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MedKoo Cat#: 563579 | Name: 5-Demethylnobiletin

Description:

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

5-Demethylnobiletin is an activator of the JNK signaling pathway, promoting the formation of polymerized tubulin, leading to G2/M phase arrest and inducing autophagy.

Chemical Structure

5-Demethylnobiletin
5-Demethylnobiletin
CAS#2174-59-6

Theoretical Analysis

MedKoo Cat#: 563579

Name: 5-Demethylnobiletin

CAS#: 2174-59-6

Chemical Formula: C20H20O8

Exact Mass: 388.1158

Molecular Weight: 388.37

Elemental Analysis: C, 61.85; H, 5.19; O, 32.96

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
5-Demethylnobiletin; 5 Demethylnobiletin;
IUPAC/Chemical Name
2-(3,4-Dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxychromen-4-one
InChi Key
DOFJNFPSMUCECH-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H20O8/c1-23-12-7-6-10(8-14(12)24-2)13-9-11(21)15-16(22)18(25-3)20(27-5)19(26-4)17(15)28-13/h6-9,22H,1-5H3
SMILES Code
O=C1C=C(C2=CC=C(OC)C(OC)=C2)OC3=C1C(O)=C(OC)C(OC)=C3OC
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 388.37 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
1: Guo R, Zhang X, Su J, Xu H, Zhang Y, Zhang F, Li D, Zhang Y, Xiao X, Ma S, Yang H. Identifying potential quality markers of Xin-Su-Ning capsules acting on arrhythmia by integrating UHPLC-LTQ-Orbitrap, ADME prediction and network target analysis. Phytomedicine. 2018 May 15;44:117-128. doi: 10.1016/j.phymed.2018.01.019. Epub 2018 Feb 10. PubMed PMID: 29526583. 2: Wang M, Meng D, Zhang P, Wang X, Du G, Brennan C, Li S, Ho CT, Zhao H. Antioxidant Protection of Nobiletin, 5-Demethylnobiletin, Tangeretin, and 5-Demethyltangeretin from Citrus Peel in Saccharomyces cerevisiae. J Agric Food Chem. 2018 Mar 28;66(12):3155-3160. doi: 10.1021/acs.jafc.8b00509. Epub 2018 Mar 16. PubMed PMID: 29526093. 3: Zhang Y, Zhao C, Tian G, Lu C, Li Y, He L, Xiao H, Zheng J. Simultaneous characterization of chemical structures and bioactivities of citrus-derived components using SERS barcodes. Food Chem. 2018 Feb 1;240:743-750. doi: 10.1016/j.foodchem.2017.07.103. Epub 2017 Jul 25. PubMed PMID: 28946337. 4: Song M, Wu X, Charoensinphon N, Wang M, Zheng J, Gao Z, Xu F, Li Z, Li F, Zhou J, Xiao H. Dietary 5-demethylnobiletin inhibits cigarette carcinogen NNK-induced lung tumorigenesis in mice. Food Funct. 2017 Mar 22;8(3):954-963. doi: 10.1039/c6fo01367h. PubMed PMID: 28154877. 5: Zhang H, Zheng J, Liu A, Xiao H, He L. Label-free Imaging and Characterization of Cancer Cell Responses to Polymethoxyflavones Using Raman Microscopy. J Agric Food Chem. 2016 Dec 28;64(51):9708-9713. doi: 10.1021/acs.jafc.6b03899. Epub 2016 Dec 15. PubMed PMID: 27977189. 6: Cao X, Ma C, Gao Z, Zheng J, He L, McClements DJ, Xiao H. Characterization of the Interactions between Titanium Dioxide Nanoparticles and Polymethoxyflavones Using Surface-Enhanced Raman Spectroscopy. J Agric Food Chem. 2016 Dec 14;64(49):9436-9441. Epub 2016 Dec 5. PubMed PMID: 27960290. 7: Cheung TK, Li W, Ho HM, Liang ZT, Huang CQ. [Chemical variation in Aurantii Fructus before and after processing based on UHPLC-Q-TOF-MS]. Zhongguo Zhong Yao Za Zhi. 2016 Jun;41(11):2070-2080. doi: 10.4268/cjcmm20161116. Chinese. PubMed PMID: 28901103. 