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

MedKoo CAT#: 562062

CAS#: 36052-37-6

Description: Alpinetin is a natural UCK2 inhibitor. It has been shown to bind to the cavity of R273H mutant p53 and restore wild-type p53 functions.


Chemical Structure

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Alpinetin
CAS# 36052-37-6

Theoretical Analysis

MedKoo Cat#: 562062
Name: Alpinetin
CAS#: 36052-37-6
Chemical Formula: C16H14O4
Exact Mass: 270.08
Molecular Weight: 270.284
Elemental Analysis: C, 71.10; H, 5.22; O, 23.68

Price and Availability

Size Price Availability Quantity
10.0mg USD 530.0 2 Weeks
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Synonym: Alpinetin;

IUPAC/Chemical Name: (2S)-7-Hydroxy-5-methoxy-2-phenyl-2,3-dihydrochromen-4-one

InChi Key: QQQCWVDPMPFUGF-ZDUSSCGKSA-N

InChi Code: InChI=1S/C16H14O4/c1-19-14-7-11(17)8-15-16(14)12(18)9-13(20-15)10-5-3-2-4-6-10/h2-8,13,17H,9H2,1H3/t13-/m0/s1

SMILES Code: O=C1C[C@@H](C2=CC=CC=C2)OC3=C1C(OC)=CC(O)=C3

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: >2 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: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 270.284 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

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1: Qi C, Fu J, Zhao H, Xing H, Dong D, Wu B. Identification of UGTs and BCRP as potential pharmacokinetic determinants of the natural flavonoid alpinetin. Xenobiotica. 2018 Feb 13:1-32. doi: 10.1080/00498254.2018.1440657. [Epub ahead of print] PubMed PMID: 29436891.

2: Ye W, Lin X, Zhang Y, Xu Y, Sun R, Wen C, Wang X, Bao S, Chen R. Quantification and pharmacokinetics of alpinetin in rat plasma by UHPLC-MS/MS using protein precipitation coupled with dilution approach to eliminate matrix effects. J Pharm Biomed Anal. 2017 Dec 27;152:242-247. doi: 10.1016/j.jpba.2017.12.046. [Epub ahead of print] PubMed PMID: 29433096.

3: Hu K, Liu L, Qian H, Zhou T, Li Y, Yu J, Tan B. [Alpinetin promotes the binding of PPAR and methyltransferase]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2017 Dec;33(12):1610-1614. Chinese. PubMed PMID: 29382419.

4: Malami I, Muhammad A, Etti IC, Waziri PM, Alhassan AM. An in silico approach in predicting the possible mechanism involving restoration of wild-type p53 functions by small molecular weight compounds in tumor cells expressing R273H mutant p53. EXCLI J. 2017 Dec 8;16:1276-1287. doi: 10.17179/excli2017-299. eCollection 2017. PubMed PMID: 29333130; PubMed Central PMCID: PMC5763090.

5: Burmańczuk A, Hola P, Milczak A, Piech T, Kowalski C, Wojciechowska B, Grabowski T. Quercetin decrease somatic cells count in mastitis of dairy cows. Res Vet Sci. 2018 Jan 9;117:255-259. doi: 10.1016/j.rvsc.2018.01.006. [Epub ahead of print] PubMed PMID: 29331686.

6: Zhou Y, Ding YL, Zhang JL, Zhang P, Wang JQ, Li ZH. Alpinetin improved high fat diet-induced non-alcoholic fatty liver disease (NAFLD) through improving oxidative stress, inflammatory response and lipid metabolism. Biomed Pharmacother. 2018 Jan;97:1397-1408. doi: 10.1016/j.biopha.2017.10.035. Epub 2017 Dec 14. PubMed PMID: 29156529.

7: Ajmala Shireen P, Abdul Mujeeb VM, Muraleedharan K. Theoretical insights on flavanones as antioxidants and UV filters: A TDDFT and NLMO study. J Photochem Photobiol B. 2017 May;170:286-294. doi: 10.1016/j.jphotobiol.2017.04.021. Epub 2017 Apr 20. PubMed PMID: 28456119.

8: Malami I, Abdul AB, Abdullah R, Kassim NK, Rosli R, Yeap SK, Waziri P, Etti IC, Bello MB. Correction: Crude Extracts, Flavokawain B and Alpinetin Compounds from the Rhizome of Alpinia mutica Induce Cell Death via UCK2 Enzyme Inhibition and in Turn Reduce 18S rRNA Biosynthesis in HT-29 Cells. PLoS One. 2017 Mar 7;12(3):e0173651. doi: 10.1371/journal.pone.0173651. eCollection 2017. PubMed PMID: 28267789; PubMed Central PMCID: PMC5340395.

