93-29-8

Basic information

• Product Name: 1-ACETOXY-2-METHOXY-4-(1-PROPENYL)BENZENE
• Synonyms: ISOEUGENYL ACETATE;ISO-EUGENOL ACETATE;FEMA 2470;ACETIC ACID ISOEUGENYL ESTER;ACETO-ISO-EUGENOL;ACETYL ISOEUGENOL;4-ACETOXY-3-METHOXY-1-PROPENYLBENZENE;2-METHOXY-4-PROPENYLPHENYL ACETATE
• CAS NO: 93-29-8
• Molecular Formula: C12H14O3
• Molecular Weight: 206.24
• EINECS: 202-236-1
• Product Categories: Alphabetical Listings;Flavors and Fragrances;I-L
• Mol File: 93-29-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 79-81 °C(lit.)
• Boiling Point: 283 °C
• Flash Point: 113.9 °C
• Appearance: /
• Density: 1.1492 (rough estimate)
• Vapor Pressure: 0.00324mmHg at 25°C
• Refractive Index: 1.5080 (estimate)
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Hygroscopic, Light Sensitive
• CAS DataBase Reference: 1-ACETOXY-2-METHOXY-4-(1-PROPENYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ACETOXY-2-METHOXY-4-(1-PROPENYL)BENZENE(93-29-8)
• EPA Substance Registry System: 1-ACETOXY-2-METHOXY-4-(1-PROPENYL)BENZENE(93-29-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: SL7940000
• Hazardous Substances Data: 93-29-8(Hazardous Substances Data)

Usage

Description

1-ACETOXY-2-METHOXY-4-(1-PROPENYL)BENZENE, also known as Isoeugenyl acetate, is a white solid with a weak, rose-carnation, somewhat spicy, and clove-like odor. It is extracted from the essential oils of Alpinia galanga and Zingiber officinale and has a unique initially burning, then sweet taste. This chemical compound 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.

Uses

Used in Flavor and Fragrance Industry:
1-ACETOXY-2-METHOXY-4-(1-PROPENYL)BENZENE is used as a flavoring agent for its spicy, floral, and carnation undertones, which blend well with vanilla-type flavors. It is also used as a perfume ingredient due to its longer-lasting properties compared to other agents, providing body to the scent.
Used in Antimicrobial Applications:
1-ACETOXY-2-METHOXY-4-(1-PROPENYL)BENZENE is used as an antibacterial agent against B. subtilis, E. coli, and S. aureus, making it a valuable component in various antimicrobial products.
Used as an Alternative to Non-IFRA Compliant Products:
1-ACETOXY-2-METHOXY-4-(1-PROPENYL)BENZENE can be used as an alternative to products such as dianthine, which degrades into isoeugenol – a compound that can cause hives in some individuals from long-term exposure and has been deemed non-IFRA (International Fragrance Association) compliant. This makes it a safer and more acceptable option in the fragrance industry.

Sources

http://www.abchemicalindustries.com/acetyl-iso-eugenol-2394883.html http://www.basenotes.net/threads/413562-Iso-Eugenol-replacer http://www.organicaaroma.com/products/synthetic/acetyl-iso-eugenol https://en.wikipedia.org/wiki/Isoeugenol http://www.basenotes.net/threads/407876-Vintage-Dianthine-Base-Formula

Preparation

From isoeugenol and acetic acid by esterification.

Safety Profile

Moderately toxic by ingestion. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Metabolism

The hydrolysis of ester linkages of foreign compounds may be catalysed by many different esterases, which are to be found in all animals and bacteria and which generally have a low degree of substrate specificity(Parke, 1968).

