Isoeugenol acetate

Base Information

• Chemical Name: Isoeugenol acetate
• CAS No.: 93-29-8
• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.241
• DSSTox Substance ID: DTXSID0052625
• Wikidata: Q72485314
• Mol file: 93-29-8.mol

Synonyms:(2-methoxy-4-prop-1-enylphenyl) acetate;2-methoxy-4-prop-1-enylphenylacetat;Isoeugenol-acetat;2-Methoxy-4-[(1E)-1-propenyl]phenyl acetate;2 - methoxy - 4 - prop - 1 - enylphenyl acetate;Fenol, 2-metoxi-4-(1-propen-1-il)-, 1-acetato;SCHEMBL313563;DTXSID0052625;HMS3330F19;AKOS024319069;FT-0631464;Isoeugenol acetate 1000 microg/mL in Acetonitrile

Chemical Property of Isoeugenol acetate

Chemical Property:

• Vapor Pressure: 0.00324mmHg at 25°C
• Melting Point: 79-81 °C(lit.)
• Refractive Index: 1.539
• Boiling Point: 283 °C at 760 mmHg
• Flash Point: 113.9 °C
• PSA: 35.53000
• Density: 1.073 g/cm³
• LogP: 2.65360
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 206.094294304
• Heavy Atom Count: 15
• Complexity: 235

Purity/Quality:

Isoeugenyl acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC=CC1=CC(=C(C=C1)OC(=O)C)OC
• Description: Acetyl Isoeugenol is used as an alcohol-soluble flavoring agent with spicy, floral, and carnation undertones, blending well with vanilla-type flavors. It lasts longer in perfume than other comparable agents such as dihydroeugenol and methyl diantilis, giving body to the scent. It can be used as an alternative to products such as dianthine, which degrades into isoeugenol – which can cause hives in some individuals from long-term exposure, and has thus been deemed non-IFRA (International Fragrance Association) compliant. Isoeugenyl acetate has a weak, rose-carnation, somewhat spicy odor and an initially burning, then sweet taste. Can be prepared from isoeugenol and acetic acid by esterification.
• Uses: Isoeugenyl acetate is a useful building block extracted from the essential oils of Alpinia galanga and Zingiber officinale. Isoeugenyl acetate has antibacterial properties towards B. subtilis, E. coli and S. aureus.

Technology Process of Isoeugenol acetate

There total 27 articles about Isoeugenol acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-methoxy-4-propenylphenol (97-54-1) + acetic anhydride (108-24-7) → 2-methoxy-4-(prop-1-enyl)phenyl acetate (93-29-8)

Guidance literature:

With sodium carbonate; at 100 - 150 ℃; for 3h; Reagent/catalyst; Temperature;

Reference yield: 97.0%

eugenol acetate (93-28-7) → (E)-1-(4-acetoxy-3-methoxyphenyl)-1-propene (5912-87-8,93-29-8)

Guidance literature:

With palladium(II) trifluoroacetate; 2-(diphenylphosphino)pyridine; 2-fluoroethanol; In 1,2-dichloro-ethane; at 25 - 27 ℃; for 24h; stereoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.0c00168

Reference yield: 84.0%

eugenol acetate (93-28-7) → 3-methoxy-4-acetoxy-1-cis-propenyl-benzene (97412-23-2,93-29-8) + (E)-1-(4-acetoxy-3-methoxyphenyl)-1-propene (5912-87-8,93-29-8)

Guidance literature:

With nickel(II) iodide; 6,6'-dimethyl-2,2'-bipyridine; phosphonic acid diethyl ester; zinc; In N,N-dimethyl acetamide; at 35 ℃; for 24h;

upstream raw materials:

cis-isoeugenol

acetic anhydride

2-methoxy-4-propenylphenol

eugenol acetate

Downstream raw materials:

(+/-)-3-methoxy-4-acetoxy-1-(threo-1.2-dibromo-propyl)-benzene

(+/-)-3-methoxy-4-acetoxy-1-(erythro-1.2-dibromo-propyl)-benzene

1-acetoxy-2-methoxy-4-(2-nitro-1-nitroso-propyl)-benzene

2-methoxy-4-(3-methyl-2-oxiranyl)phenyl acetate

Refernces

• 1、 -. "Method for synthesizing E-methyl styrene compound". Page/Page column 7. . Retrieved 2020/03/25.
• 2、 -. "Method for synthesizing vanillin from eugenol through ozone oxidation". Paragraph 0053-0054; 0058-0059; 0066-0067; 0071-0072; 0078. . Retrieved 2020/12/31.