Hinokitiol (β-thujaplicin) is a natural

monoterpenoid Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen funct ...

found in the wood of trees in the family

Cupressaceae Cupressaceae or the cypress family is a family of conifers. The family includes 27–30 genera (17 monotypic), which include the junipers and redwoods, with about 130–140 species in total. They are monoecious, subdioecious or (rarely) dioecio ...

. It is a

tropolone Tropolone is an organic compound with the chemical formula . It is a pale yellow solid that is soluble in organic solvents. The compound has been of interest to research chemists because of its unusual electronic structure and its role as a liga ...

derivative and one of the

thujaplicin Thujaplicin (isopropyl cycloheptatrienolone) is any of three isomeric tropolone-related natural products that have been isolated from the softwoods of the trees of ''Cupressaceae'' family. These compounds are known for their antibacterial, antifu ...

s. Hinokitiol is used in oral and skin care products, and is a

food additive Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives, such as vinegar ( pickling), salt ( salting), smoke ( smoking) and sugar ( crystallization), have been used f ...

used in

Japan Japan is an island country in East Asia. Located in the Pacific Ocean off the northeast coast of the Asia, Asian mainland, it is bordered on the west by the Sea of Japan and extends from the Sea of Okhotsk in the north to the East China Sea ...

History

Hinokitiol was discovered by a Japanese chemist

Tetsuo Nozoe Tetsuo Nozoe (野副鉄男, 16 May 1902 – 4 April 1996) was a Japanese organic chemist. He is known for the discovery of hinokitiol, a seven-membered aromatic compound, and studying non-benzenoid aromatic compounds. Early life and career Te ...

in 1936. It was isolated from the

essential oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the ...

component of the

heartwood Wood is a structural tissue/material found as xylem in the stems and roots of trees and other woody plants. It is an organic materiala natural composite of cellulosic fibers that are strong in tension and embedded in a matrix of lignin t ...

of '' Taiwanese hinoki'', from which the compound ultimately adopted its name. Hinokitiol is the first non-

benzenoid In organic chemistry, benzenoids are a class of organic compounds with at least one benzene ring. These compounds have increased stability due to resonance in the benzene rings. Most aromatic hydrocarbons are benzenoid. Notable counterexamples are ...

aromatic compound identified. The compound has a heptagonal molecular structure and was first synthesized by

Ralph Raphael Ralph Alexander Raphael (1 January 1921 – 27 April 1998) was a British organic chemist, well known for his use of acteylene derivatives in the synthesis of natural products with biological activity. Early life and education Ralph Raphael w ...

in 1951. Due to its iron-chelating activity, hinokitiol has been called an "Iron Man molecule" in the scientific media, which is ironic because Tetsuo is translated into English as "Iron Man". Taiwanese hinoki is native to

East Asian East Asia is a geocultural region of Asia. It includes China, Japan, Mongolia, North Korea, South Korea, and Taiwan, plus two special administrative regions of China, Hong Kong and Macau. The economies of Economy of China, China, Economy of Ja ...

countries, particularly to

and

Taiwan Taiwan, officially the Republic of China (ROC), is a country in East Asia. The main geography of Taiwan, island of Taiwan, also known as ''Formosa'', lies between the East China Sea, East and South China Seas in the northwestern Pacific Ocea ...

. Hinokitiol has also been found in other trees of the ''

'' family, including ''Thuja plicata'' Donn ex D. Don which is common in the

Pacific Northwest The Pacific Northwest (PNW; ) is a geographic region in Western North America bounded by its coastal waters of the Pacific Ocean to the west and, loosely, by the Rocky Mountains to the east. Though no official boundary exists, the most common ...

. Woods that are rich in hinokitiol were used by people of ancient

for creating long-standing buildings, such as the Konjiki-dō, a japanese national treasure, one of the buildings of

Chūson-ji is a Buddhist temple in the town of Hiraizumi in southern Iwate Prefecture, Japan. It is the head temple of the Tendai sect in Tōhoku region of northern Honshu. The temple claims it was founded in 850 by Ennin, the third chief abbot of the se ...

complex, a temple in

Iwate Prefecture is a Prefectures of Japan, prefecture of Japan located in the Tōhoku region of Honshu. It is the second-largest Japanese prefecture (behind Hokkaido) at , with a population of 1,165,886 (as of July 1, 2023). Iwate Prefecture borders Aomori Pre ...

