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Details

Stereochemistry ACHIRAL
Molecular Formula C18H18O2
Molecular Weight 266.3343
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MAGNOLOL

SMILES

OC1=CC=C(CC=C)C=C1C2=CC(CC=C)=CC=C2O

InChI

InChIKey=VVOAZFWZEDHOOU-UHFFFAOYSA-N
InChI=1S/C18H18O2/c1-3-5-13-7-9-17(19)15(11-13)16-12-14(6-4-2)8-10-18(16)20/h3-4,7-12,19-20H,1-2,5-6H2

HIDE SMILES / InChI

Molecular Formula C18H18O2
Molecular Weight 266.3343
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Magnolol is a small polyphenolic molecule with low toxicity that is isolated from the herb genus Magnolia. In preclinical experiments, magnolol was found to have anti-oxidative, anti-inflammatory, anti-tumorigenic, anti-diabetic, anti-microbial, anti-neurodegenerative and anti-depressant properties. Magnolol is a dual agonist targeting both nuclear receptors retinoic X receptor α (RXRα) and peroxisome proliferator activated receptor γ (PPARγ). These proteins function potently in metabolic diseases and are both important targets for anti-diabetic drugs. In addition, was made a suggestion, that magnolol might exert antiepileptic activity by acting at the GABAA/benzodiazepine receptor complex. Magnolol might be of benefit to the treatment of refractory Candida infection. In addition, it might be a candidate as an agent for the prevention of bone disorders such as osteoporosis. It is known, that the accumulation of oxygen-free radicals and activation of neutrophils are strongly implicated as important pathophysiological mechanisms mediating myocardial ischemia/reperfusion injury. It has been proven that various antioxidants have cardioprotective effects, including magnolol. Its properties were studied in the rat model of myocardial ischemia/reperfusion injury.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P37231|||Q15179
Gene ID: 5468.0
Gene Symbol: PPARG
Target Organism: Homo sapiens (Human)
Target ID: P19793
Gene ID: 6256.0
Gene Symbol: RXRA
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effects of Magnolol and Honokiol on the activities of streptococcal glucosyltransferases both in solution and adsorbed on an experimental pellicle.
2004
Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones.
2004 Apr
Antimicrobial and cytotoxic activities of neolignans from Magnolia officinalis.
2004 Mar
Mechanisms of the influence of magnolol on eicosanoid metabolism in neutrophils.
2004 Mar 1
Isolation and purification of honokiol and magnolol from cortex Magnoliae officinalis by high-speed counter-current chromatography.
2004 May 21
Magnolol alters the course of endotoxin tolerance and provides early protection against endotoxin challenge following sublethal hemorrhage in rats.
2004 Oct
Elucidating the inhibitory mechanisms of magnolol on rat smooth muscle cell proliferation.
2005 Dec
Magnolol and honokiol enhance HL-60 human leukemia cell differentiation induced by 1,25-dihydroxyvitamin D3 and retinoic acid.
2005 Feb
Cytotoxic neolignans: an SAR study.
2005 Jan 3
[Studies on HPLC chromatogram of phenolic constituents of Cortex Magnoliae Officinalis].
2005 Jul
Magnolol induces the distributional changes of p160 and adipose differentiation-related protein in adrenal cells.
2005 Jun
Determination of honokiol and magnolol by micro HPLC with electrochemical detection and its application to the distribution analysis in branches and leaves of Magnolia obovata.
2005 Mar
Prokinetic effect of a Kampo medicine, Hange-koboku-to (Banxia-houpo-tang), on patients with functional dyspepsia.
2005 Nov
Separation and determination of honokiol and magnolol in herbal medicines by flow injection-capillary electrophoresis.
2006 Apr
[Inhibition of extracts from 17 Chinese herbs on periodontal pathogenic microbes].
2006 Aug
Carbon nanotube/poly(methyl methacrylate) composite electrode for capillary electrophoretic measurement of honokiol and magnolol in Cortex Magnoliae Officinalis.
2006 Aug
Ethnoveterinary medicines used for horses in Trinidad and in British Columbia, Canada.
2006 Aug 7
