27200-12-0

Basic information

• Product Name: Dihydromyricetin
• Synonyms: 2,3-dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4h-1-benzopyran-4-on;3,3’,4’,5,5’,7-hexahydroxy-2,3-dihydroflavanonol;3,3’,4’,5,5’,7-hexahydroxy-flavanon;ampelopsin(flavanol);ampeloptin;DIHYDROMYRICETIN(RG);(+)-Dihydromyricetin;(2R,3R)-3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-4-one
• CAS NO: 27200-12-0
• Molecular Formula: C₁₅H₁₂O₈
• Molecular Weight: 320.25
• EINECS: 200-001-8
• Product Categories: Flavanones;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product;Inhibitors
• Mol File: 27200-12-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 239-241 °C
• Boiling Point: 780.7 °C at 760 mmHg
• Flash Point: 296.7 °C
• Appearance: white to beige/
• Density: 1.808 g/cm³
• Vapor Pressure: 1.16E-25mmHg at 25°C
• Refractive Index: 1.798
• Storage Temp.: ?20°C
• Solubility: DMSO: ≥5mg/mL (warmed)
• PKA: 7.38±0.60(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Dihydromyricetin(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydromyricetin(27200-12-0)
• EPA Substance Registry System: Dihydromyricetin(27200-12-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 27200-12-0(Hazardous Substances Data)

Usage

Description

Dihydromyricetin (DHM), also known as ampelopsin, is a natural flavonoid compound, which is found in large quantities in Asian plant species. One of them – Hovenia dulcis – is known for centuries in traditional Chinese medicine as a cure for alcohol poisoning and hangover (Liang et al. 2014). DHM is sold as a supplement and is commonly marketed as a treatment for hangovers due to its ability to reduce blood alcohol levels and projected hepatoprotective properties.Dihydromyricetin had beneficial effects on health such as antimicrobial, anti-inflammatory,antioxidative, anticancer, lipid and glucose metabolism-regulatory activities，and cell death-mediating without or with minimum adverse effects on normal cells. And most importantly, DHM has been shown to provide significant hepatoprotective effects. Its positive influence on alcohol-induced and other liver diseases was suggested in the study of acute liver failure (Liu et al. 2017).

Uses

Dihydromyricetin has been used to study its effect on adipogenesis and glucose uptake in differentiated 3T3-L1 pre-adipocytes. It has also been used to study its antitumor activity against liver cancer cells.

Definition

ChEBI: (+)-dihydromyricetin is an optically active form of dihydromyricetin having (2R,3R)-configuration. It has a role as a metabolite, an antioxidant and an antineoplastic agent. It is a secondary alpha-hydroxy ketone and a dihydromyricetin. It is an enantiomer of a (-)-dihydromyricetin.

benefits

Dihydromyricetin (DHM) relieves alcohol toxicity and prevents intoxication by limiting the absorption of alcohol in the gastrointestinal tract and promoting the metabolisation of alcohol in the liver. DHM is a promising compound for kidney protection, liver protection, and neurological protection when drinking alcohol.DHM benefits can include things like:relieve hangoverrelieve anxietycardioprotective propertiesprotect the liver

Biochem/physiol Actions

Dihydromyricetin (Ampelopsin) is a flavanonol with antioxidant and anti-cancer activity, found to have anti-alcohol intoxication effects. Its anti-alcohol effects appear to be by its actions as a positive modulator of GABA-A receptors at the benzodiazepine site.

Side effects

Dihydromyricetin has been used in Asia for thousands of years as a hangover cure and anti-intoxication medicine and is considered safe for humans even in massive doses.In a DHM toxicity study, researchers failed to find any side-effects while giving mice massive doses of up to 22g/kg body weight.Acute toxicity tests showed that a single dose of oral SHE up to 22 g/kg did not result in any death or toxic side effects in mice during 14 days'observation.Conversions from rat to human pharmacology can be estimated using the HED ratio of 16%, giving DHM a safe upper limit dosage of 15.68g for a 70kg person.

InChI:InChI=1/C15H12O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,14-20,22H/t14-,15+/m0/s1

Upstream product

• 115523-90-5 (2,4,6-Tris-methoxymethoxy-phenyl)-[(2S,3R)-3-(3,4,5-tris-methoxymethoxy-phenyl)-oxiranyl]-methanone 

Downstream Products

• 529-44-2 myricetin 
• 520-18-3 kaempferol 
• 724434-08-6 dihydrokaempferol 
• 55313-03-6 1-(2',4',6'-trihydroxyphenyl)-2-hydroxyethanone 

Relevant articles and documents

Heterocycles. XXV. Sodium Borohydride Reduction of Flavanonols

Solvent effects on the stereochemistry in the sodium borohydride reduction of (+/-)-flavanonols have been examined.The effects observed for the (+/-)-flavanonols with 5-OMe in 2-propanol, dioxane and methanol are explainable by the differences between the steric interactions inherent in the product-like transition states A and B.It has been also found that 5-OAc peculiarly affects the stereochemistry in the reduction to produce the (+/-)-catechin-type compounds in a one-pot process.The solvent and temperature effects are examined using a model analogous to the above.