4'-O-Methylhonokiol
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MedKoo CAT#: 462793

CAS#: 68592-15-4

Description: 4'-O-Methylhonokiol is a phenol that has been found in M. grandiflora and has diverse biological activities. It is active against the bacteria B. subtilis, S. aureus, and M. smegmatis and the fungus T. mentagrophytes. 4'-O-Methylhonokiol inhibits LPS-induced activation of NF-kB and production of nitric oxide in RAW 264.7 macrophages. In vivo, 4'-O-Methylhonokiol reduces carrageenan-induced paw edema in mice. It reduces neuronal apoptosis and escape latency in the Morris water maze in a mouse model of Alzheimer's disease induced by amyloid-β 1-42 when administered at a dose of 1 mg/kg.3 4-O-methylhonokiol also reduces plasma cholesterol and triglyceride levels, ameliorates hepatic steatosis, and improves insulin resistance in a mouse model of high-fat diet-induced obesity.


Chemical Structure

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4'-O-Methylhonokiol
CAS# 68592-15-4

Theoretical Analysis

MedKoo Cat#: 462793
Name: 4'-O-Methylhonokiol
CAS#: 68592-15-4
Chemical Formula: C19H20O2
Exact Mass: 280.1463
Molecular Weight: 280.367
Elemental Analysis: C, 81.40; H, 7.19; O, 11.41

Price and Availability

Size Price Availability Quantity
5.0mg USD 320.0 2 Weeks
10.0mg USD 530.0 2 Weeks
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Synonym: 4-Methoxyhonokiol; NSC 293101; NSC293101; NSC-293101;

IUPAC/Chemical Name: 3',5-diallyl-4'-methoxy-[1,1'-biphenyl]-2-ol

InChi Key: OQFHJKZVOALSPV-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H20O2/c1-4-6-14-8-10-18(20)17(12-14)15-9-11-19(21-3)16(13-15)7-5-2/h4-5,8-13,20H,1-2,6-7H2,3H3

SMILES Code: C=CCC1=CC(C2=CC(CC=C)=C(C=C2)OC)=C(C=C1)O

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

Preparing Stock Solutions

The following data is based on the product molecular weight 280.367 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: Park KR, Kim JY, Kim EC, Yun HM, Hong JT. RANKL-induced osteoclastogenesis is suppressed by 4-O-methylhonokiol in bone marrow-derived macrophages. Arch Pharm Res. 2017 Aug;40(8):933-942. doi: 10.1007/s12272-017-0932-z. Epub 2017 Jul 24. PMID: 28736799.

2: Kim SC, Kang JI, Hyun JW, Kang JH, Koh YS, Kim YH, Kim KH, Ko JH, Yoo ES, Kang HK. 4-O-Methylhonokiol Protects HaCaT Cells from TGF-β1-Induced Cell Cycle Arrest by Regulating Canonical and Non-Canonical Pathways of TGF-β Signaling. Biomol Ther (Seoul). 2017 Jul 1;25(4):417-426. doi: 10.4062/biomolther.2016.003. PMID: 28190316; PMCID: PMC5499621.

3: Kim S, Ka SO, Lee Y, Park BH, Fei X, Jung JK, Seo SY, Bae EJ. The new 4-O-methylhonokiol analog GS12021 inhibits inflammation and macrophage chemotaxis: role of AMP-activated protein kinase α activation. PLoS One. 2015 Feb 23;10(2):e0117120. doi: 10.1371/journal.pone.0117120. PMID: 25706552; PMCID: PMC4338227.

4: Li MY, Tang YH, Liu X, Lü HY, Shi XY. Sensitive determination of 4-O-methylhonokiol in rabbit plasma by high performance liquid chromatography and application to its pharmacokinetic investigation. J Pharm Anal. 2011 May;1(2):108-112. doi: 10.1016/S2095-1779(11)70019-3. Epub 2012 Jan 30. PMID: 29403688; PMCID: PMC5760773.

5: Patsenker E, Chicca A, Petrucci V, Moghadamrad S, de Gottardi A, Hampe J, Gertsch J, Semmo N, Stickel F. 4-O'-methylhonokiol protects from alcohol/carbon tetrachloride-induced liver injury in mice. J Mol Med (Berl). 2017 Oct;95(10):1077-1089. doi: 10.1007/s00109-017-1556-y. Epub 2017 Jul 8. PMID: 28689299.

6: Han H, Jung JK, Han SB, Nam SY, Oh KW, Hong JT. Anxiolytic-like effects of 4-O-methylhonokiol isolated from Magnolia officinalis through enhancement of GABAergic transmission and chloride influx. J Med Food. 2011 Jul- Aug;14(7-8):724-31. doi: 10.1089/jmf.2010.1111. Epub 2011 Apr 18. PMID: 21501091.

7: Lee YJ, Choi DY, Choi IS, Kim KH, Kim YH, Kim HM, Lee K, Cho WG, Jung JK, Han SB, Han JY, Nam SY, Yun YW, Jeong JH, Oh KW, Hong JT. Inhibitory effect of 4-O-methylhonokiol on lipopolysaccharide-induced neuroinflammation, amyloidogenesis and memory impairment via inhibition of nuclear factor-kappaB in vitro and in vivo models. J Neuroinflammation. 2012 Feb 19;9:35. doi: 10.1186/1742-2094-9-35. PMID: 22339795; PMCID: PMC3323460.

8: Baur R, Schuehly W, Sigel E. Moderate concentrations of 4-O-methylhonokiol potentiate GABAA receptor currents stronger than honokiol. Biochim Biophys Acta. 2014 Oct;1840(10):3017-21. doi: 10.1016/j.bbagen.2014.06.016. Epub 2014 Jun 25. PMID: 24973566.

