552-41-0 Usage
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.
Chemical Properties
white to beige crystalline powder
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.
History
As 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.
Uses
Different sources of media describe the Uses of 552-41-0 differently. You can refer to the following data:
1. antibacterial, antimutagen, anti-alzheimer
2. An anti-inflammatory & anti-lipid peroxidation agent
3. 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.
Preparation
Preparation by reaction of methyl iodide, or dimethyl sulfate on resacetophenone in sodium hydroxide or potassium hydroxide solution (quantitative yield) (70–75%).
General Description
This 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
Pharmacology
Paeonol has a wide range of pharmacological activities, and its antibacterial, antiinflammatory, antipyretic, analgesic, and antispasmodic pharmacological effects
have been well known. With the recent further study of pharmacological effects of
paeonol, the improvement of cardiovascular and cerebrovascular function, liver and
kidney care, and antitumor, immune regulation, antioxidant, and other new pharmacological activities have also been reported successively.
Studies have shown that the protective effects of paeonol on cardiovascular and
cerebrovascular systems are displayed in three aspects: it has antiarrhythmic activity because of the blocking effect on calcium channel current; it can affect the endothelial cell inflammatory response, thus protecting the blood vessels and improving
blood circulation; and it can stabilize the cell membrane and inhibit myocardial
ischemia and membrane damage.
Paeonol inhibits the proliferation of a variety of tumor cells, such as human leukemia cell line K562, human breast cancer gene T6-17, hepatocellular carcinoma
cell line BEL-7404, hepatoma cell line HepA, human leukemia tumor cell line
K562/ADM, cervical cancer cell line HeLa, human large intestine cancer cell line
HT-29, and so on. It can also sensitize the multidrug resistance of tumor cells to the
chemotherapy drugs.
Low concentration of paeonol can increase the proportion of T lymphocytes in
the blood circulation and also make T lymphocytes play a stronger lymphokine separation function but also can promote the non-specific phagocytic removal of bacteria
function of neutrophil. The role of systemic cellular immunity and humoral immune
function has also been experimentally confirmed. In addition, paeonol has a strong
effect on scavenging free radical; its antioxidant effect also enables paeonol’s applications in the pharmaceutical field and food preservation industry.
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.
Safety Profile
Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits acrid smoke and irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 552-41-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 2 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 552-41:
(5*5)+(4*5)+(3*2)+(2*4)+(1*1)=60
60 % 10 = 0
So 552-41-0 is a valid CAS Registry Number.
552-41-0Relevant articles and documents
Synthesis, vibrational, NMR, quantum chemical and structure-activity relation studies of 2-hydroxy-4-methoxyacetophenone
Arjunan,Devi,Subbalakshmi,Rani,Mohan
, p. 164 - 177 (2014)
The stable geometry of 2-hydroxy-4-methoxyacetophenone is optimised by DFT/B3LYP method with 6-311++G* and cc-pVTZ basis sets. The structural parameters, thermodynamic properties and vibrational frequencies of the optimised geometry have been determined. The effects of substituents (hydroxyl, methoxy and acetyl groups) on the benzene ring vibrational frequencies are analysed. The vibrational frequencies of the fundamental modes of 2-hydroxy-4-methoxyacetophenone have been precisely assigned and analysed and the theoretical results are compared with the experimental vibrations. 1H and 13C NMR isotropic chemical shifts are calculated and assignments made are compared with the experimental values. The energies of important MO's, the total electron density and electrostatic potential of the compound are determined. Various reactivity and selectivity descriptors such as chemical hardness, chemical potential, softness, electrophilicity, nucleophilicity and the appropriate local quantities are calculated.
