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MedKoo Cat#: 585223 | Name: Sinensetin
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Description:

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

Sinensetin is isolated from citrus fruit and exhibits antiadhesive action on platelets.

Chemical Structure

Sinensetin
Sinensetin
CAS#2306-27-6

Theoretical Analysis

MedKoo Cat#: 585223

Name: Sinensetin

CAS#: 2306-27-6

Chemical Formula: C20H20O7

Exact Mass: 372.1209

Molecular Weight: 372.37

Elemental Analysis: C, 64.51; H, 5.41; O, 30.08

Price and Availability

Size Price Availability Quantity
5mg USD 250.00 2 weeks
10mg USD 525.00 2 weeks
25mg USD 750.00 2 weeks
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Related CAS #
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Synonym
Sinensetin
IUPAC/Chemical Name
4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-
InChi Key
LKMNXYDUQXAUCZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H20O7/c1-22-13-7-6-11(8-15(13)23-2)14-9-12(21)18-16(27-14)10-17(24-3)19(25-4)20(18)26-5/h6-10H,1-5H3
SMILES Code
O=C1C=C(C2=CC=C(OC)C(OC)=C2)OC3=CC(OC)=C(OC)C(OC)=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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Sinensetin has been shown to enhance adipogenesis and lipolysis by increasing cAMP levels in 3T3-L1 cells. Sinensetin is also reported to inhibit α-glucosidase and α-amylase activity in vitro. Sinensetin has been shown to suppress the expression of genes associated with inflammation by regulating IκBα protein levels in LPS-activated macrophages.
In vitro activity:
Sinensetin has a synergistic effect on human interferon gamma (IFNγ)-triggered anticancer action in HepG2 cells, suggesting potential therapeutic applications for ligand-protein complexes. The study found that sinensetin forms a complex with IFNγ through a static quenching mechanism, and hydrophobic forces, particularly involving amino acid residues Lys55 and Lys58, play a key role in the complex formation. The interaction does not significantly alter the protein's structure. Reference: Int J Biol Macromol. 2023 Dec 31;253(Pt 1):126392. https://pubmed.ncbi.nlm.nih.gov/37595707/
In vivo activity:
Sinensetin has the potential to reduce Cisplatin-caused adverse effects, without reversing Cisplatin-caused tumor suppression. Sinensetin was able to alleviate intestinal injury in Cisplatin-challenged mice, which was accompanied by the decrease of lytic cell death and immune cell infiltration. Reference: Biochim Biophys Acta Mol Basis Dis. 2023 Mar;1869(3):166637. https://pubmed.ncbi.nlm.nih.gov/36638874/
Solvent mg/mL mM comments
Solubility
DMF 0.5 1.34
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 372.37 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
Formulation protocol:
1. Feng F, Li T, Liang Y, Gao W, Yang L. Structural changes and anti-hepatocellular carcinoma activity of interferon-γ after interaction with sinensetin. Int J Biol Macromol. 2023 Dec 31;253(Pt 1):126392. doi: 10.1016/j.ijbiomac.2023.126392. Epub 2023 Aug 16. PMID: 37595707. 2. Lin L, Deng K, Gong Z, Fan H, Zhang D, Lu G. Sinensetin Attenuated Macrophagic NLRP3 Inflammasomes Formation via SIRT1-NRF2 Signaling. ACS Omega. 2023 Sep 7;8(37):33514-33525. doi: 10.1021/acsomega.3c03319. PMID: 37744845; PMCID: PMC10515189. 3. Kong Z, Lv W, Wang Y, Huang Y, Che K, Nan H, Xin Y, Wang J, Chen J, Wang Y, Chi J. Sinensetin ameliorates high glucose-induced diabetic nephropathy via enhancing autophagy in vitro and in vivo. J Biochem Mol Toxicol. 2023 Oct;37(10):e23445. doi: 10.1002/jbt.23445. Epub 2023 Jul 2. PMID: 37393522. 4. Li Y, Wang X, Lin J, Wang R, Zhang B, Zhang X, He W, Gao F, Song D, Zhao K, Guan J. Natural flavonoid sinensetin inhibits cisplatin-induced pyroptosis and attenuates intestinal injury. Biochim Biophys Acta Mol Basis Dis. 2023 Mar;1869(3):166637. doi: 10.1016/j.bbadis.2023.166637. Epub 2023 Jan 10. PMID: 36638874.
