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InChI:InChI=1/C17H24O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-12,19-20H,3-7,9H2,1-2H3/b15-12-

Upstream product

• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 
• 39886-76-5 [6]-gingerol 
• 123-66-0 Ethyl hexanoate 
• 121-33-5 vanillin 
• 1080-12-2 (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one 
• 91815-29-1 5-(3-Methoxy-4-trimethylsilanyloxy-phenyl)-3-oxo-pentanenitrile 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 56700-87-9 4-(3-methoxy-4-trimethylsilyloxyphenyl)butan-2-one 
• 91815-30-4 (Z)-5-Amino-1-(4-hydroxy-3-methoxy-phenyl)-dec-4-en-3-one 
• 91827-14-4 (Z)-2-Cyano-3-hydroxy-5-(4-hydroxy-3-methoxy-phenyl)-pent-2-enoic acid tert-butyl ester 
• 91827-15-5 5-(4-Hydroxy-3-methoxy-phenyl)-3-oxo-pentanenitrile 

Downstream Products

• 91815-33-7 <6>-dehydrogingerdione 

Relevant academic research and scientific papers

6-Gingerol and Semisynthetic 6-Gingerdione Counteract Oxidative Stress Induced by ROS in Zebrafish

6-Gingerol (1) is one of the major components in ginger and developing new synthetic methodologies could bring semisynthetic analogs with improved therapeutic properties. Towards this, multigram scale isolation of 6-gingerol with excellent purity was optimized using a simple and robust extraction, followed by column purification. Synthesis of 6-gingerdione, 7 from 6-gingerol was then achieved through selective –OTBDMS protection, DMP oxidation and deprotection reaction sequence for the first time. Compounds 1, 7 and 8 (dehydrozingerone) exhibited excellent cell-free antioxidant properties in DPPH, ABTS, superoxide radical scavenging assay and H2O2 assay at 10–50 μM concentrations. The hemolytic study suggests that up to 50 μM, all three compounds did not exhibit toxicity to human erythrocytes. When H2O2 treated zebrafish larvae groups (96hpf) were exposed to compounds 1, 7 and 8, it increases the SOD (19, 19.1 and 18.7 U/mg protein), CAT (18.1, 16.5, and 15.8 μmol/mg levels and decreases the lipid peroxidation level (13, 15 and 18 nmol/mg protein), respectively. In vivo ROS levels and degree of cell death were studied using DCFDA and Acridine orange assays. Compounds 1, 7 and 8 decreases the ROS and cell death level significantly. Taken together, compounds 1, 7 and 8 exhibit excellent antioxidant properties, counteract H2O2 induced oxidative stress, reduces cell death in zebrafish larvae.

Activation of the phase II enzymes for neuroprotection by ginger active constituent 6-dehydrogingerdione in PC12 cells

The cellular endogenous antioxidant system plays pivotal roles in counteracting or retarding the pathogenesis of many neurodegenerative diseases. Molecules with the ability to enhance the antioxidant defense thus are promising candidates for neuroprotective drugs. 6-Dehydrogingerdione (6-DG), one of the major components of dietary ginger, has received increasing attention due to its multiple pharmacological activities. However, how this pleiotropic molecule works on the neuronal system has not been studied. This paper reports that 6-DG efficiently scavenges various free radicals in vitro and displays remarkable cytoprotection against oxidative stress-induced neuronal cell damage in the neuron-like rat pheochromocytoma cell line, PC12 cells. Pretreatment of PC12 cells with 6-DG significantly up-regulates a panel of phase II genes as well as the corresponding gene products, such as glutathione, heme oxygenase, NAD(P)H:quinone oxidoreductase, and thioredoxin reductase. Mechanistic study indicates that activation of the Keap1-Nrf2-ARE pathway is the molecular basis for the cytoprotection of 6-DG. This is the first revelation of this novel mechanism of 6-DG as an Nrf2 activator against oxidative injury, providing the potential therapeutic use of 6-DG as neuroprotective agent.

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).