69056-21-9

Upstream product

• 881-68-5 vanillin acetate 
• 4046-02-0 ethyl 4-hydroxy-3-methoxycinnamate 
• 7382-59-4 guaiacylglycerol-β-guaiacyl ether 
• 2309-07-1 Methyl ferulate 
• 6635-27-4 acetylferulic acid ethyl ester 
• 458-36-6 trans-coniferyl aldehyde 
• 97-53-0 4-allylguaiacol 
• 121-33-5 vanillin 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 94930-81-1 (E)-3-(4-hydroxy-3-methoxyphenyl)allyl acetate 
• 113349-27-2 3-(4-hydroxy-3-methoxy)-phenyl-2E-propenyl-1β-D-glucopyranoside 
• 124151-33-3 coniferin 
• 92446-10-1 [(E)-3-(4-Hydroxy-3-methoxy-phenyl)-acryloyloxymethylene]-dimethyl-ammonium; chloride 
• 69017-41-0 (E)-3-(4-acetoxy-3-methoxyphenyl)-2-propen-1-ol 

Downstream Products

• 37791-78-9 (Z)-coniferyl alcohol diacetate 
• 53891-05-7 (+/-)-1c,4c-bis-[4-(2,4-dinitro-phenoxy)-3-methoxy-phenyl]-(3ar,6ac)-tetrahydro-furo[3,4-c]furan 
• 487-36-5 (+/-)-pinoresinol 
• 38153-27-4 (2E)-3-(4-O-benzyloxy-3-methoxyphenyl)prop-2-en-1-ol 
• 76948-72-6 cleomiscosin A 
• 76985-93-8 cleomiscosin B 
• 72328-02-0 3-(4-hydroxy-3-methoxyphenyl)benzanthracen-7-one 
• 138225-09-9 2-hydroxymethyl-3-(4-hydroxy-3-methoxyphenyl)benzanthracen-7-one 
• 828270-45-7 1-(4-hydroxy-3-methoxyphenyl)-2-(4-<2-formyl-(E)-vinyl>-2-methoxyphenoxy)-propane-1,3-diol 
• 261778-30-7 1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(E)-3-hydroxy-1-propenyl]-2-methoxyphenoxy}-1,3-propanediol 
• 68946-40-7 Acetyl-trans-3-(4-acetoxy-3-methoxyphenyl)-2-propenyldisulfid 
• 68946-43-0 1,5-Bis-(4-acetoxy-3-methoxyphenyl)-pentan 
• 68946-41-8 trans-trans-Bis-<3-(4-acetoxy-3-methoxyphenyl)-2-propenyl>-disulfid 
• 68946-44-1 1,7-Bis-(4-acetoxy-3-methoxyphenyl)-4-(4-acetoxy-3-methoxybenzyl)-heptan 

Relevant academic research and scientific papers

A new synthesis of (Z)-coniferyl alcohol, and characterization of its derived synthetic lignin

The (Z)-monolignols (hydroxycinnamyl alcohols) are found along with their predominant (E)-isomers in a number of plants. Their role in lignification is unknown. A new synthetic route to (Z)-coniferyl alcohol has been developed via Still and Gennari's modification of the Horner-Emmons olefination to produce (Z)-unsaturated esters. Although previous studies have shown that (Z)-coniferyl alcohol will polymerize by single-electron (radical) processes to produce synthetic lignins, the stereochemistry of units in the resulting structure had not been addressed. NMR analysis of a synthetic lignin from (Z)-coniferyl alcohol indicates that unsaturated sidechains in the resulting lignin retain their (Z)-geometry. Other structures are altered in their relative proportions but retain the same stereochemistry. Assignment of structures in these synthetic lignins provides the necessary database for more careful examination of real plant lignins.

Consolidated production of coniferol and other high-value aromatic alcohols directly from lignocellulosic biomass

Sustainable production of fine chemicals and biofuels from renewable biomass offers a potential alternative to the continued use of finite geological oil reserves. However, in order to compete with current petrochemical refinery processes, alternative biorefinery processes must overcome significant costs and productivity barriers. Herein, we demonstrate the biocatalytic production of the versatile chemical building block, coniferol, for the first time, directly from lignocellulosic biomass. Following the biocatalytic treatment of lignocellulose to release and convert ferulic acid with feruloyl esterase (XynZ), carboxylic acid reductase (CAR) and aldo-keto reductase (AKR), this whole cell catalytic cascade not only achieved equivalent release of ferulic acid from lignocellulose compared to alkaline hydrolysis, but also displayed efficient conversion of ferulic acid to coniferol. This system represents a consolidated biodegradation-biotransformation strategy for the production of high value fine chemicals from waste plant biomass, offering the potential to minimize environmental waste and add value to agro-industrial residues.

Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers

A simple method for the dimerization of phenylpropenoid derivatives is reported. It leverages electrochemical oxidation of p-unsaturated phenols to access the dimeric materials in a biomimetic fashion. The mild nature of the transformation provides excellent functional group tolerance, resulting in a unified approach for the synthesis of a range of natural products and related analogues with excellent regiocontrol. The operational simplicity of the method allows for greater efficiency in the synthesis of complex natural products. Interestingly, the quinone methide dimer intermediates are potent radical-trapping antioxidants; more so than the phenols from which they are derived—or transformed to—despite the fact that they do not possess a labile H-atom for transfer to the peroxyl radicals that propagate autoxidation.

Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol

Herein we describe a one-pot microwave-assisted method for the synthesis of cinnamic acid and coumarin derivatives. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. A regioselective Claisen rearrangement was also efficiently incorporated into the synthetic sequence to further increase the complexity of the product. Notably, this approach provides high product yields and selectivities without the need of a phenol protecting group.

Asymmetric Organocatalytic Stepwise [2+2] Entry to Tetra-Substituted Heterodimeric and Homochiral Cyclobutanes

An asymmetric synthesis of tetra-substituted cyclobutanes involving an organocatalytic, stepwise [2+2]-cycloaddition is described. The secondary-amine-catalyzed method allows for the hetero-dimerization of two different cinnamic-acid-derived sub-units, opening a novel one-step assembly to densely functionalized, head-to-tail coupled dimeric cyclobutanes in high enantiomeric excess. A series of selective synthetic interconversions in these sensitive cycloadducts is also described.

Anti selective glycolate aldol reactions of (: S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one: application towards the asymmetric synthesis of 8-4′-oxyneolignans

The anti selective glycolate aldol reactions of (S)-4-isopropyl-1-[(R)-1-phenylethyl]imidazolidin-2-one auxiliary have been standardized with high yields and excellent diastereoselectivities on various substituted aryl, allyl and alkyl aldehydes. The optimized reaction conditions were employed for the stereoselective synthesis of oxyneolignans.

MELANIN GENERATION INHIBITOR AND WHITENING AGENT

PROBLEM TO BE SOLVED: To provide a melanin generation inhibitor and a whitening agent that are excellent in whitening effect and also excellent in safety and temporal stability. SOLUTION: The invention provides a melanin generation inhibitor containing a compound represented by formula [1] as an active ingredient, a whitening agent, as well as a melanin generation inhibiting method and a whitening method by applying such agents to the skin. (R1, R2, R4, and R5 are each independently H, a hydroxyl group, an alkyl group of C1-4, or -O-C(=O)R6; R6 is an alkyl group of C1-4; R3 is H, an alkyl group of C1-4, or -C(=O)R7; and R7 is an alkyl group of C1-8.) SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs

A new coniferol derivative, named as tripolinolate A (1), and 11 known compounds (2-12) were isolated from whole plants of Tripolium vulgare Nees. The structure of this new compound was determined as 4-(2S-methylbutyryl)-9-acetyl-coniferol based on its NMR and HRESIMS spectral analyses. A simple and efficient method was designed to prepare tripolinolate A and its 19 analogs including nine new chemical entities for bioactive assay. Tripolinolate A and its analog 4,9-diacetyl-coniferol were found to be the two most active compounds that significantly inhibited the proliferation of different cancer cell lines with IC50 values ranging from 0.36 to 12.9 μM and induced apoptosis in tumor cells. Structure-activity relationship analysis suggested that the molecular size of acyl moieties at C-4 and C-9 position might have an effect on the activity of this type of coniferol derivatives.

A biocompatible alkene hydrogenation merges organic synthesis with microbial metabolism

Organic chemists and metabolic engineers use orthogonal technologies to construct essential small molecules such as pharmaceuticals and commodity chemicals. While chemists have leveraged the unique capabilities of biological catalysts for small-molecule production, metabolic engineers have not likewise integrated reactions from organic synthesis with the metabolism of living organisms. Reported herein is a method for alkene hydrogenation which utilizes a palladium catalyst and hydrogen gas generated directly by a living microorganism. This biocompatible transformation, which requires both catalyst and microbe, and can be used on a preparative scale, represents a new strategy for chemical synthesis that combines organic chemistry and metabolic engineering. Reduction to practice: A hydrogenation reaction has been developed that employs hydrogen generated in situ by a microorganism and a biocompatible palladium catalyst to reduce alkenes on a synthetically useful scale. This type of transformation, which directly combines tools from organic chemistry with the metabolism of a living organism for small-molecule production, represents a new strategy for chemical synthesis.

SYNTHESIS OF CATECHIN AND EPICATECHIN CONJUGATES

The present invention relates generally to catechin and epicatechin conjugates of formula (I). For example, a chemical synthesis process for the preparation of catechin and epi-catechin compounds, in particular of catechin and epi-catechin conjugates is disclosed. A further aspect of the invention pertains to new catechin and epi-catechin conjugate compounds.