. It kept it from harm against

insects Insects (from Latin ') are hexapod invertebrates of the class Insecta. They are the largest group within the arthropod phylum. Insects have a chitinous exoskeleton, a three-part body (head, thorax and abdomen), three pairs of jointed ...

, wood-rotting fungi, and molds for a long time of about 840 years. Additionally, there are some old famous Buddhist temples and

Shinto shrines A Stuart D. B. Picken, 1994. p. xxiii is a structure whose main purpose is to house ("enshrine") one or more kami, , the deities of the Shinto religion. The Also called the . is where a shrine's patron is or are enshrined.Iwanami Japanese dic ...

using trees, later known to contain hinokitiol. Beginning in the 2000s, the biological properties of hinokitiol have become of research interest, focusing on its biological properties. And the resistance of

cypress Cypress is a common name for various coniferous trees or shrubs from the ''Cupressus'' genus of the '' Cupressaceae'' family, typically found in temperate climates and subtropical regions of Asia, Europe, and North America. The word ''cypress'' ...

trees to

wood decay A wood-decay or xylophagous fungus is any species of fungus that digests moist wood, causing it to rot. Some species of wood-decay fungi attack dead wood, such as ''Serpula lacrymans'', and some, such as ''Armillaria'' (honey fungus), are paras ...

was the leading reason prompting to study their chemical content and to find the substances responsible for those properties.

Natural occurrence

Hinokitiol has been found in the heartwood of the conifer trees of the ''

'' family, including ''

Chamaecyparis obtusa ''Chamaecyparis obtusa'' (Japanese cypress, hinoki cypress or hinoki; or , ) is a species of cypress native to central Japan in East Asia, and widely cultivated in the temperate climate, temperate northern hemisphere for its high-quality timber ...

'' (Hinoki cypress), ''

Thuja plicata ''Thuja plicata'' is a large evergreen coniferous tree in the family Cupressaceae, native to the Pacific Northwest of North America. Its common name is western redcedar in the U.S. or western red cedar in the UK, and it is also called pacific re ...

'' (Western red cedar), ''Thujopsis dolabrata'' var. ''hondai'' (Hinoki asunaro), ''

Juniperus cedrus ''Juniperus cedrus'', the Canary Islands juniper, is a species of juniper, native to the western Canary Islands (Tenerife, La Palma, Gran Canaria, Gomera) and Madeira (''J. cedrus'' Webb & Berthel. subsp. ''maderensis'' (Menezes) Rivas Mart ''et ...

'' (Canary Islands juniper), ''

Cedrus atlantica ''Cedrus atlantica'', the Atlas cedar, is a species of tree in the pine family Pinaceae, native to the Rif and Atlas Mountains of Morocco ( Middle Atlas, High Atlas), and to the Tell Atlas in Algeria.Gaussen, H. (1964). Genre ''Cedrus''. Les F ...

'' (Atlas cedar), ''

Cupressus lusitanica ''Hesperocyparis lusitanica'', the Mexican cypress, cedar-of-Goa or Goa cedar, is a species of Cupressaceae, cypress native to Mexico and Central America (Guatemala, El Salvador and Honduras). It has also been introduced to Belize, Costa Rica a ...

'' (Mexican white cedar), ''

Chamaecyparis lawsoniana ''Chamaecyparis lawsoniana'', known as Port Orford cedar or Lawson's cypress, is a species of conifer in the genus ''Chamaecyparis'', family Cupressaceae. It is native to Oregon and northwestern California, and grows from sea level up to in the ...

