Paeonol

Names

[ CAS No. ]:
552-41-0

[ Name ]:
Paeonol

[Synonym ]:
1-(2-Hydroxy-4-methoxyphenyl)ethanone
2-Acetyl-5-methoxy-phenol
2-Hydroxy-4-methoxyacetophenone
EINECS 209-012-2
Acetophenone, 2'-hydroxy-4'-methoxy-
Ethanone, 1- (2-hydroxy-4-methoxyphenyl)-
2'-hydroxy-4'-methoxyacetophenone
4-Methoxy-2-hydroxyacetophenone
Paeonol
MFCD00008730
Ethanone, 1-(2-hydroxy-4-methoxyphenyl)-
1-(2-Hydroxy-4-methoxyphenyl)ethan-1-one

Biological Activity

[Description]:

Paeonol is an active extraction from the root of Paeonia suffruticosa, Paeonol inhibits MAO-A and MAO-B with IC50 of 54.6 μM and 42.5 μM, respectively.

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> Monoamine Oxidase

Research Areas >> Neurological Disease

Natural Products >> Phenols

[Target]

IC50: 42.5 μM (MAO-B), 54.6 μM (MAO-A)[1]

[In Vitro]

Paeonol is found to be inhibitory against MAO A in a dose-dependent manner with IC50 value of 54.6 μM. Paeonol is shown to inhibit MAO-B in a dose-dependent manner with the IC50 of 42.5 μM. For Paeonol, the Ki is estimated to be 51.1 μM. The inhibition of Paeonol on MAO B is of competitive type with Ki value of 38.2 μM[1].

[In Vivo]

The 200 mg/kg Paeonol+I/R group [AN/V (%): 7.6±2.2, p<0.01] and 100 mg/kg Paeonol+I/R group [AN/V (%): 9.4±2.8, p<0.05] both show lesser extents of no-reflow area in the ventricles compared with the I/R group [AN/V (%): 18.2±2.9]. In particular, the 200 mg/kg Paeonol + I/R group experienced markedly alleviated no-reflow in the whole heart [AN/WH (%): 4.6±1, p<0.05] compared with the I/R group [AN/WH (%): 10.0±1.9][2].

[Animal admin]

Mice[2] Male Wistar rats (180-220 g, average age of 8 week) are randomly divided into four groups: (1) sham group, thoracotomy without left anterior descending coronary artery (LAD) occlusion or Paeonol pretreatment; (2) I/R group, LAD occlusion (ischemia) for 4 h followed by reperfusion for 8 h; (3) Paeonol (100 mg/kg)+I/R group, oral administration of 100 mg/kg Paeonol (1 mL/kg) for 7 days using a intragastric tube prior to I/R procedure; (4) Paeonol (200 mg/kg) + I/R group, oral administration of 200 mg/kg Paeonol (1 mL/kg) for 7 days using a intragastric tube prior to I/R procedure. In addition, rats in the sham and I/R groups received a dosage of DMSO equal to that with which the Paeonol was dissolved in for the other two groups. DMSO was also administered intragastrically for 7 consecutive days. A minimum of eight rats were assigned to each group. An ischemia group without reperfusion is not included since our present study mainly focuses on the effect of Paeonol on the cardiac injuries after reperfusion, which is closely related to the real-world situation of no-reflow after coronary revascularization. However, future studies may include a group subjected only to 4 h of ischemia to differentiate, in terms of damage to the cardiac function, which was due to the ischemia and which was due to the no-reflow.

[References]

[1]. Kong LD, et al. Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones. J Ethnopharmacol. 2004 Apr;91(2-3):351-5.

[2]. Ma L, et al. Paeonol Protects Rat Heart by Improving Regional Blood Perfusion during No-Reflow. Front Physiol. 2016 Jul 21;7:298.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
301.9±22.0 °C at 760 mmHg

[ Melting Point ]:
48-50 °C(lit.)

[ Molecular Formula ]:
C₉H₁₀O₃

[ Molecular Weight ]:
166.174

[ Flash Point ]:
122.3±15.8 °C

[ Exact Mass ]:
166.062988

[ PSA ]:
46.53000

[ LogP ]:
2.16

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

[ Index of Refraction ]:
1.538

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RT1215000

CHEMICAL NAME :: Paeonol

CAS REGISTRY NUMBER :: 552-41-0

BEILSTEIN REFERENCE NO. :: 1282794

LAST UPDATED :: 199709

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C9-H10-O3

MOLECULAR WEIGHT :: 166.19

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 490 mg/kg

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

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 49,84,1953

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 781 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex)

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 89,1205,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 196 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex)

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 89,1205,1969

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H315-H319-H332-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

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

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R20/21/22;R36/37/38

[ Safety Phrases ]:
S26-S28-S36/37/39-S45

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
RT1215000

[ HS Code ]:
2914509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

Articles

Competitive molecular interaction among paeonol-loaded liposomes: differential scanning calorimetry and synchrotron X-ray diffraction studies.

Int. J. Pharm. 438(1-2) , 91-7, (2012)

Thermotropic phase behavior of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) liposomes containing 5 mol% cholesterol, or 5 mol% stigmasterol, or 5 mol% paeonol have been investigated by different...

Paeonol inhibits oxidized low density lipoprotein-induced monocyte adhesion to vascular endothelial cells by inhibiting the mitogen activated protein kinase pathway.

Biol. Pharm. Bull. 35(5) , 767-72, (2012)

Atherosclerosis is a chronic inflammatory disease characterized by increased expression of adhesion molecules, which contribute to monocytes adhesion to vascular endothelial cells (VECs). Paeonol, an ...

Influence of co-administered danshensu on pharmacokinetic fate and tissue distribution of paeonol in rats.

Planta Med. 78(2) , 135-40, (2012)

Cortex Moutan (root bark of Paeonia suffruticosa Andrew) and Radix Salviae miltiorrhizae (root and rhizome of Salvia miltiorrhiza Bunge) are two herbs widely used in traditional Chinese medicine (TCM)...

Related Compounds

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