27200-12-0,MFCD00189451
Catalog No.:AA0034E4

27200-12-0 | Dihydromyricetin

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1g
95%
in stock  
$18.00   $13.00
- +
5g
98%
in stock  
$62.00   $44.00
- +
10g
98%
in stock  
$107.00   $75.00
- +
25g
98%
in stock  
$218.00   $153.00
- +
100g
98%
in stock  
$662.00 $464.00
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA0034E4
Chemical Name:
Dihydromyricetin
CAS Number:
27200-12-0
Molecular Formula:
C15H12O8
Molecular Weight:
320.2510
MDL Number:
MFCD00189451
SMILES:
Oc1cc2O[C@H](c3cc(O)c(c(c3)O)O)[C@H](C(=O)c2c(c1)O)O
Properties
Properties
 
BP:
780.7°C at 760 mmHg  
Form:
Solid  
MP:
>210℃ (dec.)  
Solubility:
DMSO: ≥5mg/mL (warmed)  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
445  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
6  
Isotope Atom Count:
0  
Rotatable Bond Count:
1  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
1.1  

Downstream Synthesis Route

[1]JournaloftheChemicalSociety.PerkintransactionsI,1988,p.2567-2572

108-24-7    27200-12-0   
3,5,7,3',4',5'-hexaacetyldihydromyricetin 

[1]Patent:CN107236004,2017,A.Locationinpatent:Paragraph0017

[2]Phytochemistry,1980,vol.19,p.893-896

27200-12-0    77-78-1   
(2R,3R)-3-hydroxy-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-4-one 

[1]Phytochemistry,1980,vol.19,p.893-896

[1]Molecules,2010,vol.15,p.2114-2123

[1]Molecules,2010,vol.15,p.2114-2123

Literature

Title: Dihydromyricetin modulates p62 and autophagy crosstalk with the Keap-1/Nrf2 pathway to alleviate ethanol-induced hepatic injury.

Journal: Toxicology letters 20170515

Title: Suppression of reactive oxygen species-mediated ERK and JNK activation sensitizes dihydromyricetin-induced mitochondrial apoptosis in human non-small cell lung cancer.

Journal: Environmental toxicology 20170401

Title: Dihydromyricetin from Ampelopsis grossedentata inhibits melanogenesis through down-regulation of MAPK, PKA and PKC signaling pathways.

Journal: Chemico-biological interactions 20161025

Title: Dihydromyricetin induces autophagy in HepG2 cells involved in inhibition of mTOR and regulating its upstream pathways.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20140401

Title: Synthesis and characterization of ampelopsin glucosides using dextransucrase from Leuconostoc mesenteroides B-1299CB4: glucosylation enhancing physicochemical properties.

Journal: Enzyme and microbial technology 20121210

Title: Ampelopsin inhibits H₂O₂-induced apoptosis by ERK and Akt signaling pathways and up-regulation of heme oxygenase-1.

Journal: Phytotherapy research : PTR 20120701

Title: Ampelopsin sodium exhibits antitumor effects against bladder carcinoma in orthotopic xenograft models.

Journal: Anti-cancer drugs 20120701

Title: Resveratrol dimers are novel sphingosine kinase 1 inhibitors and affect sphingosine kinase 1 expression and cancer cell growth and survival.

Journal: British journal of pharmacology 20120701

Title: Spectroscopic studies on the interaction between an anticancer drug ampelopsin and bovine serum albumin.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20120215

Title: Ampelopsin reduces endotoxic inflammation via repressing ROS-mediated activation of PI3K/Akt/NF-κB signaling pathways.

Journal: International immunopharmacology 20120101

Title: Flavonoid ampelopsin inhibits the growth and metastasis of prostate cancer in vitro and in mice.

Journal: PloS one 20120101

Title: Vitisin B, a resveratrol tetramer, inhibits migration through inhibition of PDGF signaling and enhancement of cell adhesiveness in cultured vascular smooth muscle cells.

Journal: Toxicology and applied pharmacology 20111015

Title: Regioselective reactions for programmable resveratrol oligomer synthesis.

Journal: Nature 20110623

Title: Organic chemistry: Triumph for unnatural synthesis.

Journal: Nature 20110622

Title: Development and application of high-performance liquid chromatography for the study of ampelopsin pharmacokinetics in rat plasma using cloud-point extraction.

Journal: Journal of separation science 20110101

Title: cis-Ampelopsin E, a stilbene isolated from the seeds of Paeonia suffruticosa, inhibits lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 macrophages via blockade of nuclear factor-kappa B signaling pathway.

Journal: Biological & pharmaceutical bulletin 20110101

Title: Synthesis and biological evaluation of new 5-fluorouracil-substituted ampelopsin derivatives.

Journal: Molecules (Basel, Switzerland) 20100324

Title: [Reversal effect and its mechanism of ampelopsin on multidrug resistance in K562/ADR cells].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090301

Title: Ampelopsin prevents apoptosis induced by H2O2 in MT-4 lymphocytes.