'' (Port Orford cedar), ''

Chamaecyparis taiwanensis ''Chamaecyparis taiwanensis'' (Taiwan cypress; ) is a species of cypress, native to the mountains of Taiwan, where it grows at altitudes of 1300–2800 m.Rushforth, K. (1987). ''Conifers''. Helm . Description It is a slow-growing coniferous tree ...

'' (Taiwan cypress), ''

Chamaecyparis thyoides ''Chamaecyparis thyoides'' (Atlantic white cedar, Atlantic white cypress, southern white cedar, whitecedar, or false-cypress), a species of ''Cupressaceae'', is native to the Atlantic coast of North America and is found from southern Maine to Geo ...

'' (Atlantic white cedar), ''

Cupressus arizonica ''Hesperocyparis arizonica'', the Arizona cypress, is a North American species of tree in the cypress family Cupressaceae, native species, native to the southwestern United States and Mexico. Populations may be scattered rather than in large, den ...

'' (Arizona cypress), ''

Cupressus macnabiana ''Hesperocyparis macnabiana'' (MacNab cypress or Shasta cypress) is a species of western cypress in from California that was previously named ''Cupressus macnabiana''. Distribution ''Hesperocyparis macnabiana'' is endemic to northern California ...

'' (MacNab cypress), ''

Cupressus macrocarpa ''Hesperocyparis macrocarpa'' also known as ''Cupressus macrocarpa'', or the Monterey cypress is a coniferous tree, and is one of several species of Cupressaceae, cypress trees native to California. The Monterey cypress is found naturally only ...

'' (Monterey cypress), ''

Juniperus chinensis ''Juniperus chinensis'', the Chinese juniper, is a species of plant in the cypress family Cupressaceae, native to China, Myanmar, Japan, Korea and the Russian Far East. Growing tall, it is a very variable coniferous evergreen tree or shrub. ...

'' (Chinese juniper), ''

Juniperus communis ''Juniperus communis'', the common juniper, is a species of small tree or shrub in the cypress family Cupressaceae. An evergreen conifer, it has the largest geographical range of any woody plant, with a circumpolar distribution throughout the coo ...

'' (Common juniper), ''

Juniperus californica ''Juniperus californica'', the California juniper, is a species of juniper native to southwestern North America. Description ''Juniperus californica'' is a shrub or small tree reaching , but rarely up to tall. The bark is ashy gray, typically t ...

'' (California juniper), ''

Juniperus occidentalis ''Juniperus occidentalis'', known as the western juniper, is a shrub or tree native to the Western United States, growing in mountains at altitudes of and rarely down to . It is listed as Least Concern on the IUCN Red List because it is a widesp ...

'' (Western juniper), ''

Juniperus oxycedrus ''Juniperus oxycedrus'', vernacularly called Cade, cade juniper, prickly juniper, prickly cedar, or sharp cedar, is a species of juniper, native across the Mediterranean region, growing on a variety of rocky sites from sea level. The specific ep ...

'' (Cade), ''

Juniperus sabina ''Juniperus sabina'', the savin juniper or savin, is a species of juniper native to the mountains of central and southern Europe and western and central Asia, from Spain to eastern Siberia, typically growing at altitudes of .Farjon, A. (2005). ' ...

'' (Savin juniper), ''

Calocedrus decurrens ''Calocedrus decurrens'', with the common names incense cedar and California incense cedar (syn. ''Libocedrus decurrens'' Torr.), is a species of coniferous tree native to western North America. It is the most widely known species in the genus, ...

'' (California incense-cedar), ''

Calocedrus formosana ''Calocedrus formosana'' (syn. ''C. macrolepis'' var. ''formosana'' (Florin) W.C.Cheng & L.K.Fu; Taiwan Incense-cedar; or ) is a conifer endemic (biology), endemic to Taiwan.Farjon, A. (2005). ''Monograph of Cupressaceae and Sciadopitys''. Royal ...

'' (Taiwan incense-cedar), '' Platycladus orientalis'' (Chinese thuja), ''

Thuja occidentalis ''Thuja occidentalis'', also known as northern white-cedar, eastern white-cedar, or arborvitae, is an evergreen coniferous tree, in the cypress family Cupressaceae, which is native to eastern Canada and much of the north-central and northeastern ...

