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MedKoo Cat#: 592851 | Name: Ampelopsin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ampelopsin is a Hepatoprotective agent.

Chemical Structure

Ampelopsin
Ampelopsin
CAS#27200-12-0

Theoretical Analysis

MedKoo Cat#: 592851

Name: Ampelopsin

CAS#: 27200-12-0

Chemical Formula: C15H12O8

Exact Mass: 320.0532

Molecular Weight: 320.25

Elemental Analysis: C, 56.26; H, 3.78; O, 39.97

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
10g USD 450.00 2 Weeks
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Related CAS #
No Data
Synonym
Ampelopsin, Ampeloptin, DHM, Dihydromyricetin
IUPAC/Chemical Name
4H-1-Benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-, (2R-trans)-
InChi Key
KJXSIXMJHKAJOD-LSDHHAIUSA-N
InChi Code
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
SMILES Code
O=C1[C@H](O)[C@@H](C2=CC(O)=C(O)C(O)=C2)OC3=CC(O)=CC(O)=C13
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 320.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Ul Hoque MS, Chowdhury MS, Paul A, Barua J, Zannat SS, Hasan MM, Gupta SD, Barua S, Ahmed S, Kabir MSH. In vivo analgesic effect of different extracts of Hopea odorata leaves in mice and in silico molecular docking and ADME/T property analysis of some isolated compounds from this plant. J Basic Clin Physiol Pharmacol. 2018 Aug 7. pii: /j/jbcpp.ahead-of-print/jbcpp-2018-0046/jbcpp-2018-0046.xml. doi: 10.1515/jbcpp-2018-0046. [Epub ahead of print] PubMed PMID: 30085930. 2: Sáez V, Pastene E, Vergara C, Mardones C, Hermosín-Gutiérrez I, Gómez-Alonso S, Gómez MV, Theoduloz C, Riquelme S, von Baer D. Oligostilbenoids in Vitis vinifera L. Pinot Noir grape cane extract: Isolation, characterization, in vitro antioxidant capacity and anti-proliferative effect on cancer cells. Food Chem. 2018 Nov 1;265:101-110. doi: 10.1016/j.foodchem.2018.05.050. Epub 2018 May 10. PubMed PMID: 29884360. 3: Sáez V, Gayoso C, Riquelme S, Pérez J, Vergara C, Mardones C, von Baer D. C18 core-shell column with in-series absorbance and fluorescence detection for simultaneous monitoring of changes in stilbenoid and proanthocyanidin concentrations during grape cane storage. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Feb 1;1074-1075:70-78. doi: 10.1016/j.jchromb.2017.12.028. Epub 2017 Dec 29. PubMed PMID: 29331860. 4: Park GB, Jeong JY, Kim D. Ampelopsin-induced reactive oxygen species enhance the apoptosis of colon cancer cells by activating endoplasmic reticulum stress-mediated AMPK/MAPK/XAF1 signaling. Oncol Lett. 2017 Dec;14(6):7947-7956. doi: 10.3892/ol.2017.7255. Epub 2017 Oct 23. PubMed PMID: 29250183; PubMed Central PMCID: PMC5727598. 5: Chen J, Liu S, Huang Z, Huang W, Li Q, Ye Y. Molecular inhibitory mechanism of dihydromyricetin on mushroom tyrosinase. J Biomol Struct Dyn. 2017 Nov 6:1-13. doi: 10.1080/07391102.2017.1397059. [Epub ahead of print] PubMed PMID: 29067862. 6: Han JM, Lim HN, Jung HJ. Hovenia dulcis Thunb. and its active compound ampelopsin inhibit angiogenesis through suppression of VEGFR2 signaling and HIF-1α expression. Oncol Rep. 2017 Dec;38(6):3430-3438. doi: 10.3892/or.2017.6021. Epub 2017 Oct 11. PubMed PMID: 29039561. 7: Biler M, Biedermann D, Valentová K, Křen V, Kubala M. Quercetin and its analogues: optical and acido-basic properties. Phys Chem Chem Phys. 2017 Oct 11;19(39):26870-26879. doi: 10.1039/c7cp03845c. PubMed PMID: 28952614. 8: Billet K, Houillé B, Besseau S, Mélin C, Oudin A, Papon N, Courdavault V, Clastre M, Giglioli-Guivarc'h N, Lanoue A. Mechanical stress rapidly induces E-resveratrol and E-piceatannol biosynthesis in grape canes stored as a freshly-pruned byproduct. Food Chem. 2018 Feb 1;240:1022-1027. doi: 10.1016/j.foodchem.2017.07.105. Epub 2017 Jul 25. PubMed PMID: 28946218. 