Journal: Planta medica 20080201

Title: [Study on preparation of ampelopsin liposomes].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080101

Title: [Optimizing the extracting technique of ampelopsin from Ampelopsis cantoniensis Planch by a uniform design method].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20060701

Title: [The chemotaxis effect of ampelopsin on the immunocytes].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20060301

Title: [Inhibitory effects of ampelopsin on angiogenesis].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20060201

Title: Improving the solubility of ampelopsin by solid dispersions and inclusion complexes.

Journal: Journal of pharmaceutical and biomedical analysis 20050701

Title: [Anti-tumor effects of ampelopsin on human lung cancer GLC-82 implanted in nude mice].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20041101

Title: Ampelopsin, a small molecule inhibitor of HIV-1 infection targeting HIV entry.

Journal: Biomedical and environmental sciences : BES 20040601

Title: [Effects of ampelopsin on invasion and metastasis of B16 mouse melanoma in vivo and in vitro].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20031001

Title: [Anti-invasive and anti-metastatic effect of ampelopsin on melanoma].

Journal: Ai zheng = Aizheng = Chinese journal of cancer 20030401

Title: [Studies on the chemical constituents from Ampelopsis grossedentata].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20020401

Title: [Determination of ampelopsin in the different parts of Ampelopsis grossedentata in different seasons by RP-HPLC].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20020101

Title: [Study on inhibitory effect of ampelopsin on melanoma by serologic pharmacological method].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20010501

Title: Huang CY. Inhibition of a Putative Dihydropyrimidinase from Pseudomonas aeruginosa PAO1 by Flavonoids and Substrates of Cyclic Amidohydrolases. PLoS One. 2015 May 19;10(5):e0127634.

Title: Chang H, et al. Ampelopsin suppresses breast carcinogenesis by inhibiting the mTOR signalling pathway. Carcinogenesis. 2014 Aug;35(8):1847-54.

Title: Kou X, et al. Ampelopsin attenuates brain aging of D-gal-induced rats through miR-34a-mediated SIRT1/mTORsignal pathway. Oncotarget. 2016 Nov 15;7(46):74484-74495.

Title: Václav Zima, et al. Unraveling the Anti-Influenza Effect of Flavonoids: Experimental Validation of Luteolin and its Congeners as Potent Influenza Endonuclease Inhibitors. Eur J Med Chem. 22 August 2020, 112754.

Quotation Request
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Additional Info:
SDS
Tags:27200-12-0 Molecular Formula|27200-12-0 MDL|27200-12-0 SMILES|27200-12-0 Dihydromyricetin
Catalog No.: AA0034E4
27200-12-0,MFCD00189451
27200-12-0 | Dihydromyricetin
Pack Size: 1g
Purity: 95%
in stock
$18.00 $13.00
Pack Size: 5g
Purity: 98%
in stock
$62.00 $44.00
Pack Size: 10g
Purity: 98%
in stock
$107.00 $75.00
Pack Size: 25g
Purity: 98%
in stock
$218.00 $153.00
Pack Size: 100g
Purity: 98%
in stock
$662.00 $464.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA0034E4
Chemical Name: Dihydromyricetin
CAS Number: 27200-12-0
Molecular Formula: C15H12O8
Molecular Weight: 320.2510
MDL Number: MFCD00189451
SMILES: Oc1cc2O[C@H](c3cc(O)c(c(c3)O)O)[C@H](C(=O)c2c(c1)O)O
Properties
BP: 780.7°C at 760 mmHg  
Form: Solid  
MP: >210℃ (dec.)  
Solubility: DMSO: ≥5mg/mL (warmed)  
Storage: Keep in dry area;-20 ℃;  
Complexity: 445  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 2  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 23  
Hydrogen Bond Acceptor Count: 8  
Hydrogen Bond Donor Count: 6  
Isotope Atom Count: 0  
Rotatable Bond Count: 1  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 1.1  
Downstream Synthesis Route
186581-53-3    108-24-7    117479-83-1    27200-12-0    117479-80-8 

[1]JournaloftheChemicalSociety.PerkintransactionsI,1988,p.2567-2572

108-24-7    27200-12-0   
3,5,7,3',4',5'-hexaacetyldihydromyricetin 

[1]Patent:CN107236004,2017,A.Locationinpatent:Paragraph0017

[2]Phytochemistry,1980,vol.19,p.893-896

27200-12-0    77-78-1   
(2R,3R)-3-hydroxy-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)chroman-4-one 

[1]Phytochemistry,1980,vol.19,p.893-896

27200-12-0    56059-30-4    1032930-66-7 

[1]Molecules,2010,vol.15,p.2114-2123

27200-12-0    56059-30-4    1032930-66-7    1032930-70-3 

[1]Molecules,2010,vol.15,p.2114-2123

Literature fold

Title: Dihydromyricetin modulates p62 and autophagy crosstalk with the Keap-1/Nrf2 pathway to alleviate ethanol-induced hepatic injury.

Journal: Toxicology letters20170515

Title: Suppression of reactive oxygen species-mediated ERK and JNK activation sensitizes dihydromyricetin-induced mitochondrial apoptosis in human non-small cell lung cancer.

Journal: Environmental toxicology20170401

Title: Dihydromyricetin from Ampelopsis grossedentata inhibits melanogenesis through down-regulation of MAPK, PKA and PKC signaling pathways.

