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CAS 18979-61-8 4 Butylresorcinol/4-n-Butylresorcinol
High Quality 4-n-butylresorcinol/4-butylresorcinol
Prodcut name: 4-n-butylresorcinol
CAS No.: 18979-61-8
Content: 4-n-butylresorcinol
Specification: 95% Min
Appearance: White or whitish powder
Test Method: HPLC
4 n Butylresorcinol (BR) is considered the most potent inhibitor of tyrosinase, which is why it is used in cosmetics as a depigmenting agent. However, this work demonstrates that BR is a substrate of this enzyme. The Em (met tyrosinase) form is not active on BR, but Eox (oxy tyrosinase) can act on this molecule, hydroxylating it to o diphenol. In turn, this is oxidized to an o quinone, which isomerizes to a red p quinone. Thus, for tyrosinase to act on this compound, a mechanism to generate Eox in the medium is required, which can be achieved by means of hydrogen peroxide or ascorbic acid. A kinetic analysis of the proposed mechanism allows its kinetic characterization: catalytic constant (8.49 ± 0.20 s−1) and Michaelis constant (60.26 ± 8.76 μM). These findings are compared with those for other monophenolic substrates of tyrosinase. Studies of BR docking to the Em form of the enzyme show that the hydroxyl group in C 1 position is oriented toward the copper atom A (CuA), as in it is L tyrosine. As regards Eox, BR is oriented with the carbon in C 6 position ready to be hydroxylated. The reaction of BR originates o quinones, which isomerize to p quinones, which in turn, could react with thiol compounds, a finding that could have important implications for pharmacology and the cosmetic industry.
Items | Standard |
Appearance | Off-white to pale yellow |
odor | Characteristic smells |
Solubility | Soluble in most organic solvents. Slightly soluble in |
Iron Content | ≤100ppm |
Ash Content | ≤0.5%(w/w) |
Purity by GC | ≥99.0% |
Currently, 4 n butylresorcinol (BR) is considered the most potent inhibitor of human tyrosinase, as tested in vitro and in vivo 8-12. This inhibition gives it a strong hypopigmenting effect, so it can be used in cosmetics against pigmentary disorders 8. Such is the case of a cosmetic product from Sesderma (Valencia, Spain), whose effectiveness has been demonstrated against melasma, based on the presence of azelaic acid, although BR is also present 13. Furthermore, a recent study discussed the action of tyrosinase on BR, describing this compound as an inhibitor of the enzyme 14. However, some of the compounds that were formerly catalogued as inhibitors, such as m diphenols analogous to BR, have recently been described as alternative substrates 15, 16. This is because tyrosinase cannot act through its diphenolase activity on the nonadjacent disposition of the two hydroxyl groups of these compounds. This meta disposition of the hydroxyl groups means that Em is not active on BR and only the monophenolase activity of tyrosinase can act on this molecule, hydroxylating its ortho position. The Eox form of tyrosinase is therefore necessary for the activity. To obtain this form of tyrosinase, the presence of certain compounds is necessary, as our group demonstrated in previous studies 17-19. These compounds are: (a) hydrogen peroxide (H2O2), which allows the enzyme form Em (met tyrosinase) to become Eox, which is active on monophenols; (b) a reductant such as ascorbic acid (AH2) able to transform Em into Ed (deoxy tyrosinase), which, with oxygen, produces the Eox form; or (c) catalytic quantities of o diphenol (to bring about the transformation of Em into Ed, which, with oxygen, becomes Eox) and ascorbic acid to keep the quantity of o diphenol constant in the reaction medium and ensure that Eox does not cease to be generated. Moreover, various resorcinols analogous to BR have been proposed as inactivators of tyrosinase through a suicide inactivation mechanism 20.
By effectively inhibiting tyrosinase, it can prevent the formation of melanin on the skin surface, improve the gloss of the skin, make the skin more uniform, and reduce the deposition of skin pigments. It is widely used in skin care products, skin astringency products and skin repair products, and is easily soluble in oil or water-based formulations.