67483-49-2

Usage

Uses

Used in Flavor and Fragrance Industry:
3-ALLYL-4,5-DIMETHOXY-BENZALDEHYDE is used as a flavoring agent for its sweet and pleasant aroma in food and beverages.
Used in Pharmaceutical Industry:
3-ALLYL-4,5-DIMETHOXY-BENZALDEHYDE is used in the synthesis of pharmaceuticals and other organic compounds, contributing to the development of new medications.
Used in Agriculture:
3-ALLYL-4,5-DIMETHOXY-BENZALDEHYDE has shown potential as a natural insecticide and antimicrobial agent, offering an alternative to synthetic chemicals in pest and disease control.
However, it is important to handle 3-ALLYL-4,5-DIMETHOXY-BENZALDEHYDE with caution as it may cause irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C12H14O3/c1-4-5-10-6-9(8-13)7-11(14-2)12(10)15-3/h4,6-8H,1,5H2,2-3H3

Upstream product

• 20240-58-8 3-allyl-4-hydroxy-5-methoxybenzaldehyde 
• 121-33-5 vanillin 
• 77-78-1 dimethyl sulfate 
• 22280-95-1 4-allyloxy-3-methoxybenzaldehyde 
• 32024-15-0 3,4-dimethoxy-5-iodobenzaldehyde 
• 106-95-6 allyl bromide 
• 74-88-4 methyl iodide 
• 19754-21-3 1-allyl-2,3-dimethoxy-benzene 
• 93-61-8 N-methyl-N-phenylformamide 

Downstream Products

• 578020-87-8 (5-dimethoxymethyl)-1,2-dimethoxy-3-(prop-2-enyl)benzene 
• 128139-70-8 di-(2-ethylhexyl) 3-allyl-4,5-dimethoxybenzalmalonate 
• 1072928-21-2 E-1-allyl-2,3-dimethoxy-5-(20-nitrovinyl)benzene 
• 1609627-91-9 (2E)-1-(4-chlorophenyl)-3-[3,4-dimethoxy-5-(prop-2-en-1-yl)phenyl]prop-2-en-1-one 
• 1609627-93-1 (2E)-3-[3,4-dimethoxy-5-(prop-2-en-1-yl)phenyl]-1-(4-methoxyphenyl)prop-2-en-1-one 
• 1609627-97-5 (2E)-1-(1,3-benzodioxol-5-yl)-3-[3,4-dimethoxy-5-(prop-2-en-1-yl)phenyl]prop-2-en-1-one 
• 1609627-98-6 (2E)-1-(4-bromophenyl)-3-[3,4-dimethoxy-5-(prop-2-en-1-yl)phenyl]prop-2-en-1-one 
• 1609628-00-3 (2E)-3-[3,4-dimethoxy-5-(prop-2-en-1-yl)phenyl]-1-(4-nitrophenyl)prop-2-en-1-one 
• 1309974-71-7 C₁₅H₁₈O₃ 
• 578020-90-3 methyl 2-[5-(dimethoxymethyl)-2,3-dimethoxyphenyl]-3-hydroxy-3-(4-methoxyphenyl)propanoate 
• 578020-89-0 methyl [5-(dimethoxymethyl)-2,3-dimethoxyphenyl]acetate 
• 578020-88-9 (5-formyl-2,3-dimethoxyphenyl)acetic acid 
• 578020-86-7 methyl (5-formyl-2,3-dimethoxyphenyl)acetate 
• 485-38-1 4,5-dimethoxy-isophthalic acid 

Relevant academic research and scientific papers

Preparation and reactions of highly functionalized bis-arylzinc reagents using a Li(acac)-catalyzed iodine-zinc exchange

Polyfunctional bis-arylzinc reagents are accessible via a new lithium acetylacetonate-catalyzed iodine-zinc exchange. This protocol tolerates sensitive functional groups (ketones, aldehydes or isothiocyanates) in the aryl iodides and allows the formation of highly functionalized zinc reagents. These zinc reagents can be used in a variety of catalyzed and uncatalyzed transformations. Georg Thieme Verlag Stuttgart.

Facile synthesis of vanillin-based novel bischalcones identifies one that induces apoptosis and displays synergy with Artemisinin in killing chloroquine resistant Plasmodium falciparum

The inherent affinity of natural compounds for biological receptors has been comprehensively exploited with great success for the development of many drugs, including antimalarials. Here the natural flavoring compound vanillin has been used as an economical precursor for the synthesis of a series of novel bischalcones whose in vitro antiplasmodial activities have been evaluated against erythrocytic stages of Plasmodium falciparum. Bischalcones 9, 11 and 13 showed promising antiplasmodial activity {Chloroquine (CQ) sensitive Pf3D7 IC50 (μM): 2.0, 1.5 and 2.5 respectively}but only 13 displayed potent activities also against CQ resistant PfDd2 and PfIndo strains exhibiting resistance indices of 1.4 and 1.5 respectively. IC90 (8 μM) of 13 showed killing activity against ring, trophozoite and schizont stages. Further, 13 initiated the cascade of reactions that culminates in programmed cell death of parasites including translocation of phosphatidylserine from inner to outer membrane leaflet, loss of mitochondrial membrane potential, activation of caspase like enzyme, DNA fragmentation and chromatin condensation. The combinations of 13 + Artemisinin (ART) exhibited strong synergy (ΣFIC50:0.46 to 0.58) while 13 + CQ exhibited mild synergy (ΣFIC50: 0.7 to 0.98) to mild antagonism (ΣFIC50: 1.08 to 1.23) against PfIndo. In contrast, both combinations showed marked antagonism against Pf3D7(ΣFIC50: 1.33 to 3.34). These features of apoptosis and strong synergy with Artemisinin suggest that bischalcones possess promising antimalarial drug-like properties and may also act as a good partner drugs for artemisinin based combination therapies (ACTs) against Chloroquine resistant P. falciparum.

