34000-39-0

Basic information

• Product Name: HOMOBUTEIN
• Synonyms: 2',4,4'-TRIHYDROXY-3-METHOXY CHALCONE;3-METHOXY-2',4',4-TRIHYDROXYCHALCONE;HOMOBUTEIN;(E)-2',4,4'-trihydroxy-3-methoxychalcone;3-O-methylbutein;HOMOBUTEIN WITH HPLC;HOMOBUTEIN hplc;(E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-one
• CAS NO: 34000-39-0
• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28
• EINECS: 251-782-7
• Product Categories: Chalcones
• Mol File: 34000-39-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 207-212°C
• Boiling Point: 523.8 °C at 760 mmHg
• Flash Point: 197.6 °C
• Appearance: /
• Density: 1.369 g/cm³
• CAS DataBase Reference: HOMOBUTEIN(CAS DataBase Reference)
• NIST Chemistry Reference: HOMOBUTEIN(34000-39-0)
• EPA Substance Registry System: HOMOBUTEIN(34000-39-0)

Safety Data

• Hazardous Substances Data: 34000-39-0(Hazardous Substances Data)

Usage

General Description

HOMOBUTEIN is a chemical compound with the molecular formula C10H11NO3. It is a synthetic derivative of the amino acid tyrosine and is used as a precursor in the synthesis of various pharmaceutical drugs and research chemicals. HOMOBUTEIN has been shown to have potential anti-inflammatory and neuroprotective properties, making it a subject of interest in the development of novel therapeutic agents for the treatment of conditions such as Alzheimer's disease and other neurodegenerative disorders. Additionally, HOMOBUTEIN has also been investigated for its role in the synthesis of fluorescent and bioluminescent compounds for use in biological imaging and diagnostic applications.

Upstream product

• 6515-05-5 2',4'-bis(methoxymethoxy)acetophenone 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 13192-07-9 Liquiritigenin-5'-O-methyl ether 
• 121-33-5 vanillin 
• 5533-00-6 3-methoxy-4-methoxymethoxy-benzaldehyde 
• 65490-08-6 2-hydroxy-4-(methoxymethoxy)acetophenone 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 67756-04-1 1-(2,4-dimethoxy-phenyl)-prop-2-en-1-one 
• 100753-43-3 (E)-1-(2,4-dimethoxyphenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one 
• 64-17-5 ethanol 
• 119100-24-2 2'-Hydroxy-3-methoxy-4,4'-bis(methoxymethoxy)chalcone 
• 20034-62-2 2'-Hydroxy-4'-(aethoxy-methoxy)-acetophenon 
• 128837-27-4 4-Ethoxymethoxy-3-methoxybenzaldehyde 

Downstream Products

• 13192-07-9 Liquiritigenin-5'-O-methyl ether 
• 128837-31-0 4,4'-Di(ethoxymethoxy)-2'-hydroxy-3-methoxychalkone 
• 21583-32-4 7,4'-dihydroxy-3'-methoxyflavone 
• 1428324-85-9 1-(3-(2,4-dihydroxyphenyl)-5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one 
• 1027339-73-6 C₁₆H₁₆N₂O₄ 
• 21913-98-4 4',7-dihydroxy-3'-methoxyisoflavone 

Relevant articles and documents

Discovery of isoliquiritigenin analogues that reverse acute hepatitis by inhibiting macrophage polarization

Screening a natural product library of 850 compounds yield isoliquiritigenin as an effective anti-inflammatory agent by inhibiting the production of pro-inflammatory NO induced by Pam3CSK4, while its activity accompanied by toxicity. Further studies obtained the optimized isoliquiritigenin derivative SMU-B14, which can inhibit Pam3CSK4 triggered toll-like receptor 2 (TLR2) signaling with low toxicity and high potency. Preliminary mechanism studies indicated that SMU-B14 worked through TLR2/MyD88, phosphorylation of IKKα/β, leading to the reduce degradation of NF-κB related IKBα and p65 complex, then inhibited the production of inflammatory cytokines, such as TNF-α, IL-6, IL-1β both in human and murine cell lines. Subsequent polarization experiments showed SMU-B14 significant reversed the polarization of M1 phenotype primary macrophage activated by Pam3CSK4 in vitro, and reduced the infiltration of neutrophil and polarization of M1-type macrophage, decreased serum alanine transaminase (ALT), as a result protected liver from being injured in vivo. In summary, we obtained an optimized lead compound SMU-B14 and found it functionally blocked TLR2/MyD88/NF-κB signaling pathway to down-regulate the production of inflammatory cytokines resulted significant liver protection property.

Synthesis and evaluation of butein derivatives for in vitro and in vivo inflammatory response suppression in lymphedema

Herein, we demonstrate that butein (1) can prevent swelling in a murine lymphedema model by suppressing tumor necrosis factor α (TNF-α) production. Butein derivatives were synthesized and evaluated to identify compounds with in vitro anti-inflammatory activity. Among them, 20 μM of compounds 7j, 7m, and 14a showed 50percent suppression of TNF-α production in mouse peritoneal macrophages after lipopolysaccharide stimulation. Compound 14a, exhibited the strongest potency with an in vitro IC50 of 14.6 μM and suppressed limb volume by 70percent in a murine lymphedema model. The prodrug strategy enabled a six-fold increase in kinetic solubility of compound 1 and five-fold higher levels of active metabolite in the blood for compound 14a via oral administration in the pharmacokinetics study. We suggest that the compound 14a could be developed as a potential therapeutic agent targeting anti-inflammatory activity to alleviate lymphedema progression.

Calcium hydroxide is an efficient catalyst for synthesis of polyhydroxy chalcones

Calcium hydroxide was found to be an efficient catalyst for synthesis of polyhydroxy chalcones. This method has been employed to synthesize various 2′,4′-dihydroxychalcones having various substituents on the B ring. The merits of this method include shorter reaction time, inexpensive and easily available catalyst, high yield, and easy workup compared to other reported methods. Copyright Taylor and Francis Group, LLC.