4-Butylresorcinol

Description

4-Butylresorcinol is one of the best ingredients for treating hyperpigmentation and facilitating skin-lightening in the cosmetic industry. It even works wonders for melasma treatment which is the condition of dark patches appearing on the face due to hormonal changes during pregnancy.

The Uses of 4-Butylresorcinol

4-Butylresorcinol is recognized as a potential inhibitor of Cytochrome P450, an enzyme complex that plays a crucial role in the metabolism of various substances in the body. Its ability to inhibit tyrosinase, a key enzyme in melanin production, results in hypopigmentation, which is a lightening or loss of skin color.

What are the applications of Application

Glycerol is used both in sample preparation and gel formation for polyacrylamide gel electrophoresis. Glycerol (5-10%) increases the density of a sample so that the sample will layer at the bottom of a gel′s sample well. Glycerol is also used to aid in casting gradient gels and as a protein stabilizer and storage buffer component.

Definition

ChEBI: 4-n-Butylresorcinol is a member of resorcinols.

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.

Mechanism of action

The mechanism of action of 4-butylresorcinol depigmentation is through inhibition of tyrosinase and tyrosinase-related protein-1 (TRP-1)^[1].

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%.

References

[1] D. RESENDE. Skin Depigmenting Agents in Anti-Aging Cosmetics: A Medicinal Perspective on Emerging Ingredients[J]. Applied Sciences-Basel, 2022. DOI:10.3390/app12020775.