9: Malami I, Abdul AB, Abdullah R, Kassim NK, Rosli R, Yeap SK, Waziri P, Etti IC, Bello MB. Crude Extracts, Flavokawain B and Alpinetin Compounds from the Rhizome of Alpinia mutica Induce Cell Death via UCK2 Enzyme Inhibition and in Turn Reduce 18S rRNA Biosynthesis in HT-29 Cells. PLoS One. 2017 Jan 19;12(1):e0170233. doi: 10.1371/journal.pone.0170233. eCollection 2017. Erratum in: PLoS One. 2017 Mar 7;12 (3):e0173651. PubMed PMID: 28103302; PubMed Central PMCID: PMC5245823.

10: He X, Wei Z, Wang J, Kou J, Liu W, Fu Y, Yang Z. Alpinetin attenuates inflammatory responses by suppressing TLR4 and NLRP3 signaling pathways in DSS-induced acute colitis. Sci Rep. 2016 Jun 20;6:28370. doi: 10.1038/srep28370. PubMed PMID: 27321991; PubMed Central PMCID: PMC4913257.

11: Ng TL, Karim R, Tan YS, Teh HF, Danial AD, Ho LS, Khalid N, Appleton DR, Harikrishna JA. Amino Acid and Secondary Metabolite Production in Embryogenic and Non-Embryogenic Callus of Fingerroot Ginger (Boesenbergia rotunda). PLoS One. 2016 Jun 3;11(6):e0156714. doi: 10.1371/journal.pone.0156714. eCollection 2016. PubMed PMID: 27258536; PubMed Central PMCID: PMC4892522.

12: Malami I, Abdul AB, Abdullah R, Bt Kassim NK, Waziri P, Christopher Etti I. In Silico Discovery of Potential Uridine-Cytidine Kinase 2 Inhibitors from the Rhizome of Alpinia mutica. Molecules. 2016 Apr 8;21(4):417. doi: 10.3390/molecules21040417. PubMed PMID: 27070566.

13: Liang X, Zhang B, Chen Q, Zhang J, Lei B, Li B, Wei Y, Zhai R, Liang Z, He S, Tang B. The mechanism underlying alpinetin-mediated alleviation of pancreatitis-associated lung injury through upregulating aquaporin-1. Drug Des Devel Ther. 2016 Feb 24;10:841-50. doi: 10.2147/DDDT.S97614. eCollection 2016. PubMed PMID: 26966354; PubMed Central PMCID: PMC4771394.

14: Wang J, Yan Z, Liu X, Che S, Wang C, Yao W. Alpinetin targets glioma stem cells by suppressing Notch pathway. Tumour Biol. 2016 Jul;37(7):9243-8. doi: 10.1007/s13277-016-4827-2. Epub 2016 Jan 15. PubMed PMID: 26768745.

15: Wu L, Yang W, Zhang SN, Lu JB. Alpinetin inhibits lung cancer progression and elevates sensitization drug-resistant lung cancer cells to cis-diammined dichloridoplatium. Drug Des Devel Ther. 2015 Nov 16;9:6119-27. doi: 10.2147/DDDT.S92702. eCollection 2015. PubMed PMID: 26604699; PubMed Central PMCID: PMC4655908.

16: Huang Y, Zhou LS, Yan L, Ren J, Zhou DX, Li SS. Alpinetin inhibits lipopolysaccharide-induced acute kidney injury in mice. Int Immunopharmacol. 2015 Oct;28(2):1003-8. doi: 10.1016/j.intimp.2015.08.002. Epub 2015 Aug 28. PubMed PMID: 26321118.

17: Tan BC, Tan SK, Wong SM, Ata N, Rahman NA, Khalid N. Distribution of Flavonoids and Cyclohexenyl Chalcone Derivatives in Conventional Propagated and In Vitro-Derived Field-Grown Boesenbergia rotunda (L.) Mansf. Evid Based Complement Alternat Med. 2015;2015:451870. doi: 10.1155/2015/451870. Epub 2015 Apr 7. PubMed PMID: 25883671; PubMed Central PMCID: PMC4391327.

18: Singh M, Kamal YT, Khan MA, Parveen R, Ansari SH, Ahmad S. Matrix Solid-Phase Dispersion Extraction and Quantification of Alpinetin in Amomum Seed using Validated HPLC and HPTLC Methods. Indian J Pharm Sci. 2015 Jan-Feb;77(1):49-54. PubMed PMID: 25767318; PubMed Central PMCID: PMC4355882.

19: Jiang Z, Sang H, Fu X, Liang Y, Li L. Alpinetin enhances cholesterol efflux and inhibits lipid accumulation in oxidized low-density lipoprotein-loaded human macrophages. Biotechnol Appl Biochem. 2015 Nov-Dec;62(6):840-7. doi: 10.1002/bab.1328. Epub 2015 May 17. PubMed PMID: 25496323.

20: Kuete V, Nkuete AH, Mbaveng AT, Wiench B, Wabo HK, Tane P, Efferth T. Cytotoxicity and modes of action of 4'-hydroxy-2',6'-dimethoxychalcone and other flavonoids toward drug-sensitive and multidrug-resistant cancer cell lines. Phytomedicine. 2014 Oct 15;21(12):1651-7. doi: 10.1016/j.phymed.2014.08.001. Epub 2014 Sep 15. PubMed PMID: 25442273.