Acetyleugenol

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Contents

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
Density 1.0806 g/cm3
Melting point 27 to 29 °C (81 to 84 °F; 300 to 302 K)
Boiling point 281.2 °C (538.2 °F; 554.3 K)
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]

Uses

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

See also

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.


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