72008-03-8

Basic information

• Product Name: 2-Geranyl-4-isobutyrylphloroglucinol
• Synonyms: 2-Geranyl-4-isobutyrylphloroglucinol;3-Geranyl-1-(2'-methylpropanoyl)phloroglucinol;2-Geranyl-4-(2-methylpropanoyl)phloroglucinol
• CAS NO: 72008-03-8
• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.43392
• Mol File: 72008-03-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 491.6±45.0 °C(Predicted)
• Appearance: /
• Density: 1.103±0.06 g/cm3(Predicted)
• PKA: 7.76±0.50(Predicted)
• CAS DataBase Reference: 2-Geranyl-4-isobutyrylphloroglucinol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Geranyl-4-isobutyrylphloroglucinol(72008-03-8)
• EPA Substance Registry System: 2-Geranyl-4-isobutyrylphloroglucinol(72008-03-8)

Safety Data

• Hazardous Substances Data: 72008-03-8(Hazardous Substances Data)

Usage

General Description

2-Geranyl-4-isobutyrylphloroglucinol, also known as GBIF, is a natural chemical compound that belongs to the family of phloroglucinols. It is derived from plants such as ginger and turmeric and exhibits a wide range of medicinal properties. GBIF has antimicrobial, antioxidant, and anti-inflammatory properties, making it a valuable compound for the pharmaceutical and cosmetic industries. Studies have shown that GBIF has potential as a therapeutic agent for the treatment of various diseases, including cancer, diabetes, and inflammatory disorders. Additionally, it has been found to have insecticidal and herbicidal activities, making it useful in agricultural applications. Overall, 2-Geranyl-4-isobutyrylphloroglucinol is a versatile and valuable chemical compound with diverse potential applications in various fields.

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 763-10-0 geranyl diphosphate 
• 35458-21-0 phlorisobutyrophenone 
• 6138-90-5 trans-geranyl bromide 

Downstream Products

• 72008-22-1 (E)-2-(3,7-dimethylocta-2,6-dienyl)-4-isobutyrylbenzene-1,3,5-triyl triacetate 

Relevant articles and documents

Hits-to-lead optimization of the natural compound 2,4,6-trihydroxy-3-geranyl-acetophenone (thga) as a potent lox inhibitor: Synthesis, structure-activity relationship (sar) study, and computational assignment

A new series of 2,4,6-trihydroxy-3-geranyl-acetophenone (tHGA) analogues were synthesized and evaluated for their lipoxygenase (LOX) inhibitory activity. Prenylated analogues 4a-g (half maximal inhibitory concentration (IC50) values ranging from 35 μM to 95 μM) did not exhibit better inhibitory activity than tHGA (3a) (IC50 value: 23.6 μM) due to the reduction in hydrophobic interaction when the alkyl chain length was reduced. One geranylated analogue, 3d, with an IC50 value of 15.3 μM, exhibited better LOX inhibitory activity when compared to tHGA (3a), which was in agreement with our previous findings. Kinetics study showed that the most active analogue (3e) and tHGA (3a) acted as competitive inhibitors. The combination of in silico approaches of molecular docking and molecular dynamic simulation revealed that the lipophilic nature of these analogues further enhanced the LOX inhibitory activity. Based on absorption, distribution, metabolism, excretion, and toxicity (ADMET) and toxicity prediction by komputer assisted technology (TOPKAT) analyses, all geranylated analogues (3a-g) showed no hepatotoxicity effect and were biodegradable, which indicated that they could be potentially safe drugs for treating inflammation.

Synthesis of Natural Acylphloroglucinol-Based Antifungal Compounds against Cryptococcus Species

Thirty-three natural-product-based acylphloroglucinol derivatives were synthesized to identify antifungal compounds against Cryptococcus spp. that cause the life-threatening disseminated cryptococcosis. In vitro antifungal testing showed that 17 compounds

Synthesis and docking studies of 2,4,6-trihydroxy-3-geranylacetophenone analogs as potential lipoxygenase inhibitor

The natural product molecule 2,4,6-trihydroxy-3-geranyl-acetophenone (tHGA) isolated from the medicinal plant Melicope ptelefolia was shown to exhibit potent lipoxygenase (LOX) inhibitory activity. It is known that LOX plays an important role in inflammatory response as it catalyzes the oxidation of unsaturated fatty acids, such as linoleic acid to form hydroperoxides. The search for selective LOX inhibitors may provide new therapeutic approach for inflammatory diseases. Herein, we report the synthesis of tHGA analogs using simple Friedel-Craft acylation and alkylation reactions with the aim of obtaining a better insight into the structure-activity relationships of the compounds. All the synthesized analogs showed potent soybean 15-LOX inhibitory activity in a dose-dependent manner (IC50 = 10.31-27.61 μM) where compound 3e was two-fold more active than tHGA. Molecular docking was then applied to reveal the important binding interactions of compound 3e in soybean 15-LOX binding site. The findings suggest that the presence of longer acyl bearing aliphatic chain (5Cs) and aromatic groups could significantly affect the enzymatic activity.