Specifications
- Purity
- ≥98% (HPLC)
- Appearance
- White to beige powder
- Identity
- 1H-NMR
Properties
- Solvents
- DMSO (10 mg/ml), DMF (10 mg/ml), ethanol (1 mg/ml)
Available from stock
Dihydromyricetin
- SKU
- D0381
Categories:
- Synonyms
- (+)-Dihydromyricetin , (2R,3R)-3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one , 3,3',4',5,5',7-Hexahydroxyflavanone , Ampelopsin , Ampeloptin , DHM
- 27200-12-0
- CAS-Number
- C15H12O8
- Molecular Formula
- 320.25
- Molecular Weight
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
- Shipping
- AMBIENT
- Short Term Storage
- -20°C
- Long Term Storage
- -20°C
- Handling Advice
- Protect from light and moisture.
- Use / Stability
- Stable for at least 2 years after receipt when stored at -20°C.
- Transportation
- Not dangerous goods
- Description
- Dihydromyricetin is a flavanonol originally isolated from A. grossedentata. Dihydromyricetin has been demonstrated to show antioxidative, anti-inflammatory, anticancer, antimicrobial, cell death-mediating, neuroprotective and lipid and glucose metabolism-regulatory activities. It also has been found to have anti-alcohol intoxication effects, associated with its action as a positive modulator of GABA-A receptors at the benzodiazepine site. Dihydromyricetin may scavenge ROS to protect against oxidative stress or potentiate ROS generation to counteract cancer cells selectively without any effects on normal cells. Dihydromyricetin may be associated with several different molecules involved in cellular apoptosis, oxidative stress and inflammation, such as AMP-activated protein kinase (AMPK), mitogen-activated protein kinase (MAPK), protein kinase B (Akt), nuclear factor-?B (NF-?B), nuclear factor E2-related factor 2 (Nrf2), ATP-binding cassette transporter A1 (ABCA1) or peroxisome proliferator-activated receptor-γ (PPARγ). It has been reported to effectively modulate growth factor receptor (VEGFR2 and PDGFRβ) mediated signaling, TRAIL/TRAIL-R pathway, JAK/STAT and mTOR-driven signaling in different cancers. It has been shown to stimulate irisin secretion and to inhibit NLRP3 inflammasome-dependent pyroptosis. It also has anti-neuroinflammatory activities in Alzheimer's and Parkinson's diseases and improves conginitve deficits. It acts as a potential preventive or therapeutic agent in treating multiple diseases, such as diabetes mellitus, atherosclerosis, nonalcoholic fatty liver disease and osteoporosis.
- Smiles
- O[C@H]1C(C2=C(O)C=C(O)C=C2O[C@@H]1C3=CC(O)=C(O)C(O)=C3)=O
- InChi Key
- KJXSIXMJHKAJOD-LSDHHAIUSA-N
- References
- (1) Y.S. Zhang, et al., Yao Xue Xue Bao 38, 241 (2003) , (2) J. Xia, et al., Food Chem. Toxicol. 66, 7 (2014) , (3) J. Liang, et al., Neurochem. Res. 39, 1147 (2014) , (4) J. Liang, et al., Neurochem. Res. 39, 1171 (2014) , (5) J. Liu, et al., Oncol. Lett. 8, 1645 (2014) , (6) L. Shi, et al., Mol. Cell Endocrinol. 409, 92 (2015) , (7) S. Chen, et al., Pharmacol. Res. 99, 74 (2015) , (8) Q. Zhou, et al., Mol. Cell Endocrinol. 412, 349 (2015) , (9) Z.X. Ren, et al., Acta Pharmacol. Sin. 37, 1315 (2016) , (10) R. Wang, et al., Scanning 38, 901 (2016) , (11) B. Xu, et al., Mol. Med. Rep. 15, 3674 (2017) , (12) H. Li, et al., Evid. Based Complement Alternat. Med. 2017, 1053617 (2017) (Review) , (13) Q. Hu, et al., Biofactors 44, 123 (2018) , (14) J. Feng, et al., CNS Neurosci. Ther. 24, 1207 (2018) , (15) J. Zhang, et al., Front. Pharmacol. 9, 1204 (2018) (Review) , (16) H. Tong, et al., Eur. J. Pharmacol. 870, 172888 (2019) (Review) , (17) S. Fayyaz, et al., Cell Mol. Biol. 65, 15 (2019) (Review)
- InChi
