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Questions And Answer

• Preparation

  1. Synthesis from methoxycycloheptatriene via isopropylcycloheptatrienone and aminoisopropylcycloheptatrienone. 2. Synthesis of Hinokitiol from carvone via a six-step reaction including epoxidation and acetalization. 3. Conversion of isopropylcyclohexanone or isopropylcyclohexenone to hydroxynitriles, followed by two steps to prepare isopropylcycloheptatrienone, and then oxidation, bromination, and dehydrobromination. 4. Reaction of brominated cycloheptatrienone with an organic compound, followed by catalytic hydrogenation. 5. Addition of cyclopentadiene to a dichloroenone to prepare isopropylcyclopentadiene, followed by solvation, and then a three-step reaction to synthesize Hinokitiol. The first four methods have too many steps or the raw materials are difficult to obtain, making industrial production impractical. Therefore, recent research has mainly focused on the fifth synthetic method.;

• Chemical Properties

  Hinokitiol is a tropolone derivative containing an unsaturated seven-membered carbon ring. It is a monoterpenoid – cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. It is a enol and a cyclic ketone. It derives from a hydride of a cyclohepta-1,3,5-triene. Thujaplicins are soluble in organic solvents and aqueous buffers.Hinokitiol provides acetone on vigorous oxidation and gives the saturated monocyclic diol upon catalytic hydrogenation.It is stable to alkali and acids, forming salts or remaining unchanged, but does not convert to catechol derivatives. Hinokitiol, as other thujaplicins and tropolones, reversibly binds metal ions. It forms complex salts with metal ions.;

• benefits

  Hinokitiol (β-thujaplicin) is a naturally occurring antioxidant, found in the heartwood of certain plants. It acts as a metal chelator and, also, enhances the activity of superoxide dismutase (Huang et al., 2015). It was found to be very protective in the assay. It has not been previously studied as a HC protectant. In addition to its antioxidant properties, hinokitiol has been shown to reduce inflammation via suppression of NFκB, and metalloproteinases, and to activate caspase 3. The former activities could contribute to its protective effect.
  Hinokitiol is a superpower ingredient that has anti-inflammatory, antioxidant, antibacterial, anti-fungal and anti-melanogenic properties. Best of all, hinokitiol is as gentle as it is powerful. Hinokitiol’s properties allow it to target the inflammatory redness and blemishes seen in rosacea and acne. Hinokitiol is effective against P. acnes bacteria, and there is no known acquired resistance to it, unlike other prescription antibiotics.;

• Safety

  The safety of hinokitiol has been tested in rats and no carcinogenic effect to rats was found.In 2006, hinokitiol was categorized under the Domestic substances list (DSL) in Canada as non-persistent, non-bioaccumulative and non-toxic to aquatic organisms.;

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