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4-N-BUTYLRESORCINOL

4-Butylresorcinol

CAS: 18979-61-8

Molecular Formula: C10H14O2

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4-N-BUTYLRESORCINOL - Names and Identifiers

Name 4-Butylresorcinol
Synonyms 4-Butylresorcinol
4-N-BUTYLRESORCINOL
4-Butylbenzene-1,3-diol
4-phenylbutane-1,3-diol
1,3-Benzenediol,4-butyl-
2,4-Dihydroxy-n-bytyl benzen
2,4-DIHYDROXY-N-BUTYL BENZEN
2,4-DIHYDROXY-N-BUTYL BENZENE
4-06-00-06003 (Beilstein Handbook Reference
4-06-00-06003 (Beilstein Handbook Reference)
CAS 18979-61-8
InChI InChI=1/C10H14O2/c1-2-3-4-8-5-6-9(11)7-10(8)12/h5-7,11-12H,2-4H2,1H3
InChIKey CSHZYWUPJWVTMQ-UHFFFAOYSA-N

4-N-BUTYLRESORCINOL - Physico-chemical Properties

Molecular FormulaC10H14O2
Molar Mass166.22
Density1.092±0.06 g/cm3(Predicted)
Melting Point50.0 to 55.0 °C
Boling Point166°C/7mmHg(lit.)
Flash Point144.5°C
Vapor Presure0.041Pa at 25℃
AppearanceYellow or white powder
Colorwhite to pale yellow powder
pKa9.95±0.18(Predicted)
Storage ConditionInert atmosphere,Room Temperature
Refractive Index1.555
UseThis product is for scientific research only and shall not be used for other purposes.
In vitro study It shows that 4-Butylresorcinol (4-n-butylresorcinol) significantly inhibits melanin synthesis in a concentration-dependent manner. In addition, it is also found to inhibit the activity of tyrosinase, the rate-limiting melanogenic enzyme. 4-Butylresorcinol does not induce ERK, Akt activation, or MITF degradation, and has no effect on cAMP response element binding protein (CREB) phosphorylation, which stimulates MITF expression. 4-Butylresorcinol strongly reduces tyrosinase activity in a cell-free system. Moreover, 4-Butylresorcinol shows an additive effect in combination with hinokitiol, which reduces MITF expression.

4-N-BUTYLRESORCINOL - Risk and Safety

RTECSVH0420000

4-N-BUTYLRESORCINOL - Reference Information

LogP2.8 at 24℃ and pH7
surface tension 17.8mN/m at 1g/L and 20 ℃
Overview 4-n-butyl resorcinol, also known as Rucinol, is an active ingredient in a variety of cosmetics and can inhibit melanin production. Specifically, it can inhibit the two enzymes necessary for melanin production, namely tyrosinase and 5, 6-dihydroxyindole-2-carboxylic acid-oxidase.
synthesis method currently, there are two main methods for synthesizing 4-n-butyl resorcinol: method 1: using palladium and carbon in methanol solvent, 4-Butylresorcinol is reduced by catalytic hydrogenation method. Catalytic hydrogenation is a typical gas-liquid-solid three-phase heterogeneous reaction. In order to ensure full contact of the three phases, high temperature and high pressure (15atm) conditions are required. Not only is the energy consumption high, but also H2 in the system has flammable and explosive properties. In case of leakage, there is a huge potential safety hazard. In addition, palladium and carbon are used, and the cost is relatively high. Method 2: Zinc amalgam was used to reduce 4-butyrylresorcinol under hydrochloric acid at 120 ℃. Since the reaction is carried out on the activated zinc surface, new zinc amalgam is required every time the reaction is done; the higher the reaction temperature will cause a large loss of the concentration of hydrochloric acid, and concentrated hydrochloric acid needs to be added to maintain the acidity; produce A large amount of pollutant zinc amalgam. The two methods mentioned above are the conventional methods reported so far, and there are obvious defects in process amplification. In addition, in the traditional reaction kettle reaction, the reaction exotherms and generates a large amount of gas during feeding, which poses a great potential safety hazard and increases the difficulty of process amplification.
Application 4-n-butyl resorcinol, also known as Rucinol, is an active ingredient in a variety of cosmetics and can inhibit melanin production. Specifically, it can inhibit the two enzymes necessary for melanin production, namely tyrosinase and 5, 6-dihydroxyindole-2-carboxylic acid-oxidase.
preparation 4-n-butyl resorcinol preparation is as follows: weigh 100g 4-n-butyryl resorcinol and dissolve it in toluene, ice bath to 0 ℃, then slowly add 32g(1.5eq) sodium borohydride in batches, and react at room temperature for 12h after adding; Then inject it into preheating module 1 and preheat to 80 ℃; add 67g of Raney nickel and isopropyl alcohol to preheating module 2 and preheat to 80°C. Then the above two preheated materials are added to the reaction module, and the residence time is controlled at 200s. Collect the flowing reaction liquid, pour ice water to quench, filter out the solid, evaporate most of the toluene, add dichloromethane 330mL for extraction, evaporate dichloromethane to obtain white solid 4-n-butyl resorcinol 82g with 89% yield and 99.3% HPLC purity.
Biological activity 4-Butylresorcinol is a phenol derivative that can inhibit tyrosinase with an IC50 value of 11.27 μM.
target IC50: 11.27 μM (4-Butylresorcinol)
Last Update：2024-04-09 21:11:58
4-N-BUTYLRESORCINOL
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4-N-BUTYLRESORCINOL
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