Monoterpenes are a class of

terpene Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n > 1. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes ar ...

s that consist of two

isoprene Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. Isoprene is an unsaturated hydrocarbon. It is produced by many plants and animals ...

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 functionality or missing a methyl group, are called monoterpenoids. Monoterpenes and monoterpenoids are diverse. They have relevance to the pharmaceutical, cosmetic, agricultural, and food industries.

Biosynthesis

Monoterpenes are derived biosynthetically from units of

isopentenyl pyrophosphate Isopentenyl pyrophosphate (IPP, isopentenyl diphosphate, or IDP) is an isoprenoid precursor. IPP is an intermediate in the classical, HMG-CoA reductase pathway (commonly called the mevalonate pathway) and in the ''non-mevalonate'' MEP pathway of ...

, which is formed from

acetyl-CoA Acetyl-CoA (acetyl coenzyme A) is a molecule that participates in many biochemical reactions in protein, carbohydrate and lipid metabolism. Its main function is to deliver the acetyl group to the citric acid cycle (Krebs cycle) to be oxidized for ...

via the intermediacy of

mevalonic acid Mevalonic acid (MVA) is a key organic compound in biochemistry; the name is a contraction of dihydroxymethylvalerolactone. The carboxylate anion of mevalonic acid, which is the predominant form in biological environments, is known as ''mevalonate ...

in the

HMG-CoA reductase pathway The mevalonate pathway, also known as the isoprenoid pathway or HMG-CoA reductase pathway is an essential metabolic pathway present in eukaryotes, archaea, and some bacteria. The pathway produces two five-carbon building blocks called isopenten ...

. An alternative, unrelated biosynthesis pathway of IPP is known in some bacterial groups and the plastids of plants, the so-called MEP-(2-methyl-D-erythritol-4-phosphate) pathway, which is initiated from C₅ sugars. In both pathways, IPP is isomerized to DMAPP by the enzyme isopentenyl pyrophosphate isomerase. Geranyl pyrophosphate is the precursor to monoterpenes (and hence monoterpenoids). Elimination of the pyrophosphate group from geranyl pyrophosphate leads to the formation of acyclic monoterpenes such as

ocimene Ocimenes are a group of isomeric hydrocarbons. The ocimenes are monoterpenes found within a variety of plants and fruits. α-Ocimene and the two β-ocimenes differ in the position of the isolated double bond: it is terminal in the alpha isomer. ...

and the

myrcene Myrcene, or β-myrcene, is a monoterpene. A colorless oil, it occurs widely in essential oils. It is produced mainly semi-synthetically from '' Myrcia'', from which it gets its name. It is an intermediate in the production of several fragrances. � ...

s. Hydrolysis of the phosphate groups leads to the prototypical acyclic monoterpenoid

geraniol Geraniol is a monoterpenoid and an alcohol. It is the primary component of citronella oil and is a primary component of rose oil, palmarosa oil. It is a colorless oil, although commercial samples can appear yellow. It has low solubility in water ...

. Additional rearrangements and oxidations provide compounds such as

citral Citral is an acyclic monoterpene aldehyde, and being a monoterpene, it is made of two isoprene units. Citral is a collective term which covers two geometric isomers that have their own separate names; the ''E''-isomer is named geranial (''trans ...

citronellal Citronellal or rhodinal ( C10 H18 O) is a monoterpenoid aldehyde, the main component in the mixture of terpenoid chemical compounds that give citronella oil its distinctive lemon scent. Citronellal is a main isolate in distilled oils from the pl ...

citronellol Citronellol, or dihydrogeraniol, is a natural acyclic monoterpenoid. Both enantiomers occur in nature. (+)-Citronellol, which is found in citronella oils, including ''Cymbopogon nardus'' (50%), is the more common isomer. (−)-Citronellol is w ...

linalool Linalool () refers to two enantiomers of a naturally occurring terpene alcohol found in many flowers and spice plants. Linalool has multiple commercial applications, the majority of which are based on its pleasant scent (floral, with a touch of ...

, and many others. Many monoterpenes found in marine organisms are

halogen The halogens () are a group in the periodic table consisting of five or six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts). In the modern IUPAC nomenclature, this group is ...

ated, such as

halomon Halomon is a polyhalogenated monoterpene first isolated from the marine red algae '' Portieria hornemannii''. Halomon has attracted research interest because of its promising profile of selective cytotoxicity that suggests its potential use as ...

Main examples

Myrcen.png,

Myrcene Myrcene, or β-myrcene, is a monoterpene. A colorless oil, it occurs widely in essential oils. It is produced mainly semi-synthetically from '' Myrcia'', from which it gets its name. It is an intermediate in the production of several fragrances. � ...

is an acyclic monoterpene, an

alkene In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...

hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ex ...

