23032-48-6

Usage

Uses

Used in Pharmaceutical Industry:
Benzene, 1,3-dimethoxy-5-pentadecylis used as an intermediate compound for the synthesis of 5-Pentadecylresorcinol, which is a major active component in wheat bran. The application reason is its inhibitory activity against colon cancer cell growth, making it a potential candidate for the development of anticancer drugs.
Used in Antioxidant Applications:
Benzene, 1,3-dimethoxy-5-pentadecylis used as an antioxidant agent due to its antioxidant activity. The application reason is to provide protection against oxidative stress and maintain cell viability, particularly for PC-12 AC cells.
Used in Functional Food Industry:
Benzene, 1,3-dimethoxy-5-pentadecylis used as a component in the development of functional foods and supplements, leveraging its antioxidant and cell-protective properties to promote overall health and well-being.

Upstream product

• 34809-55-7 2-decyl-5-(3,5-dimethoxy-benzyl)-thiophene 
• 52189-66-9 2,4-dimethoxy-6-pentadecylbenzoic acid 
• 17275-82-0 ethyl 3,5-dimethoxybenzoate 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 855243-04-8 1,3-dimethoxy-5-(pentadec-1-enyl)benzene 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 3158-56-3 5-n-pentadecylresorcinol 
• 77-78-1 dimethyl sulfate 
• 765-13-9 pentadec-1-yne 
• 22910-87-8 5-<(Z)-pentadec-8-enyl>resorcinol dimethyl ether 
• 52483-34-8 5-(pentadec-8-ynyl)resorcinol dimethyl ether 
• 629-05-0 n-octyne 
• 22910-86-7 bilobol 
• 54132-76-2 3,5-dimethoxyphenyl isocyanate 

Downstream Products

• 1221234-76-9 C₂₄H₄₀O₃ 
• 1221234-78-1 C₂₄H₄₂O₂ 
• 144078-14-8 3-Methoxy-5-pentadecylphenol 
• 1450590-64-3 C₂₈H₄₄O₇ 
• 99814-68-3 5-Methoxy-3-pentadecyl-benzene-1,2,4-triol 
• 21551-64-4 2-hydroxy-5-methoxy-3-pentadecyl-1,4-benzoquinone 
• 144078-11-5 2-methoxy-6-(pentadecyl)-1,4-benzoquinone 
• 68269-86-3 6-pentadecylresorcinoldiacetate 
• 3158-56-3 5-n-pentadecylresorcinol 

Relevant academic research and scientific papers

Structure of hierridin c, synthesis of hierridins b and c, and evidence for prevalent alkylresorcinol biosynthesis in picocyanobacteria

Small, single-celled planktonic cyanobacteria are ubiquitous in the world's oceans yet tend not to be perceived as secondary metabolite-rich organisms. Here we report the isolation and structure elucidation of hierridin C, a minor metabolite obtained from

Synthesis, inhibitory activity and in silico docking of dual COX/5-LOX inhibitors with quinone and resorcinol core

Based on the significant anti-inflammatory activity of natural quinone primin (5a), series of 1,4-benzoquinones, hydroquinones, and related resorcinols were designed, synthesized, characterized and tested for their ability to inhibit the activity of cyclooxygenase (COX-1 and COX-2) and 5-lipoxygenase (5-LOX) enzymes. Structural modifications resulted in the identification of two compounds 5b (2-methoxy-6-undecyl-1,4-benzoquinone) and 6b (2-methoxy-6-undecyl-1,4-hydroquinone) as potent dual COX/5-LOX inhibitors. The IC50 values evaluated in vitro using enzymatic assay were for compound 5b IC50 = 1.07, 0.57, and 0.34 μM and for compound 6b IC50 = 1.07, 0.55, and 0.28 μM for COX-1, COX-2, and 5-LOX enzyme, respectively. In addition, compound 6d was identified as the most potent 5-LOX inhibitor (IC50 = 0.14 μM; reference inhibitor zileuton IC50 = 0.66 μM) from the tested compounds while its inhibitory potential against COX enzymes (IC50 = 2.65 and 2.71 μM for COX-1 and COX-2, respectively) was comparable with the reference inhibitor ibuprofen (IC50 = 4.50 and 2.46 μM, respectively). The most important structural modification leading to increased inhibitory activity towards both COXs and 5-LOX was the elongation of alkyl chain in position 6 from 5 to 11 carbons. Moreover, the monoacetylation in ortho position of bromo-hydroquinone 13 led to the discovery of potent (IC50 = 0.17 μM) 5-LOX inhibitor 17 (2-bromo-6-methoxy-1,4-benzoquinone) while bromination stabilized the hydroquinone form. Docking analysis revealed the interaction of compounds with Tyr355 and Arg120 in the catalytic site of COX enzymes, while the hydrophobic parts of the molecules filled the hydrophobic substrate channel leading up to Tyr385. In the allosteric catalytic site of 5-LOX, compounds bound to Tyr142 and formed aromatic interactions with Arg138. Taken together, we identified optimal alkyl chain length for dual COX/5-LOX inhibition and investigated other structural modifications influencing COX and 5-LOX inhibitory activity.

