Acetyleugenol

Names
IUPAC name

(2-methoxy-4-prop-2-enylphenyl) acetate

Other names

* Eugenol acetate
* Eugenyl acetate
* 4-Allyl-2-methoxyphenol acetate

Identifiers

CAS Number

* 93-28-7 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:34522

ChEMBL |

* ChEMBL108299

ChemSpider |

* 6869

EC Number |

* 202-235-6

KEGG |

* C14567

PubChem CID

* 7136

UNII |

* V9OSB376X8

InChI

* 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

SMILES

* CC(=O)OC1=C(C=C(C=C1)CC=C)OC

Properties

Chemical formula

| 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).

Infobox references

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

* Methyleugenol

## References

1. ↑ Nassar, Mahmoud; Gaara, Ahmed; El-Ghorab, A.; Farrag, Abdel Razik; Shen, Hui; Huq, Enamul; Mabry, Tom. "Chemical constituents of clove (Syzygium aromaticum, Fam. Myrtaceae) and their antioxidant activity". Latinoam. Quim. 35.
2. ↑ 2.0 2.1 "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. January 1991. doi:10.1016/0952-3278(91)90070-l. PMID 2011614.
3. ↑ "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. January 2019. doi:10.1007/s13205-018-1565-8. PMID 30622875.
4. ↑ "Variation in essential oil composition of Rydingia michauxii at the three developmental stages". Natural Product Research 35 (2): 342–345. January 2021. doi:10.1080/14786419.2019.1622112. PMID 31140321. https://figshare.com/articles/journal_contribution/8197898.
5. ↑ "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. August 2010. doi:10.1016/j.ijfoodmicro.2010.06.011. PMID 20621374.
6. ↑ "Antifungal potential of eugenyl acetate against clinical isolates of Candida species". Microbial Pathogenesis 99: 19–29. October 2016. doi:10.1016/j.micpath.2016.07.012. PMID 27452957.
7. ↑ "Antiplatelet principles from a food spice clove (Syzygium aromaticum L) [corrected]". Prostaglandins, Leukotrienes, and Essential Fatty Acids 48 (5): 363–72. May 1993. doi:10.1016/0952-3278(93)90116-e. PMID 8321872.
8. ↑ "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. January 2018. doi:10.1016/j.fct.2017.11.049. PMID 29191726.
9. ↑ "The Good Scents Company - Aromatic/Hydrocarbon/Inorganic Ingredients Catalog information". http://www.thegoodscentscompany.com/data/rw1005011.html.
10. ↑ "RIFM fragrance ingredient safety assessment, eugenyl acetate, CAS Registry Number 93-28-7". Food and Chemical Toxicology 144 (Suppl 1): 111630. October 2020. doi:10.1016/j.fct.2020.111630. PMID 32771453.

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*[CID]: Compound ID