title: Microwave (MW) promoted high yield expedient synthesis of steryl ferulates--A class of novel biologically active compounds: A comparative study of their antioxidant activity with that of naturally occurring γ-oryzanol.
abstract: Synthetic steryl ferulates [3-O-(trans-4-feruloyl)-sterols] are currently gaining considerable importance in recent years to be used as nutraceuticals and food additives as well as in pharmaceutical applications substituting γ-oryzanol - a class of naturally occurring steryl ferulates having potent antioxidant and other organoleptic properties. Considering the importance of this class of compounds coupled with green technology associated with microwave energy (MW) in organic synthesis, we report here an expedited and high yield synthesis of steryl ferulates from abundant steroids, viz., cholesterol, cholestanol, stigmasterol, stigmastanol, β-sitosterol, β-campesterol, β-campestanol and ergosterol applying MW energy in the crucial step of esterification process of sterols with trans-4-O-acetylferulic acid to furnish their esterified products, viz., 3-O-(trans-4-O-acetylferuloyl)-sterols for their eventual deprotection to their respective steryl ferulates. We further report an efficient and scalable process of producing acetylferulic acid. Testing of synthesized steryl ferulates against antioxidant assays has also been highlighted.
authors.affiliation: Natural Products Chemistry Division, CSIR-North East Institute of Science & Technology, Jorhat 785006, India.
authors.forename: Ashma
authors.initials: A
authors.lastname: Begum
authors.affiliation: Natural Products Chemistry Division, CSIR-North East Institute of Science & Technology, Jorhat 785006, India.
authors.forename: Preetismita
authors.initials: P
authors.lastname: Borah
authors.affiliation: Natural Products Chemistry Division, CSIR-North East Institute of Science & Technology, Jorhat 785006, India. Electronic address: pritishchowdhury@yahoo.com.
authors.forename: Pritish
authors.initials: P
authors.lastname: Chowdhury
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry; D003373:Coumaric Acids / Q000737:chemistry*; D008872:Microwaves; D010666:Phenylpropionates / Q000737:chemistry*; D013261:Sterols / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000975:Antioxidants; D003373:Coumaric Acids; D010666:Phenylpropionates; D013261:Sterols; C004999:ferulic acid; C013172:gamma-oryzanol
keywords: Acetyl ferulic acid; Antioxidants; Microwave energy; Nutraceuticals; Steryl ferulates; γ-Oryzanol