77333-95-0

Upstream product

• 1080-12-2 (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one 
• 121-33-5 vanillin 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 
• 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 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 91815-23-5 4-{2-[2-(2-Hydroxy-tridecyl)-[1,3]dioxolan-2-yl]-ethyl}-2-methoxy-phenol 
• 112-54-9 Dodecanal 
• 56700-87-9 4-(3-methoxy-4-trimethylsilyloxyphenyl)butan-2-one 

Relevant academic research and scientific papers

Influence of side chain structure changes on antioxidant potency of the [6]-gingerol related compounds

[6]-Gingerol and [6]-shogaol are the major pungent components in ginger with a variety of biological activities including antioxidant activity. To explore their structure determinants for antioxidant activity, we synthesized eight compounds differentiated by their side chains which are characteristic of the C1-C2 double bond, the C4-C5 double bond or the 5-OH, and the six- or twelve-carbon unbranched alkyl chain. Our results show that their antioxidant activity depends significantly on the side chain structure, the reaction mediums and substrates. Noticeably, existence of the 5-OH decreases their formal hydrogen-transfer and electron-donating abilities, but increases their DNA damage- and lipid peroxidation-protecting abilities. Additionally, despite significantly reducing their DNA strand breakage-inhibiting activity, extension of the chain length from six to twelve carbons enhances their anti-haemolysis activity.

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).