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

phytochemical Phytochemicals are chemical compounds produced by plants, generally to help them resist fungi, bacteria and plant virus infections, and also consumption by insects and other animals. The name comes . Some phytochemicals have been used as poisons ...

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 plants within the

family Family (from la, familia) is a Social group, group of people related either by consanguinity (by recognized birth) or Affinity (law), affinity (by marriage or other relationship). The purpose of the family is to maintain the well-being of its ...

Asteraceae The family Asteraceae, alternatively Compositae, consists of over 32,000 known species of flowering plants in over 1,900 genera within the order Asterales. Commonly referred to as the aster, daisy, composite, or sunflower family, Compositae w ...

''. 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 crypto ...

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 ...

, and

insecticidal Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to b ...

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 ''Cyclospermum leptophyllum'' (also, ''Ciclospermum l.'') is a species of plant in the family Apiaceae known by the common names marsh parsley, slender celery and fir-leaved celery. This is a plant found worldwide at warm temperate to tropical la ...

'' (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. It is noted for its large yellow flower head. The names "wolf's ...

'' (32.6%) * '' Laggera crispata'' (32.2%) * '' Blumea perrottetiana'' (30.0%) * ''

Eupatorium capillifolium ''Eupatorium capillifolium'', or dogfennel (also written "dog fennel"), is a North American perennial herbaceous plant in the family Asteraceae, native to the eastern and south-central United States. It is generally between 50 cm and 2 meter ...

'' (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 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 ...

by aromatic

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

followed by

nucleophilic substitution In chemistry, a nucleophilic substitution 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). The ...

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. Itis a widely used reagent in industry and the laboratory. It is also a dangerously caustic base. P ...

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 i ...

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