Design, economical synthesis and antiplasmodial evaluation of vanillin derived allylated chalcones and their marked synergism with artemisinin against chloroquine resistant strains of Plasmodium falciparum

The in vitro blood stage antiplasmodial activity of a series of allylated chalcones based on the licochalcone A as lead molecule was investigated against chloroquine (CQ) sensitive Pf3D7 and CQ resistant PfINDO strains of Plasmodium falciparum using SYBR Green I assay. Of the forty two chalcones tested, eight showed IC50 ≥ 5 μM. Structure-activity relationship (SAR) studies revealed 9 {1-(4-Chlorophenyl)-3-[3-methoxy-4-(prop-2-en-1-yloxy)phenyl] -prop-2-en-1-one} as the most potent (IC∑: 2.5 μM) against Pf3D7 with resistance indices of 1.2 and 6.6 against PfDd2 and PfINDO strains, respectively. Later on, the synergistic effects 9 with standard antimalarials {artemisinin (ART) and chloroquine (CQ)} were studied in order to provide the basis for the selection of the best partner drug. In vitro combinations of 9 with ART showed strong synergy against PfINDO (ΣFIC∑: 0.31-0.72) but additive to slight antagonistic effects (ΣFIC∑: 1.97-2.64) against Pf3D7. ΣFIC∑ 0.31 of ART+9 combination corresponded to a 320 fold and 3 fold reduction in IC∑ of 9 and ART, respectively. Similar combinations of 9 with CQ showed synergy to additivity to mild antagonism against the two strains {ΣFIC∑: 0.668-2.269 (PfINDO); 1.45-2.83 (Pf3D7)}. Drug exposure followed by drug withdrawal indicated that 9 taken alone at IC∑ killed rings, trophozoites and schizonts of P. falciparum. The combination of ART and 9 (1X ΣFIC∑) selectively inhibited the growth of rings while the 2X ΣFIC∑ combination of the same caused killing of rings without affecting trophozoites and schizonts. In contrast, the 1X combination of CQ and 9 (ΣFIC ∑: 0.5) killed rings and trophozoites. DNA fragmentation and loss of mitochondrial membrane potential (ΔΨm) in the 9 treated P. falciparum culture indicated apoptotic death in malaria parasites. Prediction of ADME properties revealed that most of the molecules did not violate Lipinski's parameters and have low TPSA value suggesting good absorption. The results suggest the promising drug-like properties of 9 against CQ resistant Pf and propensity for synergy with classical antimalarial drugs together with easy and economical synthesis.

A combined RCM-Bischler-Napieralski strategy towards the synthesis of the carbon skeleton of excentricine and related stephaoxocanes

A convenient synthetic approach to a cyclodeca[ij]isoquinoline derivative, which embodies the carbon skeleton of excentricine and related stephaoxocanes, is described. The synthesis involves the combined use of ring closing metathesis and Bischler-Napiera

Nucleophilic catalysis of the iodine-zinc exchange reaction: Preparation of highly functionalized diaryl zinc compounds

Sensitive functional groups are tolerated in an iodine-zinc exchange reaction catalyzed by Li(acac). Aryl and heteroaryl diorganozinc compounds with keto, aldehyde, or isothiocyanate substituents can be prepared by this method (see example in scheme; acac = acetylacetone, NMP=1-methyl-2-pyrrolidinone). Such zinc reagents serve as substrates for a wide variety of coupling reactions.

An improved and versatile method for the rapid synthesis of aryldihydrobenzofuran systems by a boron tribromide-mediated cyclization reaction

Boron tribromide is presented as a highly reactive reagent that simultaneously allows the demethylation and fully diastereoselective cyclization of different precursor molecules, obtained by an aldol-type reaction, to a series of hydroxylated aryldihydrobenzofuran systems in racemic form. The latter are often found as key structures in natural compounds of different classes. Syntheses of educts, which mainly took advantage of a versatile Rieche formylation, are also described.

Cosmetic use of benzalmalonate diorganopolysiloxanes and novel cosmetic compositions containing such compounds for the protection of skin and hair

The cosmetic use is described, in particular for use as a UV filter, of benzalmalonate diorganopolysiloxanes having either formula: STR1 where R is C1 -C10 alkyl, phenyl or 3,3,3-trifluoropropyl, B is R or A, r=0-200, s=0-50, or form

New liposoluble unsaturated benzalmalonate derivatives and their use as absorbers for ultraviolet radiation in cosmetics

The invention relates to an unsaturated benzalmalonate derivative of formula: STR1 in which: R1 and R2 denote a hydrogen atom, a hydroxyl, a trimethylsiloxy, a C1 -C6 straight or branched chain alkyl, C1/s

Vilsmeier-Haack Reaction on Methoxyallylbenzenes

Vilsmeier-Haack reaction on various methoxyallylbenzenes yields the naphthaldehydes (2, 11, 14, 17, 20, 21) when ortho-position to the allyl group is activated.In other cases only nuclear formylated products are obtained.The product analysis suggests that nuclear formylation is probably the first step in these reactions.