Name: Methyl acetate-PEG1-methyl acetate
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Please store the product under the recommended conditions in the Certificate of Analysis.

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IUPACName

methyl 2-[2-(2-methoxy-2-oxoethoxy)ethoxy]acetate

InChI Key

VGYYKZVYXBJBOU-UHFFFAOYSA-N

InChI

InChI=1S/C8H14O6/c1-11-7(9)5-13-3-4-14-6-8(10)12-2/h3-6H2,1-2H3

SMILES

COC(=O)COCCOCC(=O)OC

1. Fragrance material review on 2-methyl-4-phenyl-2-butyl acetate

D McGinty, C S Letizia, A M Api Food Chem Toxicol. 2012 Sep;50 Suppl 2:S435-8.doi: 10.1016/j.fct.2012.02.075.Epub 2012 Mar 6.

A toxicologic and dermatologic review of 2-methyl-4-phenyl-2-butyl acetate when used as a fragrance ingredient is presented. 2-Methyl-4-phenyl-2-butyl acetate is a member of the fragrance structural group Aryl Alkyl Alcohol Simple Acid Esters (AAASAE). The AAASAE fragrance ingredients are prepared by reacting an aryl alkyl alcohol with a simple carboxylic acid (a chain of 1-4 carbons) to generate formate, acetate, propionate, butyrate, isobutyrate and carbonate esters. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for 2-methyl-4-phenyl-2-butyl acetate were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, skin sensitization, and elicitation data. A safety assessment of the entire AAASAE will be published simultaneously with this document. Please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all AAASAE in fragrances.

2. Fragrance material review on 1,3-benzodioxole-5-propanol, α-methyl-, 5-acetate

D McGinty, C S Letizia, A M Api Food Chem Toxicol. 2012 Sep;50 Suppl 2:S330-2.doi: 10.1016/j.fct.2012.02.049.Epub 2012 Mar 3.

A toxicologic and dermatologic review of 1,3-benzodioxole-5-propanol, α-methyl-, 5-acetate when used as a fragrance ingredient is presented. 1,3-Benzodioxole-5-propanol, α-methyl-, 5-acetate is a member of the fragrance structural group Aryl Alkyl Alcohol Simple Acid Esters (AAASAE). The AAASAE fragrance ingredients are prepared by reacting an aryl alkyl alcohol with a simple carboxylic acid (a chain of 1-4 carbons) to generate formate, acetate, propionate, butyrate, isobutyrate and carbonate esters. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for 1,3-benzodioxole-5-propanol, α-methyl-, 5-acetate were evaluated, then summarized, and includes physical properties. A safety assessment of the entire AAASAE will be published simultaneously with this document. Please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all AAASAE in fragrances.

3. Acetate catabolism by Methanosarcina barkeri: evidence for involvement of carbon monoxide dehydrogenase, methyl coenzyme M, and methylreductase

J A Krzycki, L J Lehman, J G Zeikus J Bacteriol. 1985 Sep;163(3):1000-6.doi: 10.1128/jb.163.3.1000-1006.1985.

The pathway of acetate catabolism in Methanosarcina barkeri strain MS was studied by using a recently developed assay for methanogenesis from acetate by soluble enzymes in cell extracts. Extracts incubated with [2-14C]acetate, hydrogen, and ATP formed 14CH4 and [14C]methyl coenzyme M as products. The apparent Km for acetate conversion to methane was 5 mM. In the presence of excess acetate, both the rate and duration of methane production was dependent on ATP. Acetyl phosphate replaced the cell extract methanogenic requirement for both acetate and ATP (the Km for ATP was 2 mM). Low concentrations of bromoethanesulfonic acid and cyanide, inhibitors of methylreductase and carbon monoxide dehydrogenase, respectively, greatly reduced the rate of methanogenesis. Precipitation of CO dehydrogenase in cell extracts by antibodies raised to 95% purified enzyme inhibited both CO dehydrogenase and acetate-to-methane conversion activity. The data are consistent with a model of acetate catabolism in which methylreductase, methyl coenzyme M, CO dehydrogenase, and acetate-activating enzymes are components. These results are discussed in relation to acetate uptake and rate-limiting transformation mechanisms in methane formation.

Methyl acetate-PEG1-methyl acetate, is designed to provide a compact polyethylene glycol–based spacer flanked by ester functionalities, enabling efficient conjugation between ligand-bearing fragments. Its ether-rich segment can enhance solubility and conformational flexibility while maintaining a defined attachment geometry for targeted protein degradation workflows. The following sections describe its structure-related features and practical reactivity considerations for PROTAC assembly in detail below.

Structure: The linker contains a short PEG-derived ether segment connected through ester linkages to methyl acetate termini. Its structure features ester carbonyls and ether oxygen atoms, providing a polar, hydrogen-bond-accepting scaffold. Overall, it is expected to show moderate polarity and good compatibility with common organic synthesis conditions used for PROTAC construction.

Reactivity: Ester-terminated linkers are typically engaged via nucleophilic acyl substitution or transesterification-type strategies to form new ester or related conjugation bonds under controlled conditions. Suitable approaches often employ mild base or nucleophile activation, with solvents such as polar aprotic media or alcohol-containing systems depending on the coupling partner. Mechanistically, acyl substitution proceeds through a tetrahedral intermediate, enabling stepwise assembly of PROTAC intermediates prior to final purification.

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It is commonly abbreviated as: C₁V₁ = C₂V₂