'' (Northern white-cedar), ''

Thuja standishii ''Thuja standishii'' (Japanese thuja; Japanese: , ) is a species of thuja, an evergreen coniferous tree in the cypress family Cupressaceae. It is native to southern Japan, where it occurs on the islands of Honshū and Shikoku. It is a medium-size ...

'' (Japanese thuja), ''

Tetraclinis articulata ''Tetraclinis'' (also called arar, araar or Sictus tree) is a genus of evergreen coniferous trees in the cypress family Cupressaceae, containing only one species, ''Tetraclinis articulata'', also known as Thuja articulata, Its concentration in the trees are 0.1-0.2% in ''

'' (2 mg of hinokitiol per 1 g of dry sawdust), 0.04% in ''

'' and '' Thujopsis dolabrata'' var. ''hondai'' (0.4 mg of hinokitiol per 1 g of dry sawdust), and 0.02% in ''

'' (0.2 mg of hinokitiol per 1 g of dry sawdust). There are three naturally found

s: α-thujaplicin, β-thujaplicin (hinokitiol) and γ-thujaplicin. Hinokitiol is the most common isomer and it appears to be the only isomer that exerts all biological activities attributed to thujaplicins.

Chemical synthesis

There are different pathways to synthesize thujaplicins. Hinokitiol, as other thujaplicins, can be synthesized by

cycloaddition In organic chemistry, a cycloaddition is a chemical reaction in which "two or more Unsaturated hydrocarbon, unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of th ...

of isopropyl

cyclopentadiene Cyclopentadiene is an organic compound with the chemical formula, formula C5H6. It is often abbreviated CpH because the cyclopentadienyl anion is abbreviated Cp−. This colorless liquid has a strong and unpleasant odor. At room temperature, ...

and dichloro ketene, 1,3-dipolar cycloaddition of 5-isopropyl-1-methyl-3-oxidopyridinium, ring expansion of 2-isopropylcyclohexanone, regiocontrolled

hydroxylation In chemistry, hydroxylation refers to the installation of a hydroxyl group () into an organic compound. Hydroxylations generate alcohols and phenols, which are very common functional groups. Hydroxylation confers some degree of water-solubility ...

of oxyallyl (4+3) cycloadducts, regioselectively from (''R'')-(+)-

limonene Limonene () is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the essential oil of citrus fruit peels. The (+)-isomer, occurring more commonly in nature as the fragrance of oranges, ...

, and from troponeirontricarbonyl complex. Hinokitiol can also be isolated through plant cell suspension cultures, or readily extracted from the wood with chemical

solvents A solvent (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for p ...

and ultrasonication. (1) Synthesis of hinokitiol from troponeirontricarbonyl complex: Biosynthesis of beta-thujaplicin from troponeirontricarbonyl complex

Biosynthesis of beta-thujaplicin from troponeirontricarbonyl complex

(2) Synthesis of hinokitiol by electro-reductive alkylation of substituted cycloheptatrienes: Biosynthesis of beta-thujaplicin through electroreductive alkylation

Biosynthesis of beta-thujaplicin through electroreductive alkylation

(3) Synthesis of hinokitiol through ring expansion of 2-isopropylcyclohexanone: Biosynthesis of beta-thujaplicin from 2-isopropylcyclohexanone

Biosynthesis of beta-thujaplicin from 2-isopropylcyclohexanone

(4) Synthesis of hinokitiol through oxyallyl cation +3cyclization (Noyori's synthesis):

Chemistry

Hinokitiol is a

derivative containing an unsaturated seven-membered carbon ring. It is a

– cyclohepta-2,4,6-trien-1-one substituted by a

hydroxy group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

at position 2 and an

isopropyl group In organic chemistry, a propyl group is a three-carbon alkyl substituent with chemical formula for the linear form. This substituent form is obtained by removing one hydrogen atom attached to the terminal carbon of propane. A propyl substituent ...

at position 4. It is a

enol In organic chemistry, enols are a type of functional group or intermediate in organic chemistry containing a group with the formula (R = many substituents). The term ''enol'' is an abbreviation of ''alkenol'', a portmanteau deriving from "-ene ...

and a cyclic

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

. 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.