In vitro protocol:
1. Feng F, Li T, Liang Y, Gao W, Yang L. Structural changes and anti-hepatocellular carcinoma activity of interferon-γ after interaction with sinensetin. Int J Biol Macromol. 2023 Dec 31;253(Pt 1):126392. doi: 10.1016/j.ijbiomac.2023.126392. Epub 2023 Aug 16. PMID: 37595707. 2. Lin L, Deng K, Gong Z, Fan H, Zhang D, Lu G. Sinensetin Attenuated Macrophagic NLRP3 Inflammasomes Formation via SIRT1-NRF2 Signaling. ACS Omega. 2023 Sep 7;8(37):33514-33525. doi: 10.1021/acsomega.3c03319. PMID: 37744845; PMCID: PMC10515189.
In vivo protocol:
1. Kong Z, Lv W, Wang Y, Huang Y, Che K, Nan H, Xin Y, Wang J, Chen J, Wang Y, Chi J. Sinensetin ameliorates high glucose-induced diabetic nephropathy via enhancing autophagy in vitro and in vivo. J Biochem Mol Toxicol. 2023 Oct;37(10):e23445. doi: 10.1002/jbt.23445. Epub 2023 Jul 2. PMID: 37393522. 2. Li Y, Wang X, Lin J, Wang R, Zhang B, Zhang X, He W, Gao F, Song D, Zhao K, Guan J. Natural flavonoid sinensetin inhibits cisplatin-induced pyroptosis and attenuates intestinal injury. Biochim Biophys Acta Mol Basis Dis. 2023 Mar;1869(3):166637. doi: 10.1016/j.bbadis.2023.166637. Epub 2023 Jan 10. PMID: 36638874.
1: Kang SI, Shin HS, Kim SJ. Sinensetin enhances adipogenesis and lipolysis by increasing cyclic adenosine monophosphate levels in 3T3-L1 adipocytes. Biol Pharm Bull. 2015;38(4):552-8. doi: 10.1248/bpb.b14-00700. Epub 2015 Jan 24. PubMed PMID: 25735898. 2: Kang SI, Shin HS, Ko HC, Kim SJ. Effects of sinensetin on lipid metabolism in mature 3T3-L1 adipocytes. Phytother Res. 2013 Jan;27(1):131-4. doi: 10.1002/ptr.4683. Epub 2012 Mar 22. PubMed PMID: 22438091. 3: Yam MF, Mohamed EA, Ang LF, Pei L, Darwis Y, Mahmud R, Asmawi MZ, Basir R, Ahmad M. A simple isocratic HPLC method for the simultaneous determination of sinensetin, eupatorin, and 3'-hydroxy-5,6,7,4'-tetramethoxyflavone in Orthosiphon stamineus extracts. J Acupunct Meridian Stud. 2012 Aug;5(4):176-82. doi: 10.1016/j.jams.2012.05.005. Epub 2012 Jun 15. PubMed PMID: 22898066. 4: Choi CH, Sun KH, An CS, Yoo JC, Hahm KS, Lee IH, Sohng JK, Kim YC. Reversal of P-glycoprotein-mediated multidrug resistance by 5,6,7,3',4'-pentamethoxyflavone (Sinensetin). Biochem Biophys Res Commun. 2002 Jul 26;295(4):832-40. PubMed PMID: 12127970. 5: Wei GJ, Sheen JF, Lu WC, Hwang LS, Ho CT, Lin CI. Identification of sinensetin metabolites in rat urine by an isotope-labeling method and ultrahigh-performance liquid chromatography-electrospray ionization mass spectrometry. J Agric Food Chem. 2013 May 29;61(21):5016-21. doi: 10.1021/jf3046768. Epub 2013 May 16. PubMed PMID: 23647150. 6: Laavola M, Nieminen R, Yam MF, Sadikun A, Asmawi MZ, Basir R, Welling J, Vapaatalo H, Korhonen R, Moilanen E. Flavonoids eupatorin and sinensetin present in Orthosiphon stamineus leaves inhibit inflammatory gene expression and STAT1 activation. Planta Med. 2012 May;78(8):779-86. doi: 10.1055/s-0031-1298458. Epub 2012 Apr 19. PubMed PMID: 22516932. 7: Ashraf K, Sultan S, Adam A. Orthosiphon stamineus Benth. is an Outstanding Food Medicine: Review of Phytochemical and Pharmacological Activities. J Pharm Bioallied Sci. 2018 Jul-Sep;10(3):109-118. doi: 10.4103/jpbs.JPBS_253_17. Review. PubMed PMID: 30237681; PubMed Central PMCID: PMC6142889. 