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

• 64506-49-6 sofalcone 
• 64506-53-2 2'-(carboxymethoxy)-4-(3-methyl-2-butenyloxy)-chalcone 
• 338386-44-0 (1S,2Z,5S)-4-methyl-2-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methylene]-dispiro[1,4-diazabicyclo[3.2.1]octan-3-one-7,1'-cyclohexane-4',2''-[1,3]dioxolane] 
• 338386-49-5 (1S,2Z,5S)-4-methyl-2-[[4-[(3-methyl-2-butenyl)oxy]phenyl]methylene]-dispiro[1,4-diazabicyclo[3.2.1]octan-7,1'-cyclohexane-4',2''-[1,3]dioxolane] 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 25515-46-2 naringenin chalcone 
• 28116-98-5 rac-5,7-dihydroxy-2-[4-(3-methylbut-2-enyloxy)phenyl]chroman-4-one 
• 756891-31-3 3-hydroxy-4'-prenyloxy-furano(2'',3'':7,8)flavone 
• 624734-51-6 5,7-di(methoxymethoxy)-6,8-di-C-prenyl-4'-O-prenylflavanone 
• 32328-83-9 4-(3-methyl-2-butenoxy)phenol 
• 756891-29-9 2'-hydroxy-4-prenyloxy-furano(2'',3'':4',3')chalcone 

Relevant articles and documents

Synthesis method of isolicoflavonol

The invention provides a synthesis method of isolicoflavonol, which comprises the following steps: carrying out condensation reaction on 2,4-O-R1(protective group, the same below)-6-hydroxyacetophenone and 4-O-R2(protective group, the same below)-benzaldehyde to generate 2',4'-O-R1-6'-hydroxy-4-O-R2-chalcone; oxidizing the chalcone to generate flavonol; carrying out selective protection on 3-OH ofthe flavonol to obtain 3,5,7-O-R1-4'-O-R2-flavonol; removing the protecting group R2 from the 3,5,7-O-R1-4'-O-R2-flavonol to obtain 3,5,7-O-R1-4'-hydroxyflavonol; carrying out 1,1-dimethylpropargyl reaction on the 4,4'-OH site to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonol; carrying out partial hydrogenation on the alkynyl of the 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonolunder the action of a catalyst to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol and carrying out Claisen rearrangement on the 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol to obtain 3,5,7-O-R1-isolicoflavonol, and removing the protecting group R1 from the 3,5,7-O-R1-isolicoflavonol to obtain the isolicoflavonol.

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.

Natural and semisynthetic oxyprenylated aromatic compounds as stimulators or inhibitors of melanogenesis

It has been very recently shown how naturally occurring oxyprenylated coumarins are effective modulators of melanogenesis. In this short communication we wish to generalize the potentialities as skin tanning or whitening agents of a wider panel of natural and semisynthetic aromatic compounds, including coumarins, cinnamic and benzoic acids, cinnamaldehydes, benzaldehyde, and anthraquinone derivatives. A total number of 43 compounds have been tested assaying their capacity to inhibit or stimulate melanin biosynthesis in cultured murine Melan A cells. The wider number of chemicals herein under investigation allowed to depict a detailed structure-activity relationship, as the following: (a) benzoic acid derivatives are slightly pigmenting agent, for which the effect is more pronounced in compounds with longer O-side chains; (b) independently from the type of substitution, cinnamic acids are able to increase melanin biosynthesis, while benzaldehydes are able to decrease it; (c) coumarins with a 3,3-dimethylallyl or shorter skeletons as substituents in position 7 are tanning agents, while coumarins with farnesyloxy groups are whitening ones; (d) double oxyprenylation in position 6 and 7 and 3,3-dimethylallyl or geranyl skeletons have slight depigmenting capacities, while farnesyl skeletons tend to marginally increase the tanning effect; (e) the presence of electron withdrawing groups (acetyl, COOH, and -Cl) and geranyl or farnesyl oxyprenylated chains respectively in positions 3 and 7 of the coumarin nucleus lead to a whitening effect, and finally (f) oxyprenylated anthraquinones have only a weak depigmenting capacity.