4-Hexylresorcinol

Синонимы: 4-Hexylresorcinol, 4-Hexyl-1,3-benzenediol, 1,3-Benzenediol, 4-hexyl-, 136-77-6, HX-4, Resorcinol 4-hexyl

4-Hexylresorcinol is an alkylresorcinol featuring a hexyl chain at the 4-position of a resorcinol core. This amphiphilic structure—a polar dihydroxybenzene head and a nonpolar alkyl tail—underpins its interfacial activity, enabling interactions with lipid bilayers and proteins. The molecule is a potent inhibitor of polyphenol oxidase (tyrosinase) and exhibits broad-spectrum antimicrobial and anthelmintic properties, making it valuable in pharmaceutical, cosmetic, and food preservation applications.

Industrially, 4-Hexylresorcinol is produced via Friedel-Crafts alkylation of resorcinol with hexanol or hexene, followed by purification. It is supplied as a white to off-white crystalline powder with a purity of ≥99.0% (HPLC). The compound is stable under normal storage conditions but should be protected from light and moisture.

Key applications include its use as an anti-browning agent in fresh-cut produce, an active ingredient in anti-dandruff and oral care formulations, and a model compound in enzymatic browning studies. Its efficacy at low concentrations and favorable safety profile (GRAS status for certain uses) drive demand in the food and personal care industries.

Chemical Structure & Properties

The resorcinol moiety provides two phenolic hydroxyl groups that can participate in hydrogen bonding and redox reactions, while the hexyl chain enhances lipophilicity (logP ~3.5). This balance dictates its solubility profile and membrane affinity. The compound exists as a crystalline solid with a melting point around 66 °C and is typically assayed by HPLC or titration.

Механизм действия

• Tyrosinase inhibition: Competitively inhibits polyphenol oxidase, preventing enzymatic browning in foods and pigmentation in cosmetic applications.
• Antimicrobial activity: Disrupts microbial cell membranes and inhibits spore germination, effective against bacteria, fungi, and yeasts.
• Anthelmintic action: Interferes with energy metabolism in helminths, historically used in veterinary medicine.
• Antioxidant properties: Scavenges free radicals via phenolic hydroxyl groups, contributing to its preservative effects.

Quality Specifications

Supply & Documentation

• Capacity: 20 metric tons per year
• Срок выполнения заказа: 3–5 рабочих дней (товары, имеющиеся в наличии)
• Documentation: COA, MSDS, TDS available upon request
• Packaging: 25 kg fiber drum with inner polyethylene bag

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