Synthesis of novel isoflavone/benzo-δ-sultam hybrids as potential anti-inflammatory drugs
Mengheres, Gabriel,Rice, Craig R.,Olajide, Olumayokun A.,Hemming, Karl
supporting information, (2021/01/12)
A small series of novel isoflavone/benzo-δ-sultam hybrids was synthesised and evaluated as potential anti-inflammatory and neuroprotective drugs in LPS-activated BV2 microglia. The benzo-δ-sultam core was constructed in a two-step reaction by coupling 2-halobenzenesulfonamide derivatives with terminal alkynes, followed by a 6-endo-dig cyclisation. The synthesised compounds, including precursors and hybrids, were tested for their ability to inhibit NO and TNF-α production in LPS-stimulated BV2 microglial cells, and the results are promising. The most potent hybrid reduces the NO production to 41%, and the TNF-α to 34% at 20 μM final concentration in the well.
Anti‐melanogenic properties of velutin and its analogs?
Choe, Jung-Won,Heo, Hee-Young,Jung, Se-Hui,Kim, Jaehyun,Lee, Kooyeon
, (2021/06/03)
Velutin, one of the flavones contained in natural plants, has various beneficial activities, such as skin whitening, as well as anti‐inflammatory, anti‐allergic, antioxidant, and antimicrobial activities. However, the relationship between the structure of velutin and its anti‐melanogenesis activity is not yet investigated. In this study, we obtained 12 velutin derivatives substituted at C5, C7, C3′, and C4′ of the flavone backbone with hydrogen, hydroxyl, and methoxy functionalities by chemical synthesis, to perform SAR analysis of velutin structural analogues. The SAR study revealed that the substitution of functional groups at C5, C7, C3′, and C4′ of the flavone backbone affects biological activities related to melanin synthesis. The coexistence of hydroxyl and methoxy at the C5 and C7 position is essential for inhibiting tyrosinase activity. However, 1,2‐diol compounds substituted at C3′ and C4′ of flavone backbone induce apoptosis of melanoma cells. Further, substitution at C3′ and C4′ with methoxy or hydrogen is essential for inhibiting melanogenesis. Thus, this study would be helpful for the development of natural‐derived functional materials to regulate melanin synthesis.
Ferulin C triggers potent PAK1 and p21-mediated anti-tumor effects in breast cancer by inhibiting Tubulin polymerization in vitro and in vivo
He, Zhendan,Huang, Jian,Pan, Dabo,Wang, Jinhui,Yao, Dahong,Zhang, Jin,Zhen, Yongqi
, (2019/12/26)
Ferulin C, a natural sesquiterpene coumarin, isolated from the roots of Ferula ferulaeoides (Steud.) Korov, displaying potent antiproliferatory activity against breast cancer cells. This study aimed to elucidate the underlying molecular mechanisms of Ferulin C-induced breast cancer cells death in vitro and in vivo. Ferulin C presented potent antiproliferatory activity against MCF-7 and MDA-MB-231 cells and remarkable tubulin polymerization inhibitory activity (IC50 = 9.2 μM). Meanwhile, we predicted Ferulin C bind to the Colchicine site of tubulin through CETSA assay, molecular docking and molecular dynamics (MD) simulations. In immunofluorescence assay, Ferulin C disturbed the microtubule integrity and structure. Furthermore, Ferulin C stimulated significant cell cycle arrest in the G1/S period via p21Cip1/Waf1 - CDK2 signaling, induced classic cell apoptosis, impaired metastasis via down-regulating Ras-Raf-ERK and AKT-mTOR signaling. Intriguingly, Ferulin C treatment induced autophagy by ULK1 signaling to synergize with the inhibition of proliferation and metastasis. Based upon the RNAseq analysis, PAK1, as a novel essential modulator, was involved in the signaling regulated by Ferulin C -induced α/β-tubulin depolymerization. Additionally, Ferulin C displayed an acceptable antiproliferatory activity in an MCF-7 xenograft model without inducing obvious weight loss in the Ferulin C treated mice. Summarily, our findings substantiated that Ferulin C was a potent, colchicine site binding microtubule-destabilizing agent with anti-proliferation and anti-metastasis activity via PAK1 and p21-mediated signaling in breast cancer cells.
