Product name: Glucovanillin
Synonym name:
Catalogue No.: BP4118
Cas No.: 494-08-6
Formula: C₁₄H₁₈O₈
Mol Weight: 314.29
Botanical Source:
Type of Compound:

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle

Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.

The product could be supplied from milligrams to grams
Inquire for bulk scale.


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HPLC of Glucovanillin

HNMR of Glucovanillin

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

Glucovanillin (CAS No.: 494-08-6) is a glycoside compound naturally found in Vanilla planifolia, and has attracted widespread attention due to its unique structure and biological activity. As a precursor to vanillin, vanillin glucoside is converted into active vanillin through the synergistic action of cell wall degradation and glucosidase hydrolase. In recent years, with in-depth research into the pharmacological effects of natural products, vanillin glucoside has been found to possess potential lipase inhibitory activity and significant antioxidant capacity, demonstrating its potential for application in metabolic diseases and oxidative stress-related conditions.

This paper aims to systematically review the chemical structure and physicochemical properties of vanillin glucoside, plant origin, and extraction methods. Combined with the latest pharmacological activity studies, it will delve into its mechanism of action and molecular targets, evaluate its druggability and pharmacokinetic characteristics, and look ahead to its clinical application prospects, providing a theoretical basis and research direction for further development and application of this compound.

Chemical structure and physicochemical properties

The molecular formula of vanillin glucoside is C14H18O8, with a molecular weight of 314.2900. Its chemical structure consists of a vanillin group connected to the glucoside part via β-glycosidic bonds. Its structural characteristics combine the aromatic aldehyde activity of vanillin with the water solubility of glucosides, demonstrating good hydrophilicity and biocompatibility.

In terms of physicochemical properties, the LogP value of vanillin glucoside is -0.5439, indicating strong hydrophilicity. Its water solubility is 27.2663 mg/mL, with good water solubility, facilitating absorption and distribution in the body. Its topological polar surface area (TPSA) is 125.68 Ų, indicating that the molecule has high polarity, which may affect its cell membrane permeability. The blood-brain barrier has a low penetration capacity, indicating limited penetration in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames mutagenic test result was 0.0, indicating no significant genotoxicity risk.

Overall, the physicochemical properties of vanillin glucoside are suitable for development into well-soluble and safe drug molecules, especially suitable for therapeutic strategies targeting peripheral tissues.

Plant Origins and Extraction Methods

Vanillin glucoside is mainly found in the fruit pods of Vanilla and is one of the precursors to its aroma. As an important cash crop, the pod is fermented and dried, where vanillin glucosides are hydrolyzed by enzymes to produce vanillin, giving vanilla a unique aroma.

The main methods for extracting vanillin glucoside include water extraction, alcohol extraction, and enzymatic hydrolysis. Traditional water extraction methods utilize their excellent water solubility, combined with hot water soaking and ultrasound-assisted extraction, to effectively recover vanillin glucosides. The alcohol extraction method mostly uses methanol or ethanol as solvents and is suitable for extracting other glycoside compounds simultaneously. Enzymatic hydrolysis promotes the hydrolysis of vanillin glucoside by adding β-glucosidase, improving the release efficiency of vanillin.

In recent years, supercritical CO2 extraction and membrane separation technologies have gradually been applied in the extraction and purification of vanillin glucosides, significantly improving extraction efficiency and purity, reducing the use of organic solvents, and aligning with the trend toward green extraction.

Pharmacological activity research

lipase inhibitory activity

Lipase is a key enzyme in lipid metabolism, regulating the hydrolysis and absorption of fats. As a potential lipase inhibitor, vanillin glucoside can reduce fat breakdown and absorption by suppressing lipase activity, thereby positively impacting obesity and related metabolic diseases. In vitro experiments have shown that vanillin glucoside can significantly inhibit pancreatic lipase activity, exhibiting dose-dependent inhibition.

Antioxidant activity

Oxidative stress is the pathological basis of many chronic diseases. Antioxidants play a protective role by scavenging free radicals and regulating antioxidant enzyme systems. Vanillin glucoside demonstrates good free radical scavenging ability and potential to regulate intracellular antioxidant enzyme expression. Both cell and animal model studies have confirmed that it can activate the NFE2L2/NRF2 signaling pathway, inducing the expression of downstream antioxidant enzymes such as SOD1, SOD2, CAT, GPX1, and HMOX1, thereby enhancing cellular antioxidant defense and reducing oxidative damage.

