71629-15-7

Upstream product

• 74345-31-6 2,4,4-trimethyl-3-(3-oxobut-1-enyl)cyclohex-2-enyl acetate 
• 113308-77-3 3-oxo-butyric acid 2,4,4-trimethyl-3-((E)-3-oxo-but-1-enyl)-cyclohex-2-enyl ester 
• 37677-81-9 (rac)-4-(2,3-epoxy-2,6,6-trimethylcyclohexyl)-3-buten-2-one 
• 79-77-6 (E)-β-ionone 
• 108-05-4 vinyl acetate 
• 14398-34-6 4-(3-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-one 
• 71629-13-5 (-)-(R)-4-hydroxy-β-ionone 
• 71596-98-0 (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (S)-2,4,4-trimethyl-3-((E)-3-oxo-but-1-enyl)-cyclohex-2-enyl ester 
• 151726-13-5 4-Nitro-benzoic acid (S)-2,4,4-trimethyl-3-((E)-3-oxo-but-1-enyl)-cyclohex-2-enyl ester 

Downstream Products

• 160335-16-0 (4S)-4-<(tert-Butyldimethylsilyl)oxy>-β-ionone 
• 112893-58-0 4-<3-(1-Ethoxy-2-bromoethoxy)-2,6,6-trimethylcyclohexen-1-yl>-but-3-en-2-one 

Relevant academic research and scientific papers

SYNTHESIS AND PLANT GROWTH INHIBITORY ACTIVITIES OF (+)- AND (-)-(2Z,4E)-5-(1',2'-EPOXY-2',6',6'-TRIMETHYLCYCLOHEXYL)-3-METHYL-2,4-PENTADIENOIC ACID

Chiral (+)- and (-)-enantiomers of (2Z,4E)-5-(1',2'-epoxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienoic acid have been synthesized from the chiral epoxy alcohols (+)- and (-)-1',2'-dihydro-1',2'-epoxy-β-ionone, which were prepared by Katsuki-Sharpless'asymmetric epoxidation of β-cyclogeraniol.The (+)-enantiomer showed strong inhibitory activity in a rice seedling and lettuce germination assay, whereas the (-)-enantiomer was 103 times less active. - Key Word Index - Plant growth inhibitor; absolute configuration; relationship between enantiomers and biological activity; rice seedling growth; lettuce seed germination; abscisic acid analogue; (2Z,4E)-5-(1',2'-epoxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienoic acid.

In Vitro Regio- and Stereoselective Oxidation of β-Ionone by Human Liver Microsomes

The metabolism of the norisoprenoid β-ionone was investigated in vitro using human liver microsomes and 11 different recombinant cytochrome P450 enzymes expressed in Trichoplusia ni cells. β-Ionone was found to be oxidized via 4S-hydroxylation by CYP2B6 i

Facile lipase catalysed syntheses of (S)-(+)-4-hydroxy-β-ionone and (S)-(+)-4-hydroxy-β-damascone: Chiral flavorants and synthons

Enantioselective syntheses of (S)-(+)-4-hydroxy-β-ionone and (S)-(+)-4-hydroxy-β-damascone have been achieved through pig pancreatic lipase catalysed trans-esterification. These molecules find utility as constituent in fruit-type fragrance and flavor form

Studies on the enantioselective oxidation of β-ionone with a whole E. coli system expressing cytochrome P450 monooxygenase BM3

Recombinant Escherichia coli cells, expressing an NADH-dependent cytochrome P450 monooxygenase BM-3 mutant, were used for the hydroxyalation of the sesquiterpenoid β-ionone to (R)-4-hydroxy-β-ionone. The decrease in enantioselectivity of cytochrome P450 monooxygenase BM-3 catalyzed hydroxylation of β-ionone can be ascribed to the overoxidation of the desired product. In this initial study we report, that by addressing reaction conditions the enantiomeric excess can be increased and the overoxidation can be reduced. Furthermore, we report herein the kinetic resolution of racemic 4-hydroxy-β-ionone using the same P450 monooxygenase for the production of (S)-4-hydroxy-β-ionone. Although the enantioselectivity of the enzyme is rather low for this reaction, this reaction could be of interest with improved P450 BM-3 variants. Both systems need further investigations and optimizations for preparative application.

Synthesis of (+)-(4S)- and (-)-(4R)-(11Z)-4-hydroxyretinals and determination of the absolute stereochemistry of a visual pigment chromophore in the firefly squid, Watasenia scintillans

First syntheses of (+)-(4S)- and (-)-(4R)-(11Z)-4-hydroxyretinals (4-OH-RALs) (4a and 4b) were accomplished from (4S)- and (4R)-4-hydroxy-β-ionones, respectively, to determine the absolute configuration of a visual pigment chromophore in Watasenia scintillans, which has been isolated as a new chromophore in the animal kingdom. The CD spectra of the native chromophore and its anti-oxime agreed with those of synthetic (4R)-compounds. Application of the CD exciton chirality method to the p-(dimethylamino)cinnamate of (4R)-4-OH-RAL also established the absolute configuration of the native chromophore as 4b.

Synthesis of (+)-(4S)- and (-)-(4R)11 Z-4-hydroxyretinals and determination of the absolute stereochemistry of a visual pigment chromophore in the bioluminescent squid, Watasenia scintillans

Synthesis of (+)-(4S)- and (-)-(4R)-11Z-4-hydroxyretinals (4-OH-RALs) 1a and 1b was accomplished from (4S)- and (4R)-4-hydroxy-β-ionones, respectively, to determine the absolute configuration of a visual pigment chromophore in Watasenia scintillans. The C

Easy access to an optically pure precursor of forskolin

The PLE catalysed resolution of the (+/-)-1-hydroxy-β-ionone acetoacetate resulted in the (-)-enantiomer 2 with high optical purity (95percent e.e.).Cyclisation of this material gives access to the (-)-lactone 1 in an optically pure form.

A NEW SYNTHETIC ROUTE TO (+/-)-FORSKOLIN

The trans-decalin lactone (35) has been elaborated in five steps from the bromo-acetal (10) using a novel stereoselective intramolecular radical mediated cyclisation reaction, viz (10)->(12) in tandem with an intramolecular Mukaiyama aldolisation, viz (34

2. Synthese von (-)-(R)-4-Hydroxy-β-ionon und (-)-(5R,6S)-5-Hydroxy-4,5-dihydro-α-ionon aus (-)-(S)-α-Ionon

The absolute configuration of the chiral 4-hydroxy-β-ionones and 5-hydroxy-4,5-dihydro-α-ionones has been determined by chemical connection with (-)-(S)-α-ionone i.e. by stereoselective epoxidation of the latter, followed by base catalyzed opening of the epoxide as well as by its hydride reduction.