Journal: Chemico-biological interactions20161025

Title: Dihydromyricetin induces autophagy in HepG2 cells involved in inhibition of mTOR and regulating its upstream pathways.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association20140401

Title: Synthesis and characterization of ampelopsin glucosides using dextransucrase from Leuconostoc mesenteroides B-1299CB4: glucosylation enhancing physicochemical properties.

Journal: Enzyme and microbial technology20121210

Title: Ampelopsin inhibits H₂O₂-induced apoptosis by ERK and Akt signaling pathways and up-regulation of heme oxygenase-1.

Journal: Phytotherapy research : PTR20120701

Title: Ampelopsin sodium exhibits antitumor effects against bladder carcinoma in orthotopic xenograft models.

Journal: Anti-cancer drugs20120701

Title: Resveratrol dimers are novel sphingosine kinase 1 inhibitors and affect sphingosine kinase 1 expression and cancer cell growth and survival.

Journal: British journal of pharmacology20120701

Title: Spectroscopic studies on the interaction between an anticancer drug ampelopsin and bovine serum albumin.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy20120215

Title: Ampelopsin reduces endotoxic inflammation via repressing ROS-mediated activation of PI3K/Akt/NF-κB signaling pathways.

Journal: International immunopharmacology20120101

Title: Flavonoid ampelopsin inhibits the growth and metastasis of prostate cancer in vitro and in mice.

Journal: PloS one20120101

Title: Vitisin B, a resveratrol tetramer, inhibits migration through inhibition of PDGF signaling and enhancement of cell adhesiveness in cultured vascular smooth muscle cells.

Journal: Toxicology and applied pharmacology20111015

Title: Regioselective reactions for programmable resveratrol oligomer synthesis.

Journal: Nature20110623

Title: Organic chemistry: Triumph for unnatural synthesis.

Journal: Nature20110622

Title: Development and application of high-performance liquid chromatography for the study of ampelopsin pharmacokinetics in rat plasma using cloud-point extraction.

Journal: Journal of separation science20110101

Title: cis-Ampelopsin E, a stilbene isolated from the seeds of Paeonia suffruticosa, inhibits lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 macrophages via blockade of nuclear factor-kappa B signaling pathway.

Journal: Biological & pharmaceutical bulletin20110101

Title: Synthesis and biological evaluation of new 5-fluorouracil-substituted ampelopsin derivatives.

Journal: Molecules (Basel, Switzerland)20100324

Title: [Reversal effect and its mechanism of ampelopsin on multidrug resistance in K562/ADR cells].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica20090301

Title: Ampelopsin prevents apoptosis induced by H2O2 in MT-4 lymphocytes.

Journal: Planta medica20080201

Title: [Study on preparation of ampelopsin liposomes].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica20080101

Title: [Optimizing the extracting technique of ampelopsin from Ampelopsis cantoniensis Planch by a uniform design method].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials20060701

Title: [The chemotaxis effect of ampelopsin on the immunocytes].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials20060301

Title: [Inhibitory effects of ampelopsin on angiogenesis].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials20060201

Title: Improving the solubility of ampelopsin by solid dispersions and inclusion complexes.

Journal: Journal of pharmaceutical and biomedical analysis20050701

Title: [Anti-tumor effects of ampelopsin on human lung cancer GLC-82 implanted in nude mice].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials20041101

Title: Ampelopsin, a small molecule inhibitor of HIV-1 infection targeting HIV entry.

Journal: Biomedical and environmental sciences : BES20040601

Title: [Effects of ampelopsin on invasion and metastasis of B16 mouse melanoma in vivo and in vitro].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica20031001

Title: [Anti-invasive and anti-metastatic effect of ampelopsin on melanoma].

Journal: Ai zheng = Aizheng = Chinese journal of cancer20030401

Title: [Studies on the chemical constituents from Ampelopsis grossedentata].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials20020401

Title: [Determination of ampelopsin in the different parts of Ampelopsis grossedentata in different seasons by RP-HPLC].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials20020101

Title: [Study on inhibitory effect of ampelopsin on melanoma by serologic pharmacological method].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials20010501

Title: Huang CY. Inhibition of a Putative Dihydropyrimidinase from Pseudomonas aeruginosa PAO1 by Flavonoids and Substrates of Cyclic Amidohydrolases. PLoS One. 2015 May 19;10(5):e0127634.

Title: Chang H, et al. Ampelopsin suppresses breast carcinogenesis by inhibiting the mTOR signalling pathway. Carcinogenesis. 2014 Aug;35(8):1847-54.

Title: Kou X, et al. Ampelopsin attenuates brain aging of D-gal-induced rats through miR-34a-mediated SIRT1/mTORsignal pathway. Oncotarget. 2016 Nov 15;7(46):74484-74495.

Title: Václav Zima, et al. Unraveling the Anti-Influenza Effect of Flavonoids: Experimental Validation of Luteolin and its Congeners as Potent Influenza Endonuclease Inhibitors. Eur J Med Chem. 22 August 2020, 112754.

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