18979-61-8

Basic information

• Product Name: 4-Butylresorcinol
• Synonyms: 4-BUTYLRESORCINOL,98+%;4-Butylbenzene-1,3-diol;4-Butylresorcinol;1,3-Benzenediol,4-butyl-;4-phenylbutane-1,3-diol;4-N-BUTYLRESORCINOL;2,4-DIHYDROXY-N-BUTYL BENZENE;2,4-DIHYDROXY-N-BUTYL BENZEN
• CAS NO: 18979-61-8
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• Product Categories: Benzene derivates;Miscellaneous
• Mol File: 18979-61-8.mol

Chemical Properties

• Melting Point: 50.0 to 55.0 °C
• Boiling Point: 166°C/7mmHg(lit.)
• Flash Point: 144.5 °C
• Appearance: /
• Density: 1.092 g/cm³
• Vapor Pressure: 0.000616mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.95±0.18(Predicted)
• CAS DataBase Reference: 4-Butylresorcinol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Butylresorcinol(18979-61-8)
• EPA Substance Registry System: 4-Butylresorcinol(18979-61-8)

Safety Data

• RTECS: VH0420000
• Hazardous Substances Data: 18979-61-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Butylresorcinol is used as a Cytochrome P450 inhibitor for its potential to modulate the activity of this enzyme, which plays a crucial role in drug metabolism and detoxification processes.
Used in Cosmetic Industry:
4-Butylresorcinol is used as a skin lightening agent for its ability to cause hypopigmentation due to its direct inhibition of tyrosinase, an enzyme involved in melanin production. This property makes it a valuable ingredient in skincare products aimed at reducing the appearance of dark spots and promoting an even skin tone.
Used in Research Applications:
4-Butylresorcinol is used as a sample preparation and gel formation component in polyacrylamide gel electrophoresis. It is used in concentrations of 5-10% to increase the density of a sample, ensuring that the sample layers at the bottom of a gel's sample well. Additionally, it aids in casting gradient gels and serves as a protein stabilizer and storage buffer component, making it an essential tool in molecular biology research.

resorcinol derivative

4-n-Butylresorcinol is a resorcinol derivative that inhibits both tyrosinase and tyrosinase-related protein-1 (TRP-1). It may be used to decrease skin irritation and is also known to inhibit melanin production. Its hypopigmenting action was first reported in 1995, and many following studies have documented its efficacy and safety in melasma treatment with the 0.1% cream, but there is paucity of clinical studies that used the 0.3% cream. The biochemical assay on inhibition of human tyrosinase activity has revealed the superiority of 4-n-butylresorcinol over other hypopigmenting agents. Many studies show good efficacy and safety in treating melisma. 4-n-Butylresorcinol may be used to produce a safe cosmetic agent, with the clinical efficacy required of a pharmacological agent. Furthermore, 4-n-butylresorcinol acts mainly by inhibition of tyrosinase activity and has no effect on MITF. 4-n-butylresorcinol showed an additive effect in combination with hinokitiol, which reduces MITF expression.

History

4-n-Butylresorcinol (Rucinol? ) (Obtained by POLA in 1998) was selected by screening synthetic resorcinol derivatives that can elicit strong competitive inhibition of tyrosinase activity. Melanin synthesis is catalyzed by tyrosinase, together with tyrosinase-related proteins (TRP) -1 and -2, and Rucinol? has been shown to inhibit melanin synthesis in cultured mouse melanocytes via direct inhibition not only of tyrosinase activity, but also of TRP-1 activity. A 0.3% Rucinol? -containing lotion was shown to be effective for treating hyperpigmentary disorders, such as melasma.

tyrosinase inhibitor

4-butylresorcinol is use as an effective treatment option for topical hyperpigmentation management. Similar to hydroquinone, 4-n-butylresorcinol is also a tyrosinase inhibitor. It has been characterized as a strong tyrosinase25 and TRP‐126 inhibitor. We measured an IC50 in the human tyrosinase assay of 21μmol/L for 4‐butylresorcinol compared with 94 and 131?μmol/L for 4‐hexylresorcinol and 4‐phenylethylresorcinol respectively. Also on skin models, 4‐butylresorcinol was most effective of all tested substances with an IC50 of 13.5 μmol/L. Therefore, 4‐butylresorcinol was selected for several clinical studies to prove in vivo efficacy. In comparison with 4‐hexylresorcinol and 4‐phenylethylresorcinol, 4‐butylresorcinol treated age spots showed a faster onset of improvement and also a higher degree of lightening after 12 weeks of treatment.

Biological Activity

Glutathione reductase IGR) is a crucial flavoenzyme in the antioxidant defense system. Reduced glutathione (GSH) is used by glutathione peroxidase to detoxify hydrogen peroxide and in the process is converted to oxidized glutathione (GSSG). The GSSG is then recycled back to GSH by glutathione reductase (GR) using NADPH that is then converted to NADP+. The regenerated GSH is then available to detoxify more hydrogen peroxide. The enzyme uses FAD as a cofactor. GR and glutathione peroxidase may inhibit lipid peroxidation by functioning as antioxidant enzymes in sperm. Glutathione reductase shares a structural motif with a number of other proteins including aspartyl proteases, citrate synthase, EF hands, hemoglobins, lipocalins, and α/β hydrolases. GR is stimulated by melatonin and is reportedly irreversibly inhibited by a number of oxygen radical generating systems.A sweet tastant for mammals. A glycerol taste receptor binding site specific for glucose has been proposed in drosophila.