Menthol_skeletal.svg,

Menthol Menthol is an organic compound, more specifically a monoterpenoid, made synthetically or obtained from the oils of corn mint, peppermint, or other mints. It is a waxy, clear or white crystalline substance, which is solid at room temperature and ...

is a monocyclic monoterpenoid Limonene-2D-skeletal.svg,

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

is a monocyclic monoterpene Carvone.svg,

Carvone Carvone is a member of a family of chemicals called terpenoids. Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway (''Carum carvi''), spearmint (''Mentha spicata''), and dill. Uses Both carvo ...

is a monoterpenoid Beta-thujaplicin.png,

Hinokitiol Hinokitiol (β-thujaplicin) is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins. Hinokitiol is used in oral and skin care products, and is a food additive used ...

is a monoterpenoid, 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 ligan ...

derivative Linalool_skeletal.svg,

Linalool Linalool () refers to two enantiomers of a naturally occurring terpene alcohol found in many flowers and spice plants. Linalool has multiple commercial applications, the majority of which are based on its pleasant scent (floral, with a touch of ...

is an acyclic monoterpenoid Bicyclic monoterpenes include

carene 3-Carene is a bicyclic monoterpene consisting of fused cyclohexene and cyclopropane rings. It occurs as a constituent of turpentine, with a content as high as 42% depending on the source. Carene has a sweet and pungent odor, best described as a c ...

sabinene Sabinene is a natural bicyclic monoterpene with the molecular formula C10H16. It is isolated from the essential oils of a variety of plants including Marjoram, holm oak (''Quercus ilex'') and Norway spruce (''Picea abies''). It has a strained ...

camphene Camphene is a bicyclic organic compound. It is one of the most pervasive monoterpenes. As for other terpenes, it is insoluble in water, flammable, colorless, and has a pungent smell. It is a minor constituent of many essential oils such as tur ...

, and

thujene Thujene (or α-thujene) is a natural organic compound classified as a monoterpene. It is found in the essential oils of a variety of plants, and contributes pungency to the flavor of some herbs such as Summer savory.''PDR for Herbal Medicines'', ...

Camphor Camphor () is a waxy, colorless solid with a strong aroma. It is classified as a terpenoid and a cyclic ketone. It is found in the wood of the camphor laurel ('' Cinnamomum camphora''), a large evergreen tree found in East Asia; and in the k ...

borneol Borneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an '' endo'' position. The exo diastereomer is called isoborneol. Being chiral, borneol exists as enantiomers, both of which are foun ...

eucalyptol Eucalyptol is a monoterpenoid. A colorless liquid, it is a bicyclic ether. Eucalyptol has a fresh mint-like smell and a spicy, cooling taste. It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up ~70% - 90% of eucaly ...

and

ascaridole Ascaridole is a natural organic compound classified as a bicyclic monoterpenoid that has an unusual bridging peroxide functional group. It is a colorless liquid with a pungent smell and taste that is soluble in most organic solvents. Like other lo ...

are examples of bicyclic monoterpenoids containing ketone, alcohol, ether, and bridging

peroxide In chemistry, peroxides are a group of compounds with the structure , where R = any element. The group in a peroxide is called the peroxide group or peroxo group. The nomenclature is somewhat variable. The most common peroxide is hydrogen p ...

functional groups, respectively.

Umbellulone Umbellulone is a headache-inducing monoterpene ketone found in the leaves of the tree ''Umbellularia californica'', sometimes known as the "headache tree". It is hypothesized to cause headaches by influencing the trigeminovascular system via TRPA ...

is another example of bicyclic monoterpene ketone.

Natural roles

Monoterpenes are found in many parts of different plants, such as

barks Barks may refer to: * Carl Barks (1901 – 2000) was an American cartoonist, author, and painter * Coleman Barks (b. 1937), an American poet, and former literature faculty at the University of Georgia * Samantha Barks (b. 1990), a Manx actress and ...

heartwood Wood is a porous and fibrous structural tissue found in the stems and roots of trees and other woody plants. It is an organic materiala natural composite of cellulose fibers that are strong in tension and embedded in a matrix of lignin tha ...

, bark and leaves of coniferous trees, in

vegetable Vegetables are parts of plants that are consumed by humans or other animals as food. The original meaning is still commonly used and is applied to plants collectively to refer to all edible plant matter, including the flowers, fruits, stems, ...

fruit In botany, a fruit is the seed-bearing structure in flowering plants that is formed from the ovary after flowering. Fruits are the means by which flowering plants (also known as angiosperms) disseminate their seeds. Edible fruits in particu ...

s and

herb In general use, herbs are a widely distributed and widespread group of plants, excluding vegetables and other plants consumed for macronutrients, with savory or aromatic properties that are used for flavoring and garnishing food, for medicinal ...

