Acetyleugenol

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34522;
ChEMBL	ChEMBL108299;
ChemSpider	6869;
ECHA InfoCard	100.002.033
EC Number	202-235-6;
KEGG	C14567;
PubChem CID	7136;
UNII	V9OSB376X8;
CompTox Dashboard (EPA)	DTXSID5052624 ;
	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]

References

^ 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.
^ ^a ^b 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ "The Good Scents Company - Aromatic/Hydrocarbon/Inorganic Ingredients Catalog information".
^ 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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[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.

[pmid2011614-2] 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.

[pmid30622875-3] 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.

[pmid31140321-4] 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.

[pmid20621374-5] 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.

[pmid27452957-6] 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.

[pmid8321872-7] 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.

[pmid29191726-8] 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".

[pmid32771453-10] 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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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
ECHA InfoCard	100.002.033
EC Number	202-235-6
KEGG	C14567
PubChem CID	7136
UNII	V9OSB376X8
CompTox Dashboard (EPA)	DTXSID5052624
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

Uses

See also

References