Concise access to primin, miconidin and related natural resorcinols

An efficient and short synthetic procedures affording the biologically active natural products primin, miconidin, olivetol, grevillol, and cardol (adipostatin A) in high yields are reported. The two strategies involve Sonogashira and Suzuki cross-couplings as the crucial steps for the installation of the alkyl side-chains. Syntheses start from cheap, commercially available 1-bromo-3,5-dimethoxybenezene to obtain 1,3-dimethoxy-5-(alk-1-yn-1-yl)benzene as the key intermediate. This intermediate can be easily and economically oxidized to provide primin in excellent overall yield while avoiding undesired side products by the virtue of its symmetry. The demethylation of the key intermediate affords natural resorcinols olivetol, grevillol, and cardol, respectively. The reduction of primin provides its hydroquinone derivative miconidin.

METHOD FOR PREPARING A HERBICIDAL COMPOUND

The present invention discloses a simple method for transforming cashew nut shell liquid into an active herbicidal composition.

METHOD FOR PREPARING A HERBICIDAL COMPOUND

The present invention discloses a simple method for transforming cashew nut shell liquid into an active herbicidal composition.

Synthesis and inhibitory activities against colon cancer cell growth and proteasome of alkylresorcinols

We have identified alkylresorcinols (ARs) as the major active components in wheat bran against human colon cancer cell growth (HCT-116 and HT-29) using a bioassay-guided approach. To further study the structure-activity relationships, 15 ARs and their intermediates (1-15) were synthesized expediently by the modified Wittig reaction in aqueous media, and six 5-alkylpyrogallols and their analogues (16-21) were prepared by the general Grignard reaction. The synthetic AR analogues were evaluated for activities against the growth of human colon cancer cells HCT-116 and HT-29 and the chymotrypsin-like activity of the human 20S proteasome. Our results found that (1) AR C13:0 and C15:0 (13 and 14) had the greatest inhibitory effects in human colon cancer cells HCT-116 and HT-29, while decreasing or increasing the side chain lengths diminished the activities; (2) two free meta-hydroxyl groups at C-1 and C-3 on the aromatic ring of the AR analogues greatly contributed to their antitumor activity; (3) the introduction of a third hydroxyl group at C-2 (20 and 21) into the aromatic ring of the AR analogues yielded no significant enhancement in activity against HCT-116 cells and decimated the effects against HT-29 cells, but dramatically increased the activity against the chymotrypsin-like activity of the human 20S proteasome; and (4) AR C11:0 (12) was found to have the greatest effect in a series of AR C9:0-C17:0 against the chymotrypsin-like activity of the human 20S proteasome.

Synthesis and biological evaluation of bilobol and adipostatin A

Concise total synthesis of bilobol 5-pentadecenylresorcinol (1), isolated from Gingko biloba fruits, has been achieved in 10 steps with 51% overall yield from 3,5-dihydroxybenzoic acid (3). Adipostatin A (2), isolated from the fruits as well as from Streptomyces cyaneus 2299-SV1, has also been synthesized in two steps from methylated bilobol (10). The structure-activity relationship study of synthetic products was described by means of cytotoxic assay against human KB carcinoma cell lines.

Phytotoxic activity of quinones and resorcinolic lipid derivatives

On the basis of the reported phytotoxic activity of sorgoleone and resorcinolic lipids identified from the root extracts of Sorghum bicolor, 8 resorcinolic lipid derivatives and 10 quinones with various side chain sizes were synthesized. The phytotoxicity of the compounds was tested against a monocot and a dicot species. The quinones were phytotoxic, whereas the resorcinolic lipids were not. Of the quinones, 2-hydroxy-5-methoxy-3- pentylcyclohexa-2,5-diene-1,4-dione, having a five-carbon side chain, showed phytotoxic activity similar to that of natural compound sorgoleone. This article not subject to U.S. Copyright. Published 2010 by the American Chemical Society.

An expedient synthesis of 5-n-alkylresorcinols and novel 5-n-alkylresorcinol haptens

The first synthesis of bioactive long alkyl chain 5-n-alkylresorcinols, present in whole grain products, by a novel modification of the Wittig reaction is described. All the main long chain 5-n-alkylresorcinols present in rye and wheat, including C23 and C25 analogues and haptens, which have not been previously prepared, were synthesised. Microwave-promoted reactions of a semistabilized ylid and alkanals in water gave good yields in both pressurized and open systems. An alternative microwave-promoted synthesis starting from non-stabilized alkyltriphenylphosphonium salts and 3,5-dimethoxybenzaldehyde worked as well. Aqueous media were suitable for the reactions even if the starting materials were not soluble in water. The 5-n-alkylresorcinols are potential biomarkers of whole grain intake, and the new hapten derivatives of 5-n-alkylresorcinols will open the way for the immunochemical detection techniques of alkylresorcinols.