3144-54-5

Usage

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 
• 95-88-5 4-Chlororesorcinol 
• 693-02-7 hex-1-yne 
• 7780-16-7 phenyl hexanoate 

Downstream Products

• 100972-54-1 1-(4-acetoxy-2-hydroxy-phenyl)-hexan-1-one 
• 136-77-6 4-Hexylresorcinol 
• 103981-28-8 1-[2-Hydroxy-4-(3-nitro-benzyloxy)-phenyl]-hexan-1-one 
• 103981-23-3 1-[4-(3-Amino-benzyloxy)-2-hydroxy-phenyl]-hexan-1-one 
• 98618-96-3 3-[[3-[[3-hydroxy-4-(1-oxohexyl)phenoxy]methyl]phenyl]amino]-3-oxopropanoic acid, methyl ester 
• 98618-97-4 4-[[3-[[3-hydroxy-4-(1-oxohexyl)phenoxy]methyl]phenyl]amino]-4-oxobutanoic acid, methyl ester 
• 101002-19-1 4-pentoxy-2-hydroxycaprophenone oxime 
• 143286-81-1 1-(4-Benzyloxy-2-hydroxy-phenyl)-hexan-1-one oxime 
• 101002-20-4 4-decyloxy-2-hydroxycaprophenone oxime 
• 63411-88-1 1-(5-hexyl-2,4-dihydroxyphenyl) ethan-1-one 

Relevant academic research and scientific papers

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.

Synthesis and evaluation of aromatic methoxime derivatives against five postharvest phytopathogenic fungi of fruits. Main structure–activity relationships

The antifungal activity of a library of twenty-four aromatic methoximes was examined against five representative postharvest phytopathogenic fungi. The panel included Penicillium digitatum, Penicillium italicum, Rhizopus stolonifer, Botrytis cinerea and Monilinia fructicola, all of which cause relevant economic losses worldwide as a result of affecting harvested fruits. The minimum inhibitory concentrations and minimum fungicidal concentrations of each compound were defined and the main structure–activity relationships were determined. Although other congeners were more potent, drug likeliness considerations pointed to the methoxime derived from 2,4-dihydroxypropiophenone as the compound with the most suitable profile. The morphology of the colonies of the fungal strains treated with the methoxime was examined microscopically and the compound was also tested in freshly harvested peaches and oranges, exhibiting promising control profiles in both fruits, similar to those of the commercial agents Imazalil and Carbendazim.

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.

Preparation method of 4-alkylresorcinol

The invention discloses a preparation method of 4-alkylresorcinol. The preparation method comprises the steps: carrying out a reaction on resorcinol and alkyl acid to prepare acyl resorcinol, and then, catalyzing a hydrogenation reaction to obtain 4-alkylresorcinol. By using the method, the dosages of a catalyst and alkyl groups are controlled in an acylation process, so that the yield is remarkably increased, byproducts are reduced, and the production cost is reduced; and hydrogen reduction is adopted in a reduction process, and a high-toxicity and high-pollution zinc amalgam reducing agent is prevented from being used, so that the preparation method is green and environment-friendly; and the aftertreatment is simple, the prepared product is high in purity, the total yield of the two steps reaches up to 77%, and the preparation method has a remarkable significance for industrial production of 4-alkylresorcinol.

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.

Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging

Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ～ 205.19, λab ～ 350 nm, λem ～ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is

Discovery and SAR study of hydroxyacetophenone derivatives as potent, non-steroidal farnesoid X receptor (FXR) antagonists

Compound 1 (IC50 = 35.2 ± 7.2 μM), a moderate FXR antagonist was discovered via high-throughput screening. Structure-activity relationship studies indicated that the shape and the lipophilicity of the substituents of the aromatic ring affect the activity dramatically, increasing the shape and the lipophilicity of the substituents of the aromatic ring enhances the potency of FXR antagonists. Especially, when the OH at C2 position of the aromatic ring was replaced by the OBn substituent (analog 2b), its activity could be improved to IC50 = 1.1 ± 0.1 μM. Besides, the length of the linker and the tetrazole structure are essential for retaining the activity.

A photochemical route to 2-substituted benzo[b]furans

2-Substituted benzo[b]furans were synthesized by a one-step metal-free photochemical reaction between 2-chlorophenol derivatives and terminal alkynes by tandem formation of an aryl-C and a C-O bond via an aryl cation intermediate. The mild conditions and the application to chlorophenols rather of the more expensive bromo or iodo analogues makes this procedure environmentally convenient.

SKIN LIGHTENING COMPOSITIONS AND METHODS

Skin lightening/even toning compositions are provided for reducing skin pigmentation of normal skin and for lightening hyper-pigmented skin said compositions comprising (i) highly purified hexylresorcinol which is substantially free or resorcinol, (ii) optionally, at least one other skin lightening agent, and (iii) a dermatologically acceptable carrier.

Process for the synthesis of alkylresorcinols

The invention provides a process for the production of 4-(C2-C16)alkylresorcinol. 4-(C2-C16)alkylresorcinol is produced by reacting resorcinol with a (C2-C16)alkyloic acid in the presence of a zinc chloride catalyst to produce an intermediate comprising a 4-(C2-C16)acylresorcinol and zinc ions. Then the intermediate is adjusted such that the zinc ion content is from about 0.1 to about 150 parts per million based on the weight of the intermediate to form an adjusted intermediate. Then the produced 4-(C2-C16)acylresorcinol is hydrogenated in the presence of the zinc ions and a base metal hydrogenation catalyst to produce a crude product comprising 4-(C2-C16)alkylresorcinol, which may thereafter be isolated.