3144-54-5

Basic information

• Product Name: 4-Hexanoylresorcinol
• Synonyms: 4-HEXANOYLRESORCINOL;2',4'-DIHYDROXYHEXANOPHENONE;1-(2,4-DIHYDROXYPHENYL)-1-HEXANONE;1-(2,4-Dihydroxyphenyl)hexan-1-one;2,4-Dihydroxyphenyl(pentyl) ketone;2,4-Dihydroxyphenylpentyl ketone
• CAS NO: 3144-54-5
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25
• EINECS: 221-555-7
• Mol File: 3144-54-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 53-56 °C(lit.)
• Boiling Point: 217 °C14 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: solid or liquid
• Density: 1.0989 (rough estimate)
• Vapor Pressure: 1.39E-05mmHg at 25°C
• Refractive Index: 1.5141 (estimate)
• PKA: 7.83±0.35(Predicted)
• CAS DataBase Reference: 4-Hexanoylresorcinol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hexanoylresorcinol(3144-54-5)
• EPA Substance Registry System: 4-Hexanoylresorcinol(3144-54-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 3144-54-5(Hazardous Substances Data)

Usage

Description

4-Hexanoylresorcinol is a chemical compound that possesses unique properties, making it a valuable component in various industrial applications. It is characterized by its ability to interact with lignin, a complex organic polymer found in the cell walls of plants, and facilitate its depolymerization.

Uses

Used in Chemical Industry:
4-Hexanoylresorcinol is used as a catalyst for the efficient depolymerization of alkaline lignin. This application is particularly relevant in the chemical industry, where the breakdown of lignin is crucial for the production of valuable chemicals and materials from renewable resources.
Used in Bioenergy Production:
In the bioenergy sector, 4-Hexanoylresorcinol serves as a catalyst to enhance the depolymerization of lignin, which is an essential step in the conversion of lignocellulosic biomass into biofuels and other bioproducts. This process contributes to the development of sustainable energy sources and reduces reliance on fossil fuels.
Used in Material Science:
4-Hexanoylresorcinol is utilized as a component in the synthesis of advanced materials, such as polymers and composites, that exhibit improved properties due to the incorporation of depolymerized lignin. This application is significant in material science, where the development of innovative materials with enhanced performance is a key area of research and development.
Overall, 4-Hexanoylresorcinol plays a vital role in various industries, particularly in the chemical, bioenergy, and material science sectors, due to its ability to promote the depolymerization of lignin and contribute to the development of sustainable and high-performance products.

InChI:InChI=1/C12H16O3/c1-2-3-4-5-11(14)10-7-6-9(13)8-12(10)15/h6-8,13,15H,2-5H2,1H3

Upstream product

• 408538-95-4 3-Hexanoyloxy-phenol 
• 142-61-0 Hexanoyl chloride 
• 108-46-3 recorcinol 
• 142-62-1 hexanoic acid 
• 534-59-8 n-butylmalonic acid 
• 2051-49-2 n-hexanoic anhydride 
• 7780-16-7 phenyl hexanoate 
• 95-88-5 4-Chlororesorcinol 
• 693-02-7 hex-1-yne 

Downstream Products

• 101002-33-9 1-(4-Decyloxy-2-hydroxy-phenyl)-hexan-1-one 
• 136-77-6 4-Hexylresorcinol 
• 101002-20-4 4-decyloxy-2-hydroxycaprophenone oxime 
• 143286-81-1 1-(4-Benzyloxy-2-hydroxy-phenyl)-hexan-1-one oxime 
• 101002-19-1 4-pentoxy-2-hydroxycaprophenone oxime 
• 63411-88-1 1-(5-hexyl-2,4-dihydroxyphenyl) ethan-1-one 
• 98618-97-4 4-[[3-[[3-hydroxy-4-(1-oxohexyl)phenoxy]methyl]phenyl]amino]-4-oxobutanoic acid, methyl ester 
• 98618-96-3 3-[[3-[[3-hydroxy-4-(1-oxohexyl)phenoxy]methyl]phenyl]amino]-3-oxopropanoic acid, methyl ester 
• 103981-23-3 1-[4-(3-Amino-benzyloxy)-2-hydroxy-phenyl]-hexan-1-one 

Relevant articles and documents

Exploring efficacy of natural-derived acetylphenol scaffold inhibitors for α-glucosidase: Synthesis, in vitro and in vivo biochemical studies

The discovery of novel α-glucosidase inhibitors and anti-diabetic candidates from natural or natural-derived products represents an attractive therapeutic option. Here, a collection of acetylphenol analogues derived from paeonol and acetophenone were synthesized and evaluated for their α-glucosidase inhibitory activity. Most of derivatives, such as 9a–9e, 9i, 9m–9n and 11d–1e, (IC50 = 0.57 ± 0.01 μM to 8.45 ± 0.57 μM), exhibited higher inhibitory activity than the parent natural products and were by far more potent than the antidiabetic drug acarbose (IC50 = 57.01 ± 0.03 μM). Among these, 9e and 11d showed the most potent activity in a non-competitive manner. The binding processes between the two most potent compounds and α-glucosidase were spontaneous. Hydrophobic interactions were the main forces for the formation and stabilization of the enzyme - acetylphenol scaffold inhibitor complex, and induced the topography image changes and aggregation of α-glucosidase. In addition, everted intestinal sleeves in vitro and the maltose loading test in vivo further demonstrated the α-glucosidase inhibition of the two compounds, and our findings proved that they have significant postprandial hypoglycemic effects.

Rational Engineered C-Acyltransferase Transforms Sterically Demanding Acyl Donors

The biocatalytic Friedel-Crafts acylation has been identified recently for the acetylation of resorcinol using activated acetic acid esters for the synthesis of acetophenone derivatives catalyzed by an acyltransferase. Because the wild-type enzyme is limited to acetic and propionic derivatives as the substrate, variants were designed to extend the substrate scope of this enzyme. By rational protein engineering, the key residue in the active site was identified which can be replaced to allow binding of bulkier acyl moieties. The single-point variant F148V enabled the transformation of previously inaccessible medium chain length alkyl and alkoxyalkyl carboxylic esters as donor substrates with up to 99% conversion and up to >99% isolated yield.

Primulin derivative as well as synthesis method and application of primulin derivative

The invention discloses a primulin derivative with antibacterial activity shown as the structural general formula (I), wherein R is selected from C2-C20 alkyls. The primulin derivative is prepared from raw materials including m-dihydroxybenzene and a fatty acid derivative by the steps: carrying out Friedel-Crafts acylation and methylation to synthesize a paeonol derivative, and carrying out oxidization after carrying out carbonyl reduction. The primulin derivative has good antibacterial activity and can be used as a potential antibacterial agent.