39728-80-8

Usage

InChI:InChI=1/C11H16O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-8,12-13H,3-4H2,1-2H3

Upstream product

• 1080-12-2 Dehydrozingerone 
• 56700-87-9 4-(3-methoxy-4-trimethylsilyloxyphenyl)butan-2-one 
• 66-25-1 hexanal 
• 64-17-5 ethanol 
• 1080-12-2 (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one 
• 917-64-6 methyl magnesium iodide 
• 80638-48-8 3-(3'-methoxy-4'-hydroxyphenyl)propionaldehyde 
• 121-33-5 vanillin 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 
• 141-78-6 ethyl acetate 

Downstream Products

• 960357-42-0 4-[2-(4-nitrobenzyl)-4-hydroxy-5-methoxyphenyl]butan-2-one 
• 960357-43-1 4-(2-benzyl-4-hydroxy-5-methoxyphenyl)butan-2-one 
• 1443152-51-9 (R)-4-(4'-hydroxy-3'-methoxyphenyl)-2-butyl acetate 
• 1450832-91-3 (S)-4-(4'-hydroxy-3'-methoxyphenyl)-2-butyl acetate 
• 1443152-50-8 (S)-4-(4'-acetyloxy-3'-methoxyphenyl)-2-butanol 

Relevant academic research and scientific papers

Zingerone in the flower of passiflora maliformis attracts an australian fruit fly, bactrocera jarvisi (Tryon)

Passiflora maliformis is an introduced plant in Australia but its flowers are known to attract the native Jarvis’s fruit fly, Bactrocera jarvisi (Tryon). The present study identifies and quantifies likely attractant(s) of male B. jarvisi in P. maliformis

Phenyl trimethyl ammonium tribromide mediated robust one-pot synthesis of spiro-oxacycles-an economic route-stereoselective synthesis of oxaspirohexacyclodieneones

This paper entails the first recognition of Phenyl Trimethyl Ammonium Tribromide (PTAB) as an effective reagent for spiro-cyclizations proceeding via oxidative dearomatization. The experiment exhibits economical, metal and ligand free one-pot accomplishment of these significant transformations. The described protocol presents the first generalised methodology of spiro-oxacycle synthesis which can be applied towards various directions. A stereoselective synthesis of oxa-spirocyclooxadieneones has been accomplished.

Synthesis of raspberry and ginger ketones by nickel boride-catalyzed hydrogenation of 4-arylbut-3-en-2-ones

Raspberry and ginger ketones have been synthesized in good yield by the hydrogenation of the corresponding unsaturated precursors 4-(4′- hydroxyphenyl)but-3-en-2-one and 4-(4′-hydroxy-3′-methoxyphenyl)but- 3-en-2-one, respectively, using a freshly prepared suspension of nickel boride in methanol as catalyst.

Glycerol/Hypophosphorous acid and PhSeSePh: An efficient and selective system for reactions in the carbon-carbon double bond of (E)-chalcones

We describe herein our results for the reaction of benzeneselenol, generated in situ by reaction of diphenyl diselenide with H3PO 2, with various (E)-chalcones using glycerol as solvent. Using our optimized reaction conditions, a range of chemoselective 1,4-reduction products could be obtained in good yields. The glycerol/H3PO2 system can be easily recovered and reused in chemoselective 1,4-reductions for successive cycles without loss of efficiency. Additionally, under 1,4-reducing reaction conditions, the natural product zingerone can be synthesized in good yield. ?2014 Sociedade Brasileira de Qui?mica.

Asymmetric synthesis of enantiomerically pure zingerols by lipase-catalyzed transesterification and efficient synthesis of their analogues

The achiral zingerone 1, readily available from ginger, can be easily transformed into chiral derivatives. Zingerol 2, a reduced product of zingerone 1 is expected to be an important new medicinal lead compound. We have achieved a concise synthesis of optically active zingerol (R)-2 and (S)-2 by the lipase-catalyzed stereoselective transesterification of racemic 2. Under the optimized conditions, a lipase from Alcaligenes sp. (Meito QLM) and vinyl acetate in i-Pr2O or hexane at 35 C within 1 h gave the alcohol (S)-2 and the acetate (R)-9 with high enantioselectivity without producing acetylated by-products. Since optically active (S)-2 and (R)-9 were obtained through lipase-catalyzed transesterification, other enantiomerically pure novel compounds could all be synthesized.

Protection-, salt-, and metal-free syntheses of [n]-shogaols by use of dimethylammonium dimethyl carbamate (DIMCARB) without protecting groups

Shogaols, the pungent principle of ginger, exhibit interesting bioactivities. Practical preparation of shogaols is highly desired. Here we report the protection/deprotection-, salt-, and metalfree synthesis of shogaol in three steps by use of dimethylammonium dimethyl carbamate (DIMCARB), in which DIMCARB smoothly promoted Mannich-type condensation of the ketone donor with the aldehyde acceptor through the iminium cation intermediate. Georg Thieme Verlag Stuttgart.

Studies towards the diastereoselective spiroannulation of phenolic derivatives

The oxidative spiroannulation of simple phenols bearing a chiral center was carried out. Good yields (61-83%) of spirocompounds were obtained. An increase in diastereomeric ratios from 55/45 to 81/19 was observed as the steric factor surrounding the chiral carbon increased.

Insect growth inhibition, antifeedant and antifungal activity of compounds isolated/ derived from Zingiber officinale Roscoe (ginger) rhizomes

Fresh rhizomes of Zingiber officinale (ginger), when subjected to steam distillation, yielded ginger oil in which curcumene was found to be the major constituent. The thermally labile zingiberene-rich fraction was obtained from its diethyl ether extract. Column chromatography of ginger oleoresin furnished a fraction from which [6]-gingerol was obtained by preparative TLC. Naturally occurring [6]-dehydroshogaol was synthesised following condensation of dehydrozingerone with hexanal, whereas zingerone and 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)butane were obtained by hydrogenation of dehydrozingerone with 10% Pd/C. The structures of the compounds were established by 1H NMR, 13C NMR and mass (EI-MS and ES-MS) spectral analysis. The test compounds exhibited moderate insect growth regulatory (IGR) and antifeedant activity against Spilosoma obliqua, and significant antifungal activity against Rhizoctonia solani. Among the various compounds, [6]-dehydroshogaol exhibited maximum IGR activity (EC50 3.55mg ml-1) while dehydrozingerone imparted maximum antifungal activity (EC50 86.49mg litre-1).

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).