Methoxyeugenol

Last updated
Methoxyeugenol
Methoxyeugenol.svg
Names
IUPAC name
2,6-dimethoxy-4-prop-2-enylphenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.026.910 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 229-600-2
PubChem CID
UNII
  • InChI=1S/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4,6-7,12H,1,5H2,2-3H3
    Key: FWMPKHMKIJDEMJ-UHFFFAOYSA-N
  • COC1=CC(=CC(=C1O)OC)CC=C
Properties
C11H14O3
Molar mass 194.230 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H317, H319, H335
P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methoxyeugenol is a naturall occurring allylbenzene and eugenol derivative. It is found in toxic Japanese star anise pericarp [1] and leaves. [2] as well as in nutmeg crude extract but not in nutmeg essential oil. [3] It also activates PPAR-gamma in vivo. [4]

See also

Related Research Articles

<span class="mw-page-title-main">Anise</span> Species of flowering plant

Anise, also called aniseed or rarely anix is a flowering plant in the family Apiaceae native to the eastern Mediterranean region and Southwest Asia.

<span class="mw-page-title-main">Clove</span> Spice, flower buds of Syzygium aromaticum

Cloves are the aromatic flower buds of a tree in the family Myrtaceae, Syzygium aromaticum. They are native to the Maluku Islands, or Moluccas, in Indonesia, and are commonly used as a spice, flavoring, or fragrance in consumer products, such as toothpaste, soaps, or cosmetics. Cloves are available throughout the year owing to different harvest seasons across various countries.

<i>Illicium verum</i> Star anise, a medium-sized evergreen tree native to northeast Vietnam and southeast China

Illicium verum is a medium-sized evergreen tree native to northeast Vietnam and South China. It is a spice that closely resembles anise in flavor and is obtained from the star-shaped pericarps of the fruit of I. verum which are harvested just before ripening. Star anise oil is a highly fragrant oil used in cooking, perfumery, soaps, toothpastes, mouthwashes, and skin creams. Until 2012, when they switched to using a bacterial source, Roche Pharmaceuticals used up to 90% of the world's annual star anise crop to produce shikimic acid, a chemical intermediate used in the synthesis of oseltamivir (Tamiflu).

<span class="mw-page-title-main">Safrole</span> Chemical compound

Safrole is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among others. Small amounts are found in a wide variety of plants, where it functions as a natural antifeedant. Ocotea pretiosa, which grows in Brazil, and Sassafras albidum, which grows in eastern North America, are the main natural sources of safrole. It has a characteristic "sweet-shop" aroma.

<span class="mw-page-title-main">Myristicin</span> Chemical compound

Myristicin is a naturally occurring compound found in common herbs and spices, such as nutmeg. It is an insecticide, and has been shown to enhance the effectiveness of other insecticides.

<span class="mw-page-title-main">Cinnamaldehyde</span> Chemical compound

Cinnamaldehyde is an organic compound with the formula or C6H5CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90% cinnamaldehyde. Cinnamaldehyde decomposes to styrene because of oxidation as a result of bad storage or transport conditions. Styrene especially forms in high humidity and high temperatures. This is the reason why cinnamon contains small amounts of styrene.

<span class="mw-page-title-main">Thymol</span> Chemical compound found in plants including thyme

Thymol, C10H14O, is a natural monoterpenoid phenol derivative of p-Cymene, isomeric with carvacrol, found in oil of thyme, and extracted from Thymus vulgaris, ajwain, and various other plants as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. Thymol also provides the distinctive, strong flavor of the culinary herb thyme, also produced from T. vulgaris. Thymol is only slightly soluble in water at neutral pH, but it is extremely soluble in alcohols and other organic solvents. It is also soluble in strongly alkaline aqueous solutions due to deprotonation of the phenol. Its dissociation constant (pKa) is 10.59±0.10. Thymol absorbs maximum UV radiation at 274 nm.

<span class="mw-page-title-main">Eugenol</span> Chemical compound

Eugenol is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove, nutmeg, cinnamon, basil and bay leaf. It is present in concentrations of 80–90% in clove bud oil and at 82–88% in clove leaf oil. Eugenol has a pleasant, spicy, clove-like scent. The name is derived from Eugenia caryophyllata, the former Linnean nomenclature term for cloves. The currently accepted name is Syzygium aromaticum.

<span class="mw-page-title-main">Anethole</span> Chemical compound

Anethole is an organic compound that is widely used as a flavoring substance. It is a derivative of the aromatic compound allylbenzene and occurs widely in plants in essential oils. It is in the class of phenylpropanoid organic compounds. It contributes a large component of the odor and flavor of anise and fennel, anise myrtle (Myrtaceae), liquorice (Fabaceae), magnolia blossoms, and star anise (Schisandraceae). Closely related to anethole is its isomer estragole, which is abundant in tarragon (Asteraceae) and basil (Lamiaceae),and has a flavor reminiscent of anise. It is a colorless, fragrant, mildly volatile liquid. Anethole is only slightly soluble in water but exhibits high solubility in ethanol. This trait causes certain anise-flavored liqueurs to become opaque when diluted with water; the ouzo effect.

<i>Ocimum tenuiflorum</i> Species of flowering plant

Ocimum tenuiflorum, commonly known as holy basil or tulsi, is an aromatic perennial plant in the family Lamiaceae. It is native to tropical and subtropical regions of Australia, Malesia, Asia, and the western Pacific. It is widely cultivated throughout the Southeast Asian tropics. This plant has escaped from cultivation and has naturalized in many tropical regions of the Americas. It is an agricultural and environmental weed.

Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower shikimi, from which it was first isolated in 1885 by Johan Fredrik Eykman. The elucidation of its structure was made nearly 50 years later.

<i>Illicium anisatum</i> Species of plant

Illicium anisatum, with common names Japanese star anise, Aniseed tree, and sacred Anise tree, known in Japan as shikimi, is a tree closely related to the Chinese star anise. Since it is highly toxic, the fruit is not edible; instead, the dried and powdered leaves are burned as incense in Japan. Its branches and evergreen leaves are considered highly sacred by Japanese Buddhists due to aversion from insects and their ability to remain fresh after pruning.

<span class="mw-page-title-main">Myrcene</span> Chemical compound

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. α-Myrcene is the name for the isomer 2-methyl-6-methylene-1,7-octadiene, which has not been found in nature.

<i>Phellodendron amurense</i> Species of tree

Phellodendron amurense is a species of tree in the family Rutaceae, commonly called the Amur cork tree. It is a major source of huáng bò, one of the 50 fundamental herbs used in traditional Chinese medicine. The Ainu people used this plant, called shikerebe-ni, as a painkiller. It is known as hwangbyeok in Korean and (キハダ) kihada in Japanese.

α-Eleostearic acid Chemical compound

α-Eleostearic acid or (9Z,11E,13E)-octadeca-9,11,13-trienoic acid, is an organic compound, a conjugated fatty acid and one of the isomers of octadecatrienoic acid. It is often called simply eleostearic acid although there is also a β-eleostearic acid. Its high degree of unsaturation gives tung oil its properties as a drying oil.

<i>Kaempferia galanga</i> Species of flowering plant

Kaempferia galanga, commonly known as kencur, aromatic ginger, sand ginger, cutcherry, is a monocotyledonous plant in the ginger family, and one of four plants called galangal. It is found primarily in open areas in Indonesia, southern China, Taiwan, Cambodia, and India, but is also widely cultivated throughout Southeast Asia.

<span class="mw-page-title-main">Peroxisome proliferator-activated receptor alpha</span> Nuclear receptor protein found in humans

Peroxisome proliferator-activated receptor alpha (PPAR-α), also known as NR1C1, is a nuclear receptor protein functioning as a transcription factor that in humans is encoded by the PPARA gene. Together with peroxisome proliferator-activated receptor delta and peroxisome proliferator-activated receptor gamma, PPAR-alpha is part of the subfamily of peroxisome proliferator-activated receptors. It was the first member of the PPAR family to be cloned in 1990 by Stephen Green and has been identified as the nuclear receptor for a diverse class of rodent hepatocarcinogens that causes proliferation of peroxisomes.

<span class="mw-page-title-main">Peroxisome proliferator-activated receptor delta</span> Nuclear receptor protein found in humans

Peroxisome proliferator-activated receptor delta(PPAR-delta), or (PPAR-beta), also known as Nuclear hormone receptor 1(NUC1) is a nuclear receptor that in humans is encoded by the PPARD gene.

<span class="mw-page-title-main">Magnoliids</span> Clade of flowering plants

Magnoliids are a clade of flowering plants. With more than 10,000 species, including magnolias, nutmeg, bay laurel, cinnamon, avocado, black pepper, tulip tree and many others, it is the third-largest group of angiosperms after the eudicots and monocots. The group is characterized by trimerous flowers, pollen with one pore, and usually branching-veined leaves.

References

  1. Howes MJ, Kite GC, Simmonds MS (July 2009). "Distinguishing chinese star anise from Japanese star anise using thermal desorption-gas chromatography-mass spectrometry". Journal of Agricultural and Food Chemistry . 57 (13): 5783–9. doi:10.1021/jf9009153. PMID   19507874.
  2. Koeduka T, Sugimoto K, Watanabe B, Someya N, Kawanishi D, Gotoh T, Ozawa R, Takabayashi J, Matsui K, Hiratake J (March 2014). "Bioactivity of natural O-prenylated phenylpropenes from Illicium anisatum leaves and their derivatives against spider mites and fungal pathogens". Plant Biology . 16 (2): 451–6. doi:10.1111/plb.12054. PMID   23889818.
  3. Oo T, Saiboonjan B, Srijampa S, Srisrattakarn A, Sutthanut K, Tavichakorntrakool R, Chanawong A, Lulitanond A, Tippayawat P (July 2021). "Inhibition of Bacterial Efflux Pumps by Crude Extracts and Essential Oil from Myristica fragrans Houtt. (Nutmeg) Seeds against Methicillin-Resistant Staphylococcus aureus". Molecules (Basel, Switzerland) . 26 (15): 4662. doi: 10.3390/molecules26154662 . PMC   8348620 . PMID   34361815.
  4. de Souza Basso B, Haute GV, OrtegaRibera M, Luft C, Antunes GL, Bastos MS, Carlessi LP, Levorse VG, Cassel E, Donadio MV, Santarém ER, GraciaSancho J, Rodrigues de Oliveira J (July 2021). "Methoxyeugenol deactivates hepatic stellate cells and attenuates liver fibrosis and inflammation through a PPAR-ɣ and NF-kB mechanism". Journal of Ethnopharmacology . 280: 114433. doi: 10.1016/j.jep.2021.114433 . hdl: 10923/18540 . PMID   34280502.