2,5-Dimethoxy-''p''-cymene, or thymohydroquinone dimethyl ether, is a

phytochemical Phytochemicals are naturally-occurring chemicals present in or extracted from plants. Some phytochemicals are nutrients for the plant, while others are metabolites produced to enhance plant survivability and reproduction. The fields of ext ...

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 ...

s of plants within the

family Family (from ) is a Social group, group of people related either by consanguinity (by recognized birth) or Affinity (law), affinity (by marriage or other relationship). It forms the basis for social order. Ideally, families offer predictabili ...

Asteraceae Asteraceae () is a large family (biology), family of flowering plants that consists of over 32,000 known species in over 1,900 genera within the Order (biology), order Asterales. The number of species in Asteraceae is rivaled only by the Orchi ...

''. These essential oils, which contain the compound as a major component of the oil, have

antifungal An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as ...

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 ...

, and

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 ...

properties.

Natural occurrence

2,5-Dimethoxy-''p''-cymene occurs in a variety of different plants' essential oils. Examples include: * ''

Ayapana triplinervis ''Ayapana triplinervis'' (aya-pana, water hemp) is a tropical American shrub in the family Asteraceae. This plant has long slender leaves which are often used in traditional medicine. The flowers are pale pink and the thin, hairless stem is redd ...

'' (92.8%) * '' Apium leptophyllum'' (50.7 to 80.24%) * '' Cyathocline purpurea'' (57.4%) * ''

Arnica montana ''Arnica montana'', also known as wolf's bane, leopard's bane, mountain tobacco and mountain arnica, is a moderately toxic European flowering plant in the daisy family Asteraceae that has a large yellow head (botany), flower head. The names "wol ...

'' (32.6%) * '' Laggera crispata'' (32.2%) * '' Blumea perrottetiana'' (30.0%) * '' Eupatorium capillifolium'' (20.8%) * '' Sphaeranthus indicus'' (18.2%) * '' Limbarda crithmoides'' (16.4) * '' Bubonium imbricatum'' (16.2%)

Chemical synthesis

2,5-Dimethoxy-''p''-cymene can be synthesized from

carvacrol Carvacrol, or cymophenol, C6H3(CH3)(OH)C3H7, is a monoterpene, 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 t ...

by aromatic

halogenation In chemistry, halogenation is a chemical reaction which introduces one or more halogens into a chemical compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drug ...

followed by

nucleophilic substitution In chemistry, a nucleophilic substitution (SN) is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile) ...

with

sodium methoxide Sodium methoxide is the simplest sodium alkoxide. With the formula , it is a white solid, which is formed by the deprotonation of methanol. It is a widely used reagent in industry and the laboratory. It is also a dangerously caustic base. ...

and

Williamson ether synthesis The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol (alkoxide). This reaction was developed by Alexander Williamson in 1850. Typically it involves the reaction of an alkoxide ...

using

methyl iodide Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one h ...

References

{{DEFAULTSORT:Dimethoxy-p-cymene, 2,5- Hydroquinone ethers Fungicides Insecticides Alkyl-substituted benzenes Isopropyl compounds Methoxy compounds

Natural occurrence

Chemical synthesis

See also

References