20649-40-5

Upstream product

• 55226-78-3 methyl (2E)-3-[4-(acetyloxy)phenyl]-2-propenoate 
• 92446-09-8 [(E)-3-(4-Hydroxy-phenyl)-acryloyloxymethylene]-dimethyl-ammonium; chloride 
• 2979-06-8 ethyl (E)-4-hydroxycinnamate 
• 3943-97-3 methyl 4-hydroxycinnamate 
• 120442-73-1 (E)-4-hydroxycinnamyl alcohol 4-O-β-D-glucopyranoside 
• 123-08-0 4-hydroxy-benzaldehyde 
• 878-00-2 4-formylphenyl acetate 
• 58505-83-2 4‐((E)-2-formylvinyl)phenyl acetate 
• 1095624-04-6 methyl (2E)-3-[4-(aminomethoxyphosphoryloxy)phenyl]acrylate 
• 5034-68-4 4-[(2S)-2-amino-3-hydroxypropyl]phenol 
• 27542-85-4 4-acetoxycinnamic acid 
• 107-18-6 allyl alcohol 
• 27914-73-4 4-acetoxybenzoyl chloride 
• 7400-08-0 p-Coumaric Acid 

Downstream Products

• 51765-03-8 (E)-3-[4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl]-propenol 
• 58115-15-4 Acetic acid 4-acetoxy-2-[(E)-3-(4-acetoxy-phenyl)-allyl]-5-methoxy-phenyl ester 
• 2538-87-6 trans-p-hydroxycinnamaldehyde 
• 905277-59-0 p-coumaryl alcohol 2,4-dinitrophenyl ether 
• 20649-39-2 (E)-1-(4-hydroxyphenyl)propene 
• 501-92-8 4-(prop-2-enyl)phenol 
• 20238-83-9 dihydro-p-coumaryl aldehyde 
• 10210-17-0 3-(4-hydroxyphenyl)propan-1-ol 
• 132294-76-9 p-coumaryl alcohol-γ-O-β-D-glucopyranoside 
• 4361-22-2 4-(3-hydroxypropyl)cyclohexan-1-ol 
• 108-93-0 cyclohexanol 

Relevant academic research and scientific papers

A one-pot synthesis of coumaryl, coniferyl and sinapyl alcohol

The side chain of 4-allylphenol can be easily deprotonated if the butyl-lithium/potassium tert-butoxide superbase is employed. Consecutive treatment with fluorodimethoxyboron and hydrogen peroxide affords directly 3-(4-hydroxy-phenyl)-2-propen-1-ol ('coumaryl alcohol'). In the same way, 4-allyl-2-methoxyphenol can be converted to coniferyl alcohol and 4-allyl-2,6-dimethoxyphenol to sinapyl alcohol.

Total synthesis of (±)-sinaiticin

(±)-Sinaiticin (12) was first synthesized from 4-hydroxybenzoaldehyde (1) and caffeic acid (4). This synthesis involves the construction of flavon ring with DDQ and the formation of 1,4-benzodioxane ring by coupling reaction in which a epimerization was t

Arabidopsis thaliana β-Glucosidases BGLU45 and BGLU46 hydrolyse monolignol glucosides

In higher plants, β-glucosidases belonging to glycoside hydrolase (GH) Family 1 have been implicated in several fundamental processes including lignification. Phylogenetic analysis of Arabidopsis thaliana GH Family 1 has revealed that At1g61810 (BGLU45), At1g61820 (BGLU46), and At4g21760 (BGLU47) cluster with Pinus contorta coniferin β-glucosidase, leading to the hypothesis that their respective gene products may be involved in lignification by hydrolysing monolignol glucosides. To test this hypothesis, we cloned cDNAs encoding BGLU45 and BGLU46 and expressed them in Pichia pastoris. The recombinant enzymes were purified to apparent homogeneity by ammonium sulfate fractionation and hydrophobic interaction chromatography. Among natural substrates tested, BGLU45 exhibited narrow specificity toward the monolignol glucosides syringin (Km, 5.1 mM), coniferin (Km, 7 mM), and p-coumaryl glucoside, with relative hydrolytic rates of 100%, 87%, and 7%, respectively. BGLU46 exhibited broader substrate specificity, cleaving salicin (100%), p-coumaryl glucoside (71%; Km, 2.2 mM), phenyl-β-d-glucoside (62%), coniferin (8%), syringin (6%), and arbutin (6%). Both enzymes also hydrolysed p- and o-nitrophenyl-β-d-glucosides. Using RT-PCR, we showed that BGLU45 and BGLU46 are expressed strongly in organs that are major sites of lignin deposition. In inflorescence stems, both genes display increasing levels of expression from apex to base, matching the known increase in lignification. BGLU45, but not BGLU46, is expressed in siliques, whereas only BGLU46 is expressed in roots. Taken together with recently described monolignol glucosyltransferases [Lim et al., J. Biol. Chem. (2001) 276, 4344-4349], our enzymological and molecular data support the possibility of a monolignol glucoside/β-glucosidase system in Arabidopsis lignification.

