Product Name: Alltride
Synonym name: Diallyl trisulfide; Allitridin; Bis(2-propenyl) trisulfide
Catalogue No.: BP0141
Cas No.: 2050-87-5
Formula: C6H10S3
Mol Weight: 178.34
Botanical Source: garlic (Allium sativum) and Allium fistulosum
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℃
38.1600
2.2000
2.0000
High
No
No
No
No
No
Negative
Alltride (CAS number: 2050-87-5) is a typical sulfur-containing natural organic compound, belonging to the class of trisulfines, characterized by the substitution of two hydrogens with allyl groups. As one of the main components of garlic (Allium sativum L.) essential oil, allicin is widely used in traditional Chinese medicine and has attracted much attention due to its significant biological activity. In recent years, with the deepening development of natural product pharmacology, allicin has become an important object of drug development and disease treatment research due to its diverse pharmacological effects, such as antifungal, anti-tumor, and antioxidant activities.
This review aims to systematically summarize the chemical structure and physicochemical properties, plant sources, and extraction methods of allicin, explore its pharmacological activity and mechanism of action, evaluate its pharmacological parameters and pharmacokinetic characteristics, and prospect its clinical application potential. By integrating and analyzing existing literature, it is expected to provide comprehensive theoretical support and practical guidance for researchers in the field of natural product pharmacology.
The chemical structure of allicin is a trisulfide skeleton, in which two hydrogen atoms are replaced by allyl groups. The molecular formula is C6H10S3 and the molecular weight is 162.34. Its structure contains a chain like structure composed of three sulfur atoms, which endows it with unique chemical reactivity. The LogP value of allicin is 2.2, indicating its moderate lipid solubility, which is beneficial for membrane penetration and in vivo distribution. The polar surface area (TPSA) is 38.16 Å ² and the number of hydrogen bond acceptors is 3, indicating its affinity for intermolecular forces.
The physicochemical properties of allicin give it good bioavailability and pharmacokinetic characteristics. The allyl groups and polysulfide bonds in its molecular structure provide a chemical basis for its biological activity, especially exhibiting significant activity in redox reactions. In addition, allicin can cross the blood-brain barrier (BBB) in the body, indicating its potential application value in central nervous system diseases.
Allicin is mainly present in garlic essential oil and is a key component of the volatile compounds in garlic. Garlic, as a widely cultivated vegetable and medicinal plant, has a wide variety of sulfur-containing compounds, among which the content and composition of allicin are greatly affected by variety, cultivation conditions, harvesting time, and processing technology.
The traditional extraction methods mainly include steam distillation and organic solvent extraction. The steam distillation method can effectively extract garlic essential oil and obtain volatile oils containing high-purity allicin. In recent years, supercritical CO2 extraction technology has become the preferred method for extracting allicin due to its advantages of green environmental protection, strong selectivity, and mild operation. In addition, modern technologies such as microwave-assisted extraction and ultrasound assisted extraction have also been applied to improve extraction efficiency and purity.
After extraction, allicin is often qualitatively and quantitatively analyzed using gas chromatography-mass spectrometry (GC-MS) technology to ensure its purity and stability of active ingredients. Purification processes include column chromatography and high-performance liquid chromatography (HPLC) to meet pharmaceutical and scientific research needs.
The pharmacological activities of allicin cover multiple aspects such as antifungal, anti-tumor, antioxidant, anti-inflammatory, and regulation of hypoxia response, reflecting its unique advantages as a multi-target natural product.
Allicin exhibits significant inhibitory effects on various fungal pathogens, including Candida albicans, Aspergillus spp., and others. Its antifungal mechanism mainly involves disrupting the integrity of fungal cell membranes, interfering with intracellular redox balance, and leading to cell death. Multiple in vitro experiments have shown that allicin can inhibit fungal spore germination and hyphal growth, and is equally effective against drug-resistant strains, indicating its potential in the development of antifungal drugs.
Allicin exhibits the ability to inhibit cell proliferation and induce apoptosis in various tumor cell lines. Its anti-tumor effect involves multiple signaling pathways, including regulating the cell cycle, activating mitochondrial dependent apoptosis pathways, inhibiting tumor cell migration and invasion, etc. Research has shown that allicin can downregulate the expression of tumor related genes such as PTGS2 (COX-2) and NOS2 (iNOS), alleviate inflammatory responses in the tumor microenvironment, and enhance immune surveillance function.
