162290-05-3

Basic information

• Product Name: 7,3'-Dihydroxy-4'-Methoxyflavan
• Synonyms: 7,3'-Dihydroxy-4'-Methoxyflavan;(2S)-3',7-Dihydroxy-4'-methoxyflavan;(S)-2-(3-Hydroxy-4-Methoxyphenyl)chroMan-7-ol
• CAS NO: 162290-05-3
• Molecular Formula: C16H16O4
• Molecular Weight: 272.29584
• Mol File: 162290-05-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 482.6±45.0 °C(Predicted)
• Appearance: /
• Density: 1.282±0.06 g/cm3(Predicted)
• PKA: 9.73±0.10(Predicted)
• CAS DataBase Reference: 7,3'-Dihydroxy-4'-Methoxyflavan(CAS DataBase Reference)
• NIST Chemistry Reference: 7,3'-Dihydroxy-4'-Methoxyflavan(162290-05-3)
• EPA Substance Registry System: 7,3'-Dihydroxy-4'-Methoxyflavan(162290-05-3)

Safety Data

• Hazardous Substances Data: 162290-05-3(Hazardous Substances Data)

Usage

Description

7,3'-Dihydroxy-4'-Methoxyflavan is a flavan class of flavonoids, a plant-derived compound with antioxidant properties. It is found in various natural sources such as fruits, vegetables, and tea, and has potential health benefits including anti-inflammatory and cardioprotective effects. Its antioxidant activity helps protect cells from free radical damage, and it shows promise in treating various diseases and conditions, making it a subject of interest for research and development in the pharmaceutical and nutraceutical industries.

Uses

Used in Pharmaceutical Industry:
7,3'-Dihydroxy-4'-Methoxyflavan is used as a pharmaceutical agent for its potential health benefits, including anti-inflammatory and cardioprotective effects. Its antioxidant properties may help protect cells from damage caused by free radicals, and it has shown potential in the treatment of various diseases and conditions.
Used in Nutraceutical Industry:
7,3'-Dihydroxy-4'-Methoxyflavan is used as a nutraceutical ingredient for its antioxidant properties, which may help protect cells from free radical damage. It is also used for its potential health benefits, including anti-inflammatory and cardioprotective effects, making it a valuable component in dietary supplements and functional foods.

Upstream product

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• 618895-97-9 1-(4-methoxy-3-methoxymethoxyphenyl)ethanol 
• 618896-04-1 1-(4-methoxy-3-methoxymethoxyphenyl)-3-(2,4-dimethoxyphenyl)-1-propanol 
• 634922-71-7 2,3',4-trimethoxymethoxy-4'-methoxychalcone 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 520-33-2 (S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone 
• 13246-46-3 2,4-dibenzyloxybenzaldehyde 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 154490-49-0 1-(3-benzyloxy-4-methoxyphenyl)ethanol 
• 23428-77-5 1‐(3‐(benzyloxy)‐4‐methoxyphenyl)ethanone 

Relevant articles and documents

Enantioselective Synthesis of 2′- and 3′-Substituted Natural Flavans by Domino Asymmetric Transfer Hydrogenation/Deoxygenation

A concise and highly enantioselective synthesis of the natural flavans kazinol U and (2S)-7,3′-dihydroxy-4′-methoxyflavan is reported for the first time. The key transformation is a single-step conversion of a racemic flavanone to a flavan by means of an asymmetric transfer hydrogenation/deoxygenation cascade with kinetic resolution.

Identification of Interleukin-8-Reducing Lead Compounds Based on SAR Studies on Dihydrochalcone-Related Compounds in Human Gingival Fibroblasts (HGF-1 cells) in Vitro

Background: In order to identify potential activities against periodontal diseases, eighteen dihydrochalcones and structurally related compounds were tested in an established biological in vitro cell model of periodontal inflammation using human gingival fibroblasts (HGF-1 cells). Methods: Subsequently to co-incubation of HGF-1 cells with a bacterial endotoxin (Porphyromonas gingivalis lipopolysaccharide, pgLPS) and each individual dihydrochalcone in a concentration range of 1 μM to 100 μM, gene expression of interleukin-8 (IL-8) was determined by qPCR and cellular interleukin-8 (IL-8) release by ELISA. Results: Structure–activity analysis based on the dihydrochalcone backbone and various substitution patterns at its aromatic ring revealed moieties 20,4,40,60-tetrahydroxy 3-methoxydihydrochalcone (7) to be the most effective anti-inflammatory compound, reducing the pgLPS-induced IL-8 release concentration between 1 μM and 100 μM up to 94%. In general, a 2,4,6-trihydroxy substitution at the A-ring and concomitant vanilloyl (4-hydroxy-3-methoxy) pattern at the B-ring revealed to be preferable for IL-8 release inhibition. Furthermore, the introduction of an electronegative atom in the A,B-linker chain led to an increased anti-inflammatory activity, shown by the potency of 4-hydroxybenzoic acid N-vanillylamide (13). Conclusions: Our data may be feasible to be used for further lead structure designs for the development of potent anti-inflammatory additives in oral care products.

Studies on flavans. III. The total synthesis of (±)-7,4′ -dihydroxy-3′-methoxyflavan, (±)-7,3′-dihydroxy-4′ -methoxyflavan, and (±)-7,4′-dihdroxyflavan

The first total synthesis of (±)-7,3′-dihydroxy-4′ -methoxyflavan (1) and (±)-7,4′-dihydroxy-3′-methoxyflavan (2), along with the synthesis of (±)-7,4′-dihydroxyflavan (3), three naturally occurring flavans, were described. The key step is the cyclization of 1,3-diaryl-1-propanol by BF3·Et2O.