Acetyleugenol

Last updated
Acetyleugenol
Acetyleugenol.png
Names
IUPAC name
(2-methoxy-4-prop-2-enylphenyl) acetate
Other names
  • Eugenol acetate
  • Eugenyl acetate
  • 4-Allyl-2-methoxyphenol acetate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.033 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-235-6
KEGG
PubChem CID
UNII
  • InChI=1S/C12H14O3/c1-4-5-10-6-7-11(15-9(2)13)12(8-10)14-3/h4,6-8H,1,5H2,2-3H3
    Key: SCCDQYPEOIRVGX-UHFFFAOYSA-N
  • CC(=O)OC1=C(C=C(C=C1)CC=C)OC
Properties
C12H14O3
Molar mass 206.241 g·mol−1
Related compounds
Related compounds
Methoxyeugenol
Methyleugenol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Acetyleugenol is a phenylpropanoid compound found in cloves. It is the second in abundance to the related compound eugenol in certain extract preparations. [1] [2] Like eugenol, its found in several plants such as Acacia nilotica and Piper betle [3] [4] [5] and has similar antibacterial and antifungal properties on C. albicans and S. mutans . [6] It inhibits aggregation of platelets and has partial agonistic activity on AhR. [2] [7] [8]

Contents

Uses

Acetyleugenol has characteristic odor reminiscent of cloves and thus used as fragrance. [9] [10]

See also

Related Research Articles

<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.

<span class="mw-page-title-main">Basil</span> Important culinary herb

Basil, also called great basil, is a culinary herb of the family Lamiaceae (mints). It is a tender plant, and is used in cuisines worldwide. In Western cuisine, the generic term "basil" refers to the variety also known as sweet basil or Genovese basil. Basil is native to tropical regions from Central Africa to Southeast Asia. In temperate climates basil is treated as an annual plant, however, basil can be grown as a short-lived perennial or biennial in warmer horticultural zones with tropical or Mediterranean climates.

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

The betel, Piper betle, is a species of flowering plant in the pepper family Piperaceae, native to Southeast Asia. It is an evergreen, dioecious vine, with glossy heart-shaped leaves and white catkins. Betel plants are cultivated for their leaves which are most commonly used as flavoring in chewing areca nut.

<span class="mw-page-title-main">Eicosanoid</span> Class of compounds

Eicosanoids are signaling molecules made by the enzymatic or non-enzymatic oxidation of arachidonic acid or other polyunsaturated fatty acids (PUFAs) that are, similar to arachidonic acid, around 20 carbon units in length. Eicosanoids are a sub-category of oxylipins, i.e. oxidized fatty acids of diverse carbon units in length, and are distinguished from other oxylipins by their overwhelming importance as cell signaling molecules. Eicosanoids function in diverse physiological systems and pathological processes such as: mounting or inhibiting inflammation, allergy, fever and other immune responses; regulating the abortion of pregnancy and normal childbirth; contributing to the perception of pain; regulating cell growth; controlling blood pressure; and modulating the regional flow of blood to tissues. In performing these roles, eicosanoids most often act as autocrine signaling agents to impact their cells of origin or as paracrine signaling agents to impact cells in the proximity of their cells of origin. Eicosanoids may also act as endocrine agents to control the function of distant cells.

Linoleic acid (LA) is an organic compound with the formula HOOC(CH
2
)
7
CH=CHCH
2
CH=CH(CH
2
)
4
CH
3
. Both alkene groups are cis. It is a fatty acid sometimes denoted 18:2 (n-6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.

<span class="mw-page-title-main">Food browning</span> Food process

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 health, nutrition, and food technology. Though there are many different ways food chemically changes over time, browning in particular falls into two main categories: enzymatic versus non-enzymatic browning processes.

<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">Ferulic acid</span> Chemical compound

Ferulic acid is a hydroxycinnamic acid, is an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis). Classified as a phenolic phytochemical or polyphenol, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plant cell walls, covalently bonded to hemicellulose such as arabinoxylans. Salts and esters derived from ferulic acid are called ferulates.

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

Caryophyllene, more formally (−)-β-caryophyllene,(BCP), is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, copaiba, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.

