5-OH-HxMF

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

MedKoo CAT#: 525794

CAS#: 1176-88-1

Description: 5-OH-HxMF is an inducer of neurite outgrowth via cAMP/PKA/CREB pathway in PC12 cells.


Price and Availability

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5-OH-HxMF is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 525794
Name: 5-OH-HxMF
CAS#: 1176-88-1
Chemical Formula: C21H22O9
Exact Mass: 418.1264
Molecular Weight: 418.398
Elemental Analysis: C, 60.28; H, 5.30; O, 34.41


Synonym: 5-OH-HxMF

IUPAC/Chemical Name: 5-Hydroxy-3,6,7,8,3',4'-hexamethoxyflavone

InChi Key: JDVPHCLYMGBZLE-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H22O9/c1-24-11-8-7-10(9-12(11)25-2)16-18(26-3)14(22)13-15(23)19(27-4)21(29-6)20(28-5)17(13)30-16/h7-9,23H,1-6H3

SMILES Code: O=C1C(OC)=C(C2=CC=C(OC)C(OC)=C2)OC3=C1C(O)=C(OC)C(OC)=C3OC


Technical Data

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).

Harmonized System Code:
293490


References

1: Wang Y, Lee PS, Chen YF, Ho CT, Pan MH. Suppression of Adipogenesis by 5-Hydroxy-3,6,7,8,3',4'-Hexamethoxyflavone from Orange Peel in 3T3-L1 Cells. J Med Food. 2016 Sep;19(9):830-5. doi: 10.1089/jmf.2016.0060. Epub 2016 Aug 19. PubMed PMID: 27542074.

2: Wang X, Xia M. 5-Hydroxy-3,6,7,8,3',4'-hexamethoxyflavone, a polymethoxyflavone, exerts antitumor effect on PI3K/Akt signaling pathway in human gastric cancer cell BGC-7901. J Recept Signal Transduct Res. 2016 Oct;36(5):471-7. doi: 10.3109/10799893.2015.1122046. Epub 2015 Dec 16. PubMed PMID: 26671739.

3: Wu CH, Hong BH, Ho CT, Yen GC. Targeting cancer stem cells in breast cancer: potential anticancer properties of 6-shogaol and pterostilbene. J Agric Food Chem. 2015 Mar 11;63(9):2432-41. doi: 10.1021/acs.jafc.5b00002. Epub 2015 Feb 25. PubMed PMID: 25686711.

4: Kim MJ, Lee HH, Jeong JW, Seo MJ, Kang BW, Park JU, Kim KS, Cho YS, Seo KI, Kim GY, Kim JI, Choi YH, Jeong YK. Anti-inflammatory effects of 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone via NF-κB inactivation in lipopolysaccharide-stimulated RAW 264.7 macrophage. Mol Med Rep. 2014 Apr;9(4):1197-203. doi: 10.3892/mmr.2014.1922. Epub 2014 Jan 28. PubMed PMID: 24481726.

5: Kang CH, Kim MJ, Seo MJ, Choi YH, Jo WS, Lee KT, Jeong YK, Kim GY. 5-Hydroxy-3,6,7,8,3'4'-hexamethoxyflavone inhibits nitric oxide production in lipopolysaccharide-stimulated BV2 microglia via NF-κB suppression and Nrf-2-dependent heme oxygenase-1 induction. Food Chem Toxicol. 2013 Jul;57:119-25. doi: 10.1016/j.fct.2013.03.019. Epub 2013 Mar 29. PubMed PMID: 23542513.

6: Kou MC, Fu SH, Yen JH, Weng CY, Li S, Ho CT, Wu MJ. Effects of citrus flavonoids, 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone and 3,5,6,7,8,3',4'-heptamethoxyflavone, on the activities of macrophage scavenger receptors and the hepatic LDL receptor. Food Funct. 2013 Apr 25;4(4):602-9. doi: 10.1039/c3fo30301b. Epub 2013 Jan 31. PubMed PMID: 23370792.

7: Kim MJ, Lee HH, Seo MJ, Kang BW, Park JU, Kim KS, Kim GY, Joo WH, Choi YH, Cho YS, Jeong YK. Identification of 5-hydroxy-3,6,7,8,3´,4´-hexamethoxyflavone from Hizikia fusiforme involved in the induction of the apoptosis mediators in human AGS carcinoma cells. J Microbiol Biotechnol. 2012 Dec;22(12):1665-72. PubMed PMID: 23221529.

8: Lai HC, Wu MJ, Chen PY, Sheu TT, Chiu SP, Lin MH, Ho CT, Yen JH. Neurotrophic effect of citrus 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone: promotion of neurite outgrowth via cAMP/PKA/CREB pathway in PC12 cells. PLoS One. 2011;6(11):e28280. doi: 10.1371/journal.pone.0028280. Epub 2011 Nov 29. PubMed PMID: 22140566; PubMed Central PMCID: PMC3226691.

