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

• 60-35-5 acetamide 
• 97-54-1 2-methoxy-4-propenylphenol 
• 97-53-0 4-allylguaiacol 
• 121-33-5 vanillin 
• 6997-34-8 1-(4-hydroxy-3-methoxyphenyl)propan-1-ol 
• 75-36-5 acetyl chloride 
• 120-11-6 2-methoxy-1-(phenylmethoxy)-4-(1-propenyl)-benzene 
• 506-96-7 Acetyl bromide 
• 108-24-7 acetic anhydride 
• 201230-82-2 carbon monoxide 
• 93-28-7 eugenol acetate 
• 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 

Downstream Products

• 1215-30-1 1,2-dibromo-1-(4-acetoxy-3-methoxyphenyl)-propane 
• 54514-38-4 2-methoxy-4-(3-methyl-2-oxiranyl)phenyl acetate 
• 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.

Method for synthesizing E-methyl styrene compound

The method for preparing E-pyridyl or alkyl-substituted,bipyridine, in a solvent, in the presence of nitrogen protection, in, reaction 0 °C -50 °C in the presence of a metal nickel salt 24 - 36h, ligand and an additive is E, and the preparation method disclosed by the invention has the advantages, cheap 2,2 ’ - raw materials, easiness in obtaining 2,2 ’ - and the like. The ligand is,bipyridine or an alkyl-substituted bipyridyl compound, in the. presence of a nitrogen, protection agent, in a solvent.

Free Radical Scavenging Activity of Essential Oil of Eugenia caryophylata from Amboina Island and Derivatives of Eugenol

Essential oil from Eugenia caryophylata was normally used to heal many different deseaces. Various chemical compositions of essential oil distilled and steamed of Moluccas Eugenia caryophylata has been investigated by many different researchers. Even though an intensive research has been carried out of the local chemotypes, a very detail study has not been fully investigated to find out the complete chemical compounds from the plant essential oil and its content associated with their biological activities. In present paper, we assess the free radical scavenging of E. caryophylata collected from Moluccas islands, Indonesia. Essential oil was extracted from leaves, buds, and stems of plant by steam distillation and analyzed using GC-FID and GC-MS. The result showed that free radical activity of essential oil, main constituent and its derivatives were analized using in vitro method. Essential oil activity from stem obtained as (0.82±0.15 μg/mL) was higher than that from bud and leaf possessing both 1,1-diphenyl-2-picrylhydrazyl (DPPH) and (2,2'-azino-bis-3-ethylbenzthizoline-6-sulphonic acid (ABTS) radical scavenging assays by sinergism of eugenol, eugenyl acetate, β-caryophylene and humulene. The activity of isoeugenol (2) (3.59±0.54 μM) and (5.0±0.53 μM) scavenging DPPH and ABTS, respectively, as derivatives eugenol was higher than (3), (4) and (5). Although (6) was active originally, it was inactive after conversion of the ester. While the change of the double bond of location to conjungation structure caused more activity scavenging radicals than the starting molecule.