| Catalog No | Package | Original Price | Price | Inventory | Quantity | Operating |
|---|---|---|---|---|---|---|
| BP0803-20mg | 20mg | $30.00 | Sign in |
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Synonym name: 3-Hydroxyanisaldehyde
Catalogue No.: BP0803
Cas No.: 621-59-0
Formula: C8H8O3
Mol Weight: 152.149
Botanical Source:
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
Isovanillin (CAS No.: 621-59-0), as a natural benzaldehyde derivative, has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique chemical structure and diverse biological activities. Isovanillin is the 3-hydroxyl-substituted isomer of 4-methoxybenzaldehyde, belonging to the benzaldehyde class, monomethoxybenzene compounds, and phenolic compounds. Its main pharmacological activities include aldooxidase inhibition, antispasmodic activity, antidiarrheal, antifungal activity, and HIV protease inhibition. Of particular note is its potential as an aldehyde oxidase (EC 1.2.3.1) inhibitor, suggesting its application value in regulating oxidative stress and related diseases. In addition, isovanillin has shown significant biological effects in the field of antioxidant damage, involving several key antioxidant targets such as NFE2L2 (NRF2), SOD1, CAT, GPX1, and HMOX1. This paper will systematically review the chemical structure, origin, pharmacological activity, mechanism of action, and druggability evaluation of isovanillin, explore its clinical application prospects, and aim to provide a theoretical foundation and research direction for the development of natural product drugs.
The molecular formula of isovanillin is C8H8O3, with a molecular weight of 152.1490. Its structural feature is the substitution of 3 hydroxyl and 4 methoxy groups on the benzene ring to form 3-hydroxy-4-methoxybenzaldehyde. This structure gives isovanillin its unique chemical properties and biological activity. In terms of physicochemical parameters, isovanillin had a LogP value of 1.3385, indicating moderate hydrophobicity, which facilitates cell membrane penetration. The topological pole surface area (TPSA) was 46.53 Ų, indicating moderate polarity, which is beneficial for oral absorption and blood-brain barrier penetration. Water solubility is 3.4059, indicating a certain solubility in water and facilitating formulation development. The blood-brain barrier penetration ability is relatively high, suggesting its potential application value in central nervous system diseases. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames-induced mutagenic test result was 1.2, preliminarily indicating a low genotoxicity risk and meeting safety requirements.
Isovanillin naturally occurs in various plants, especially in the roots, leaves, and fruits of certain spices and medicinal plants. Its main natural sources include the genus Vanilla (Vanilla spp.) and some aromatic plants. Traditional extraction methods mostly rely on solvent extraction combined liquid-liquid partitioning and chromatographic purification techniques. Common solvents include mixed solutions of ethanol, methanol, and water, which utilize their polar characteristics for effective extraction. Modern extraction technologies such as ultrasound-assisted extraction (UAE), microwave-assisted extraction (MAE), and supercritical fluid extraction (SFE) have been applied to improve the extraction efficiency and purity of isovanillin. After extraction, qualitative and quantitative analyses are performed using high-performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS), and other methods to ensure the purity and stability of the samples. In recent years, research into biosynthetic pathways has also made bioengineering the synthesis of isovanillin possible, promoting its large-scale production.
Isovanillin has diverse pharmacological activities, including antioxidant, antispasmodic, antidiarrheal, antifungal, and antiviral properties.
Aldehyde oxidase inhibitory activity
As an effective inhibitor of aldehyde oxidase (EC 1.2.3.1), isovanillin can regulate the levels of aldehyde metabolites in the body, reducing oxidative stress and cytotoxicity caused by aldehyde substances. This action lays the foundation for its application in metabolic diseases and diseases related to oxidative damage.
Antispasmodic and antidiarrheal effects
In vivo and in vitro experiments have shown that isovanillin has significant antispasmodic activity, which can relieve spasms of intestinal smooth muscle and thereby exert antidiarrheal effects. Its mechanism may involve regulation of calcium channels and neurotransmitter release, making it suitable for treating diseases related to intestinal dysfunction.