- InChI=1S/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
Dihydromyricetin is a flavanonol originally isolated from A. grossedentata. Dihydromyricetin has been demonstrated to show antioxidative, anti-inflammatory, anticancer, antimicrobial, cell death-mediating, neuroprotective and lipid and glucose metabolism-regulatory activities. It also has been found to have anti-alcohol intoxication effects, associated with its action as a positive modulator of GABA-A receptors at the benzodiazepine site. Dihydromyricetin may scavenge ROS to protect against oxidative stress or potentiate ROS generation to counteract cancer cells selectively without any effects on normal cells. Dihydromyricetin may be associated with several different molecules involved in cellular apoptosis, oxidative stress and inflammation, such as AMP-activated protein kinase (AMPK), mitogen-activated protein kinase (MAPK), protein kinase B (Akt), nuclear factor-?B (NF-?B), nuclear factor E2-related factor 2 (Nrf2), ATP-binding cassette transporter A1 (ABCA1) or peroxisome proliferator-activated receptor-γ (PPARγ). It has been reported to effectively modulate growth factor receptor (VEGFR2 and PDGFRβ) mediated signaling, TRAIL/TRAIL-R pathway, JAK/STAT and mTOR-driven signaling in different cancers. It has been shown to stimulate irisin secretion and to inhibit NLRP3 inflammasome-dependent pyroptosis. It also has anti-neuroinflammatory activities in Alzheimer’s and Parkinson’s diseases and improves conginitve deficits. It acts as a potential preventive or therapeutic agent in treating multiple diseases, such as diabetes mellitus, atherosclerosis, nonalcoholic fatty liver disease and osteoporosis.
Additional information
| Synonyms | (+)-Dihydromyricetin, (2R,3R)-3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one, 3,3',4',5,5',7-Hexahydroxyflavanone, Ampelopsin, Ampeloptin, DHM |
|---|---|
| Purity | ≥98% (HPLC) |
| Appearance | White to beige powder |
| CAS-Number | 27200-12-0 |
| Molecular Formula | C15H12O8 |
| Molecular Weight | 320.25 |
| Identity | 1H-NMR |
| Solvents | DMSO (10 mg/ml), DMF (10 mg/ml), ethanol (1 mg/ml) |
| Smiles | O[C@H]1C(C2=C(O)C=C(O)C=C2O[C@@H]1C3=CC(O)=C(O)C(O)=C3)=O |
| InChi Key | KJXSIXMJHKAJOD-LSDHHAIUSA-N |
| Shipping | AMBIENT |
| Short Term Storage | -20°C |
| Long Term Storage | -20°C |
| Handling Advice | Protect from light and moisture. |
| Use / Stability | Stable for at least 2 years after receipt when stored at -20°C. |
| Transportation | Not dangerous goods |
| References | (1) Y.S. Zhang, et al., Yao Xue Xue Bao 38, 241 (2003), (2) J. Xia, et al., Food Chem. Toxicol. 66, 7 (2014), (3) J. Liang, et al., Neurochem. Res. 39, 1147 (2014), (4) J. Liang, et al., Neurochem. Res. 39, 1171 (2014), (5) J. Liu, et al., Oncol. Lett. 8, 1645 (2014), (6) L. Shi, et al., Mol. Cell Endocrinol. 409, 92 (2015), (7) S. Chen, et al., Pharmacol. Res. 99, 74 (2015), (8) Q. Zhou, et al., Mol. Cell Endocrinol. 412, 349 (2015), (9) Z.X. Ren, et al., Acta Pharmacol. Sin. 37, 1315 (2016), (10) R. Wang, et al., Scanning 38, 901 (2016), (11) B. Xu, et al., Mol. Med. Rep. 15, 3674 (2017), (12) H. Li, et al., Evid. Based Complement Alternat. Med. 2017, 1053617 (2017) (Review), (13) Q. Hu, et al., Biofactors 44, 123 (2018), (14) J. Feng, et al., CNS Neurosci. Ther. 24, 1207 (2018), (15) J. Zhang, et al., Front. Pharmacol. 9, 1204 (2018) (Review), (16) H. Tong, et al., Eur. J. Pharmacol. 870, 172888 (2019) (Review), (17) S. Fayyaz, et al., Cell Mol. Biol. 65, 15 (2019) (Review) |
| InChi | InChI=1S/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 |
| Quantity | 5 mg, 25 mg, Bulk |
