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
Show more names
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
- Formal charge
- 0
- Complexity
- 167
Experimental & physicochemical properties
Collision Cross Section
123.8 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
124.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
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
- solubility
- Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
- form
- Crystalline Powder
- pka
- 9.79 · 9.79±0.10(Predicted)
- color
- White to beige
- Odor
- Warm-aromatic odor
- Odor Type
- pungent
- BRN
- 1282794 · 1282794
- Cosmetics Ingredients Functions
- SKIN CONDITIONINGANTIOXIDANT
- InChI
- InChI=1S/C9H10O3/c1-6(10)8-4-3-7(12-2)5-9(8)11/h3-5,11H,1-2H3
- InChIKey
- UILPJVPSNHJFIK-UHFFFAOYSA-N
- SMILES
- C(=O)(C1=CC=C(OC)C=C1O)C
- LogP
- 1.98 · 1.980
- CAS DataBase Reference
- 552 · 552-41-0(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 3 R834EPI82 · 3R834EPI82
- NIST Chemistry Reference
- 1 · Ethanone, 1-(2-hydroxy-4-methoxyphenyl)-(552-41-0)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302+H312+H332-H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P280-P302+P352+P312-P304+P340+P312-P337+P313
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 20 · 20/21/22-36/37/38
- Safety Statements
- 26 · 26-28-36/37/39-45
- WGK Germany
- 3 · 3
- RTECS
- 1215000 · RT1215000
- Hazard Note
- Irritant
- HS Code
- 29145090 · 29145090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Toxicity
- 50 orl-mus: · LD50 orl-mus: 3430 mg/kg YKKZAJ 89,1205,69
Safety & regulation
GHS classification
GHS Classification
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
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.
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
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-28-36/37/39-45
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H302+H312+H332-H315-H319-H335
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P280-P302+P352+P312-P304+P340+P312-P337+P313
Chemistry & industry
Pharmacology
Applications
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%).
Upstream & downstream products
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: A natural product found in Paeonia rockii subspecies rockii.
Related reactions
Compound notes
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