28090-12-2

Basic information

• Product Name: 4'-(3-Methyl-2-butyenyloxy)benzaldehyde
• Synonyms: MBBA;4(3-METHYL-2-BUTENYLOXY) BENZALDEHYDE;4'-(3-METHYL-2-BUTENYLOXY)BENZALDEHYDE;4'-(3-METHYL-2-BUTYENYL-OXY)BENZALDEHYDE;4-(3-METHYLBUT-2-ENYLOXY)BENZALDEHYDE;4-prenyloxybenzaldehyde;SOFALCONE'S INTERMEDIATES;4'-(3-METHYL-2-BUTENYL-OXY)BENZALDEHYDE (MBBA)
• CAS NO: 28090-12-2
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.24
• EINECS: 1312995-182-4
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);INTERMEDIATESOFSOFALCONE;(intermediate of sofalcone)
• Mol File: 28090-12-2.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 313°C
• Flash Point: 137°C
• Appearance: /
• Density: 1.030
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 4'-(3-Methyl-2-butyenyloxy)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-(3-Methyl-2-butyenyloxy)benzaldehyde(28090-12-2)
• EPA Substance Registry System: 4'-(3-Methyl-2-butyenyloxy)benzaldehyde(28090-12-2)

Safety Data

• Hazardous Substances Data: 28090-12-2(Hazardous Substances Data)

Usage

Description

4'-(3-Methyl-2-butyenyloxy)benzaldehyde, also known as an analog of Curcumin, is a natural phenolic compound derived from the Curcuma longa plant. It exhibits potent anti-tumor, anti-inflammatory, and antioxidant properties. 4'-(3-Methyl-2-butyenyloxy)benzaldehyde is characterized by its pale yellow to colorless liquid appearance and is known for its ability to induce apoptosis in cancer cells, inhibit protein kinase C (PKC) activity, and modulate various signaling pathways related to inflammation and cancer progression.

Uses

Used in Pharmaceutical Industry:
4'-(3-Methyl-2-butyenyloxy)benzaldehyde is used as an anti-tumor agent for its ability to induce apoptosis in cancer cells and inhibit the production of inflammatory cytokines by peripheral blood monocytes and alveolar macrophages. Its potent inhibitory effects on EGFR tyrosine kinase and IκB kinase contribute to its potential as a therapeutic agent in cancer treatment.
Used in Anti-inflammatory Applications:
As an anti-inflammatory agent, 4'-(3-Methyl-2-butyenyloxy)benzaldehyde is used to inhibit inducible nitric oxide synthase (iNOS), cycloxygenase, and lipoxygenase, which are key enzymes involved in the inflammatory response. This property makes it a valuable compound for the development of anti-inflammatory drugs.
Used in Antioxidant Formulations:
Due to its antioxidant properties, 4'-(3-Methyl-2-butyenyloxy)benzaldehyde is used in the development of antioxidant formulations that can help protect cells from oxidative stress and damage, which are common factors in various diseases, including cancer and neurodegenerative disorders.
Used in Alzheimer's Disease Research:
4'-(3-Methyl-2-butyenyloxy)benzaldehyde is being examined as a potential therapeutic agent for the treatment of Alzheimer's disease, given its ability to easily penetrate into the cytoplasm of cells and accumulate in membranous structures such as the plasma membrane, endoplasmic reticulum, and nuclear envelope. This characteristic allows it to potentially modulate cellular processes involved in the pathology of Alzheimer's disease.

InChI:InChI=1/C12H14O2/c1-10(2)7-8-14-12-5-3-11(9-13)4-6-12/h3-7,9H,8H2,1-2H3

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 870-63-3 prenyl bromide 
• 503-60-6 3,3-dimethyl-allyl chloride 

Downstream Products

• 61370-75-0 3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carboxaldehyde 
• 756891-29-9 2'-hydroxy-4-prenyloxy-furano(2'',3'':4',3')chalcone 
• 32328-83-9 4-(3-methyl-2-butenoxy)phenol 
• 338386-43-9 (1R,2S,5S)-2-[hydroxy-[4-[(3-methyl-2-butenyl)oxy]phenyl]methyl]-4-methyl-dispiro[1,4-diazabicyclo[3.2.1]octan-3-one-7,1'-cyclohexane-4',2''-[1,3]dioxolane] 
• 943860-45-5 C₂₁H₂₂O₄ 
• 624734-51-6 5,7-di(methoxymethoxy)-6,8-di-C-prenyl-4'-O-prenylflavanone 
• 756891-31-3 3-hydroxy-4'-prenyloxy-furano(2'',3'':7,8)flavone 
• 28116-98-5 rac-5,7-dihydroxy-2-[4-(3-methylbut-2-enyloxy)phenyl]chroman-4-one 
• 25515-46-2 naringenin chalcone 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 

Relevant articles and documents

Ancillary ligands switch the activity of Ru–NHC-based oxidation precatalysts

Herein we demonstrate how the inner-sphere coordinating ligands switch the activity of Ru–NHC-based oxidation precatalysts in the oxidative conversion of olefins to carbonyl compounds, with the help of a series of systematically varied imidazolydene-NHC (Im-NHC) and triazolydene-NHC (Tz-NHC)-based ruthenium(II)-complexes. It is shown that the catalytic activity of the para-cymene-containing precatalysts varies in the order of [(Tz-NHC)Ru(para-cymene)Cl]+ > [(Im-NHC)Ru(para-cymene)Cl]+, while the order of activity of the MeCN-containing precatalysts is found to be reversed, i.e., [(Im-NHC)Ru(MeCN)4]2+ > [(Tz-NHC)Ru(MeCN)4]2+. Along with the electronic influence of the NHC ligands, the effect of the lability of the para-cymene and MeCN ligands, and the overall charge of the complexes might be attributed toward such a switching of catalytic activity. This finding led to develop a new precatalyst with improved activity which was further utilized in selective oxidation of a series of styrene substrates containing other oxidation-sensitive functionalities.

Butenolide derivative as well as preparation method and application thereof

The invention discloses a butenolide compound as well as a preparation method and an application thereof. The butenolide derivative has the inhibitory activity of protein tyrosine phosphatase 1B (PTP1B), improves insulin resistance of HepG2 cells, generates a remarkable hypoglycemic effect and can be used for preparing a medicine for treating diabetes mellitus.

Prenylated Curcumin Analogues as Multipotent Tools to Tackle Alzheimer's Disease

Alzheimer's disease is likely to be caused by copathogenic factors including aggregation of Aβ peptides into oligomers and fibrils, neuroinflammation, and oxidative stress. To date, no effective treatments are available, and because of the multifactorial nature of the disease, it emerges the need to act on different and simultaneous fronts. Despite the multiple biological activities ascribed to curcumin as neuroprotector, its poor bioavailability and toxicity limit the success in clinical outcomes. To tackle Alzheimer's disease on these aspects, the curcumin template was suitably modified and a small set of analogues was attained. In particular, derivative 1 turned out to be less toxic than curcumin. As evidenced by capillary electrophoresis and transmission electron microscopy studies, 1 proved to inhibit the formation of large toxic Aβ oligomers, by shifting the equilibrium toward smaller nontoxic assemblies and to limit the formation of insoluble fibrils. These findings were supported by molecular docking and steered molecular dynamics simulations which confirmed the superior capacity of 1 to bind Aβ structures of different complexity. Remarkably, 1 also showed in vitro anti-inflammatory and antioxidant properties. In summary, the curcumin-based analogue 1 emerged as multipotent compound worthy to be further investigated and exploited in the Alzheimer's disease multitarget context.