Paeonol

HCID 11092

Basic information

CAS
552-41-0
Standard SMILES
COc1ccc(C(C)=O)c(O)c1
InChIKey
UILPJVPSNHJFIK-UHFFFAOYSA-N
Molecular formula
C9H10O3
Average molar mass
166.17 g/mol
Monoisotopic mass
166.06299418

Overview

Paeonol is a member of phenols and a member of methoxybenzenes. It has a role as a metabolite.

Names & identifiers

Preferred name
Paeonol
IUPAC
1-(2-hydroxy-4-methoxyphenyl)ethanone
English name
Paeonol
Molecular formula
C9H10O3
Molecular weight
166.17

Names & synonyms

PAEONOL552-41-01-(2-Hydroxy-4-methoxyphenyl)ethanone2'-Hydroxy-4'-methoxyacetophenonePeonol2-Hydroxy-4-methoxyacetophenoneEthanone, 1-(2-hydroxy-4-methoxyphenyl)-4-O-Methylresacetophenone1-(2-hydroxy-4-methoxy-phenyl)ethanoneDTXSID10220593R834EPI82NSC-401442
Show more names
Paeonol std.2-Hydroxy-4-methoxyPaeonol (white powder)Paeol
RefChem:45051DTXCID302059209-012-21-(2-hydroxy-4-methoxyphenyl)ethan-1-onePaeonalMFCD00008730Resacetophenone-4-methyl etherAcetophenone, 2'-hydroxy-4'-methoxy-

Database identifiers

CAS
552-41-0
PubChem CID
11092
DTXSID
DTXSID1022059
ChEMBL
CHEMBL1079227
ChEBI
CHEBI:69581
UNII
3R834EPI82
EC Number
209-012-2
Nikkaji
J4.483K

Properties

Computed structural properties

XLogP
2
Topological polar surface area
46.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
12

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Aromatic Ketones
SpringerMaterials PropertiesChemical shift
LogP1.98
Endocrine DisruptorsPotential endocrine disrupting compound
Vapor Pressure0.000683 [mmHg]
Physical DescriptionOff-white crystalline solid; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
48 · 48-50 °C(lit.)
Boiling point
154 °C · 154 °C / 20mmHg
Density
1.3102 · 1.3102
refractive index
1.5452 · 1.5452 (estimate)
Flash point
230 °F · >230 °F
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 52 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards Summary · 1 item

Causes altered sleep time in intraperitoneal and intravenous lethal-dose studies of mice; Causes analgesia and effects on inflammation in acute intraperitoneal studies of rats; [RTECS] A skin and strong eye irritant; Prolonged or repeated exposure may cause eye injury; Toxic by ingestion; [Sigma-Aldrich MSDS] See Acetophenone and Anisole.

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
3
rtecs
RT1215000
hs_code
29145090
Toxicity
LD50 orl-mus: 3430 mg/kg YKKZAJ 89,1205,69
risk_code
20/21/22-36/37/38

Chemistry & industry

Pharmacology

Metabolism/MetabolitesPaeonol has known human metabolites that include (2-Acetyl-5-methoxyphenyl) hydrogen sulfate.
Applications · 6 items

DescriptionPaeonol is the main active ingredient of the cortex of thePaeonol raw materials with high purity can be derived from plant extracts by chemical synthesis. The commonly used extraction methods of paeonol include boiling method, alcohol extraction, steam distillation, and CO2 supercritical fluid extraction . But due to the limitation of plant resources and the lower content of paeonol in the natural plants, there are many separation and purification difficulties existed in the extraction methods. The chemical synthesis process is relatively easy, and the final product usually can be obtained through two- to three-step reaction and separation process . Ranunculaceae plants including Paeonia suffruticosa Andr. (Moutan cortex, Mudanpi) and Rhododendron plant Cynanchum paniculatum (Bge.) Kitag. (Cynanchi paniculati radix et rhizome, Xuchangqing). Moutan cortex and Xuchangqing are commonly used as traditional Chinese medicine. Moutan cortex has the effects on clearing heat, cooling blood, activating blood, resolving stasis, and retreating heat; Xuchangqing also has many effects, such as dispelling wind, relieving pain and itching, and so on.

HistoryAs the main active ingredient of Moutan cortex and Xuchangqing, paeonol has been used in clinical practice since ancient times. Paeonol was first isolated from Moutan cortex by Japanese scholar Changjing Changyi in 1884 . This clinical observation was proceeded at more than 10 medical units in Shanghai and other places and lasted more than 1 year since 1971. Paeonol injection was the earliest recorded in the Chinese pharmacopoeia 1977 edition; it is the main formulation until now. But because of the poor water solubility of paeonol, it is necessary to improve its solubility to be used as injection. Ten times amount of Tween compared to paeonol was used in the injection to increase the dissolution. In the 1970s, paeonol was made into oil solution for intramuscular injection. But these are with security risks and the use of inconvenience and other shortcomings. Pharmacist obtained paeonol sodium sulfonate by sulfonated paeonol, so the problem of water solubility had been resolved, and the injection of paeonol sodium sulfonate also came into being . In 2003, the quality standard of paeonol sodium sulfonate was also promoted from the local standard to the national standard. The dosage form of paeonol for skin is mainly ointment.

UsesPaeonol acting as a β-Secretase inhibitor an anti-apoptotic agent is used in the treatment of memory loss after ischemic stroke. Anti-inflammatory and analgesic.

Usesantibacterial, antimutagen, anti-alzheimer

UsesAn anti-inflammatory & anti-lipid peroxidation agent

General DescriptionThis substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Preparation methods

PreparationPreparation by reaction of methyl iodide, or dimethyl sulfate on resacetophenone in sodium hydroxide or potassium hydroxide solution (quantitative yield) (70–75%).

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北常奥药业有限公司027-87058617 13419515565

Additional notes

DefinitionChEBI: A natural product found in Paeonia rockii subspecies rockii.

Related reactions

21 records

Compound notes

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CAS 552-41-0 Paeonol (HCID 11092)|Huagongshe