeonia suffruticosa prevents TNF-alpha-induced monocytic cell adhesion to rat aortic endothelial cells by suppression of VCAM-1 expression.
2009 Nov
Action potential bursts in central snail neurons elicited by paeonol: roles of ionic currents.
2010 Dec
Paeonol from Hippocampus kuda Bleeler suppressed the neuro-inflammatory responses in vitro via NF-κB and MAPK signaling pathways.
2012 Sep
The protective effects of paeonol against epirubicin-induced hepatotoxicity in 4T1-tumor bearing mice via inhibition of the PI3K/Akt/NF-kB pathway.
2016 Jan 25
Patents

Sample Use Guides

Each volunteer was given a single 80-mg oral dose of paeonol (two tablets), three times a day for 2 days (clinical dosage: 120–240 mg/day)
Route of Administration: Oral
Human umbilical vein endothelial cells (HUVECs, ScienCell, Corte Del Cedro Carlsbad, CA, USA) were cultured in endothelial cell medium (ECM) supplemented with 5% fetal bovine serum, 1% penicillin-streptomycin and 1% endothelial cell growth supplement, maintained at 37 °C and aerated with 5% CO2, 95% O2. The cells (passage 4 to 6) were used when reaching 80-90% confluence. For all experiments, HUVECs were seeded and grown overnight to sub-confluence level before incubation (24 hours), in ECM, with LPS, (0.1, 0.5 and 1μg/mL), hydrogen peroxide (H2O2, 200 μM) and various concentrations of paeonol (0.01, 0.1 and 1 μM,) before collection for apoptosis and protein assays. For other drug treatments, HUVECs were co-treated during 24 hours with one of the following: recombinant BMP4 (100 ng/mL, dissolved in 4 mM HCl with 0.1% BSA), noggin (100 ng/mL, BMP4 antagonist), apocynin (20 μM, NADPH oxidase inhibitor), SP600125 (10 μM, JNK inhibitor), SB202190 (10 μM, p38 MAPK inhibitor), aminoguanidine (100 μM, selective inhibitor of inducible NOS) and TAK242 (1 μM, TLR4 antagonist).
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:27:36 UTC 2021
Edited
by admin
on Sat Jun 26 02:27:36 UTC 2021
Record UNII
3R834EPI82
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PAEONOL
INCI  
INCI  
Official Name English
2-HYDROXY-4-METHOXYPHENYL METHYL KETONE
Systematic Name English
PAEONOL [WHO-DD]
Common Name English
4-O-METHYLRESACETOPHENONE
Common Name English
2-ACETYL-5-METHOXYPHENOL
Systematic Name English
1-(2-HYDROXY-4-METHOXYPHENYL)ETHAN-1-ONE
Systematic Name English
NSC-401442
Code English
ETHANONE, 1-(2-HYDROXY-4-METHOXYPHENYL)-
Systematic Name English
ACETOPHENONE, 2'-HYDROXY-4'-METHOXY-
Systematic Name English
1-(4-METHOXY-2-HYDROXYPHENYL)ETHANONE
Systematic Name English
PAEONOL [INCI]
Common Name English
RESACETOPHENONE 4-O-METHYL ETHER
Common Name English
4'-METHOXY-2'-HYDROXYACETOPHENONE
Systematic Name English
PA
Common Name English
1-(2-HYDROXY-4-METHOXYPHENYL)ETHANONE
Systematic Name English
Code System Code Type Description
MESH
C013638
Created by admin on Sat Jun 26 02:27:37 UTC 2021 , Edited by admin on Sat Jun 26 02:27:37 UTC 2021
PRIMARY
CAS
552-41-0
Created by admin on Sat Jun 26 02:27:37 UTC 2021 , Edited by admin on Sat Jun 26 02:27:37 UTC 2021
PRIMARY
WIKIPEDIA
Paeonol
Created by admin on Sat Jun 26 02:27:37 UTC 2021 , Edited by admin on Sat Jun 26 02:27:37 UTC 2021
PRIMARY
EVMPD
SUB195783
Created by admin on Sat Jun 26 02:27:37 UTC 2021 , Edited by admin on Sat Jun 26 02:27:37 UTC 2021
PRIMARY
FDA UNII
3R834EPI82
Created by admin on Sat Jun 26 02:27:37 UTC 2021 , Edited by admin on Sat Jun 26 02:27:37 UTC 2021
PRIMARY
PUBCHEM
11092
Created by admin on Sat Jun 26 02:27:37 UTC 2021 , Edited by admin on Sat Jun 26 02:27:37 UTC 2021
PRIMARY
ECHA (EC/EINECS)
209-012-2
Created by admin on Sat Jun 26 02:27:37 UTC 2021 , Edited by admin on Sat Jun 26 02:27:37 UTC 2021
PRIMARY
EPA CompTox
552-41-0
Created by admin on Sat Jun 26 02:27:37 UTC 2021 , Edited by admin on Sat Jun 26 02:27:37 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Effect of paeonol on degranulation of rat peritoneal mast cells (IC50 = 90.3 uM) and RBL-2H3 (IC50 = >100 uM) cells.
PARENT -> CONSTITUENT ALWAYS PRESENT
Compound was measured as protective rate against sepsis-induced lethality in mice. Showed 2/5 survival rate for 24 and 48 hr.
PARENT -> CONSTITUENT ALWAYS PRESENT
MIC 160 mg/L for ATCC 700392 and ATCC 700824 strains of H. pylori.