8: Song M, Charoensinphon N, Wu X, Zheng J, Gao Z, Xu F, Wang M, Xiao H. Inhibitory Effects of Metabolites of 5-Demethylnobiletin on Human Nonsmall Cell Lung Cancer Cells. J Agric Food Chem. 2016 Jun 22;64(24):4943-9. doi: 10.1021/acs.jafc.6b01367. Epub 2016 Jun 7. PubMed PMID: 27219898. 9: Tung YC, Li S, Huang Q, Hung WL, Ho CT, Wei GJ, Pan MH. 5-Demethylnobiletin and 5-Acetoxy-6,7,8,3',4'-pentamethoxyflavone Suppress Lipid Accumulation by Activating the LKB1-AMPK Pathway in 3T3-L1 Preadipocytes and High Fat Diet-Fed C57BL/6 Mice. J Agric Food Chem. 2016 Apr 27;64(16):3196-205. doi: 10.1021/acs.jafc.6b00706. Epub 2016 Apr 15. PubMed PMID: 27041493. 10: Ye X, Song F, Fan G, Wu F. [Simultaneous determination of 11 constituents in Citrus reticulate 'Chachi' by high performance liquid chromatography]. Se Pu. 2015 Apr;33(4):423-7. Chinese. PubMed PMID: 26292415. 11: Chen YK, Wang HC, Ho CT, Chen HY, Li S, Chan HL, Chung TW, Tan KT, Li YR, Lin CC. 5-demethylnobiletin promotes the formation of polymerized tubulin, leads to G2/M phase arrest and induces autophagy via JNK activation in human lung cancer cells. J Nutr Biochem. 2015 May;26(5):484-504. doi: 10.1016/j.jnutbio.2014.12.003. Epub 2015 Jan 29. PubMed PMID: 25765513. 12: Ye X, Cao D, Zhao X, Song F, Huang Q, Fan G, Wu F. Chemical fingerprint and metabolic profile analysis of Citrus reticulate 'Chachi' decoction by HPLC-PDA-IT-MS(n) and HPLC-Quadrupole-Orbitrap-MS method. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Nov 1;970:108-20. doi: 10.1016/j.jchromb.2014.06.035. Epub 2014 Jul 6. PubMed PMID: 25255155. 13: Chiu SP, Wu MJ, Chen PY, Ho YR, Tai MH, Ho CT, Yen JH. Neurotrophic action of 5-hydroxylated polymethoxyflavones: 5-demethylnobiletin and gardenin A stimulate neuritogenesis in PC12 cells. J Agric Food Chem. 2013 Oct 2;61(39):9453-63. doi: 10.1021/jf4024678. Epub 2013 Sep 23. PubMed PMID: 24003765. 14: 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. 15: Zheng J, Song M, Dong P, Qiu P, Guo S, Zhong Z, Li S, Ho CT, Xiao H. Identification of novel bioactive metabolites of 5-demethylnobiletin in mice. Mol Nutr Food Res. 2013 Nov;57(11):1999-2007. doi: 10.1002/mnfr.201300211. Epub 2013 Jul 26. PubMed PMID: 23894027. 16: Zheng J, Fang X, Cao Y, Xiao H, He L. Monitoring the chemical production of citrus-derived bioactive 5-demethylnobiletin using surface-enhanced Raman spectroscopy. J Agric Food Chem. 2013 Aug 28;61(34):8079-83. doi: 10.1021/jf4027475. Epub 2013 Aug 20. PubMed PMID: 23885986; PubMed Central PMCID: PMC3786449. 17: Yen JH, Weng CY, Li S, Lo YH, Pan MH, Fu SH, Ho CT, Wu MJ. Citrus flavonoid 5-demethylnobiletin suppresses scavenger receptor expression in THP-1 cells and alters lipid homeostasis in HepG2 liver cells. Mol Nutr Food Res. 2011 May;55(5):733-48. doi: 10.1002/mnfr.201000226. Epub 2011 Jan 10. PubMed PMID: 21225617. 18: 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. 19: Wang D, Wang J, Huang X, Tu Y, Ni K. Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques. J Pharm Biomed Anal. 2007 May 9;44(1):63-9. Epub 2007 Feb 3. PubMed PMID: 17367982. 20: Nagase H, Omae N, Omori A, Nakagawasai O, Tadano T, Yokosuka A, Sashida Y, Mimaki Y, Yamakuni T, Ohizumi Y. Nobiletin and its related flavonoids with CRE-dependent transcription-stimulating and neuritegenic activities. Biochem Biophys Res Commun. 2005 Dec 2;337(4):1330-6. Epub 2005 Oct 10. PubMed PMID: 16253614.

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