Gram-scale economical synthesis of trans-coniferyl alcohol and its corresponding thiol

Abstract

Coniferyl alcohol is considered to be a potent antioxidant and a precursor of several bioactive products. In addition, it is a frequently used as a model compound in lignin chemistry. Coniferyl thiol is used analogously to study the sulfur chemistry in technical lignins. Coniferyl alcohol was synthesized in a large scale from commercially available ferulic acid by a mixed anhydride reduction method which affords high yields (84%) under very mild conditions and allows using sodium borohydride. The nucleophilic substitution of 4-O-acetylated coniferyl alcohol (3) with thioacetic acid in the presence of dimethylformamide (DMF) dineopentylacetal afforded 4-O-acetylated coniferyl thioacetate (5) in a 70% yield, which, in a 72% yield, was deprotected to the respective thiol (6). Both coniferyl alcohol and coniferyl thiol were comprehensively analytically characterized [one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) spectroscopy]. The presented approach renders the two model substances readily available on a gram scale and according to low-risk, environmentally compatible protocols.

Volatile Compounds from Flowers of Elaeagnus x submacrophylla Servett.: Extraction, Identification of Flavonoids, and Antioxidant Capacity

“…Some of which are widely described for their ability to trap free radicals, especially guaiacol derivatives (no. 56, 59, 68, 72, 78, 79, 81), [57,58] benzyl salicylate (no. 86), [59] chavicol moieties (no.…”

Xylochemicals and where to find them

“…Sassafras oil [195] (80-93%) [196][197] , Ocotea odorifera oil (42%) [198] S O O Me isosafrol from safrol (98%) [199] P OH HO MeO coniferyl alcohol reduction of ferulic acid (68%), [200] lignin depol. [185] P OH HO MeO O ferulic acid rice straw (0.87%), [187] rice bran [201] (178.3 µg/mg), [202] grapevine pruning (0.41 mg/g), [186] wheat straw (1.24%) [187] S OH O OMe MeO MeO asaronic acid oxidation of asarone (65%) [203][204]…”