77333-92-7

Upstream product

• 56700-87-9 4-(3-methoxy-4-trimethylsilyloxyphenyl)butan-2-one 
• 75-07-0 acetaldehyde 
• 91815-18-8 4-{2-[2-(2-Hydroxy-propyl)-[1,3]dioxolan-2-yl]-ethyl}-2-methoxy-phenol 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 121-33-5 vanillin 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 
• 1080-12-2 (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one 
• 91827-14-4 (Z)-2-Cyano-3-hydroxy-5-(4-hydroxy-3-methoxy-phenyl)-pent-2-enoic acid tert-butyl ester 
• 91827-16-6 {2-[2-(4-Hydroxy-3-methoxy-phenyl)-ethyl]-[1,3]dioxolan-2-yl}-acetonitrile 
• 91827-15-5 5-(4-Hydroxy-3-methoxy-phenyl)-3-oxo-pentanenitrile 
• 91827-17-7 {2-[2-(4-Hydroxy-3-methoxy-phenyl)-ethyl]-[1,3]dioxolan-2-yl}-acetaldehyde 
• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 

Relevant academic research and scientific papers

NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 44. A NEW GENERAL EFFICIENT SYNTHESIS OF DL--GINGEROLS AND RELATIVES THROUGH DIRECT C-ACYLATION USING DIETHYL PHOSPHOROCYANIDATE (DEPC)

DL--Gingerols (1) and their relatives, which have various interesting physiological actions, have been conveniently and efficiently prepared from ferulic acid (2) through direct C-acylation using diethyl phosphorocyanidate (DEPC) in the presence of triethylamine.KEYWORDS - -gingerol; C-acylation; diethyl phosphorocyanidate; β-ketonitrile; Grignard reaction; β-ketol

Syntheses of the (+/-)--Gingerols (Pungent Principles of Ginger) and Related Compounds through Regioselective Aldol Condensations: Relative Pungency Assays

The deprotonation of trimethylsilylzingerone (13) by lithium di-isopropylamide at -78 deg C has been found to be regioselective (92 : 8 in favour of less-substituted enolate): the anion was condensed with alkanals and acyl imidazoles to give convenient syntheses of (+/-)--- and --gingerols (1) and -, -, and -gingerdiones (9).Similary, 3-methoxy-4-trimethylsilyloxybenzylideneacetone (17) gave the (+/-)---dehydrogingerols (8) and -, -, and -dehydrogingerdiones (10).The aldol reaction to -gingerol and methyl -gingerol was also conducted through a vinyloxyborane or through the enol silyl ether (TiCl4 catalysis).Results of organoleptic assays on these compounds are discussed, and the relation between pungency in the gingerols and in capsaicin is commented on.The aldol method was also used to synthesise the natural β-ketols(+/-)-daphneolone (25) and (+/-)-hexahydrocurcumin (4).