Dirigent Proteins Guide Asymmetric Heterocoupling for the Synthesis of Complex Natural Product Analogues

Phenylpropanoids are a class of abundant building blocks found in plants and derived from phenylalanine and tyrosine. Phenylpropanoid polymerization leads to the second most abundant biopolymer lignin while stereo- and site-selective coupling generates an array of lignan natural products with potent biological activity, including the topoisomerase inhibitor and chemotherapeutic etoposide. A key step in etoposide biosynthesis involves a plant dirigent protein that promotes selective dimerization of coniferyl alcohol, a common phenylpropanoid, to form (+)-pinoresinol, a critical C2 symmetric pathway intermediate. Despite the power of this coupling reaction for the elegant and rapid assembly of the etoposide scaffold, dirigent proteins have not been utilized to generate other complex lignan natural products. Here, we demonstrate that dirigent proteins from Podophyllum hexandrum in combination with a laccase guide the heterocoupling of natural and synthetic coniferyl alcohol analogues for the enantioselective synthesis of pinoresinol analogues. This route for complexity generation is remarkably direct and efficient: three new bonds and four stereocenters are produced from two different achiral monomers in a single step. We anticipate our results will enable biocatalytic routes to difficult-to-access non-natural lignan analogues and etoposide derivatives. Furthermore, these dirigent protein and laccase-promoted reactions of coniferyl alcohol analogues represent new regio- and enantioselective oxidative heterocouplings for which no other chemical methods have been reported.

(±)-trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents: Synthesis, in vitro evaluation and SAR analysis

Leishmaniasis, a neglected tropical disease caused by parasites of the genus Leishmania, causes a serious burden of disease around the world, represents a threat to the life of millions of people, and therefore is a major public health problem. More effective and non-toxic new treatments are required, especially for visceral leishmaniasis, the most severe form of the disease. On the backdrop that dihydrobenzofurans have previously shown antileishmanial activity, we present here the synthesis of a set of seventy trans-2-phenyl-2,3-dihydrobenzofurans and evaluation of their in vitro activity against Leishmania donovani as well as a discussion of structure-activity relationships. Compounds 8m-o and 8r displayed the highest potency (IC50 4.6). Nonetheless, structural optimization as further requirement was inferred from the high clearance of the most potent compound (8m) observed during determination in vitro of its metabolic stability. On the other hand, chiral separation of 8m and subsequent biological evaluation of its enantiomers demonstrated no effect of chirality on activity and cytotoxicity. Holistic analysis of in silico ADME-like properties and ligand efficiency metrics by a simple scoring function estimating druglikeness highlighted compounds 16c, 18 and 23 as promising candidates for further development. Overall, the potential of trans-2-phenyl-2,3-dihydrobenzofurans as leishmanicidal agents was confirmed.

Controllable synthesis of 2- And 3-aryl-benzomorpholines from 2-aminophenols and 4-vinylphenols

We present herein a method for the controllable synthesis of 3-aryl-benzomorpholine and 2-aryl-benzomorpholine cycloadducts via cross-coupling/annulation between electron-rich 2-aminophenols and 4-vinylphenols. Molecular oxygen was successfully used in the reaction as the terminal oxidant and the complete inversion of chemoselectivity was achieved by the adjustment of the solvents and bases at room temperature.

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.

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

In vitro analysis of the monolignol coupling mechanism using dehydrogenative polymerization in the presence of peroxidases and controlled feeding ratios of coniferyl and sinapyl alcohol

In this study, dehydrogenative polymers (DHP) were synthesized in vitro through dehydrogenative polymerization using different ratios of coniferyl alcohol (CA) and sinapyl alcohol (SA) (10:0, 8:2, 6:4, 2:8, 0:10), in order to investigate the monolignol coupling mechanism in the presence of horseradish peroxidase (HRP), Coprinus cinereus peroxidase (CiP) or soybean peroxidase (SBP) with H2O2, respectively. The turnover capacities of HRP, CiP and SBP were also measured for coniferyl alcohol (CA) and sinapyl alcohol (SA), and CiP and SBP were found to have the highest turnover capacity for CA and SA, respectively. The yields of HRP-catalyzed DHP (DHP-H) and CiP-catalyzed DHP (DHP-C) were estimated between ca. 7% and 72% based on the original weights of CA/SA in these synthetic conditions. However, a much lower yield of SBP-catalyzed DHP (DHP-S) was produced compared to that of DHP-H and DHP-C. In general, the DHP yields gradually increased as the ratio of CA/SA increased. The average molecular weight of DHP-H also increased with increasing CA/SA ratios, while those of DHP-C and DHP-S were not influenced by the ratios of monolignols. The frequency of β-O-4 linkages in the DHPs decreased with increasing CA/SA ratios, indicating that the formation of β-O-4 linkages during DHP synthesis was influenced by peroxidase type.

Identification and initial SAR of silybin: An Hsp90 inhibitor

Through Hsp90-dependent firefly luciferase refolding and Hsp90-dependent heme-regulated eIF2α kinase (HRI) activation assays, silybin was identified as a novel Hsp90 inhibitor. Subsequently, a library of silybin analogues was designed, synthesized and evaluated. Initial SAR studies identified the essential, non-essential and detrimental functionalities on silybin that contribute to Hsp90 inhibition.