1036-72-2

Basic information

• Product Name: 5,7-DIMETHOXYFLAVANONE
• Synonyms: DIMETHOXYFLAVANONE,5,7-;5,7-DIMETHOXYFLAVANONE;PINOCEMBRIN DIMETHYL ETHER;5,7-DIMETHOXYFLAVANONE 97%;2,3-Dihydro-5,7-dimethoxy-2-phenyl-4H-1-benzopyran-4-one;2-Phenyl-5,7-dimethoxy-2,3-dihydro-4H-1-benzopyran-4-one;5,7-Dimethylpinocembrin;5,7-dimethoxy-2-phenyl-2,3-dihydrochromen-4-one
• CAS NO: 1036-72-2
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.31
• Mol File: 1036-72-2.mol

Chemical Properties

• Melting Point: 144-146°C
• Boiling Point: 468.8°Cat760mmHg
• Flash Point: 209.4°C
• Appearance: /
• Density: 1.204g/cm³
• Vapor Pressure: 5.79E-09mmHg at 25°C
• Refractive Index: 1.574
• CAS DataBase Reference: 5,7-DIMETHOXYFLAVANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-DIMETHOXYFLAVANONE(1036-72-2)
• EPA Substance Registry System: 5,7-DIMETHOXYFLAVANONE(1036-72-2)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 1036-72-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5,7-DIMETHOXYFLAVANONE is used as a therapeutic agent for its antioxidant, anti-inflammatory, and anticancer properties, targeting a variety of diseases and conditions.
Used in Neuroprotective Applications:
5,7-DIMETHOXYFLAVANONE is used as a neuroprotective agent for its potential to protect the nervous system and prevent neurodegenerative diseases due to its neuroprotective effects.
Used in Immunomodulatory Applications:
5,7-DIMETHOXYFLAVANONE is used as an immunomodulatory agent to modulate the immune response, which can be beneficial in treating autoimmune diseases and inflammatory conditions.
Used in Antioxidant Formulations:
5,7-DIMETHOXYFLAVANONE is used as an antioxidant in formulations to combat oxidative stress and protect cells from damage, which can contribute to aging and various diseases.
Used in Cancer Treatment:
5,7-DIMETHOXYFLAVANONE is used as a component in cancer treatment regimens for its anticancer properties, potentially enhancing the effectiveness of existing therapies and providing a novel approach to cancer management.

InChI:InChI=1/C17H16O4/c1-19-12-8-15(20-2)17-13(18)10-14(21-16(17)9-12)11-6-4-3-5-7-11/h3-9,14H,10H2,1-2H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 75291-74-6 pinostrobin 
• 1775-97-9 flavokawain B 
• 480-39-7 pinocembrin 
• 74-88-4 methyl iodide 
• 59887-91-1 5,7-dimethoxy-4H-chromen-4-one 
• 98-80-6 phenylboronic acid 
• 187877-87-8 3-dimethylamino-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 351458-87-2 (R)-1-[2,4-dimethoxy-6-(methoxymethoxy)phenyl]-3-phenyl-3-(tert-butyldimethylsilyl)oxy-propan-1-one 
• 131294-12-7 ethyl [(3R)-(tert-butyldimethylsilyloxy)-3-phenyl]propionate 
• 351458-82-7 (R)-3-(tert-butyldimethylsylil)oxy-N-methoxy-N-methyl-benzenepropanamide 
• 271600-97-6 3,5-dimethoxyphenyl-1-methoxymethyl ether 
• 72656-47-4 ethyl (R)-3-hydroxy-3-phenylpropanoate 

Downstream Products

• 26964-35-2 5,7-dimethoxyisoflavone 
• 1193346-73-4 5,7-dimethoxyflavanone oxime 
• 124259-95-6 2-(1,5-diphenyl-1H-pyrazol-3-yl)-3,5-dimethoxyphenol 
• 99111-06-5 5,7-dimethoxy-3-N,N-dimethylaminomethylidene-flavanone 
• 98770-02-6 4-chloro-3,8-diformyl-5,7-dimethoxy-flav-3-ene 
• 15236-07-4 3-Hydroxy-5,7-dimethoxyflavone 
• 2569-86-0 5,8-dihydroxy-7-methoxyflavanone 
• 851606-11-6 5,7-dimethoxy-2-phenylchroman-4-one (4-nitrophenyl)hydrazone 
• 18956-15-5 pinostrobin chalcone 
• 480-39-7 pinocembrin 
• 1775-97-9 flavokawain B 
• 42508-82-7 2,4-trans-5,7-dimethoxyflavan-4-ol 
• 42508-82-7 5,7-dimethoxyflavan-4β-ol 
• 101441-50-3 3-iodo-5,7-dimethoxy-2-phenyl-chroman-4-one 

Relevant articles and documents

Antimutagenic activity of flavonoids from Sozuku

Pinocembrin (1) and cardamonin (2) from Sozuku showed a suppressive effect on umu gene expression of SOS response in Salmonella typhimurium TA1535/pSK1002 against the mutagen furylfuramide. Compounds 1 and 2 suppressed 52% and 36% of SOS-inducing activity at a concentration of 0.20?μmol/mL. The ID50 value of 1 was 0.18?μmol/mL. These compounds showed the suppression of 2-amino-3,4-dimethylimidazo-[4,5-f]quinolone (MeIQ) and UV irradiation-induced SOS response. Pinostrobin (3) and 5,7-dimethoxyflavanone (4), methyl ethers of 1, showed similar activity to 1 against MeIQ-induced SOS response, but that of furylfuramide and UV irradiation were decreased. On the other hand, compounds 1–4 did not show the suppression of activated MeIQ-induced SOS response. Furthermore, compounds 1–4 showed potent antimutagenic activity against MeIQ mutagenesis in Ames test using the S. typhimurium TA100 and TA98 strains.