InChI:InChI=1/C12H14O3/c1-4-5-10-6-7-11(15-9(2)13)12(8-10)14-3/h4-8H,1-3H3/b5-4+

Upstream product

• 97-54-1 2-methoxy-4-propenylphenol 
• 108-24-7 acetic anhydride 
• 93-28-7 eugenol acetate 
• 97-53-0 4-allylguaiacol 
• 75-36-5 acetyl chloride 
• 201230-82-2 carbon monoxide 
• 5932-68-3 (E)-2-methoxy-4-(1-propenyl)phenol 
• 58343-58-1 9,10-dihydro-9,10-dihydroxyanthracene 
• 36382-85-1 2-Methoxy-4-[2-(2-methoxy-phenoxy)-prop-(Z)-ylidene]-cyclohexa-2,5-dienone 
• 60-35-5 acetamide 
• 5912-86-7 cis-isoeugenol 
• 121-33-5 vanillin 
• 6997-34-8 1-(4-hydroxy-3-methoxyphenyl)propan-1-ol 
• 120-11-6 2-methoxy-1-(phenylmethoxy)-4-(1-propenyl)-benzene 

Downstream Products

• 54514-38-4 2-methoxy-4-(3-methyl-2-oxiranyl)phenyl acetate 
• 1215-30-1 1,2-dibromo-1-(4-acetoxy-3-methoxyphenyl)-propane 
• 859188-25-3 1-acetoxy-2-methoxy-4-(2-nitro-1-nitroso-propyl)-benzene 
• 1215-30-1 (+/-)-3-methoxy-4-acetoxy-1-(threo-1.2-dibromo-propyl)-benzene 
• 1215-30-1 (+/-)-3-methoxy-4-acetoxy-1-(erythro-1.2-dibromo-propyl)-benzene 

Relevant articles and documents

One-pot hydroformylation/O-acylation of propenylbenzenes for the synthesis of polyfunctionalized fragrances

A process involving the hydroformylation/O-acylation of propenylbenzenes with a phenolic group is described for eugenol, isoeugenol, chavicol, propenyl guaethol, 2-allylphenol, and 2-allyl-6-methylphenol. The reactions occur in parallel, under the same reaction conditions in anisole, a solvent with an impressive sustainability rank comparable to those of ethanol and water. The products contain formyl and acetoxy moieties, both established olfactory groups in flavor and fragrance industry, and present potential as new fragrance components with less allergenic properties. To the best of our knowledge, this is the first time that a one-pot process involving hydroformylation combined with further functionalization in a remote site is described.

A Pd-Catalyzed Site-Controlled Isomerization of Terminal Olefins

An effective Pd-catalyzed isomerization of olefins with 2-PyPPh2 as the ligand is described. A wide variety of trans-2-olefins bearing various functional groups can be obtained with high regio- A nd stereoselectivity under mild reaction conditions. The ligand is crucial for the reaction.

Hydrophilic (ν6-Arene)-Ruthenium(II) Complexes with P-OH ligands as catalysts for the isomerization of allylbenzenes and C-H bond arylation reactions in water

Half-sandwich ruthenium(II) complexes containing ν6-coordinated 3-phenylpropanol and phosphinous-acid-type ligands, namely, [RuCl2(ν6-C6H5CH2CH2CH2OH){P(OH)R2}] (R = Me (2a), Ph (2b), 4-C6H4CF3 (2c), 4-C6H4OMe (2d), OMe (2e), OEt (2f), and OPh (2g), have been synthesized in 44-88% yield by reacting [RuCl2{ν6:κ1(O)-C6H5CH2CH2CH2OH}] (1) with the appropriate pentavalent phosphorus oxide R2P(═O)H. The structure of [RuCl2(ν6-C6H5CH2CH2CH2OH){P(OH)Me2}] (2a) was unequivocally confirmed by X-ray diffraction methods. Compounds 2a-g proved to be catalytically active in the isomerization of allylbenzenes into the corresponding (1-propenyl)benzene derivatives employing water as the sole reaction solvent, with [RuCl2(ν6-C6H5CH2CH2CH2OH){P(OH)(OPh)2}] (2g) showing the best performance and a broad substrate scope (73-93% isolated yields with E/Z ratios around 90:10 employing 1 mol % of 2g and 3 mol % of K2CO3, and performing the catalytic reactions at 80 °C for 4-24 h). The results herein presented show for the first time the utility of phosphinous acids as auxiliary ligands for metal-catalyzed olefin isomerization processes, reactions in which a cooperative role for the P - OH unit is proposed. On the other hand, the utility of complexes 2a-g as catalysts for ortho-arylation reactions of 2-phenylpyridine in water is also briefly discussed.