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 o ...

s are very rich in monoterpenes. Several monoterpenes produced by trees, such as

hinokitiol Hinokitiol (β-thujaplicin) is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins. Hinokitiol is used in oral and skin care products, and is a food additive used ...

, and

have

fungicidal Fungicides are biocidal chemical compounds or biological organisms used to kill parasitic fungi or their spores. A fungistatic inhibits their growth. Fungi can cause serious damage in agriculture, resulting in critical losses of yield, quality, ...

and

antibacterial An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of ...

activities and participate in wound healing. Some of these compounds are produced to protect the trees from

insect Insects (from Latin ') are pancrustacean 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 ...

attacks. Monoterpenes are emitted by

forest A forest is an area of land dominated by trees. Hundreds of definitions of forest are used throughout the world, incorporating factors such as tree density, tree height, land use, legal standing, and ecological function. The United Nations' ...

s and form

aerosol An aerosol is a suspension (chemistry), suspension of fine solid particles or liquid Drop (liquid), droplets in air or another gas. Aerosols can be natural or Human impact on the environment, anthropogenic. Examples of natural aerosols are fog o ...

s that are proposed to serve as

cloud condensation nuclei Cloud condensation nuclei (CCNs), also known as cloud seeds, are small particles typically 0.2 µm, or one hundredth the size of a cloud droplet. CCNs are a unique subset of aerosols in the atmosphere on which water vapour condenses. This c ...

(CCN). Such aerosols can increase the brightness of clouds and cool the climate. Many monoterpenes have unique smell and flavor. For example,

contributes to the

spicy Pungency () refers to the taste of food commonly referred to as spiciness, hotness or heat, found in foods such as chili peppers. Highly pungent tastes may be experienced as unpleasant. The term piquancy () is sometimes applied to foods with a l ...

taste of

black pepper Black pepper (''Piper nigrum'') is a flowering vine in the family Piperaceae, cultivated for its fruit, known as a peppercorn, which is usually dried and used as a spice and seasoning. The fruit is a drupe (stonefruit) which is about in diame ...

3-carene 3-Carene is a bicyclic monoterpene consisting of fused cyclohexene and cyclopropane rings. It occurs as a constituent of turpentine, with a content as high as 42% depending on the source. Carene has a sweet and pungent odor, best described as a ...

gives

cannabis ''Cannabis'' () is a genus of flowering plants in the family Cannabaceae. The number of species within the genus is disputed. Three species may be recognized: ''Cannabis sativa'', '' C. indica'', and '' C. ruderalis''. Alternatively ...

an earthy taste and smell,

has a lemon-like pleasant odor and contributes to the distinctive smell of

citrus ''Citrus'' is a genus of flowering plant, flowering trees and shrubs in the rue family, Rutaceae. Plants in the genus produce citrus fruits, including important crops such as Orange (fruit), oranges, Lemon, lemons, grapefruits, pomelos, and lim ...

fruits, and

and

carvacrol Carvacrol, or cymophenol, C6H3(CH3)(OH)C3H7, is a monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano. Natural occurrence Carvacrol is present in the essential oil of ''Origanum vulgare'' (oregano), oil of thyme, oil ob ...

are responsible for the

pungent Pungency () refers to the taste of food commonly referred to as spiciness, hotness or heat, found in foods such as chili peppers. Highly pungent tastes may be experienced as unpleasant. The term piquancy () is sometimes applied to foods with a l ...

flavors of

summer savory Summer savory (''Satureja hortensis'') is among the best known of the savory genus. It is an annual, but otherwise is similar in use and flavor to the perennial winter savory. It is used more often than winter savory, which has a slightly more ...

and

oregano Oregano (, ; ''Origanum vulgare'') is a species of flowering plant in the mint family Lamiaceae. It was native to the Mediterranean region, but widely naturalised elsewhere in the temperate Northern Hemisphere. Oregano is a woody perennial pla ...

, respectively. Monoterpenes are considered

allelochemicals Allelopathy is a biological phenomenon by which an organism produces one or more biochemicals that influence the germination, growth, survival, and reproduction of other organisms. These biochemicals are known as allelochemicals and can have be ...

Uses

Many monoterpenes are volatile compounds and some of them are well-known fragrants found in 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 o ...

s of many plants. For example,

camphor Camphor () is a waxy, colorless solid with a strong aroma. It is classified as a terpenoid and a cyclic ketone. It is found in the wood of the camphor laurel ('' Cinnamomum camphora''), a large evergreen tree found in East Asia; and in the k ...

grapefruit mercaptan Grapefruit mercaptan is the common name for a natural organic compound found in grapefruit. It is a monoterpenoid that contains a thiol (also known as a mercaptan) functional group. Structurally a hydroxy group of terpineol is replaced by the th ...

