21422-02-6

Basic information

• Product Name: Benzaldehyde, 2,4-dihydroxy-5-(3-methyl-2-butenyl)-
• CAS NO: 21422-02-6
• Molecular Formula: C12H14O3
• Molecular Weight: 206.241
• Mol File: 21422-02-6.mol

Chemical Properties

• CAS DataBase Reference: Benzaldehyde, 2,4-dihydroxy-5-(3-methyl-2-butenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, 2,4-dihydroxy-5-(3-methyl-2-butenyl)-(21422-02-6)
• EPA Substance Registry System: Benzaldehyde, 2,4-dihydroxy-5-(3-methyl-2-butenyl)-(21422-02-6)

Safety Data

• Hazardous Substances Data: 21422-02-6(Hazardous Substances Data)

Upstream product

• 115-18-4 2-methyl-3-buten-2-ol 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 556-82-1 3-methyl-2-buten-1-ol 
• 870-63-3 prenyl bromide 

Downstream Products

• 1422971-03-6 2-(4'-methoxyphenyl)-7,7-dimethyl-7H-furo[3,2-g]chromene 
• 1422971-02-5 2-(4-hydroxyphenyl)-7,7-dimethyl-7H-furo[3,2-g]chromene 
• 130740-35-1 4',2-dibenzyloxy-2'-hydroxy-3'',4''-dihydro-2'',2''-dimethyl-2H-pyrano<2,3-c>chalcone 
• 96909-25-0 7-benzyloxy-6-formyl-2,2-dimethyldihydrobenzo[1,2-b]pyran 
• 263902-88-1 3-benzoyl-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-one 

Relevant articles and documents

Concise synthesis of licochalcone C and its regioisomer, licochalcone H

Licochalone C (7a) is a retrochalcone isolated from Glycyrrhiza inflata, which shows potent antioxidant properties and inhibition of bacterial growth and cellular respiration. Biological studies have suggested that licochalcone C attenuates the lipopolysaccharide and interferon-gamma induced inflammatory response by decreasing the expression and activity of inducible nitric oxide synthase and modulating the antioxidant network activity of superoxide dismutase, catalase, and glutathione peroxidase activity. Licochalcone C also inhibits NADH-cytochrome C reductase in the membrane fraction of Micrococcus luteus. Since pharmacological activity studies of licochalcone C are ongoing and the yield of the compound is poor from natural product, we report a concise four step synthesis of licochalcone C (7a) and its regioisomer, tentatively called licochalcone H (7b), by employing acid-mediated Claisen-Schmidt condensation as a key step with 6 and 20 % overall yield, respectively.

Synthesis and biological activity evaluation of coumarin-3-carboxamide derivatives

A series of novel coumarin-3-carboxamide derivatives were designed and synthesized to evaluate their biological activities. The compounds showed little to no activity against gram-positive and gram-negative bacteria but specifically showed potential to inhibit the growth of cancer cells. In particular, among the tested compounds, 4-fluoro and 2,5-difluoro benzamide derivatives (14b and 14e, respectively) were found to be the most potent derivatives against HepG2 cancer cell lines (IC50 = 2.62–4.85 μM) and HeLa cancer cell lines (IC50 = 0.39–0.75 μM). The activities of these two compounds were comparable to that of the positive control doxorubicin; especially, 4-flurobenzamide derivative (14b) exhibited low cytotoxic activity against LLC-MK2 normal cell lines, with IC50 more than 100 μM. The molecular docking study of the synthesized compounds revealed the binding to the active site of the CK2 enzyme, indicating that the presence of the benzamide functionality is an important feature for anticancer activity.

Synthetic methods for Gramniphenols F and G, Cicerfuran, Morunigrol C and its Derivative

The present invention relates to a method for preparing natural benzofurans including gramniphenol F, gramniphenol G, morunigrol C and 3andprime;,5andprime;-di-O-methyl analogues thereof and cicerfuran by using 2,4-dihydroxybenzaldehyde, 5-bromoresorcinol and sesamol. In the method according to the present invention, region-selective prenylation, Ramirez gem-dibromo olefination, Miyaura borylation and Suzuki coupling are used. In addition, the compounds were determined for anti-inflammatory effects through a test for production of nitrogen oxide in liposaccharide-induced RAW-264.7 macrophages. All of the compounds show weak to medium (16-42%) inhibitory activities, are not toxic and have an IC_50 value of 9.1 to 25.2 andmu;M.COPYRIGHT KIPO 2017

Synthesis, anti-phytopathogenic and DPPH radical scavenging activities of C-prenylated acetophenones and benzaldehydes

The syntheses of six prenylated acetophenone and benzaldehyde derivatives and their anti-phytopathogenic and antioxidant activities are reported. These compounds were obtained by electrophilic aromatic substitution (SEAr) of the corresponding arenes and 3-methyl-2-buten-1-ol using ZnCl2 as a Lewis acid catalyst in ethyl acetate. Reasonable to good yields were obtained based on unrecovered aromatic starting material (45-73%). All the synthesized compounds were evaluated against phytopathogenic gram-negative bacteria Agrobacterium tumefaciens, Pseudomonas syringae and Erwinia carotovora and plant fungal pathogens Botrytis cinerea, Phytophthora cinnamomi and Gibberella fujikuroi. The antioxidant activity was evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity assay and expressed as half maximal inhibitory concentration (IC50) values in μM concentrations. The antioxidant activity went from 27.20 μM to >100 μM. Compound 11 showed statistically significant inhibition of the growth of Botrytis cinerea, and compounds 13 and 15 showed statistically significant inhibition of the growth of Phytophthora cinnamomi, with respect to negative control fungal growth. All six compounds showed bacteriostatic effects against gram-negative plant pathogenic bacteria with IC50 values between 250 and 3.9 μM.

Synthetic method for licochalcone C

According to the present invention, licochalcone C is produced by performing C-prenylation using A_2O_3, position selective deprotection and methylation, and general Claisen-Schmidt condensation under a base condition. A [3,3]-sigma bond position transferring reaction promoted by water cannot be applied to licochalcone C synthesis due to a decomposition problem. According to the present invention, it has been confirmed that position selective C-prenylation using Al_2O_3 is a novel method for synthesizing licochalcone C.COPYRIGHT KIPO 2015

Facile synthesis of licochalcone C

Licochalcone C was synthesized from commercially available 2,4-dihydroxybenzaldehde by using regioselective Al2O 3-mediated C-prenylation followed by conventional Claisen-Schmidt condensation in basic condition.

Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid-phase synthesis of benzopyrans

Herein we report a novel strategy for the design and construction of natural and natural product-like libraries based on the principle of privileged structures, a term originally introduced to describe structural motifs capable of interacting with a variety of unrelated molecular targets. The identification of such privileged structures in natural products is discussed, and subsequently the 2,2-dimethylbenzopyran moiety is selected as an inaugural template for the construction of natural product-like libraries via this strategy. Initially, a novel solid-phase synthesis of the benzopyran motif is developed employing a unique cycloloading strategy that relies on the use of a new, polystyrene-based selenenyl bromide resin. Once the loading, elaboration, and cleavage of these benzopyrans was established, this new solid-phase method was then thoroughly validated through the construction of six focused combinatorial libraries designed around natural and designed molecules of recent biological interest.

STRUCTURES OF CUDRAFLAVANONE A AND EUCHRESTAFLAVANONE C

From the benzene extract of the root bark of Cudrania tricuspidata (Carr.) Bur. (Japanese name "Hariguwa", Moraceae), an isoprene substituted flavanone derivative, named cudraflavanone A, was isolated, for which structure (I) was determined on the basis o