39953-41-8

Usage

Structure

Benzaldehyde derivative with a methoxy group at the 3-position and an allyl group at the 4-position

Common uses

Flavor and fragrance ingredient in perfumes and cosmetic products

Potential applications

Pharmaceuticals and agrochemicals

Aroma

Sweet and floral

Handling precautions

Requires care and following safety guidelines

Health hazards

Possible risks associated with use, requiring controlled environments for handling

Upstream product

• 121-33-5 vanillin 
• 870-63-3 prenyl bromide 
• 85738-96-1 E/Z-1-Brom-3-methyl-1-buten 

Downstream Products

• 259267-38-4 methyl (E)-3-(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)phenyl)acrylate 
• 121-33-5 vanillin 
• 1412939-10-6 (E)-3-[5-(1,2-dimethyl-2-propenyl)-4-hydroxy-3-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one 
• 1412939-08-2 (E)-3-[5-(1,2-dimethyl-2-propenyl)-4-hydroxy-3-methoxyphenyl]-1-(2,4-dihydroxyphenyl)-2-propen-1-one 
• 1412939-09-3 (E)-3-[5-(1,2-dimethyl-2-propenyl)-4-hydroxy-3-methoxyphenyl]-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one 
• 1412939-06-0 C₁₃H₁₆O₃ 
• 1412939-07-1 C₁₅H₂₀O₄ 
• 1548331-46-9 (2E,5E)-2,5-bis{3-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]benzylidene}cyclopentanone 

Relevant academic research and scientific papers

Synthesis, experimental and theoretical study of the spectroscopic properties in (2E)-3-{3-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-1-(3,4,5- trimethoxyphenyl)prop-2-en-1-one

We reported the synthesis of (2E)-3-{3-methoxy-4-[(3-methylbut-2-en-1-yl) oxy]phenyl}-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one. The molecular structure and spectroscopic properties of this compound were calculated using the density functional theory (DFT

Excavating precursors from the traditional Chinese herb Polygala tenuifolia and Gastrodia elata: Synthesis, anticonvulsant activity evaluation of 3,4,5-trimethoxycinnamic acid (TMCA)ester derivatives

Epilepsy is a group of neurological disorders characterized by recurrent seizures that disturbs about 60 million people worldwide. In this article, a novel series of 3,4,5-trimethoxycinnamic acid (TMCA)ester derivatives 1–35 were designed inspired from the traditional Chinese herb pair drugs Polygala tenuifolia and Gastrodia elata and synthesized followed by in vivo and in silico evaluation of their anticonvulsant potential. All the synthesized derivatives were biologically evaluated for their anticonvulsant potential using two acute model of seizures induced in mice, the maximal electroshock (MES)and sc-pentylenetetrazole (PTZ)models. Simultaneously, the motor impairment as a surrogate of acute neurotoxicity and in vitro screening of cytotoxicity against HepG-2 cells line were assessed through the rotarod performance test and CCK-8 assay, respectively. In addition, the physicochemical and pharmacokinetic parameters of the active compounds were determined. Our results showed that compounds 5, 7, 8, 13, 20, 25, 28, 30 and 32 exhibited preferable anticonvulsant activity in primary evaluation, with compounds 28 and 32 being the most promising anticonvulsant agents in according to results of subsequent pharmacology and toxicity evaluation. Additionally, the molecular modeling experiments predicted good binding interactions of part of the obtained active molecules with the gamma-aminobutyric acid (GABA)transferas. Therefore, it could be concluded that the synthesized derivatives 28 and 32 would represent useful lead compounds for further investigation in the development of anticonvulsant agents.

NOVEL SUGAR-DERIVED GELATOR

There is provided a novel gelator containing a sugar derivative. A gelator including a compound of Formula (1) or Formula (2): wherein each of R1 and R3 is independently a linear or branched alkyl group having a carbon atom number of 1 to 20, a cyclic C3-20 alkyl group, or a linear or branched alkenyl group having a carbon atom number of 2 to 20, n is 0 or an integer of 1 to 4, R2 is a hydrogen atom, a linear or branched alkyl group having a carbon atom number of 1 to 10, or an aryl group optionally having a substituent, and R4 and R5 are each a hydroxy group.