Anti-inflammatory effects of different drugs/agents with antioxidant property on endothelial expression of adhesion molecules.
2006 Dec
[Investigate into of effective constituent transference of herba Ephedrae and cortex Magnoliae officinalis in preparation course of Shujin Kechuan capsule].
2006 Dec
Targeting signal-transducer-and-activator-of-transcription-3 for prevention and therapy of cancer: modern target but ancient solution.
2006 Dec
Magnolol-induced apoptosis is mediated via the intrinsic pathway with release of AIF from mitochondria in U937 cells.
2006 Dec
A comparative study of upright counter-current chromatography and high-performance liquid chromatograpohy for preparative isolation and purification ofphenolic compounds from Magnoliae officinalis.
2006 Feb
Facile purification of honokiol and its antiviral and cytotoxic properties.
2006 Jun 1
Herbal remedy magnolol suppresses IL-6-induced STAT3 activation and gene expression in endothelial cells.
2006 May
Determination of liquiritin, naringin, hesperidin, thymol, imperatorin, honokiol, isoimperatorin, and magnolol in the traditional Chinese medicinal preparation Huoxiang-zhengqi liquid using high-performance liquid chromatography.
2006 Nov
Nitric oxide-independent lipid metabolism in RAW 264.7 macrophages loaded with oleic acid.
2006 Nov
[Optimization of preparative technique for banxia-houpu effervescent tablets by orthogonal design].
2006 Oct
[Evaluation of antioxidant activity of Radix Linderae and other two Chinese drugs using TLC-bioautography].
2006 Oct
The inhibitory effect of magnolol from Magnolia officinalis on glucosyltransferase.
2006 Oct
Simultaneous determination of honokiol and magnolol in Magnolia officinalis by liquid chromatography with tandem mass spectrometric detection.
2006 Oct
In vitro anti-mutagenic effect of magnolol against direct and indirect mutagens.
2006 Oct 10
Honokiol potentiates apoptosis, suppresses osteoclastogenesis, and inhibits invasion through modulation of nuclear factor-kappaB activation pathway.
2006 Sep
Oxidative stress and ischemic injuries in heat stroke.
2007
Involvement of Ras/Raf-1/ERK actions in the magnolol-induced upregulation of p21 and cell-cycle arrest in colon cancer cells.
2007 Apr
Magnolol suppresses NF-kappaB activation and NF-kappaB regulated gene expression through inhibition of IkappaB kinase activation.
2007 Apr
Inhibitory role of magnolol on proliferative capacity and matrix metalloproteinase-9 expression in TNF-alpha-induced vascular smooth muscle cells.
2007 Aug
Synthesis, cytotoxicity, and antiviral activities of new neolignans related to honokiol and magnolol.
2007 Aug 15
Evaluation of the in vitro and in vivo genotoxicity of magnolia bark extract.
2007 Dec
Spectroscopic investigation of inner filter effect by magnolol solutions.
2007 Dec 31
Analysis of magnolol and honokiol in biological fluids by capillary zone electrophoresis.
2007 Feb 23
Rapid purification and scale-up of honokiol and magnolol using high-capacity high-speed counter-current chromatography.
2007 Feb 23
Antiproliferative and pro-apoptotic activity of eugenol-related biphenyls on malignant melanoma cells.
2007 Jan 18
Effects of magnolol (5,5'-diallyl-2,2'-dihydroxybiphenyl) on diabetic nephropathy in type 2 diabetic Goto-Kakizaki rats.
2007 Jan 9
Protective effect of magnolol on TBHP-induced injury in H460 cells partially via a p53 dependent mechanism.
2007 Jul
Mechanisms for the magnolol-induced cell death of CGTH W-2 thyroid carcinoma cells.
2007 Jul 1
[Effects of the active compounds of M. officinalis on cariogenic bacteria].
2007 Jun
Protective effects of magnolol against oxidized LDL-induced apoptosis in endothelial cells.
2007 Jun
Magnolia ovovata extract and its active component magnolol prevent skin photoaging via inhibition of nuclear factor kappaB.
2007 Jun 22
Effect of magnolol on TGF-beta1 and fibronectin expression in human retinal pigment epithelial cells under diabetic conditions.
2007 May 7
Effects of honokiol and magnolol on acute and inflammatory pain models in mice.
2007 Sep 8
Patents