Synthesis

Under the protection of nitrogen, 110 g (1 mol) of resorcinol and 220 g of n-heptane were mixed in the reaction flask, heated and dissolved, and the temperature was lowered to 10 ° C. A turbid solution of 40.8 g (1.02 mol) of sodium hydroxide and 100 g of n-butanol was added in portions. , And control the temperature of 10 to 15 , after TLC (EA developing agent) detection of almost no remaining raw materials, add n-butanol (2.5mol), tris (pentafluorobenzene) borane 17.5g (0.1mol) and calcium chloride 1.1 g, raise the temperature to 40-45 ° C for 1 hour, then raise the temperature to 98 ° C for reflux and water separation. After 8 hours of water separation, take a sample and quench the GC to detect resorcinol <1%, cool to room temperature, add a small amount of water to quench It is extinguished, and then dilute sulfuric acid is added to adjust the pH = 1-2. The insoluble solids are filtered through diatomaceous earth, and the organic phase is concentrated to a stagnant liquid. Water is added for replacement, and then 660 g of water, 2.2 g of sodium thiosulfate, and 5.5 g are added. Activated carbon was heated to reflux for 1 hour, and was hot-filtered to obtain a pale yellow solution. Then, flaky crystals were precipitated by cooling, and 151 g of 4-n-butylresorcinol was obtained by filtration, GC: 99.3%, and yield: 90.9%.

InChI:InChI=1/C10H14O2/c1-2-3-4-8-5-6-9(11)7-10(8)12/h5-7,11-12H,2-4H2,1H3

Upstream product

• 4390-92-5 1-(2,4-dihydroxyphenyl)butan-1-one 
• 51754-69-9 3-butyl-2,6-dihydroxy-benzoic acid 
• 7647-01-0 hydrogenchloride 
• 108-46-3 recorcinol 
• 2150-45-0 methyl 2,6-dihydroxybenzoate 
• 51798-17-5 3-Butyryl-2,6-dihydroxy-benzoic acid methyl ester 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 13246-46-3 2,4-dibenzyloxybenzaldehyde 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 54494-87-0 resorcinol; sodium-compound 
• 71-36-3 butan-1-ol 

Downstream Products

• 51754-69-9 3-butyl-2,6-dihydroxy-benzoic acid 
• 99188-05-3 4-butyl-6-chloro-resorcinol 
• 55605-58-8 5-butyl-2,4-dihydroxy-benzoic acid 
• 96643-96-8 5-butyl-2,4-dihydroxy-deoxybenzoin 
• 81468-73-7 1-(5-butyl-2,4-dihydroxyphenyl)ethan-1-one 
• 717910-17-3 1-(5-butyl-2,4-dihydroxy-phenyl)-2-chloro-ethanone 
• 65239-71-6 1-(5-Butyl-2,4-dihydroxy-phenyl)-2,2,2-trifluoro-ethanone 
• 170466-80-5 1-(5-Butyl-2,4-dihydroxy-phenyl)-2-(4-methyl-thiazol-2-yl)-ethanone 
• 130182-22-8 6-Butyl-7-hydroxy-4-phenyl-chromen-2-one 
• 178754-69-3 6-Butyl-7-methoxy-4-phenyl-chromen-2-one 

Relevant articles and documents

Preparation method of 4-alkylresorcinol

The invention discloses a preparation method of 4-alkyl resorcinol, and belongs to the field of organic synthetic chemistry. The method comprises the following steps: carrying out Claisen-Schmidt condensation reaction on 4-acetyl resorcinol and alkyl aldehyde to obtain an intermediate III, and carrying out catalytic hydrogenation reduction to obtain 4-alkyl resorcinol; the synthetic reaction route of the method is as follows: raw and auxiliary materials and reagents used in the method are low in toxicity, safe, low in price and easy to obtain; the yield is obviously improved, byproducts are reduced, and the production cost is reduced; high-toxicity and high-pollution reagents are prevented from being used in the reduction process, and environmental protection is achieved; different 4-alkyl resorcinol can be obtained by using alkyl aldehydes with different carbon atom numbers; the product prepared by the method is high in quality, and the method has a significant meaning for industrial production of 4-alkylresorcinol.

Method for preparing 4-butyl resorcinol

The invention discloses a method for preparing 4-butyl resorcinol. The method comprises the following steps: (1) preparing 2, 4-dihydroxy benzaldehyde; (2) preparing 2, 4-dihydroxy benzylidene acetone; and (3) preparing the 4-butyl resorcinol. The method has the advantages as follows: firstly, raw materials and reagents used in the method are lower in toxicity, safer, cheaper, easier to obtain andconvenient to store, and the raw material cost and operation cost are greatly reduced; secondly, the method has few reaction steps, is convenient to operate, and is easier for large-scale production;and thirdly, high-toxicity three wastes are not generated, environmental pollution is reduced, and the ecological environment is protected. Meanwhile, the yield of the prepared product is high and can reach 90% or above.

