136-77-6

Pale-yellow viscous liquid (that becomes solid on standing at room temperature) or a peach colored powder. Pungent faintly fatty odor. Sharp astringent taste.

P-HEXYLRESORCINOL(136-77-6) may be sensitive to prolonged exposure to light. Incompatible with acid chlorides, acid anhydrides and oxidizing agents .

Insoluble in water.

Irritant to respiratory tract and skin, concentrated solutions are vesicant.

Flash point data for this chemical are not available. P-HEXYLRESORCINOL is probably combustible.

slightly red powder

4-Hexylresorcinol is used as the starting material to synthesize a potent immune suppressor, celastramycin A. It is a precursor to prepare resorcinol-sn-glycerol derivatives, that exhibit high affinity for cannabinoid type 1 receptor. It can also be incorporated as a linker while building catenanes. p-Hexylresorcinol shows antiimnflammatory activity acting on the human 5-LO (5-Lipoxygenase) proinflammatory enzyme.

4-Hexylresorcinol(136-77-6) is an inhibitor of transglutaminase-2 in KB cells. Studies indicate that 4-Hexylresorcinol reduces DNA oxidative damage in human lymphocytes. is a substituted dihydroxybenzene used topically as an antiseptic for the treatment of minor skin infections. is a substituted phenol with bactericidal, antihelminthic and potential antineoplastic activities. The combination of 4-Hexylresorcinol and Cisplatin has been shown to inhibit tumor growth, cell growth, and KB cell viability.

ChEBI: 4-hexylbenzene-1,3-diol is a member of resorcinols.

The preparation of 4-Hexylresorcinol involves two methods:
The reaction of caproic acid and resorcinol in the presence of a catalyst.
Reduction of hexanoylresorcinol with zinc amalgam and dilute hydrochloric acid.

hexylresorcinol is a mushroom tyrosinase inhibitor.tyrosinase, a copper-containing enzyme, is distributed in microorganisms, animals, and plants widely. mushroom tyrosinase has been becoming popular due to its availability and usages in various applications.

4-Hexylresorcinol, or “hexylresorcinol,” is a white crystallinesubstance with a faint phenolic odor. When appliedto the tongue it produces a sensation of numbness. It isfreely soluble in alcohol but only slightly soluble in water(1–20,000 parts). Hexylresorcinol is an effective antiseptic,possessing both bactericidal and fungicidal properties.The phenol coefficient of hexylresorcinol against S. aureusis 98. As is typical for alkylated phenols, hexylresorcinolpossesses surfactant properties. The compound also haslocal anesthetic activity. Hexylresorcinol is formulatedinto throat lozenges because of its local anesthetic and antisepticproperties. These preparations are probably of littlevalue. Hexylresorcinol (in the concentration in thelozenge) is probably not antiseptic, and the local anestheticproperty can anesthetize the larynx, causing temporarylaryngitis.

General procedure for the synthesis of 4-hexylresorcinol from 2',4'-dihydroxybenzenehexanone: In a 1.0 L autoclave, 104.1 g (0.5 mol) of 4-hexanoylresorcinol, 500 mL of methanol, and 10% wet Pd/C catalyst (20.0 g) were added in sequence. The reaction system was heated to 80 °C and the hydrogenation reaction was carried out under hydrogen pressure of 1.5 MPa. The reaction process was monitored by gas chromatography (GC) until the reaction was complete. Upon completion of the reaction, the reaction mixture was filtered to recover the Pd/C catalyst. The filtrate was concentrated under reduced pressure to give a light brown-red oily liquid. Finally, the product was recrystallized using a solvent mixture of dichloromethane and hexane to give 83.7 g of 4-hexylresorcinol, which was analyzed by GC for purity >99.0% in 86.2% yield, and the total yield of the two-step reaction was 77.5%.

previous results showed hexylresorcinol could inhibit both mono- and di-phenolase activity of mushroom tyrosinase. moreover, hexylresorcinol at 2 μm lengthened the lag period from 98 s to 26. hexylresorcinol could also display reversible inhibition of the enzyme. in addition, the kinetic analyses showed that hexylresorcinol was a competitive inhibitor with the apparent inhibition constant binding with free enzyme to be 0.443 μm for diphenolase [1].

previous in vivo study showed that hexylresorcinol could induce chromosome aberrations in mouse eukaryotic cells at doses of 0.5, 0.05, and 0.005 mg/g and the metabolic transformation of hexylresorcinol decreased its genotoxic effect in mice. moreover, the mutagenic effect lasted for 3 days only at the highest dose of hexylresorcinol (0.5 mg/g). thus, hexylresorcinol doses less than 0.5 mg/g were metabolized within two days to the extent of the cytotoxic effect. in addition, hexylresorcinol was transformed at a rate of 0.0025–0.025 mg/day after a single administration to mice [2].

1.24 μm

Store at -20°C

[1] chen qx,ke ln,song kk,huang h,liu xd. inhibitory effects of hexylresorcinol and dodecylresorcinol on mushroom (agaricus bisporus) tyrosinase. protein j.2004 feb;23(2):135-41.
[2] margulis ab,ozhiganova iv,bushmanova ov,kolpakov ai,il'inskaia on. hexylresorcinol induces chromosome aberrations in mouse peripheral blood cells. genetika. 2005 aug;41(8):1045-8.