Monomethyl adipate

clear colorless liquid

Methyl hydrogen adipate is a useful synthetic intermediate. It can be used to prepare 1,3,4-thiadiazole hydroxamic acid derivatives as novel histone deacetylase inhibitors which show potential antitumor activities. It can be also used to synthesize mannose-linked biphenylylacetic acid derivatives as novel inhibitors of selectin-mediated cell adhesion.

ChEBI: Monomethyl adipate is a dicarboxylic acid monoester that is the monomethyl ester of adipic acid. It has a role as a metabolite and a plasticiser.

According to the general procedure described above, a has been synthesized from adipic acid (730mg, 5 mmol) and methanol (10 ml). Yield: 80%.
The synthetic method of Monomethyl adipate mainly contains following three kinds:
The one, under alkaline condition or issue the first portion hydrolysis reaction in the catalysis of bioactive enzyme (pork liver lipase etc.) and obtain Monomethyl adipate (such as document Blaise; Koehler; Bulletin de la Societe Chimique deFrance; Vol. (4) 7; (1910); P.219).
The 2nd, by hexanodioic acid or adipic anhydride and ethanol, as catalyzer, the control reaction conditions carries out esterification and obtains Monomethyl adipate (such as document Chem.Zentralbl. with acid; Vol.97; (1926; P.126));
The 3rd, by the people such as Swann nineteen forty-three with hexanodioic acid, diethylene adipate and ethanol with the condition of acid as catalyst under control reaction conditions obtain monomethyl adipate(document such as Swann; Oehler; Buswell; Org.synth.Coll.Vol.11; (1943); P.227).
Synthetic method of monomethyl adipate
http://www.orgsyn.org/demo.aspx?prep=CV2P0264