Ionophore

Hinokitiol, as other

s, reversibly binds metal ions (i.e. Zn²⁺, Fe²⁺, Cu²⁺, Co²⁺, Mn²⁺, Ag²⁺) and form complex

salts In chemistry, a salt or ionic compound is a chemical compound consisting of an assembly of positively charged ions ( cations) and negatively charged ions (anions), which results in a compound with no net electric charge (electrically neutral). ...

. It is considered as a broad-spectrum metallophore, and an efficient

iron Iron is a chemical element; it has symbol Fe () and atomic number 26. It is a metal that belongs to the first transition series and group 8 of the periodic table. It is, by mass, the most common element on Earth, forming much of Earth's o ...

chelating agent Chelation () is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These l ...

. The iron complex with hinokitiol with the formula (C₁₀H₁₁O₂)₃Fe is called hinokitin.

Hinoki ''Chamaecyparis obtusa'' (Japanese cypress, hinoki cypress or hinoki; or , ) is a species of cypress native to central Japan in East Asia, and widely cultivated in the temperate northern hemisphere for its high-quality timber and ornamental qu ...

oil is rich in hinokitin which has an appearance of dark red crystals. The complexes made of iron and tropolones display high thermodynamic stability and has shown to have a stronger binding constant than the transferrin-iron complex. It is believed that metal-binding activity may be the principal mechanism of action underlying the most part of its biological activities, especially binding iron, zinc, and copper ions. By binding different metal ions and serving as an

ionophore In chemistry, an ionophore () is a chemical species that reversibly binds ions. Many ionophores are lipid-soluble entities that transport ions across the cell membrane. Ionophores catalyze ion transport across hydrophobic membranes, such as l ...

, it accelerates the intracellular uptake of those ions and increases their intracellular levels, thus influencing on different biological activities. It is shown that a synergistic effect in some biological activities and settings may occur when ionophores are combined with the ions they bind. As an ionophore, its molecule has an hydrophilic center and a hydrophobic part. The hydrophobic part interacts with biological membranes. The hydrophilic center binds metal ions and form ionophore-ion complexes.

Biological properties

Hinokitiol and other

s have been mainly investigated in ''in-vitro'' studies and animal models for their possible biological properties, such as antimicrobial, antifungal, antiviral, antiproliferative, anti-inflammatory, antiplasmodial effects. However, no evidence exists from clinical studies to support these findings. It has also shown to have insecticidal, pesticidal and antibrowning effects. The vast majority of these properties are thought to be due to the metal ion-binding activity. Hinokitiol appeared to exert all ''in-vitro'' activities attributed to thujaplicins. Hinokitiol has been shown to possess inhibitory effects on ''

Chlamydia trachomatis ''Chlamydia trachomatis'' () is a Gram-negative, Anaerobic organism, anaerobic bacterium responsible for Chlamydia infection, chlamydia and trachoma. ''C. trachomatis'' exists in two forms, an extracellular infectious elementary body (EB) and an ...

'' and may be clinically useful as a topical drug.

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.

Uses

Skin and oral care products

Hinokitiol is used in a range of consumer products intended for skin care, such as

soap Soap is a salt (chemistry), salt of a fatty acid (sometimes other carboxylic acids) used for cleaning and lubricating products as well as other applications. In a domestic setting, soaps, specifically "toilet soaps", are surfactants usually u ...

s, skin lotions, eyelid cleanser,

shampoos Shampoo () is a hair care product, typically in the form of a Viscosity, viscous liquid, that is formulated to be used for cleaning (scalp) hair. Less commonly, it is available in solid bar format. ("Dry shampoo" is a separate product.) Shamp ...

and hair tonics; for oral care, such as

toothpaste Toothpaste is a paste or gel dentifrice that is used with a toothbrush to clean and maintain the aesthetics of Human tooth, teeth. Toothpaste is used to promote oral hygiene: it is an abrasive that aids in removing dental plaque and food from th ...

s, breath sprays. In April 2020, Advance Nanotek, an Australian producer of zinc oxide, filed a joint patent application with AstiVita Limited, for an anti-viral composition that included oral care products.

