Honokiol

Base Information

• Chemical Name: Honokiol
• CAS No.: 35354-74-6
• Molecular Formula: C18H18O2
• Molecular Weight: 266.34
• Hs Code.: 29072990
• European Community (EC) Number: 609-119-8
• NSC Number: 293100
• UNII: 11513CCO0N
• DSSTox Substance ID: DTXSID30188845
• Nikkaji Number: J138.358B
• Wikipedia: Honokiol
• Wikidata: Q5896650
• Pharos Ligand ID: LVAHNHT76Z1P
• Metabolomics Workbench ID: 67873
• ChEMBL ID: CHEMBL16901
• Mol file: 35354-74-6.mol

Synonyms:(1,1'-biphenyl)-2,4'-diol, 3',5-di-2-propen-1-yl-;3,5'-diallyl-4,2'-dihydroxybiphenyl;honokiol

Chemical Property of Honokiol

Chemical Property:

• Appearance/Colour: Dark brown to white fine powder with pleasant odor, spicy and slightly bitter taste.
• Vapor Pressure: 5.65E-07mmHg at 25°C
• Melting Point: 87.5ºC
• Refractive Index: 1.601
• Boiling Point: 400.1 °C at 760 mmHg
• PKA: 9.89±0.48(Predicted)
• Flash Point: 184 °C
• PSA: 40.46000
• Density: 1.107 g/cm³
• LogP: 4.22180
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 36 mg/mL
• XLogP3: 5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 266.130679813
• Heavy Atom Count: 20
• Complexity: 325

Purity/Quality:

98%, ^*data from raw suppliers

Honokiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 41-51/53
• Safety Statements: 26-39-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CCC1=CC(=C(C=C1)O)C2=CC(=C(C=C2)O)CC=C
• Description: Magnolol is derived from the root bark and branch bark of magnolia or Magnolia officinalis. Magnolia officinalis was first written in the《ben jing》, it prefers cool and humid climate and well-drained acid soil. Cortex magnoliae officinalis (hou po) is mainly produced in Sichuan (Wan quan, Shizhu, Guanxian), Hubei (Shien,Yichang, Lichuan), Zhejiang (Longquan, Anhui), and other places. It is also distributed in Fujian, Jiangxi, Hunan, Guangxi, Yunnan, Guizhou, Shanxi, Gansu, and other places. Cortex magnoliae officinalis from Sichuan and Hubei is called “chuan pu,” with better quality, while in Zhejiang, it is called “warm park,” with a larger output.
• Physical properties: Appearance: white fine powder. Solubility: practically insoluble in water; very soluble in benzene, ethyl ether, chloroform, and acetone. Melting point: magnolol is 102 °C. Honokiol is 87.5 °C.
• Uses: Honokiol has been used:to study its effects on plasmid hSirt3102-399 deacetylation activityas an antioxidant to study its cytoprotective role in human ovarian cancer cells (SKOV-3) and Chinese hamster ovary cells (CHOK1)to explore its effects on oxidative stress and mitochondrial dysfunction via a sirt3-dependent mannerfor intracerebroventricular (ICV) cannulation Honokiol is a small-molecule polyphenol isolated from the genus Magnolia. Recent studies show that Honokiol displays antiangiogenic, antiinflammatory, and antitumor properties in preclinical models, w ithout appreciable toxicity. Honokiol has been shown to inhibit the bone metastatic growth of human prostate cancer cells.
• Indications: These compounds are recorded in the British Pharmacopoeia (2017) and European Pharmacopoeia (8.7th ed.). They are mainly used as antibacterial and antifungal agents.

Technology Process of Honokiol

There total 65 articles about Honokiol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

C28H34O4 → Honokiol (35354-74-6)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 - -20 ℃; Inert atmosphere;

DOI:10.1080/00304948.2021.1993685

Reference yield: 97.0%

Dimethylhonokiol (68592-18-7) → Honokiol (35354-74-6)

Guidance literature:

With aluminum (III) chloride; at -5 - 0 ℃; for 0.333333h;

DOI:10.1016/j.tetlet.2014.04.084

Reference yield: 91.0%

3,5′-diallyl-2′-methoxy-[1,1′-biphenyl]-4-ol (68592-19-8) → Honokiol (35354-74-6)

Guidance literature:

With boron trichloride - methyl sulfide complex; In dichloromethane; 1,2-dichloro-ethane; for 18h; Reflux;

DOI:10.1016/j.tet.2010.08.005

upstream raw materials:

eudeshonokiol A

5-allyl-4'-(allyloxy)-[1,1'-biphenyl]-2-ol

5,3'-diallyl-2,4'-bis-methoxymethoxy-biphenyl

5-bromosalicyclic acid

Downstream raw materials:

3,5'-diallyl-2'-[3-(methylamino)-1-phenylpropoxy]biphenyl-4-ol hydrochloride

Refernces

• 1、 Srinivas, Jada,Singh, Parvinder Pal,Varma, Yogesh Kumar,Hyder, Irfan,Kumar, Halmuthur M. Sampath. "Concise total synthesis of honokiol via Kumada cross coupling". . p. 4295 - 4297. Retrieved 2014.
• 2、 Wright, Alicia M.,O'Neil, Gregory W.. "Total synthesis of honokiol by selective samarium-mediated allylic benzoate reduction". . p. 3441 - 3443. Retrieved 2016.
• 3、 Schuehly, Wolfgang,Paredes, Juan Manuel Viveros,Kleyer, Jonas,Huefner, Antje,Anavi-Goffer, Sharon,Raduner, Stefan,Altmann, Karl-Heinz,Gertsch, Juerg. "Mechanisms of osteoclastogenesis inhibition by a novel class of biphenyl-type cannabinoid CB2 receptor inverse agonists". . p. 1053 - 1064. Retrieved 2011.
• 4、 Che, Chi-Ming,Wu, Kai,Wu, Liang-Liang,Zhou, Cong-Ying. "Transition-Metal-Free C(sp2)–C(sp2) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters". supporting information. p. 16202 - 16208. Retrieved 2020/07/17.
• 5、 -. "SYNTHESIS OF HONOKIOL". Paragraph 0212; 0213; 0214; 0215; 0236; 0237; 0238. . Retrieved 2017/06/01.