Paeonol

Base Information

• Chemical Name: Paeonol
• CAS No.: 552-41-0
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 29145090
• European Community (EC) Number: 209-012-2
• NSC Number: 401442
• UNII: 3R834EPI82
• DSSTox Substance ID: DTXSID1022059
• Nikkaji Number: J4.483K
• Wikipedia: Paeonol
• Wikidata: Q7124105
• Metabolomics Workbench ID: 67613
• ChEMBL ID: CHEMBL1079227
• Mol file: 552-41-0.mol

Synonyms:2-hydroxy-4-methoxyacetophenone;paeonol;peonol

Chemical Property of Paeonol

Chemical Property:

• Appearance/Colour: white to beige crystalline powder
• Melting Point: 48-50 °C(lit.)
• Refractive Index: 1.5452 (estimate)
• Boiling Point: 301.9 °C at 760 mmHg
• PKA: 9.79±0.10(Predicted)
• Flash Point: 122.3 °C
• PSA: 46.53000
• Density: 1.158 g/cm³
• LogP: 1.60340
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 166.062994177
• Heavy Atom Count: 12
• Complexity: 167

Purity/Quality:

99% ^*data from raw suppliers

Paeonol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones
• Canonical SMILES: CC(=O)C1=C(C=C(C=C1)OC)O
• Recent EU Clinical Trials: A placebo-controlled, double-blinded, randomized, trial using a combination of apocynin and paeonol (APPA) for the treatment of knee osteoarthritis
• Description: Paeonol 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.
• Physical properties: Appearance: white or light yellow, shining, needlelike crystals. Solubility: freely soluble in ethanol and methanol; soluble in diethyl ether, acetone, benzene, chloroform, and carbon disulfide; slightly soluble in water; and soluble in hot water, practically insoluble in cold water, and volatilizing in water vapor. Melting point: 48–51?°C.
• Uses: antibacterial, antimutagen, anti-alzheimer An anti-inflammatory & anti-lipid peroxidation agent Paeonol 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.
• Indications: This drug has been recorded in Pharmacopoeia of the People’s Republic of China (1977). At present, the dosage forms of paeonol for clinical use include tablet, ointment, injection, and plaster. Paeonol is clinically used for the treatment of fever, headache, neuralgia, muscle pain, abdominal pain, rheumatoid arthritis and rheumatoid arthritis; its ointment can also be used for a variety of eczema, dermatitis, skin itching, mosquito bite redness, and other skin diseases, also has a certain effect for allergic rhinitis, and is used for prevention of cold.
• Clinical Use: In clinical practice, paeonol is mainly used as a major active ingredient of multiflavor traditional Chinese medicine. For example, paeonol is the main active ingredient and quality control index of more than ten kinds of commonly used Chinese medicine preparations, such as Feng Shi Ding tablets, Liu Wei Di Huang pills, Zheng Gu Shui water, Gui Shao Di Huang Tang pills, Mai Wei Di Huang pills, Qi Ju Di Huang tablets, Ming Mu Di Huang pills, Zhi Bai Di Huang pills, Gu Ci pills, Gu Ci Xiao Tong tablets, Fu Fang Yi Gan pills, Yang Yin Qing Fei Tang pills, JiSheng Shen Qi Wan pills, and Danggui Yangxue pills. In addition, paeonol can also be administered as a monomeric drug. The listed preparations are mainly paeonol injection, paeonol tablets, and paeonol ointment, clinically for the treatment of rheumatism, stomachache, and other pains, eczema, allergic dermatitis, etc. Paeonol and its preparations have the characteristics of less side effect, no addictive, nonrebound, and high security.

Technology Process of Paeonol

There total 52 articles about Paeonol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 2',4'-dihydroxy-4-acetophenone (89-84-9) → 1-(2-hydroxy-4-methoxyphenyl)ethanone (552-41-0)

Guidance literature:

In methanol; diethyl ether;

DOI:10.1016/S0040-4020(98)01076-X

Reference yield: 93.0%

C9H12O3 → 1-(2-hydroxy-4-methoxyphenyl)ethanone (552-41-0)

Guidance literature:

With C₆H₄MoNO₇^(1-)*C₁₉H₄₂N⁽¹⁺⁾; oxygen; In water; at 100 ℃; for 20h; chemoselective reaction; Green chemistry;

DOI:10.1016/j.jcat.2019.06.013

Reference yield: 90.0%

1-(2-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)ethan-1-one (462610-98-6) → 1-(2-hydroxy-4-methoxyphenyl)ethanone (552-41-0)

Guidance literature:

With N,N,N',N'-tetramethylguanidine; In acetonitrile; at 20 ℃; for 0.333333h;

DOI:10.1021/ol027263d

upstream raw materials:

2',4'-dihydroxy-4-acetophenone

acetic acid 3-methoxyphenyl ester

2-hydroxy-4-methoxyacetophenone-OAc

O-methylresorcine

Downstream raw materials:

2',4'-dimethoxyacetophenone

2'-hydroxy-4'-methoxy-ω-cinnamylidene acetophenone

3-ethyl-7-methoxy-4-methyl-chromen-2-one

(E)-3-(4-(benzyloxy)phenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one

Refernces

• 1、 Finlayson. "". . p. 2763,2767. Retrieved 1926.
• 2、 Sang, Zhipei,Song, Qing,Cao, Zhongcheng,Deng, Yong,Tan, Zhenghuai,Zhang, Li. "Design, synthesis and evaluation of novel dimethylamino chalcone-O-alkylamines derivatives as potential multifunctional agents against Alzheimer's disease". . . Retrieved 2021/03/04.
• 3、 He, Zhendan,Huang, Jian,Pan, Dabo,Wang, Jinhui,Yao, Dahong,Zhang, Jin,Zhen, Yongqi. "Ferulin C triggers potent PAK1 and p21-mediated anti-tumor effects in breast cancer by inhibiting Tubulin polymerization in vitro and in vivo". . . Retrieved 2019/12/26.