Acetyleugenol

Names

[ CAS No. ]:
93-28-7

[ Name ]:
Acetyleugenol

[Synonym ]:
O-Acetyleugenol
Acetyl eugenol
Eugenol Acetate
EINECS 202-235-6
1-Acetoxy-2-methoxy-4-allylbenzene
Phenol, 2-methoxy-4- (2-propenyl)-, acetate
2-methoxy-4-(prop-2-en-1-yl)phenyl acetate
MFCD00026191
4-Allyl-2-methoxyphenol acetate
Acetyleugenol
Eugenyl acetate
(2-methoxy-4-prop-2-enylphenyl) acetate
Phenol, 2-methoxy-4-(2-propen-1-yl)-, acetate
acetic acid eugenyl ester
Phenol, 4-allyl-2-methoxy-, acetate
4-Allyl-2-methoxyphenyl acetate
Phenol, 2-methoxy-4-(2-propenyl)-, acetate

Biological Activity

[Description]:

Eugenol acetate (Eugenyl acetate), a major phytochemical constituent of the essential oil exhibits antibacterial, antioxidant, and anti-virulence activities. Eugenol acetate (Eugenyl acetate), a phytochemical in clove essential oil, against clinical isolates of Candida albicans, Candida parapsilosis, Candida tropicalis, and Candida glabrata.

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Musthafa KS, et al. Antifungal potential of eugenyl acetate against clinical isolates of Candida species. Microb Pathog. 2016 Oct;99:19-29.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
268.0±28.0 °C at 760 mmHg

[ Melting Point ]:
26°C

[ Molecular Formula ]:
C₁₂H₁₄O₃

[ Molecular Weight ]:
206.238

[ Flash Point ]:
106.8±18.6 °C

[ Exact Mass ]:
206.094299

[ PSA ]:
35.53000

[ LogP ]:
2.40

[ Vapour Pressure ]:
0.0±0.5 mmHg at 25°C

[ Index of Refraction ]:
1.507

[ Stability ]:
Stable. Combustible. Incompatible with strong oxidizing agents.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: SJ4550000

CHEMICAL NAME :: Phenol, 4-allyl-2-methoxy-, acetate

CAS REGISTRY NUMBER :: 93-28-7

BEILSTEIN REFERENCE NO. :: 1964745

LAST UPDATED :: 199701

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C12-H14-O3

MOLECULAR WEIGHT :: 206.26

WISWESSER LINE NOTATION :: 1VOR BO1 D2U1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 12,877,1974 ** ACUTE TOXICITY DATA **

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1670 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Skin and Appendages - hair

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 2,327,1964

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intratracheal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 48 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - structural or functional change in trachea or bronchi Lungs, Thorax, or Respiration - acute pulmonary edema Lungs, Thorax, or Respiration - chronic pulmonary edema

REFERENCE :: ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 59,78,1986

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 12,877,1974

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22;R38

[ Safety Phrases ]:
S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
SJ4550000

[ HS Code ]:
2915390090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2915390090

[ Summary ]:
2915390090. esters of acetic acid. VAT:17.0%. Tax rebate rate:13.0%. Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward). MFN tariff:5.5%. General tariff:30.0%

Articles

Preparation and characterization of clove essential oil-loaded liposomes.

Food Chem. 178 , 52-62, (2015)

In this study, suitable formulations of natural soybean phospholipid vesicles were developed to improve the stability of clove essential oil and its main component, eugenol. Using an ethanol injection...

Lipozyme TL IM as Catalyst for the Synthesis of Eugenyl Acetate in Solvent-Free Acetylation.

Appl. Biochem. Biotechnol. , (2015)

The ability of commercial immobilized lipase from Thermomyces lanuginosus (Lipozyme TL IM) to catalyze the acetylation of essential clove oil with acetic anhydride in a solvent-free system was studied...

Acaricidal activity of clove bud oil compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).

J. Agric. Food Chem. 51(4) , 885-9, (2003)

The acaricidal activity of clove (Eugenia caryophyllata) bud oil-derived eugenol and its congeners (acetyleugenol, isoeugenol, and methyleugenol) against adults of Dermatophagoides farinae and Dermato...