9: Yu HE, Oh SJ, Ryu JK, Kang JS, Hong JT, Jung JK, Han SB, Seo SY, Kim YH, Park SK, Kim HM, Lee K. Pharmacokinetics and metabolism of 4-O-methylhonokiol in rats. Phytother Res. 2014 Apr;28(4):568-78. doi: 10.1002/ptr.5033. Epub 2013 Jul 3. PMID: 23824979.

10: Lee YK, Choi IS, Kim YH, Kim KH, Nam SY, Yun YW, Lee MS, Oh KW, Hong JT. Neurite outgrowth effect of 4-O-methylhonokiol by induction of neurotrophic factors through ERK activation. Neurochem Res. 2009 Dec;34(12):2251-60. doi: 10.1007/s11064-009-0024-7. PMID: 19557513.

11: Choi IS, Lee YJ, Choi DY, Lee YK, Lee YH, Kim KH, Kim YH, Jeon YH, Kim EH, Han SB, Jung JK, Yun YP, Oh KW, Hwang DY, Hong JT. 4-O-methylhonokiol attenuated memory impairment through modulation of oxidative damage of enzymes involving amyloid-β generation and accumulation in a mouse model of Alzheimer's disease. J Alzheimers Dis. 2011;27(1):127-41. doi: 10.3233/JAD-2011-110545. PMID: 21799245.

12: Oh JH, Kang LL, Ban JO, Kim YH, Kim KH, Han SB, Hong JT. Anti-inflammatory effect of 4-O-methylhonokiol, compound isolated from Magnolia officinalis through inhibition of NF-kappaB [corrected]. Chem Biol Interact. 2009 Aug 14;180(3):506-14. doi: 10.1016/j.cbi.2009.03.014. Epub 2009 Mar 27. Erratum in: Chem Biol Interact. 2010 Dec 5;188(3):677. PMID: 19539808.

13: Han JY, Ahn SY, Yoo JH, Nam SY, Hong JT, Oh KW. Alleviation of kainic acid- induced brain barrier dysfunction by 4-o-methylhonokiol in in vitro and in vivo models. Biomed Res Int. 2015;2015:893163. doi: 10.1155/2015/893163. Epub 2015 Jan 20. PMID: 25688368; PMCID: PMC4320858.

14: Lin C, Yon JM, Hong JT, Lee JK, Jeong J, Baek IJ, Lee BJ, Yun YW, Nam SY. 4-O-methylhonokiol inhibits serious embryo anomalies caused by nicotine via modulations of oxidative stress, apoptosis, and inflammation. Birth Defects Res B Dev Reprod Toxicol. 2014 Apr;101(2):125-34. doi: 10.1002/bdrb.21092. Epub 2014 Apr 1. PMID: 24692394.

15: Lee YK, Yuk DY, Kim TI, Kim YH, Kim KT, Kim KH, Lee BJ, Nam SY, Hong JT. Protective effect of the ethanol extract of Magnolia officinalis and 4-O-methylhonokiol on scopolamine-induced memory impairment and the inhibition of acetylcholinesterase activity. J Nat Med. 2009 Jul;63(3):274-82. doi: 10.1007/s11418-009-0330-z. Epub 2009 Apr 4. PMID: 19343477; PMCID: PMC2690856.

16: Xiao S, Chen F, Gao C. Antitumor activity of 4-O-Methylhonokiol in human oral cancer cells is mediated via ROS generation, disruption of mitochondrial potential, cell cycle arrest and modulation of Bcl-2/Bax proteins. J BUON. 2017 Nov-Dec;22(6):1577-1581. PMID: 29332355.

17: Lee YJ, Choi IS, Park MH, Lee YM, Song JK, Kim YH, Kim KH, Hwang DY, Jeong JH, Yun YP, Oh KW, Jung JK, Han SB, Hong JT. 4-O-Methylhonokiol attenuates memory impairment in presenilin 2 mutant mice through reduction of oxidative damage and inactivation of astrocytes and the ERK pathway. Free Radic Biol Med. 2011 Jan 1;50(1):66-77. doi: 10.1016/j.freeradbiomed.2010.10.698. Epub 2010 Oct 23. PMID: 20974250.

18: Lee YK, Choi IS, Ban JO, Lee HJ, Lee US, Han SB, Jung JK, Kim YH, Kim KH, Oh KW, Hong JT. 4-O-methylhonokiol attenuated β-amyloid-induced memory impairment through reduction of oxidative damages via inactivation of p38 MAP kinase. J Nutr Biochem. 2011 May;22(5):476-86. doi: 10.1016/j.jnutbio.2010.04.002. Epub 2010 Aug 5. PMID: 20688501.

19: Singha SK, Muhammad I, Ibrahim MA, Wang M, Ashpole NM, Shariat-Madar Z. 4-O-Methylhonokiol Influences Normal Cardiovascular Development in Medaka Embryo. Molecules. 2019 Jan 29;24(3):475. doi: 10.3390/molecules24030475. PMID: 30699965; PMCID: PMC6384692.

20: Oh JH, Ban JO, Cho MC, Jo M, Jung JK, Ahn B, Yoon DY, Han SB, Hong JT. 4-O-methylhonokiol inhibits colon tumor growth via p21-mediated suppression of NF-κB activity. J Nutr Biochem. 2012 Jul;23(7):706-15. doi: 10.1016/j.jnutbio.2011.03.013. Epub 2011 Aug 4. PMID: 21820300.