<span class="mw-page-title-main">Oil of clove</span> Oil of cloves

Oil of clove, also known as clove oil, is an essential oil extracted from the clove plant, Syzygium aromaticum. Clove oil is commonly used in aromatherapy and for flavoring food and some medicines. Madagascar and Indonesia are the main producers of clove oil.

<span class="mw-page-title-main">Essential fatty acid interactions</span>

There are many fatty acids found in nature. Two types of fatty acids considered essential for human health are the omega-3 and omega-6 types. These two essential fatty acids are necessary for some cellular signalling pathways and are involved in mediating inflammation, protein synthesis, and metabolic pathways in the human body.

<span class="mw-page-title-main">Antioxidant effect of polyphenols and natural phenols</span>

A polyphenol antioxidant is a hypothetized type of antioxidant, in which each instance would contain a polyphenolic substructure; such instances which have been studied in vitro. Numbering over 4,000 distinct chemical structures, such polyphenols may have antioxidant activity {{{1}}} in vitro (although they are unlikely to be antioxidants in vivo). Hypothetically, they may affect cell-to-cell signaling, receptor sensitivity, inflammatory enzyme activity or gene regulation, although high-quality clinical research has not confirmed any of these possible effects in humans as of 2020.

<span class="mw-page-title-main">Linoleoyl-CoA desaturase</span> Class of enzymes

Linoleoyl-CoA desaturase (also Delta 6 desaturase, EC 1.14.19.3) is an enzyme that converts between types of fatty acids, which are essential nutrients in the human body. The enzyme mainly catalyzes the chemical reaction

<span class="mw-page-title-main">ALOX12</span> Protein-coding gene in the species Homo sapiens

ALOX12, also known as arachidonate 12-lipoxygenase, 12-lipoxygenase, 12S-Lipoxygenase, 12-LOX, and 12S-LOX is a lipoxygenase-type enzyme that in humans is encoded by the ALOX12 gene which is located along with other lipoyxgenases on chromosome 17p13.3. ALOX12 is 75 kilodalton protein composed of 663 amino acids.

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

Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies.

<span class="mw-page-title-main">Depside</span> Class of chemical compounds

A depside is a type of polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester group. Depsides are most often found in lichens, but have also been isolated from higher plants, including species of the Ericaceae, Lamiaceae, Papaveraceae and Myrtaceae.

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

Tellimagrandin II is the first of the ellagitannins formed from 1,2,3,4,6-pentagalloyl-glucose. It can be found in Geum japonicum and Syzygium aromaticum (clove).

Eoxins are proposed to be a family of proinflammatory eicosanoids. They are produced by human eosinophils, mast cells, the L1236 Reed–Sternberg cell line derived from Hodgkin's lymphoma, and certain other tissues. These cells produce the eoxins by initially metabolizing arachidonic acid, an omega-6 (ω-6) fatty acid, via any enzyme possessing 15-lipoxygenase activity. The product of this initial metabolic step, 15(S)-hydroperoxyeicosatetraenoic acid, is then converted to a series of eoxins by the same enzymes that metabolize the 5-lipoxygenase product of arachidonic acid metabolism, i.e. 5-Hydroperoxy-eicosatetraenoic acid to a series of leukotrienes. That is, the eoxins are 14,15-disubstituted analogs of the 5,6-disubstituted leukotrienes.

<span class="mw-page-title-main">12-Hydroxyheptadecatrienoic acid</span> Chemical compound

12-Hydroxyheptadecatrienoic acid (also termed 12-HHT, 12(S)-hydroxyheptadeca-5Z,8E,10E-trienoic acid, or 12(S)-HHTrE) is a 17 carbon metabolite of the 20 carbon polyunsaturated fatty acid, arachidonic acid. It was discovered and structurally defined in 1973 by P. Wlodawer, Bengt I. Samuelsson, and M. Hamberg, as a product of arachidonic acid metabolism made by microsomes (i.e. endoplasmic reticulum) isolated from sheep seminal vesicle glands and by intact human platelets. 12-HHT is less ambiguously termed 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid to indicate the S stereoisomerism of its 12-hydroxyl residue and the Z, E, and E cis-trans isomerism of its three double bonds. The metabolite was for many years thought to be merely a biologically inactive byproduct of prostaglandin synthesis. More recent studies, however, have attached potentially important activity to it.

