2-[2-hydroxy-5-(prop-2-en-1-yl)phenyl]-4-(prop-2-en-1-yl)phenol

• ChemBase ID: 70535
• Molecular Formular: C18H18O2
• Molecular Mass: 266.33432
• Monoisotopic Mass: 266.13067982
• SMILES: c1(c(ccc(c1)CC=C)O)c1c(ccc(c1)CC=C)O
• Canonical SMILES: C=CCc1ccc(c(c1)c1cc(CC=C)ccc1O)O
• InChI: 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
• InChIKey: VVOAZFWZEDHOOU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-hydroxy-5-(prop-2-en-1-yl)phenyl]-4-(prop-2-en-1-yl)phenol
• IUPAC Traditional name: magnolol; 2-[2-hydroxy-5-(prop-2-en-1-yl)phenyl]-4-(prop-2-en-1-yl)phenol
• Synonyms: 5,5′-Diallyl-2,2′-biphenyldiol; Magnolol; 5,5'-Diallyl-[1,1'-biphenyl]-2,2'-diol; 2; 2'-Bichavicol; Magnolol

Database IDs

• CAS Number: 528-43-8
• MDL Number: MFCD00016658
• PubChem SID: 24896843; 162036250
• PubChem CID: 72300

CALCULATED PROPERTIES

• Acid pKa: 8.690145
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.2102036
• LogD (pH = 7.4): 5.1887584
• Log P: 5.210482
• Molar Refractivity: 83.7306 cm^3
• Polarizability: 33.158566 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Powder

Safety Information

• Storage Condition: -20°C
• Storage Warning: IRRITANT
• European Hazard Symbols: Nature polluting (N)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 37/38-41-51/53
• Safety Statements: 26-39-61
• TSCA Listed: false
• GHS Pictograms: GHS05; GHS07; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H318-H335-H411
• GHS Precautionary statements: P261-P273-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: CNS depressant with serotonergic activity; Inhibition of calcium influx through voltage gated channels; Reported from in-vitro study in rat aorta to produce relaxation of vascular smooth-muscle mediated by: release of endothelium derived relaxant factor

Product Information

• Purity: ≥95% (HPLC); 95+%
• Salt Data: Free Base
• Biological Source: Constit. of Sassafras randaiense and Magnolia spp.; from plant
• Application(s): Antibacterial, antifungal agent; Antiplatelet agent; Relaxant; Sedative; Shows antiinflammatory and analgesic effects
• Empirical Formula (Hill Notation): C18H18O2

DETAILS

Selleck Chemicals - S2321

Research Area: Infection , Inflammation
Biological Activity:
Magnolol (2,2’-Bichavicol) is a bioactive compound found in the bark of the Houpu magnolia(Magnolia officinalis).

Sigma Aldrich - M3445

Biochem/physiol Actions
Bioactive plant component with antifungal,1 antibacterial2 and antioxidant effects.3 Magnolol also demonstrates anti-inflammatory activity by interferring with NF-κB signaling.4

REFERENCES

• Runeberg, J. et al., Acta Chem. Scand., 1957, 11, 1060; 1958, 12, 188
• Clark, A.M. et al., J. Pharm. Sci., 1981, 70, 951, (props)
• Wang, Y. et al., J. Chin. Chem. Soc. (Peking), 1982, 30, 215, (cryst struct)
• El-Feraly, F.S. et al., J. Nat. Prod., 1983, 46, 493
• Watanabe, K. et al., Planta Med., 1983, 49, 103, (isol, pharmacol)
• Hattori, M. et al., Chem. Pharm. Bull., 1984, 32, 5010; 1986, 34, 158, (metab)
• Ho, T.I. et al., CA, 1986, 105, 152803, (synth)
• Teng, C.-M. et al., Thromb. Res., 1988, 50, 757, (pharmacol)
• Wang, J.-P. et al., Naunyn-Schmiedeberg's Arch. Pharmacol., 1992, 346, 707, (pharmacol)
• Tsai, T.-H. et al., Drug Metab. Dispos., 1994, 22, 518, (hplc, pharmacokinet)
• Agharahimi, M.R. et al., J.O.C., 1995, 60, 1856, (synth, ir, pmr, cmr, ms)
• Tsai, T.-H. et al., Neurosci. Lett., 1995, 186, 49, (pharmacol)
• Kim, Y.-K. et al., Planta Med., 1996, 65, 291-292, (activity)