Sample Use Guides

in mice: magnolol protects against trimethyltin-induced neuronal damage and glial activation: 25 mg/kg i.p in rats: pretreatment with magnolol (0.2 and 0.5 microg/kg, i.v. bolus) at 10 min before 45 min of left coronary artery occlusion, significantly suppressed the incidence of ventricular fibrillation and mortality when compared with the control group
Route of Administration: Other
The antifungal activity of magnolol was demonstrated in planktonic C. albicans and non-albicans Candida species, especially fluconazole-resistant Candida krusei, with the minimum inhibitory concentrations ranging from 10 to 40 μg/mL. The BMIC90 (minimum concentration with 90% Candida biofilm inhibited) values of magnolol ranged from 20 to 160 μg/mL. As an alternative and broad-spectrum antifungal agent, magnolol might be of benefit to the treatment of refractory Candida infection. Susceptibility testing of planktonic yeast cells to magnolol was performed following the CLSI M-27A broth micro-dilution method. The frozen magnolol solution was thawed and diluted in Roswell Park Memorial Institute (RPMI) 1640, which was buffered to pH =7.0 using 0.165 M 3-morpholinopropane-1-sulfonic acid. The magnolol solution (100 μL of a 2-fold dilution) was pipetted into each well of a 96-well microtiter plate. The final concentration of magnolol ranged from 2.5 to 1,280 μg/mL.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:32:56 GMT 2023
Edited
by admin
on Fri Dec 15 18:32:56 GMT 2023
Record UNII
001E35HGVF
Record Status Validated (UNII)
Record Version
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Name Type Language
MAGNOLOL
HSDB   INCI   MI  
INCI  
Official Name English
MAGNOLOL [INCI]
Common Name English
DEHYDRODICHAVICOL
Common Name English
5,5'-DIALLYL-2,2'-BIPHENYLDIOL
Systematic Name English
FEMA NO. 4559
Code English
MAGNOLOL [HSDB]
Common Name English
5,5'-DI-2-PROPEN-1-YL-(1,1'-BIPHENYL)-2,2'-DIOL
Systematic Name English
MAGNOLOL [MI]
Common Name English
2,2'-BICHAVICOL
Common Name English
NSC-293099
Code English
2,2'-DIHYDROXY-5,5'-DIALLYLBIPHENYL
Systematic Name English
Classification Tree Code System Code
JECFA EVALUATION MAGNOLOL
Created by admin on Fri Dec 15 18:32:56 GMT 2023 , Edited by admin on Fri Dec 15 18:32:56 GMT 2023
Code System Code Type Description
MERCK INDEX
m7031
Created by admin on Fri Dec 15 18:32:56 GMT 2023 , Edited by admin on Fri Dec 15 18:32:56 GMT 2023
PRIMARY Merck Index
DAILYMED
001E35HGVF
Created by admin on Fri Dec 15 18:32:56 GMT 2023 , Edited by admin on Fri Dec 15 18:32:56 GMT 2023
PRIMARY
RXCUI
2562549
Created by admin on Fri Dec 15 18:32:56 GMT 2023 , Edited by admin on Fri Dec 15 18:32:56 GMT 2023
PRIMARY
JECFA MONOGRAPH
2001
Created by admin on Fri Dec 15 18:32:56 GMT 2023 , Edited by admin on Fri Dec 15 18:32:56 GMT 2023
PRIMARY
MESH
C005498
Created by admin on Fri Dec 15 18:32:56 GMT 2023 , Edited by admin on Fri Dec 15 18:32:56 GMT 2023
PRIMARY
SMS_ID
100000176429
Created by admin on Fri Dec 15 18:32:56 GMT 2023 , Edited by admin on Fri Dec 15 18:32:56 GMT 2023
PRIMARY
CAS
528-43-8
Created by admin on Fri Dec 15 18:32:56 GMT 2023 , Edited by admin on Fri Dec 15 18:32:56 GMT 2023
PRIMARY
HSDB
7686
Created by admin on Fri Dec 15 18:32:56 GMT 2023 , Edited by admin on Fri Dec 15 18:32:56 GMT 2023
PRIMARY
PUBCHEM
72300
Created by admin on Fri Dec 15 18:32:56 GMT 2023 , Edited by admin on Fri Dec 15 18:32:56 GMT 2023
PRIMARY
EPA CompTox
DTXSID0044076
Created by admin on Fri Dec 15 18:32:56 GMT 2023 , Edited by admin on Fri Dec 15 18:32:56 GMT 2023
PRIMARY
FDA UNII
001E35HGVF
Created by admin on Fri Dec 15 18:32:56 GMT 2023 , Edited by admin on Fri Dec 15 18:32:56 GMT 2023
PRIMARY
NSC
293099
Created by admin on Fri Dec 15 18:32:56 GMT 2023 , Edited by admin on Fri Dec 15 18:32:56 GMT 2023
PRIMARY
WIKIPEDIA
MAGNOLOL
Created by admin on Fri Dec 15 18:32:56 GMT 2023 , Edited by admin on Fri Dec 15 18:32:56 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
MAJOR
Related Record Type Details
METABOLITE -> PARENT
Name Property Type Amount Referenced Substance Defining Parameters References
ORAL BIOAVAILABILITY PHARMACOKINETIC SPECIES
BIOLOGICAL