8: Shin HS, Kang SI, Yoon SA, Ko HC, Kim SJ. Sinensetin attenuates LPS-induced inflammation by regulating the protein level of IκB-α. Biosci Biotechnol Biochem. 2012;76(4):847-9. Epub 2012 Apr 7. PubMed PMID: 22484952. 9: Yam MF, Tan CS, Shibao R. Vasorelaxant effect of sinensetin via the NO/sGC/cGMP pathway and potassium and calcium channels. Hypertens Res. 2018 Oct;41(10):787-797. doi: 10.1038/s41440-018-0083-8. Epub 2018 Aug 15. PubMed PMID: 30111856. 10: Dong Y, Ji G, Cao A, Shi J, Shi H, Xie J, Wu D. [Effects of sinensetin on proliferation and apoptosis of human gastric cancer AGS cells]. Zhongguo Zhong Yao Za Zhi. 2011 Mar;36(6):790-4. Chinese. PubMed PMID: 21710752. 11: Mohamed EA, Siddiqui MJ, Ang LF, Sadikun A, Chan SH, Tan SC, Asmawi MZ, Yam MF. Potent α-glucosidase and α-amylase inhibitory activities of standardized 50% ethanolic extracts and sinensetin from Orthosiphon stamineus Benth as anti-diabetic mechanism. BMC Complement Altern Med. 2012 Oct 8;12:176. doi: 10.1186/1472-6882-12-176. PubMed PMID: 23039079; PubMed Central PMCID: PMC3533584. 12: Lam IK, Alex D, Wang YH, Liu P, Liu AL, Du GH, Lee SM. In vitro and in vivo structure and activity relationship analysis of polymethoxylated flavonoids: identifying sinensetin as a novel antiangiogenesis agent. Mol Nutr Food Res. 2012 Jun;56(6):945-56. doi: 10.1002/mnfr.201100680. PubMed PMID: 22707269. 13: Tan KT, Lin MX, Lin SC, Tung YT, Lin SH, Lin CC. Sinensetin induces apoptosis and autophagy in the treatment of human T-cell lymphoma. Anticancer Drugs. 2019 Jun;30(5):485-494. doi: 10.1097/CAD.0000000000000756. PubMed PMID: 30702500. 14: Jiang Y, Wong JH, Fu M, Ng TB, Liu ZK, Wang CR, Li N, Qiao WT, Wen TY, Liu F. Isolation of adenosine, iso-sinensetin and dimethylguanosine with antioxidant and HIV-1 protease inhibiting activities from fruiting bodies of Cordyceps militaris. Phytomedicine. 2011 Jan 15;18(2-3):189-93. doi: 10.1016/j.phymed.2010.04.010. Epub 2010 Jun 23. PubMed PMID: 20576416. 15: Youn K, Yu Y, Lee J, Jeong WS, Ho CT, Jun M. Polymethoxyflavones: Novel β-Secretase (BACE1) Inhibitors from Citrus Peels. Nutrients. 2017 Sep 4;9(9). pii: E973. doi: 10.3390/nu9090973. PubMed PMID: 28869548; PubMed Central PMCID: PMC5622733. 16: Pan Y, Tiong KH, Abd-Rashid BA, Ismail Z, Ismail R, Mak JW, Ong CE. In vitro effect of important herbal active constituents on human cytochrome P450 1A2 (CYP1A2) activity. Phytomedicine. 2014 Oct 15;21(12):1645-50. doi: 10.1016/j.phymed.2014.08.003. Epub 2014 Sep 16. PubMed PMID: 25442272. 17: Xiong YJ, Deng ZB, Liu JN, Qiu JJ, Guo L, Feng PP, Sui JR, Chen DP, Guo HS. Enhancement of epithelial cell autophagy induced by sinensetin alleviates epithelial barrier dysfunction in colitis. Pharmacol Res. 2019 Oct;148:104461. doi: 10.1016/j.phrs.2019.104461. Epub 2019 Sep 19. PubMed PMID: 31542404. 18: Ding YQ, Xiong Y, Zhou B, Deng MZ, Deng KZ. [Isolation and structural identification of flavonoids from Aurantii Fructus]. Zhongguo Zhong Yao Za Zhi. 2015 Jun;40(12):2352-6. Chinese. PubMed PMID: 26591524. 19: Saidan NH, Aisha AF, Hamil MS, Majid AM, Ismail Z. A novel reverse phase high-performance liquid chromatography method for standardization of Orthosiphon stamineus leaf extracts. Pharmacognosy Res. 2015 Jan-Mar;7(1):23-31. doi: 10.4103/0974-8490.147195. PubMed PMID: 25598631; PubMed Central PMCID: PMC4285645. 20: Kimura J, Nemoto K, Yokosuka A, Mimaki Y, Degawa M, Ohizumi Y. 6-demethoxynobiletin, a nobiletin-analog citrus flavonoid, enhances extracellular signal-regulated kinase phosphorylation in PC12D cells. Biol Pharm Bull. 2013;36(10):1646-9. Epub 2013 Aug 9. PubMed PMID: 23934345.

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