Synthesis of licochalcones and inhibition effects on radical-induced oxidation of DNA

This study deals with the influence of phenolic hydroxyl groups on the antioxidant capacities of licochalcones. (E)-3-[5-(1,2-Dimethyl-2-propenyl)-4- hydroxy-3-methoxyphenyl]-1-(4-hydroxyphenyl)-2-propen-1-one (HMP), (E)-3-[5-(1,2-dimethyl-2-propenyl)-4-hydroxy-3-methoxyphenyl]-1-(2, 4-dihydroxyphenyl)-2-propen-1-one (DHM), and (E)-3-[5-(1,2-dimethyl-2-propenyl)- 4-hydroxy-3-methoxyphenyl]-1-(2,4,6-trihydroxyphenyl)-2-propen-1-one (HMT) were synthesized via abnormal Claisen rearrangement and Claisen-Schmidt condensation. The antioxidant capacities were evaluated in hydroxyl radical ( ?OH)-, Cu2+/glutathione (GSH)-, and 2,2′-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. It was found that only HMP possessed weak ability to inhibit ?OH-induced oxidation of DNA, and DHM and HMT cannot protect DNA against the oxidation. All the licochalcones employed herein can retard Cu 2+/GSH-induced oxidation of DNA, the activity followed the order of HMP > DHM > HMT. Hence, more hydroxyl groups did not ameliorate the antioxidant effectiveness in the aforementioned experimental systems. On the other hand, HMT, DHM, and HMP can scavenge 5.61, 2.42, and 1.68 radicals, respectively, when they were applied to protect DNA against AAPH-induced oxidation. This result demonstrated that more hydroxyl groups enhanced the antioxidant capacities of licochalcones in this case. The obtained information was beneficial for designing novel licochalcones.

Highly efficient and selective deprotection method for prenyl, geranyl, and phytyl ethers and esters using borontrifluoride-etherate

An efficient, simple, and practical method has been developed for the deprotection of prenyl, geranyl, and phytyl ethers and esters of aromatic and aliphatic compounds using borontrifluoride-etherate (BF3· OEt2) at room temperature in good to excellent yields for the first time. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

Synthesis of O-prenylated and O-geranylated derivatives of 5-benzylidene2,4-thiazolidinediones and evaluation of their free radical scavenging activity as well as effect on some phase II antioxidant/detoxifying enzymes

A series of 5-arylidene-2,4-thiazolidinediones and its geranyloxy or prenyloxy derivative were synthesized and studied for their radical scavenging activity using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Their comparable scavenging activities were expr

Convenient synthesis of (E)-methyl O-alkylferulates: Formal synthesis of O-geranylconiferyl alcohol, a metabolite of Fagara rhetza

A convenient two step stereoselective synthesis of (E)-methyl O-alkylferulate 5a-c is described from vanillin 1. Reaction of vanillin 1 with allyl-, prenyl- or geranyl- bromide 2a-c has afforded alkyl ethers 3a-c which on reaction with phosphorane 4, under microwave irradiation, gives (E)-methyl O-alkylferulates 5a-c in high yield. In an alternative approach vanillin 1 on reaction with phosphorane 4 provides (E)-methyl ferulate 6 which on reaction with the corresponding bromides 2a-c gives (E)-methyl O-alkylferulates 5a-c.

Antitumor agents. 250. Design and synthesis of new curcumin analogues as potential anti-prostate cancer agents

In a continuing study of curcumin analogues as potential drug candidates to treat prostate cancer at both androgen-dependent and androgen-refractory stages, we designed and synthesized over 40 new analogues classified into four series: monophenyl analogues (series A), heterocycle-containing analogues (series B), analogues bearing various substituents on the phenyl rings (series C), and analogues with various linkers (series D). These new compounds were tested for cytotoxicity against two human prostate cancer cell lines, androgen-dependent LNCaP and androgen-independent PC-3. Antiandrogenic activity was also evaluated in LNCaP cells and PC-3 cells transfected with wild-type androgen receptor. Ten compounds possessed potent cytotoxicity against both LNCaP and PC-3 cells, seven only against LNCaP, and one solely against PC-3. This study established an advanced structure-activity relationship (SAR), and these correlations will guide the further design of new curcumin analogues with better anti-prostate cancer activity.

Claisen rearrangement of 2'-hydroxy-3,4'-dimethoxy-4-prenyloxychalcone

Claisen rearrangement of 2'-hydroxy-3,4'-dimethoxy-4-prenyloxychalcone (III) using acetic anhydride in dimethylaniline gives three major compounds, 2'-acetoxy-3,4'-dimethoxy-4'',4'',5''-trimethyldihydrofuranochalcone (IV), 2',4-diacetaoxy-3,4