9: Cheng P, Gui C, Huang J, Xia Y, Fang Y, Da G, Zhang X. Molecular mechanisms of ampelopsin from Ampelopsis megalophylla induces apoptosis in HeLa cells. Oncol Lett. 2017 Sep;14(3):2691-2698. doi: 10.3892/ol.2017.6520. Epub 2017 Jul 4. PubMed PMID: 28928812; PubMed Central PMCID: PMC5588129. 10: Chitarrini G, Soini E, Riccadonna S, Franceschi P, Zulini L, Masuero D, Vecchione A, Stefanini M, Di Gaspero G, Mattivi F, Vrhovsek U. Identification of Biomarkers for Defense Response to Plasmopara viticola in a Resistant Grape Variety. Front Plant Sci. 2017 Sep 5;8:1524. doi: 10.3389/fpls.2017.01524. eCollection 2017. PubMed PMID: 28928759; PubMed Central PMCID: PMC5591819. 11: Ye XL, Lu LQ, Li W, Lou Q, Guo HG, Shi QJ. Oral administration of ampelopsin protects against acute brain injury in rats following focal cerebral ischemia. Exp Ther Med. 2017 May;13(5):1725-1734. doi: 10.3892/etm.2017.4197. Epub 2017 Mar 8. PubMed PMID: 28565759; PubMed Central PMCID: PMC5443315. 12: Biais B, Krisa S, Cluzet S, Da Costa G, Waffo-Teguo P, Mérillon JM, Richard T. Antioxidant and Cytoprotective Activities of Grapevine Stilbenes. J Agric Food Chem. 2017 Jun 21;65(24):4952-4960. doi: 10.1021/acs.jafc.7b01254. Epub 2017 Jun 7. PubMed PMID: 28551990. 13: Kou X, Fan J, Chen N. Potential Molecular Targets of Ampelopsin in Prevention and Treatment of Cancers. Anticancer Agents Med Chem. 2017;17(12):1610-1616. doi: 10.2174/1871521409666170412130529. PubMed PMID: 28403777. 14: Kou X, Li J, Liu X, Yang X, Fan J, Chen N. Ampelopsin attenuates the atrophy of skeletal muscle from d-gal-induced aging rats through activating AMPK/SIRT1/PGC-1α signaling cascade. Biomed Pharmacother. 2017 Jun;90:311-320. doi: 10.1016/j.biopha.2017.03.070. Epub 2017 Mar 30. PubMed PMID: 28364603. 15: Chitarrini G, Zulini L, Masuero D, Vrhovsek U. Lipid, phenol and carotenoid changes in 'Bianca' grapevine leaves after mechanical wounding: a case study. Protoplasma. 2017 Nov;254(6):2095-2106. doi: 10.1007/s00709-017-1100-5. Epub 2017 Mar 21. PubMed PMID: 28324165. 16: Gabaston J, Cantos-Villar E, Biais B, Waffo-Teguo P, Renouf E, Corio-Costet MF, Richard T, Mérillon JM. Stilbenes from Vitis vinifera L. Waste: A Sustainable Tool for Controlling Plasmopara Viticola. J Agric Food Chem. 2017 Apr 5;65(13):2711-2718. doi: 10.1021/acs.jafc.7b00241. Epub 2017 Mar 24. PubMed PMID: 28288509. 17: Hong SW, Park NS, Noh MH, Shim JA, Ahn BN, Kim YS, Kim D, Lee HK, Hur DY. Combination treatment with erlotinib and ampelopsin overcomes erlotinib resistance in NSCLC cells via the Nox2-ROS-Bim pathway. Lung Cancer. 2017 Apr;106:115-124. doi: 10.1016/j.lungcan.2017.02.009. Epub 2017 Feb 14. PubMed PMID: 28285685. 18: Ninomiya K, Chaipech S, Kunikata Y, Yagi R, Pongpiriyadacha Y, Muraoka O, Morikawa T. Quantitative Determination of Stilbenoids and Dihydroisocoumarins in Shorea roxburghii and Evaluation of Their Hepatoprotective Activity. Int J Mol Sci. 2017 Feb 20;18(2). pii: E451. doi: 10.3390/ijms18020451. PubMed PMID: 28230758; PubMed Central PMCID: PMC5343985. 19: Weng L, Zhang H, Li X, Zhan H, Chen F, Han L, Xu Y, Cao X. Ampelopsin attenuates lipopolysaccharide-induced inflammatory response through the inhibition of the NF-κB and JAK2/STAT3 signaling pathways in microglia. Int Immunopharmacol. 2017 Mar;44:1-8. doi: 10.1016/j.intimp.2016.12.018. Epub 2016 Dec 18. PubMed PMID: 27998743. 20: Kabir MS, Hossain MM, Kabir MI, Ahmad S, Chakrabarty N, Rahman MA, Rahman MM. Antioxidant, antidiarrheal, hypoglycemic and thrombolytic activities of organic and aqueous extracts of Hopea odorata leaves and in silico PASS prediction of its isolated compounds. BMC Complement Altern Med. 2016 Nov 21;16(1):474. PubMed PMID: 27871266; PubMed Central PMCID: PMC5117591.