9: Hamdan D, El-Readi MZ, Tahrani A, Herrmann F, Kaufmann D, Farrag N, El-Shazly A, Wink M. Chemical composition and biological activity of Citrus jambhiri Lush. Food Chem. 2011 Jul 15;127(2):394-403. doi: 10.1016/j.foodchem.2010.12.129. Epub 2011 Jan 8. PubMed PMID: 23140678.

10: Qiu P, Guan H, Dong P, Guo S, Zheng J, Li S, Chen Y, Ho CT, Pan MH, McClements DJ, Xiao H. The inhibitory effects of 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone on human colon cancer cells. Mol Nutr Food Res. 2011 Oct;55(10):1523-32. doi: 10.1002/mnfr.201100070. Epub 2011 Jun 6. PubMed PMID: 21648071; PubMed Central PMCID: PMC3449327.

11: Qiu P, Guan H, Dong P, Li S, Ho CT, Pan MH, McClements DJ, Xiao H. The p53-, Bax- and p21-dependent inhibition of colon cancer cell growth by 5-hydroxy polymethoxyflavones. Mol Nutr Food Res. 2011 Apr;55(4):613-22. doi: 10.1002/mnfr.201000269. Epub 2010 Nov 23. PubMed PMID: 21462329; PubMed Central PMCID: PMC3139001.

12: Qiu P, Dong P, Guan H, Li S, Ho CT, Pan MH, McClements DJ, Xiao H. Inhibitory effects of 5-hydroxy polymethoxyflavones on colon cancer cells. Mol Nutr Food Res. 2010 Jul;54 Suppl 2:S244-52. doi: 10.1002/mnfr.200900605. PubMed PMID: 20397199.

13: Li S, Wang Y, Wang Z, Xiao H, Lo CY, Rawson N, Ho CT. Quantitative analysis of hydroxylated polymethoxyflavones by high-performance liquid chromatography. Biomed Chromatogr. 2010 Aug;24(8):838-45. doi: 10.1002/bmc.1372. PubMed PMID: 20033889.

14: Dong P, Qiu P, Zhu Y, Li S, Ho CT, McClements DJ, Xiao H. Simultaneous determination of four 5-hydroxy polymethoxyflavones by reversed-phase high performance liquid chromatography with electrochemical detection. J Chromatogr A. 2010 Jan 29;1217(5):642-7. doi: 10.1016/j.chroma.2009.11.097. Epub 2009 Dec 4. PubMed PMID: 20022018.

15: Sergeev IN, Li S, Ho CT, Rawson NE, Dushenkov S. Polymethoxyflavones activate Ca2+-dependent apoptotic targets in adipocytes. J Agric Food Chem. 2009 Jul 8;57(13):5771-6. doi: 10.1021/jf901071k. PubMed PMID: 19522510.

16: Xiao H, Yang CS, Li S, Jin H, Ho CT, Patel T. Monodemethylated polymethoxyflavones from sweet orange (Citrus sinensis) peel inhibit growth of human lung cancer cells by apoptosis. Mol Nutr Food Res. 2009 Mar;53(3):398-406. doi: 10.1002/mnfr.200800057. PubMed PMID: 19065586.

17: Lai CS, Li S, Chai CY, Lo CY, Ho CT, Wang YJ, Pan MH. Inhibitory effect of citrus 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone on 12-O-tetradecanoylphorbol 13-acetate-induced skin inflammation and tumor promotion in mice. Carcinogenesis. 2007 Dec;28(12):2581-8. Epub 2007 Oct 24. PubMed PMID: 17962218.

18: Pan MH, Lai YS, Lai CS, Wang YJ, Li S, Lo CY, Dushenkov S, Ho CT. 5-Hydroxy-3,6,7,8,3',4'-hexamethoxyflavone induces apoptosis through reactive oxygen species production, growth arrest and DNA damage-inducible gene 153 expression, and caspase activation in human leukemia cells. J Agric Food Chem. 2007 Jun 27;55(13):5081-91. Epub 2007 May 31. PubMed PMID: 17536822.

19: Li S, Pan MH, Lai CS, Lo CY, Dushenkov S, Ho CT. Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines. Bioorg Med Chem. 2007 May 15;15(10):3381-9. Epub 2007 Mar 13. PubMed PMID: 17391969.

20: Sergeev IN, Li S, Colby J, Ho CT, Dushenkov S. Polymethoxylated flavones induce Ca(2+)-mediated apoptosis in breast cancer cells. Life Sci. 2006 Dec 23;80(3):245-53. Epub 2006 Sep 15. PubMed PMID: 17046027.