Insect repellent

Hinokitiol is found to have

insecticidal Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, in ...

and pesticidal activities against crop-damaging

termite Termites are a group of detritivore, detritophagous Eusociality, eusocial cockroaches which consume a variety of Detritus, decaying plant material, generally in the form of wood, Plant litter, leaf litter, and Humus, soil humus. They are dist ...

s (''

Reticulitermes speratus ''Reticulitermes speratus'', the Japanese termite, is a species of subterranean termite found in Japan, North Korea, and South Korea. It eats decayed wood. It is adapted to withstand the cold temperatures of the temperate regions it inhabits. T ...

'', ''

Coptotermes formosanus ''Coptotermes'' is a genus of termites in the family Heterotermitidae. Many of the roughly 71 species are economically destructive pests. The genus is thought to have originated in Southeast Asia. Worker termites from this genus forage undergroun ...

'') and beetles (''

Lasioderma serricorne ''Lasioderma serricorne'', more commonly referred to as the cigarette beetle, cigar beetle, or tobacco beetle, is a small beetle that shares a resemblance with the drugstore beetle (''Stegobium paniceum)'' and the common furniture beetle (''Anobi ...

'', ''

Callosobruchus chinensis ''Callosobruchus chinensis'', also known as the adzuki bean weevil, pulse beetle, Chinese bruchid or cowpea bruchid, is a common species of beetle found in the bean weevil subfamily. Although it is commonly known as the "adzuki bean weevil" it i ...

''). It has also shown to act against certain mites (''

Dermatophagoides farinae ''Dermatophagoides farinae'', the American house dust mite, is one of the best-known species of house dust mite.Tyrophagus putrescentiae ''Tyrophagus putrescentiae'' is a cosmopolitan mite species. Together with the related species '' T. longior'', it is commonly referred to as the mould mite or the cheese mite. The genus name translates from Greek to "cheese eater." Ecology In t ...

'') and mosquito larvae (''

Aedes aegypti ''Aedes aegypti'' ( or from Greek 'hateful' and from Latin, meaning 'of Egypt'), sometimes called the Egyptian mosquito, dengue mosquito or yellow fever mosquito, is a mosquito that spreads diseases like dengue fever, yellow fever, malar ...

'', ''

Culex pipiens ''Culex pipiens'' is a species of mosquito commonly referred to as the common house mosquito or northern house mosquito. Native to Africa, Asia and Europe, it is now widely distributed in temperate regions on every continent except Antarctica an ...

''). Hinokitiol is supplemented in commercial tick and

insect repellent An insect repellent (also commonly called "bug spray" or "bug deterrent") is a substance applied to the skin, clothing, or other surfaces to discourage insects (and arthropods in general) from landing or climbing on that surface. Insect repellent ...

Food preservative

In experimental studies hinokitiol has been shown to act against ''

Botrytis cinerea ''Botrytis cinerea'' is a necrotrophic fungus that affects many plant species, although its most notable hosts may be wine grapes. In viticulture, it is commonly known as "botrytis bunch rot"; in horticulture, it is usually called "grey mould" ...

'', a necrotrophic fungus causing gray mold in many plant species and known to damage

horticultural Horticulture (from ) is the art and science of growing fruits, vegetables, flowers, trees, shrubs and ornamental plants. Horticulture is commonly associated with the more professional and technical aspects of plant cultivation on a smaller and mo ...

crop A crop is a plant that can be grown and harvested extensively for profit or subsistence. In other words, a crop is a plant or plant product that is grown for a specific purpose such as food, Fiber, fibre, or fuel. When plants of the same spe ...

s. Thus it has been suggested to be used for post-harvest

waxing Waxing is the process of hair removal from the root by using a covering of a sticky substance, such as wax, to adhere to body hair, and then removing this covering and pulling out the hair from the follicle. New hair will not grow back in the pr ...