<span class="mw-page-title-main">Asim Duttaroy</span> Indian American medical scientist

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References

  1. Nassar M, Gaara A, El-Ghorab A, Farrag AR, Shen H, Huq E, Mabry T. "Chemical constituents of clove (Syzygium aromaticum, Fam. Myrtaceae) and their antioxidant activity". Latinoam. Quim. 35.
  2. 1 2 Srivastava KC, Malhotra N (January 1991). "Acetyl eugenol, a component of oil of cloves (Syzygium aromaticum L.) inhibits aggregation and alters arachidonic acid metabolism in human blood platelets". Prostaglandins, Leukotrienes, and Essential Fatty Acids . 42 (1): 73–81. doi:10.1016/0952-3278(91)90070-l. PMID   2011614.
  3. Das S, Ray A, Nasim N, Nayak S, Mohanty S (January 2019). "Effect of different extraction techniques on total phenolic and flavonoid contents, and antioxidant activity of betelvine and quantification of its phenolic constituents by validated HPTLC method". 3 Biotech . 9 (1): 37. doi:10.1007/s13205-018-1565-8. PMC   6320704 . PMID   30622875.
  4. Tahmasebi A, Hosseini SM, Karami A, Afsharifar A, Sharifi Olounabadi AR (January 2021). "Variation in essential oil composition of Rydingia michauxii at the three developmental stages" . Natural Product Research . 35 (2): 342–345. doi:10.1080/14786419.2019.1622112. PMID   31140321. S2CID   169032297.
  5. Prakash B, Shukla R, Singh P, Kumar A, Mishra PK, Dubey NK (August 2010). "Efficacy of chemically characterized Piper betle L. essential oil against fungal and aflatoxin contamination of some edible commodities and its antioxidant activity". International Journal of Food Microbiology . 142 (1–2): 114–9. doi:10.1016/j.ijfoodmicro.2010.06.011. PMID   20621374.
  6. Musthafa KS, Hmoteh J, Thamjarungwong B, Voravuthikunchai SP (October 2016). "Antifungal potential of eugenyl acetate against clinical isolates of Candida species". Microbial Pathogenesis . 99: 19–29. doi:10.1016/j.micpath.2016.07.012. PMID   27452957.
  7. Srivastava KC (May 1993). "Antiplatelet principles from a food spice clove (Syzygium aromaticum L) [corrected]". Prostaglandins, Leukotrienes, and Essential Fatty Acids . 48 (5): 363–72. doi:10.1016/0952-3278(93)90116-e. PMID   8321872.
  8. Bartoňková I, Dvořák Z (January 2018). "Essential oils of culinary herbs and spices display agonist and antagonist activities at human aryl hydrocarbon receptor AhR". Food and Chemical Toxicology . 111: 374–384. doi:10.1016/j.fct.2017.11.049. PMID   29191726.
  9. "The Good Scents Company - Aromatic/Hydrocarbon/Inorganic Ingredients Catalog information".
  10. Api AM, Belmonte F, Belsito D, Biserta S, Botelho D, Bruze M, Burton GA, Buschmann J, Cancellieri MA, Dagli ML, Date M, Dekant W, Deodhar C, Fryer AD, Gadhia S, Jones L, Joshi K, Lapczynski A, Lavelle M, Liebler DC, Na M, O'Brien D, Patel A, Penning TM, Ritacco G, Rodriguez-Ropero F, Romine J, Sadekar N, Salvito D, Schultz TW, Sipes IG, Sullivan G, Thakkar Y, Tokura Y, Tsang S (October 2020). "RIFM fragrance ingredient safety assessment, eugenyl acetate, CAS Registry Number 93-28-7". Food and Chemical Toxicology . 144 (Suppl 1): 111630. doi:10.1016/j.fct.2020.111630. PMID   32771453. S2CID   221093220.