2174-64-3

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Dihydroxyanisole hydrate is used as an intermediate in the synthesis of various pharmaceutical compounds, such as isorobustin and substituted linear and angular benzofurocoumarins. These synthesized compounds have potential applications in the development of new drugs for treating various diseases.
Used in Cosmetic Industry:
Due to its antioxidant properties, 3,5-dihydroxyanisole hydrate can be used as an additive in the cosmetic industry to enhance the shelf life and stability of products. It can help protect cosmetics from oxidation, which can lead to rancidity and degradation of the product's quality.
Used in Research and Development:
3,5-Dihydroxyanisole hydrate is used as a research compound for studying the kinetics of aroxyl radical-scavenging actions. The investigation of its reaction with other radicals, such as the 5,7-diisopropyl-tocopheroxyl radical (Toc), can provide valuable insights into the development of new antioxidants and their potential applications in various industries.

InChI:InChI=1/C7H8O3/c1-10-7-3-5(8)2-6(9)4-7/h2-4,8-9H,1H3

Upstream product

• 67-56-1 methanol 
• 108-73-6 3,5-dihydroxyphenol 
• 479-21-0 cotoin 
• 77-78-1 dimethyl sulfate 
• 672-89-9 4-methoxy-6-methyl-2H-pyran-2-one 
• 621-23-8 1,2,3-trimethoxybenzene 
• 121869-54-3 2,4,6-tribromo-5-methoxyresorcinol 
• 116-11-0 2-Methoxypropene 
• 1663-67-8 malonoyl dichloride 
• 37971-69-0 7-O-Methyldihydrokaempferol, 7-O-methylaromadendrin 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 1245-15-4 retusin 
• 90-19-7 rhamnetin 
• 552-54-5 rhamnazin 

Downstream Products

• 855839-17-7 3-ethoxy-5-methoxyphenol 
• 176386-29-1 bis(2,4-dihydroxy-6-methoxyphenyl)methane 
• 111316-17-7 4,2′,4′-trihydroxy-6′-methoxydihydrochalcone 
• 119-84-6 C₆H₄(CH₂CH₂C(O)O) 
• 3519-76-4 2,4-dihydroxy-6-methoxybenzaldehyde 
• 62330-14-7 2,4-dihydroxy-ω,6-dimethoxyacetophenone 
• 387-24-6 2,2,2-trifluoro-1-(2,4-dihydroxy-6-methoxy-phenyl)-ethanone 
• 56308-11-3 2,4,4'-trihydroxy-6-methoxy-deoxybenzoin 
• 857617-60-8 2-benzoyloxy-1-(2,4-dihydroxy-6-methoxy-phenyl)-ethanone 
• 109092-83-3 2,4-Dihydroxy-6-methoxyphenyl-3,4-dimethoxybenzyl ketone 
• 857564-02-4 3',4'-diethoxy-2,4-dihydroxy-6-methoxy-deoxybenzoin 
• 109091-12-5 2,4-dihydroxy-6,2',4'-trimethoxy-deoxybenzoin 
• 101252-83-9 2-chloro-5-methoxy-resorcinol 
• 101251-22-3 4-chloro-5-methoxy-resorcinol 

Relevant academic research and scientific papers

Structural elucidation, total synthesis, and cytotoxic activity of effphenol A

A highly substituted phenol derivative, effphenol A (1), was isolated from the deep-sea-derived fungus Trichobotrys effuse FS524. Its complete structural assignment was established through a combination of spectroscopic analysis together with single-crystal X-ray diffraction experiments and further unequivocally confirmed by a biomimetic total synthesis. Structurally, effphenol A possesses a poly-substituted 6-5/6/6 tetracyclic ring system, which represents the first case of such a skeleton found in nature. Furthermore, the cytotoxic activity of effphenol A (1) toward four human cancer cell lines was assayed. This journal is

Selective methylation of phloroglucinol in the presence of a glycoluril clip

Methylation of phloroglucinol was performed using dimethyl sulfate as the methylating agent in the presence and absence of a glycoluril clip. The results showed that the yield of the di-methylated product decreased significantly in the presence of a glycoluril clip (host), due to the formation of a host-guest complex between the clip and phloroglucinol. Also, the reaction was conducted with different quantities (mol %) of the host.

Selective Catalytic Methylation of Phloroglucinol with Dimethyl Carbonate in the Presence of Heterogeneous Acids

A facile process for the methylation of phloroglucinol using environmentally friendly dimethyl carbonate as methylating agent and solvent is described. Widely available and inexpensive solid acids have been used as catalysts to promote this transformation. H-Y zeolite proved particularly selective for monomethylation, hence it has been used for the convenient preparation of methoxyresorcinol (MR), with only limited co-production of dimethoxyphenol (DMP). Conversely, the use of tungstosilicic acid on silica easily afforded DMP in excellent isolated yield.