to prevent post-harvest decay. Hinokitiol is a registered

in Japan. Hinokitiol appears to suppress

food browning Browning is the process of food turning brown due to the chemical reactions that take place within. The process of browning is one of the chemical reactions that take place in food chemistry and represents an interesting research topic regarding ...

through inhibiting browning enzymes, particularly tyrosinase and other

polyphenol oxidase Polyphenol oxidase (PPO; also polyphenol oxidase i, chloroplastic), an enzyme involved in fruit browning, is a tetramer that contains four atoms of copper per molecule. PPO may accept monophenols and/or ''o''-diphenols as substrates. The ...

s by chelating

copper Copper is a chemical element; it has symbol Cu (from Latin ) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pinkish-orang ...

ions. This effect has been shown on different vegetables, fruits, mushrooms, flowers, plants, other agricultural products and seafood. Due to the latter effects, hinokitiol is used in

food packaging Food packaging is a packaging system specifically designed for food and represents one of the most important aspects among the processes involved in the food industry, as it provides protection from chemical, biological and physical alterations ...

as a

shelf-life Shelf life is the length of time that a commodity may be stored without becoming unfit for use, consumption, or sale. In other words, it might refer to whether a commodity should no longer be on a pantry shelf (unfit for use), or no longer on a s ...

extending agent.

Wood preservative

Hinokitiol is one of the chemical compounds isolated from trees, known as '' extractives'', responsible for natural durability of certain trees. Hinokitiol is found in the

of naturally durable trees belonging to the ''

'' family. These compounds give the wood natural resistance to

decay Decay may refer to: Science and technology * Bit decay, in computing * Decay time (fall time), in electronics * Distance decay, in geography * Software decay, in computing Biology * Decomposition of organic matter * Mitochondrial decay, in g ...

and insect attacks due to their fungicidal, insecticidal and pesticidal activities. Thereby, hinokitiol, as some other natural extractives, is suggested to be used as a

wood preservative Wood preservation refers to any method or process, or even technique, used to protect the wood and extend its service life. Most wood species are susceptible to both biological (''biotic'') and non-biological (''abiotic'') factors that cause d ...

for

timber Lumber is wood that has been processed into uniform and useful sizes (dimensional lumber), including beams and planks or boards. Lumber is mainly used for construction framing, as well as finishing (floors, wall panels, window frames). ...

treatment.

Research directions

Iron transport

Researchers screening a library of small biomolecules for signs of iron transport found that hinokitiol restored cell functionality. Further work by the team suggested a mechanism by which hinokitiol restores or reduces cell iron.

Cancer research

Different ''in-vitro'' studies have investigated the effects of hinokitiol on various tumor

cell line An immortalised cell line is a population of cells from a multicellular organism that would normally not proliferate indefinitely but, due to mutation, have evaded normal cellular senescence and instead can keep undergoing division. The cells ...

References

External links

Hinokitiol
at

PubChem PubChem is a database of Chemistry, chemical molecules and their activities against biological assays. The system is maintained by the National Center for Biotechnology Information (NCBI), a component of the National Library of Medicine, which ...

β-Thujaplicin
at

Sigma-Aldrich Sigma-Aldrich (formally MilliporeSigma) is an American chemical, life science, and biotechnology company owned by the multinational chemical conglomerate Merck Group. Sigma-Aldrich was created in 1975 by the merger of Sigma Chemical Company and ...

Hinokitiol
at ChemicalBook {{Terpenoids Isopropyl compounds Monoterpenes Tropolones Non-benzenoid aromatic carbocycles Ionophores Chelating agents Skin care Oral hygiene Food additives Preservatives Wood extracts Tree-derived bioactive compounds

History

Natural occurrence

Chemical synthesis

Chemistry

Ionophore

Biological properties

Safety

Uses

Skin and oral care products

Insect repellent

Food preservative

Wood preservative

Research directions

Iron transport

Cancer research

See also

References

External links