Additionally, the regulatory effects of vanillin glucoside on matrix metalloproteinases (MMP1, MMP3) and tyrosinase (TYR) suggest potential application value in tissue remodeling and melanin production regulation.

Other activities

Preliminary studies have also found that vanillin glucoside may have anti-inflammatory, antibacterial, and neuroprotective effects, but the related mechanisms remain unclear and require further systematic study.

Mechanism of action and molecular targets

The biological activity of vanillin glucoside is mainly realized through its metabolite vanillin and its interactions with various molecular targets.

Antioxidant-related targets

Vanillin glucoside promotes transcriptional expression of antioxidant enzyme genes by activating the nuclear factor E2-related factor 2 (NFE2L2/NRF2) signaling pathway, enhancing intracellular antioxidant enzyme activity, including superoxide dismutase (SOD1, SOD2), catalase (CAT), glutathione peroxidase (GPX1), and heme oxygenase 1 (HMOX1). These enzymes work together to eliminate reactive oxygen species (ROS), maintain cellular redox homeostasis, and reduce cell damage caused by oxidative stress.

lipase inhibition mechanism

Vanillin glucoside binds to the active site of pancreatic lipase, blocking the binding and hydrolysis of fat substrates, reducing the release of fatty acids and glycerol, and decreasing lipid absorption. Molecular docking and kinetic simulations show that the glycoside portion of vanillin glucoside forms a stable hydrogen bond network with the enzyme's hydrophilic pocket, enhancing binding affinity.

Other molecular targets

Vanillin glucoside regulates matrix metalloproteinases (MMP1, MMP3) and tyrosinase (TYR) by directly inhibiting enzymes or modulating related signaling pathways, affecting extracellular matrix degradation and melanin synthesis, and has potential anti-aging and whitening effects.

Druggability evaluation and pharmacokinetics

Vanillin glucoside has a low LogP value and high water solubility, which is beneficial for dissolution and absorption after oral administration, but its higher TPSA and polarity may limit its cell membrane permeability and affect bioavailability. The low penetration capacity of the blood-brain barrier suggests it mainly acts on peripheral tissues, reducing the risk of central nervous system side effects.

In terms of safety, vanillin glucoside does not inhibit hERG channels, reducing the risk of arrhythmias. The Ames test was negative, indicating no significant genotoxicity and good safety.

Pharmacokinetic studies show that vanillin glucoside can be hydrolyzed in the body by β-glucosidase to produce vanillin, which has high bioactivity and good membrane permeability. The synergistic effect of the two may be key to the pharmacological effects of vanillin glucoside.

However, the metabolic stability and in vivo half-life of vanillin glucoside still require further systematic evaluation to guide dosage formulation design and administration regimen optimization.

Prospects and outlooks for clinical applications

The lipase inhibition and antioxidant activity of vanillin glucoside are noteworthy for their therapeutic potential in obesity, metabolic syndrome, diabetes, and oxidative stress-related diseases (such as cardiovascular disease and neurodegenerative diseases). Its excellent safety and natural origin make it possible to develop it as a functional food additive or adjunct therapy.

Future research should focus on:

1. Precise mechanism analysis: In-depth revealing the molecular mechanisms of vanillin glucoside and its metabolites, clarifying their target networks and signaling pathway regulation.
2. Pharmacokinetic optimization: Enhancing bioavailability and targeting through structural modification or nanocarrier technology.
3. Preclinical and clinical research: Conduct systematic toxicological evaluations and clinical trials to verify efficacy and safety.
4. Multi-target synergistic application: combining with other natural products or drugs to exert synergistic effects and expand its range of applications.

In addition, the antioxidant and whitening potential of vanillin glucoside in cosmetics is also worth further development.

Conclusion

Vanillin glucoside, a widely sourced and structurally unique natural glycoside compound, shows broad pharmacological application prospects thanks to its lipase inhibition and multi-target antioxidant activity. Its excellent safety and druggability lay the foundation for clinical translation. In the future, through multidisciplinary research combined with modern drug development technologies, it is expected to promote vanillin glucoside from the laboratory to clinical practice, becoming an important research subject and application resource in the field of natural product pharmacology.