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

menthol Menthol is an organic compound, more specifically a monoterpenoid, made synthetically or obtained from the oils of corn mint, peppermint, or other mints. It is a waxy, clear or white crystalline substance, which is solid at room temperature and ...

and

pinene Pinene is a collection of unsaturated bicyclic monoterpenes. Two geometric isomers of pinene are found in nature, α-pinene and β-pinene. Both are chiral. As the name suggests, pinenes are found in pines. Specifically, pinene is the major compo ...

s are used in

perfume Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Th ...

s and

cosmetic Cosmetic may refer to: *Cosmetics, or make-up, substances to enhance the beauty of the human body, apart from simple cleaning *Cosmetic, an adjective describing beauty, aesthetics, or appearance, especially concerning the human body *Cosmetic, a t ...

products.

and

perillyl alcohol Perillyl alcohol (IUPAC name: -(prop-1-en-2-yl)cyclohex-1-en-1-ylethanol) and its precursor limonene are naturally occurring monocyclic terpenes derived from the mevalonate pathway in plants. Perillyl alcohol can be found in the essential oils of ...

are used in

cleaning Cleaning is the process of removing unwanted substances, such as dirt, infectious agents, and other impurities, from an object or environment. Cleaning is often performed for aesthetic, hygienic, functional, environmental, or safety purposes. Cl ...

products. Many monoterpenes are used as food

flavor Flavor or flavour is either the sensory perception of taste or smell, or a flavoring in food that produces such perception. Flavor or flavour may also refer to: Science *Flavors (programming language), an early object-oriented extension to Lis ...

s and

food additive Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (salt ...

s, such as

bornyl acetate Bornyl acetate is a chemical compound. Its molecular formula is C12H20O2 and its molecular weight is 196.29 g/mol. It is the acetate ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least o ...

and

thymol Thymol (also known as 2-isopropyl-5-methylphenol, IPMP), , is a natural monoterpenoid phenol derivative of ''p''-Cymene, isomeric with carvacrol, found in oil of thyme, and extracted from ''Thymus vulgaris'' (common thyme), ajwain, and vario ...

are also used in

oral hygiene Oral hygiene is the practice of keeping one's mouth clean and free of disease and other problems (e.g. bad breath) by regular brushing of the teeth (dental hygiene) and cleaning between the teeth. It is important that oral hygiene be carried out ...

products.

Thymol Thymol (also known as 2-isopropyl-5-methylphenol, IPMP), , is a natural monoterpenoid phenol derivative of ''p''-Cymene, isomeric with carvacrol, found in oil of thyme, and extracted from ''Thymus vulgaris'' (common thyme), ajwain, and vario ...

also has

antiseptic An antiseptic (from Greek ἀντί ''anti'', "against" and σηπτικός ''sēptikos'', "putrefactive") is an antimicrobial substance or compound that is applied to living tissue/skin to reduce the possibility of infection, sepsis, or putre ...

and

disinfectant A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than st ...

properties. Volatile monoterpenes produced by plants can attract or repel insects, thus some of them are used in

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

s, such as

and

Ascaridole Ascaridole is a natural organic compound classified as a bicyclic monoterpenoid that has an unusual bridging peroxide functional group. It is a colorless liquid with a pungent smell and taste that is soluble in most organic solvents. Like other lo ...

and

are monoterpenes that have pharmaceutical use.

Health effects

A study suggests that a range of floor cleaners with certain monoterpenes may cause indoor

air pollution Air pollution is the contamination of air due to the presence of substances in the atmosphere that are harmful to the health of humans and other living beings, or cause damage to the climate or to materials. There are many different types ...

equivalent or exceeding the harm to respiratory tracts when the time is spent near a busy road. This is due to

ozonolysis In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds of alkenes (), alkynes (), or azo compounds () are cleaved with ozone (). Alkenes and alkynes form organic compounds in which the multiple carbon–carbon bond ...

of monoterpenes like

leading to the production of atmospheric SOA. Another study suggests monoterpenes substantially affect ambient organic aerosol with uncertainties regarding environmental impacts. In a review, scientists concluded that they hope that these "substances will be extensively studied and used in more and more in medicine". A 2013 study found that "Based on adverse effects and risk assessments, d-limonene may be regarded as a safe ingredient. However, the potential occurrence of skin irritation necessitates regulation of this chemical as an ingredient in cosmetics." According to a review, several studies showed "that some monoterpenes (e.g., pulegone, menthofuran, camphor, and limonene) and sesquiterpenes (e.g., zederone, germacrone) exhibited liver toxicity" and that i.a. intensive research on terpenes toxicity is needed.

References

{{Terpenoids Monoterpenes Terpenes and terpenoids

Biosynthesis

Main examples

Natural roles

Uses

Health effects

See also

References