5-Demethylnobiletin

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

MedKoo CAT#: 563579

CAS#: 2174-59-6

Description: 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

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5-Demethylnobiletin
CAS# 2174-59-6
Instruction

Theoretical Analysis

MedKoo Cat#: 563579
Name: 5-Demethylnobiletin
CAS#: 2174-59-6
Chemical Formula: C20H20O8
Exact Mass: 388.12
Molecular Weight: 388.370
Elemental Analysis: C, 61.85; H, 5.19; O, 32.96

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.

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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.

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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.

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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.

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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.