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4-Hexylresorcinol

Catalog Number
ACM136776-3
CAS
136-77-6
Structure
IUPAC Name
4-hexylbenzene-1,3-diol
Synonyms
1,3-Benzenediol, 4-hexyl-;Hexylresorcinol
Molecular Weight
194.27
Molecular Formula
C12H18O2
Canonical SMILES
CCCCCCC1=C(C=C(C=C1)O)O
InChI
WFJIVOKAWHGMBH-UHFFFAOYSA-N
InChI Key
InChI=1S/C12H18O2/c1-2-3-4-5-6-10-7-8-11(13)9-12(10)14/h7-9,13-14H,2-6H2,1H3
Boiling Point
333-335 °C (lit.)
Melting Point
65-67 °C(lit.)
Purity
98%
Density
1.001g/ml
Appearance
Powder
Active Content
95%
Physical State
Solid
Typical Applications
Antioxidant
Spec Sheet
Case Study

4-Hexylresorcinol Used for the Enzymatic Grafting Modification of Pectin to Enhance Antioxidant and Antibacterial Properties

4-Hexylresorcinol Used for the Enzymatic Grafting Modification of Pectin to Enhance Antioxidant and Antibacterial Properties Liu, Jingna, et al. International Journal of Biological Macromolecules 237 (2023): 124212.

In this study, 4-hexylresorcinol was enzymatically grafted onto pectin to enhance its functional performance for food preservation applications. The modification was achieved via a lipase-catalyzed esterification reaction, where the hydroxyl group of 4-hexylresorcinol and the carboxyl group of pectin served as reactive sites.
To prepare the modified pectin (He-Pe), a solution of 10 mmol/L 4-hexylresorcinol in tetrahydrofuran (THF) and 1 g of lipase was mixed with a 3.33 g/L pectin solution in equal volumes. The grafting reaction was performed at 50 °C for 12 hours. After centrifugation to remove the enzyme, THF was eliminated by rotary evaporation. The mixture was subjected to dialysis (MWCO 7000-14,000 Da) for 96 hours to eliminate unreacted 4-hexylresorcinol. The final He-Pe product was obtained by freeze-drying.
Structural analysis confirmed successful grafting, with a grafting ratio of 10.98%. Compared to native pectin, He-Pe exhibited markedly improved antioxidant activity (DPPH clearance: 74.72%) and β-carotene bleaching inhibition (53.40%). Antibacterial assays showed increased inhibition zones against E. coli (16.78 mm) and S. aureus (14.87 mm). When applied as a coating for pork, He-Pe significantly delayed spoilage, outperforming both native and resorcinol-modified pectin.
These results demonstrate the promising utility of 4-hexylresorcinol in the green enzymatic functionalization of pectin for active food packaging applications.

4-Hexylresorcinol as a Potent Inhibitor of α-Glucosidase and Non-Enzymatic Glycation for Antidiabetic Applications

4-Hexylresorcinol as a Potent Inhibitor of α-Glucosidase and Non-Enzymatic Glycation for Antidiabetic Applications Song, Shuang, et al. Journal of bioscience and bioengineering 131.3 (2021): 241-249.

4-Hexylresorcinol, a long-chain alkylresorcinol derivative, has demonstrated significant potential in the treatment of type-2 diabetes mellitus through dual inhibition of α-glucosidase activity and non-enzymatic glycation processes. In the referenced study, a series of in vitro biochemical and spectroscopic analyses were conducted to explore its mechanism of action.
The inhibitory effect of 4-hexylresorcinol on α-glucosidase was first assessed via enzyme kinetics, revealing a dose-dependent, reversible, noncompetitive inhibition with an IC₅₀ value of 0.146 ± 1.5 mM-significantly more potent than the commercial inhibitor acarbose (IC₅₀ = 0.5 ± 1.6 mM). Fluorescence spectroscopy indicated conformational changes in the enzyme upon binding, suggesting increased enzyme hydrophobicity due to complex formation. Thermodynamic analysis confirmed that the binding was primarily driven by hydrogen bonding and hydrophobic interactions.
Molecular docking further supported these findings by showing stable interaction between 4-hexylresorcinol and key residues in the enzyme's active region. In addition, 4-hexylresorcinol inhibited the formation of fructosamine, α-dicarbonyl compounds, and advanced glycation end products (AGEs), indicating its efficacy in suppressing glycation pathways. Its interaction with bovine serum albumin was also found to be hydrophobically driven.
Overall, 4-hexylresorcinol represents a promising antidiabetic agent with dual inhibitory action, offering a novel approach for the prevention and management of type-2 diabetes.

4-Hexylresorcinol Used for the Development of Alginate-Based Active Packaging to Extend the Shelf Life of Hass Avocados

4-Hexylresorcinol Used for the Development of Alginate-Based Active Packaging to Extend the Shelf Life of Hass Avocados Hebishy, Essam, and A. A. Tas. Applied Food Research 3.1 (2023): 100289.

4-Hexylresorcinol (4-HR), a phenolic compound with potent antioxidant properties, has been effectively applied in the development of alginate-based edible coatings aimed at prolonging the shelf life of Hass avocados. In this study, 4-HR was used at two concentrations (250 and 500 mg/L), either as a standalone additive or incorporated into sodium alginate films (10 g/L). The treatment was compared to sodium metabisulphite (SMBS) and evaluated for its physicochemical and microbiological impact on avocado preservation.
Fruits were immersed in the respective solutions or coated with the alginate-additive formulations and stored for 10 days at 25 ± 1 °C and 60% RH. Experimental analyses were conducted on days 1, 5, and 10 to assess weight loss, total soluble solids (TSS), pH, firmness, bioyield point (BYP), color parameters (L*, a*, b*), and microbial growth. Alginate-coated samples showed significantly lower weight loss and better appearance retention. Although all samples maintained firmness, the BYP declined slightly in coated fruits. Notably, the incorporation of 4-HR into the alginate matrix enhanced internal and external color stability and inhibited surface microbial growth, indicating its synergistic effect with alginate.
This research highlights the potential of 4-Hexylresorcinol in active packaging systems to reduce post-harvest losses. Future studies may focus on residue analysis, antioxidant quantification, and synergistic interactions to further optimize edible coatings for fresh produce preservation.

Custom Q&A

What is the IUPAC name of 4-Hexylresorcinol?

The IUPAC name of 4-Hexylresorcinol is 4-hexylbenzene-1,3-diol.

What are some synonyms for 4-Hexylresorcinol?

Some synonyms for 4-Hexylresorcinol are 1,3-Benzenediol, 4-hexyl- and Hexylresorcinol.

What is the molecular weight of 4-Hexylresorcinol?

The molecular weight of 4-Hexylresorcinol is 194.27.

What is the molecular formula of 4-Hexylresorcinol?

The molecular formula of 4-Hexylresorcinol is C12H18O2.

What is the boiling point of 4-Hexylresorcinol?

The boiling point of 4-Hexylresorcinol is 333-335 °C.

What is the melting point of 4-Hexylresorcinol?

The melting point of 4-Hexylresorcinol is 65-67 °C.

What is the purity of 4-Hexylresorcinol?

The purity of 4-Hexylresorcinol is 98%.

What is the density of 4-Hexylresorcinol?

The density of 4-Hexylresorcinol is 1.001g/ml.

What is the physical state of 4-Hexylresorcinol?

The physical state of 4-Hexylresorcinol is solid.

What are some typical applications of 4-Hexylresorcinol?

Some typical applications of 4-Hexylresorcinol are as an antioxidant.

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