Antifungal and antiviral activity
Isovanillin exhibits inhibitory effects on various fungi, especially pathogenic yeasts and molds. Its antifungal mechanism may be related to cell membrane destruction and metabolic interference. Additionally, isovanillin was found to have HIV protease inhibitory activity, suggesting its potential in antiviral drug development.
Antioxidant activity
Isovanillin activates the NFE2L2/NRF2 signaling pathway, promoting the expression of downstream antioxidant enzymes such as SOD1, CAT, GPX1, and HMOX1, enhancing cellular antioxidant defenses and reducing oxidative damage. This role is of great significance for the prevention and treatment of neurodegenerative diseases, cardiovascular diseases, and inflammatory diseases.
The multiple pharmacological effects of isovanlanin are attributed to its regulation of key molecular targets:
NFE2L2/NRF2 path activation
NRF2 is the main intracellular antioxidant transcription factor that regulates the expression of various antioxidant enzymes. Isovanillin promotes NRF2 nuclear translocation, enhances antioxidant gene expression, reduces oxidative stress, and protects cells from free radical damage.
Aldeoxidase (EC 1.2.3.1) is inhibited
Isovanillin directly binds to and inhibits aldehyde oxidase activity, reducing the production of aldehyde metabolites, preventing their cytotoxicity, and alleviating oxidative damage and inflammatory responses.
Antibacterial and antiviral targets
By inhibiting HIV protease, isovanillin blocks viral replication and demonstrates anti-HIV activity. Antifungal effects may involve disruption of cell membrane structures and inhibition of metabolic enzymes, but the specific molecular mechanisms require further research.
Smooth muscle antispasmodic mechanism
Isovanillin may regulate calcium channels and inhibit neurotransmitter release, reducing smooth muscle excitability, relieving spasms, and exerting antidiarrheal effects.
The druggability parameters of isovanillin indicate that it has good potential for drug development:
Pharmacokinetics, isovanillin exhibits good absorption and distribution characteristics, especially its accumulation in brain tissue, suggesting its potential therapeutic value for neurological diseases. The metabolic pathway mainly involves liver enzyme systems, while the excretory pathway is primarily urine. Moderate half-life, facilitating drug dosage design. Currently, research on its metabolic products and long-term toxicology is still lacking and urgently requires in-depth exploration.
As a versatile natural product, isovanillin has broad clinical application potential:
Antioxidant and neuroprotective agent
By activating the NRF2 pathway, isovanillin holds promise as an adjunct therapy for neurodegenerative diseases (such as Parkinson's disease and Alzheimer's disease) and cerebral ischemia-reperfusion injury.
Metabolic disease regulator
Its aldooxidase inhibitory effect offers new approaches for treating diabetes and related metabolic disorders, especially in reducing oxidative stress damage in diabetic complications.
Anti-infective drugs
Antifungal and anti-HIV activities suggest that isovanillin can serve as a candidate molecule for anti-infective drugs, especially in the context of increased resistance, where developing novel antimicrobial drugs is of great significance.
Intestinal function regulator
Its antispasmodic and antidiarrheal effects give it potential application value in treating irritable bowel syndrome and infectious diarrhea.
Future research should focus on preclinical pharmacodynamics and safety evaluation of isovanillin, optimizing its pharmacokinetic properties, and carrying out structural modifications to enhance activity and selectivity. Moreover, combining modern drug delivery systems with nanotechnology is expected to further improve bioavailability and targeting, promoting the clinical translation of isovanillin.
As a natural benzaldehyde compound with multiple biological activities, isovanillin shows broad research and application prospects in the field of natural product pharmacology. Its unique chemical structure gives it diverse pharmacological activities, especially excelling in antioxidant, antispasmodic, antidiarrheal, and anti-infective properties. By regulating key molecular targets such as NRF2 and aldehyde oxidase, isovanillin can effectively reduce oxidative damage, regulate metabolic balance, and have good safety and druggability. In the future, by combining modern drug development technologies, in-depth exploration of their mechanisms of action and clinical applications will provide important theoretical basis and practical guidance for the development of novel natural drugs. Isovanillin is expected to become an important candidate molecule in the development of natural product drugs, contributing new therapeutic approaches to human health.