Synthesis of flavanones using methane sulphonic acid as a greencatalystand comparision under different conditions

Flavonoids are an important class of natural products with wide range activities. Flavonoids includes flavone, flavanone, flavane & flavanol. The synthetic route invovles synthesis of chalcone followed by ring closing to give flavanone. So many catalysts were mentioned in past literature. But most efficient catalyst is methane sulphonic acid.It is easy to handle,less reaction time &easily available. Flavanones were synthesized from chalcone using methane sulphonic acid under thermal condition, microw wave and ultrasound condition.Flavanones are syntheisized in very less time compared to other conditions.

PHOTOSENSITIZED (SET) CONVERSION OF 2'-HYDROXYCHALCONES TO FLAVONOIDS A PROBABLE BIOGENETIC PATHWAY

2'-Hydroxychalcones undergo transformation to flavonoids by photoinduced single electron transfer processes.

Asymmetric Synthesis of Sakuranetin-Relevant Flavanones for the Identification of New Chiral Antifungal Leads

Discovery and efficient synthesis of new promising leads have a central role in agrochemical science. Reported herein is the sakuranetin-directed synergistic exploration of an asymmetric synthesis and an antifungal evaluation of chiral flavanones. A new palladium catalytic system with CarOx-type ligands was successfully identified for the highly enantioselective addition of arylboronic acids to chromones. This enabled the facile and programmable construction of a constellation of chiral flavanones (up to 98% yield and 97% ee), in which (R)-pinostrobin was efficiently constructed without laborious protecting/deprotecting operations. Its good performance in asymmetric induction and functional tolerance expanded the chemical space of pharmaceutically important flavanones. The chiral differentiation of flavanones based on antifungal activity and a concise structure-activity relationship model was disclosed and summarized. This synergistic project culminated with acquisition of the naturally unprecedented flavanones with better antifungal potentials than sakuranetin, in which the R-enantiomer of flavanone 54 (EC50 = 0.8 μM) demonstrated better performance than boscalid against Rhizoctonia solani. The novel scaffold and predicted new target compared with the commercial fungicides in the FRAC reinforce the value of further exploration.

Attrition-enhanced deracemization and absolute asymmetric synthesis of flavanones from prochiral precursors

Seven racemic 5,7-dimethoxyflavanones afforded conglomerate crystals upon recrystallization from a solvent. Three methodologies were investigated to achieve asymmetric transformation based on dynamic crystallization of the chiral conglomerate system. The first was chiral symmetry breaking of racemic flavanones by attrition-enhanced deracemization. Continuous suspension of racemic flavanones in a small amount of propanol in the presence of a base (1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)) and glass beads promoted chiral symmetry breaking and converted the flavanones to crystals of (+)- or (-)-enantiomers with 78 to 99% ee. The second method involved cyclization of the intermediate aldol product to give optically active flavanone with 90% ee involving a reversible oxa-Michael addition reaction with attrition-enhanced deracemization. The third was a reaction starting from prochiral 2-hydroxy-4,6-dimethoxyacetophenone and 2-naphthaldehyde under basic conditions, which gave the corresponding flavanone in 89% ee.

Enzyme-assisted cyclization of chalcones to flavanones

Enzyme catalyzed synthesis is an eco-friendly technique in organic synthesis, having several benefits over conventional methods. In the present work, we describe a simple process of laccase and chloroperoxidase assisted cyclization of chalcones, leading to the formation of flavanones. The reaction proceeds in a mixture of phosphate buffer and ethanol, under oxygen atmosphere at room temperature, yielding the corresponding flavanone in good to moderate yield. The relative configuration of the products at C2 is tentatively assigned as S*-flavanone based on the coupling constants with the methylenic protons H3α,β. In comparison to the chemical methods, we describe a process which can be achieved efficiently under mild conditions using oxygen as oxidant.

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.

Mild and efficient one-pot synthesis of diverse flavanone derivatives via an organocatalyzed Mannich-type reaction

A facile ethylenediamine diacetate (EDDA)-catalyzed one-pot synthesis of biologically interesting flavanone derivatives from 2-hydroxyacetophenones, aromatic aldehydes, and aniline via a Mannich-type reaction is described. This synthetic method provides a rapid access to biologically interesting flavanone derivatives. To demonstrate this method, several biologically interesting natural products bearing a flavanone moiety were synthesized as racemates.

Intermolecular C-O addition of carboxylic acids to arynes: Synthesis of o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones

An efficient and simple route to biologically and pharmaceutically important o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones has been developed utilizing readily available carboxylic acids and commercially available o-(trimethylsilyl)aryl tr

Highly enantioselective and efficient synthesis of flavanones including pinostrobin through the rhodium-catalyzed asymmetric 1,4-addition

An efficient synthesis of bioactive chiral flavanones (1) was achieved through the αh-catalyzed asymmetric 1,4-addition of arylboronic acid to chromone. The reaction in toluene proceeded smoothly at room temperature in the presence of 0.5% Rh catalyst with electron-poor chiral diphosphine MeO-F 12-BIPHEP. In this reaction, the 1,2-addition to (S)-1 frequently occurred to yield (2S,4α)-2,4-diaryl-4-chromanol as a byproduct, which could be reduced by changing the reaction solvent to CH2C 12 to deactivate the Rh catalyst (3% required).