Method for preparing 4-n-butyl resorcinol by one-pot method

The invention discloses a method for preparing 4-n-butyl resorcinol by a one-pot method, and belongs to the field of cosmetic intermediate synthesis. The method comprises the following steps of: reacting resorcinol serving as a raw material with an alkali in n-butyl alcohol to form monophenol salt, reacting the monophenol salt with a Lewis acid by a dehydration one-pot method, performing acidolysis to obtain a crude product, and recrystallizing to obtain the 4-n-butyl resorcinol. The method is simple and convenient to operate, mild in condition, low in cost and high in yield, the purity of theobtained product can reach 99.0% or above, and the method has a potential amplification prospect.

Preparation method of 4-butyl resorcinol

The invention belongs to the field of chemical synthesis and fine chemical manufacturing, and particularly discloses a preparation method of 4-butyl resorcinol, which comprises the following steps: byusing cheap and accessible 2, 4-dihydroxy benzaldehyde as a starting raw material and benzyl halide as an alkylation reagent, carrying out double O-benzylation under alkaline conditions to obtain 2,4-dibenzyloxy benzaldehyde; by taking triphenylpropyl phosphine halide as a reagent, carrying out Wittig alkenylation to prepare 2, 4-dibenzyloxy phenyl butene; and carrying out metal catalytic hydrogenation, and simultaneously completing alkenyl reduction and debenzylation to prepare the 4-butyl resorcinol in one pot. According to the method disclosed by the invention, a Friedel-Crafts acylationreaction and a reduction deketonization reaction which are necessary for a traditional method are abandoned, the use of excessive high-pollution reagents such as zinc chloride and hydrochloric acid isavoided, and the emission of three wastes is greatly reduced; the catalyst is reusable, free of by-products, simple and convenient to operate and suitable for large-scale production; the yield is increased, the cost is reduced, and the green upgrading of the industrial production technology of the 4-butylresorcinol is completed.

Method for synthesizing 4-alkylresorcinol through solvent-free system

The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing 4-alkylresorcinol through a solvent-free system. The method comprises the following stepsthat (1) resorcinol, zinc chloride and alkyl acid are evenly mixed, heated and stirred for a reaction, after cooling, water is added to precipitate a solid, filtering, drying and recrystallization areconducted, and thus 4-acylresorcinol is obtained; (2) the 4-acylresorcinol is dissolved into trifluoroacetic acid, triethyl silicane is added dropwise, heating and stirring are conducted for a reaction, cooling and standing are conducted for layering, an organic layer is extracted and dried, filtration and concentration are conducted to obtain a crude product, recrystallization is conducted, andthe 4-alkylresorcinol is obtained. According to the method, a triethyl silicane/trifluoroacetic acid system is applied to synthesis of the 4-alkylresorcinol for the first time, the reaction conditionis gentler and easier to control, and a post-treatment method is simple; and the system does not contain a solvent, water materials generated during industrial amplification are also greatly reduced,and thus the whole process is more environment friendly.

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.

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.

Antifungal Activity of 2,4-Dihydroxyacylophenones and Related Compounds

The antifungal activity of 2,4-dihydroxyacylophenones and related compounds against Trichophyton spp. and other fungi were investigated to determine their structure-activity relationships.The activity of these compounds was found to be closely related to the length of the acyl and alkyl substituents attached to the 1,3-dihydroxybenzene moiety.In addition, differences in activity were observed depending on the position of the alkyl substituents and on the number of substituents attached to the 1,3-dihydroxybenzene moiety.Some compounds tested showed potent antifungal activity against Trichophyton spp. and other fungi that was more active than amphotericin B.

2,6 Dihydroxybenzoic acid derivatives as anthelmintics

The 2,6 dihydroxybenzoic acid anilides have marked cesticidal properties when a specific form of substitution by halogen atoms or methyl groups is made in the anilide portion of the molecule. Optimum activity is achieved with 2,6 dihydroxybenzoic acid 4' bromanilide. This compound interferes with the energy metabolism of cestodes, inhibiting the breakdown of glucose and lowering the ATP level. The introduction of halogen atoms in the 3 and 5 position of the benzoic acid portion increases the activity but the toxicity as well. Activity against the liver fluke is also observed and prevails when an electronegative substituent is introduced in the 3 position. The most effective compounds are the 3 nitro 2,6 dihydroxybenzoic acid anilides, followed by the 3 acyl 2,6 dihydroxybenzoic acid anilides. The choice of substituents in the anilide portion is restricted to halogens, methyl groups, tri halogenated methyls, i.e. substituents which improve the lipoid solubility. Optimum efficacy is achieved with 3 nitro 2,6 dihydroxybenzoic acid 3',5' bis trifluoromethyl anilide. A description of the chemical methods of synthesis is given.