An efficient synthesis of bergapten

An efficient synthesis of the linear furanocoumarin, bergapten, is reported. In order to avoid the formation of the angular furanocoumarin, we have adopted iodine as protecting group at the 8 position of the coumarin ring.

Total syntheses of (+)-adunctins C and D: Assignment of their absolute configurations

The first total synthesis of (+)-adunctin C (ent-1) and (+)-adunctin D (2), two monoterpene-substitued dihydrochalcones isolated from Piper aduncum (Piperaceae), was achieved. A regioselective oxidative [3 + 2] cycloaddition of acylphloroglucinol with (-)-β-phellandrene was developed to construct their unique spirobenzofuran skeleton. The absolute configurations of natural adunctins 1 and 2 were thus assigned through these endeavors. This journal is

Design, synthesis, and biological activity studies of a new class of sulfonated aurones: First synthesis of acidoaurone isolated from Phyllanthus acidus

A novel series of aurones were designed by introducing sulfonic acid group on ring-A and ring-B of known natural aurones such as hispidol, sulfuretin, maritimetin, and aureusidin. These sulfonated aurones were synthesized by a unique approach. Sulfonation on ring-A or ring-B converts water-insoluble aurones into highly water-soluble aurones. The sulfonated aurones were tested for their antioxidant, antiinflammatory, and AChE inhibition activities along with their natural aurones. Ring-A sulfonated aurones displayed higher antioxidant activity, 5-LOX, and AChE inhibition in comparison with their corresponding natural aurones. Ring-B sulfonated aurones exhibited potent 5-LOX inhibitory activity and significant antioxidant activity. Acidoaurone, a first sulfonated aurone isolated from Phyllanthus acidus was synthesized for the first time and was well characterized using NMR, LC–MS, and further confirmed by HMBC.

Total syntheses of hyperaspidinols A and B enabled by a bioinspired diastereoselective cascade sequence

A bioinspired acid-triggered hemiacetalization/dehydration/[3 + 3]-type cycloaddition cascade process was disclosed, diastereoselectively furnishing furo[2,3-b]chromene skeleton under mild conditions. The viability of this approach was demonstrated by syntheses of a series of furo[2,3-b]chromene and pyrano[2,3-b]chromene derivatives. The successful total syntheses of two lignan-phloroglucinol hybrids, hyperaspidinols A and B, exemplified the synthetic utility of our biomimetic methodology.

Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo

Alzheimer′s disease (AD) is a neurological disorder with still no preventive or curative treatment. Flavonoids are phytochemicals with potential therapeutic value. Previous studies described the flavanone sterubin isolated from the Californian plant Eriodictyon californicum as a potent neuroprotectant in several in vitro assays. Herein, the resolution of synthetic racemic sterubin (1) into its two enantiomers, (R)-1 and (S)-1, is described, which has been performed on a chiral chromatographic phase, and their stereochemical assignment online by HPLC-ECD coupling. (R)-1 and (S)-1 showed comparable neuroprotection in vitro with no significant differences. While the pure stereoisomers were configurationally stable in methanol, fast racemization was observed in the presence of culture medium. We also established the occurrence of extracted sterubin as its pure (S)-enantiomer. Moreover, the activity of sterubin (1) was investigated for the first time in vivo, in an AD mouse model. Sterubin (1) showed a significant positive impact on short- and long-term memory at low dosages.

Preparation method of spirobenzofuran compounds

The invention discloses a preparation method of spirobenzofuran compounds. The method comprises the steps: taking commercially available phloroglucinol and 4-isopropyl cyclohexanone as raw materials;dihydrochalcone and beta-phellandrene with an extracyclic double bond are respectively synthesized through a Friedel-Crafts reaction and a Wittig reaction; after two fragment compounds of the hydrochalcone and the beta-phellandrene are obtained, with oxidized cycloaddition reactions, connecting the two fragment compounds, constructing a spirobenzofuran core skeleton, and thus preparing natural products adunctin C and adunctin D. According to the invention, an organic chemical synthesis means is adopted, synthesis of the target natural products adunctin C and adunctin D is used as guidance, anda new method for constructing the structural units is developed; meanwhile, the method is applied to synthesis and preparation of the natural products adunctin C and D with important physiological and pharmacological activities, the preparation yield is high, the cost is low, and the limitation of sources of the natural products is greatly broken through.

SYNTHESIS OF MORIN AND MORIN DERIVATIVES

The invention relates to a method for directly producing morin derivatives and high-purity morin of formula (I). The invention also relates to morin derivatives and high-purity morin that can be obtained using the claimed method.