Honokiol

Catalog	BBC35354746
CAS	35354-74-6
Structure
Description	Honokiol is a bioactive, biphenolic phytochemical that possesses potent antioxidative, anti-inflammatory, antiangiogenic, and anticancer activities by targeting a variety of signaling molecules. It inhibits the activation of Akt. Honokiol can readily cross the blood brain barrier.
Synonyms	3',5-Diallyl-2,4'-biphenyldiol
IUPAC Name	2-(4-Hydroxy-3-prop-2-enylphenyl)-4-prop-2-enylphenol
Molecular Weight	266.33
Molecular Formula	C18H18O2
Canonical SMILES	C=CCC1=CC(=C(C=C1)O)C2=CC(=C(C=C2)O)CC=C
InChI	InChI=1S/C18H18O2/c1-3-5-13-7-9-18(20)16(11-13)14-8-10-17(19)15(12-14)6-4-2/h3-4,7-12,19-20H,1-2,5-6H2
InChI Key	FVYXIJYOAGAUQK-UHFFFAOYSA-N
Boiling Point	400.1±40.0 °C
Melting Point	86 °C
Flash Point	184°C
Purity	98%
Density	1.107±0.06 g/ml
Appearance	White powder
pKa	9.89±0.48
Refractive Index	1.6

Case Study

Preparation of Honokiol@PF127 Crosslinked Hyaluronate-Based Hydrogel

Wei, Qingcong, et al. Carbohydrate Polymers 303 (2023): 120469.

Bacterial infection, oxidative stress, and inflammation are key barriers to effective wound healing. Hydrogels with moist and inherent properties are beneficial for enhancing wound healing. In this study, we developed a honokiol-loaded, micelle-crosslinked hyaluronate-based hydrogel by combining honokiol-laden PF127-CHO micelles, 3,3'-dithiobis(propionohydrazide) grafted hyaluronic acid, and silver ions.
Preparation of Hydrogels
First, honokiol-laden PF127-CHO micelles were prepared. To do this, 0.5 g of PF127-CHO and 5 mg of honokiol were dissolved in 50 mL of methylene chloride. The solvent was then removed using a rotary evaporator. After co-evaporation, 5 mL of deionized water was added to the mixture and heated at 40°C to obtain a light-yellow transparent solution.
Next, the hydrogel was formed by mixing the honokiol-loaded PF127-CHO micelle solution with HA-SS-NH2 solution (70 mg/mL) in a 1:2 (v/v) ratio. Silver ions were added based on the molar ratios of silver ions to disulfide bonds (1:1, 1:2, and 1:3), resulting in three hydrogel formulations: PF-HA-1, PF-HA-2, and PF-HA-3. A control hydrogel (PF-HA) was prepared by mixing PF127-CHO micelle solution and HA-SS-NH2 solution at the same concentrations, without silver ions.

Synthesis of a Novel Flame Retardant Epoxy Thermoset Based on Renewable Honokiol and Furfuryl Alcohol

Li, Mingli, et al. Construction and Building Materials 432 (2024): 136707.

This study focuses on the development of a bio-based epoxy resin system, where honokiol (HK) is directly functionalized to create honokiol epoxy resin. The resin is then combined with a furfuryl alcohol-derived flame retardant via a Diels-Alder reaction, forming a bio-based epoxy cross-linking system.
Synthesis of Honokiol Epoxy Resin (HE)
In a 1000 mL round-bottom flask, 27.96 g (105 mmol) of HK, 485.73 g (5.25 mol) of epichlorohydrin (ECH), and 2.39 g (10.5 mmol) of tetrabutylammonium bromide (TBAB) as the phase transfer catalyst were mixed. The reaction mixture was slowly heated to 80°C and stirred continuously under a nitrogen atmosphere for 3 hours. A 40 wt% aqueous sodium hydroxide solution (262.5 mmol NaOH) was added dropwise to the mixture, causing the reaction to intensify for 1 hour. The mixture was then washed several times with deionized water until the aqueous solution became neutral. Finally, the organic phase was concentrated under reduced pressure by rotary evaporation to remove excess ECH. The resulting yellow liquid, honokiol epoxy resin (HE), was obtained with an 86.4% yield after vacuum oven drying at 50°C for 24 hours.

Synthesis of Core-Shell Structured Nanocarriers Loaded with Honokiol for Bactericide Delivery

Huang, Xunliang, et al. Journal of Hazardous Materials 472 (2024): 134502.

The development of nanocarriers with controlled release properties and environmental safety supports sustainable agricultural practices and provides an effective solution for managing severe soil-borne bacterial diseases. In this study, we synthesized a core-shell structured nanocarrier, honokiol@ZnO-ZIF-8, using a one-pot method for targeted delivery to control Ralstonia solanacearum, the pathogen responsible for tobacco bacterial wilt disease.
Synthesis of Honokiol@ZnO-ZIF-8
To prepare the nanocarrier, 2 mmol of 2-methylimidazole was dissolved in 15 mL of N,N-dimethylformamide (DMF) and preheated to 70°C. Next, 5 mL of a mixture containing 0.25 mmol of ZnO nanoparticles, 100 mg of honokiol, and 0.2 mL of CTAB in DMF was added to the preheated solution while maintaining magnetic stirring at 70°C for 2 hours. The resulting white precipitate was collected by centrifugation, washed several times with water, and dried at 60°C overnight.