As a sulfur-containing compound, allicin has excellent free radical scavenging ability and can effectively resist oxidative stress. Its antioxidant effect is achieved by directly clearing reactive oxygen species (ROS) and reactive nitrogen species (RNS), as well as regulating intracellular antioxidant enzyme systems such as glutathione peroxidase and superoxide dismutase. Antioxidant activity not only protects cells from oxidative damage, but also delays cell aging and tissue degeneration.
Under hypoxic conditions, allicin participates in cellular adaptation to hypoxic environments by regulating key targets such as CA12 (carbonic anhydrase 12), NOS1 (neuronal nitric oxide synthase), NOS2 (inducible nitric oxide synthase), and PTGS2. Its mechanism of action involves regulating intracellular pH, nitric oxide signaling pathway, and inflammatory response, promoting tissue repair and functional recovery, providing new ideas for the treatment of hypoxia related diseases.
The multi-target mechanism of action of allicin is an important basis for its pharmacological activity. By interacting with various enzymes and receptors, allicin regulates the cellular signaling network and exerts its biological effects.
Carbonic anhydrase 12 (CA12) and carbonic anhydrase 1 (CA1) play critical roles in cellular acid-base balance and carbon dioxide metabolism. Allicin helps alleviate hypoxia and acidosis by inhibiting CA12 and CA1 activity, regulating intracellular pH, and improving cellular metabolic environment.
NOS1 and NOS2 are neuronal and inducible nitric oxide synthase enzymes, respectively, involved in regulating intracellular nitric oxide (NO) levels. The inhibitory effect of allicin on NOS2 reduces the excessive production of inflammatory mediator NO and alleviates hypoxia related inflammatory damage. Meanwhile, regulating NOS1 contributes to neuroprotection and vasodilation.
PTGS2 (COX-2) is a key enzyme in inflammatory response. Allicin downregulates PTGS2 expression, inhibits prostaglandin synthesis, alleviates inflammatory response, and suppresses tumor cell proliferation and metastasis.
Allicin also affects cell apoptosis, proliferation, and immune response by regulating signaling pathways such as nuclear factor kappa B (NF - κ B) and mitogen activated protein kinase (MAPK). In addition, its sulfur-containing structure enables it to form covalent bonds with thiol groups in proteins, regulating protein function and further enriching its functional spectrum.
The pharmacological parameters of allicin indicate that it has good potential for drug development. The molecular weight is moderate (162.34), with a LogP of 2.2, indicating that it has a good balance of lipid solubility and water solubility, which is beneficial for oral absorption and in vivo distribution. The TPSA is 38.16 Å ², and the low polarity surface area helps to penetrate cell membranes and the blood-brain barrier, supporting its application in central nervous system diseases.
Toxicological evaluation shows that allicin has no hepatotoxicity, no cardiotoxicity, and does not inhibit hERG channels, reducing the risk of drug-induced arrhythmia. The Ames test result is negative, indicating no significant mutagenicity and high safety.
Pharmacokinetic studies have shown that allicin is rapidly absorbed after oral administration, with good bioavailability, and can effectively distribute to various tissues, especially brain tissue. Its metabolism is mainly carried out through the liver enzyme system, and the metabolites are relatively stable. The main excretion pathways are urine and bile. The half-life of allicin is moderate, supporting the design of its clinical dosing regimen.
Based on the multiple pharmacological activities and good pharmacological properties of allicin, it has shown broad prospects in clinical applications.
The antifungal activity of allicin provides a novel candidate drug for the treatment of fungal infections, especially in the context of the increasing number of drug-resistant strains, and its unique mechanism of action is of great significance. In the future, its clinical efficacy and safety can be improved through structural modification and dosage form optimization.
The anti proliferative and pro apoptotic effects exhibited by allicin in various tumor models provide potential for adjuvant therapy of tumors. Combining modern targeted therapy and immunotherapy strategies, allicin is expected to become an important component of comprehensive cancer treatment plans.
The regulatory effect of allicin on hypoxia related targets makes it valuable in the regulation of hypoxic microenvironment in ischemic cardiovascular and cerebrovascular diseases, chronic obstructive pulmonary disease, and tumors. In the future, through in-depth mechanism research and clinical trial verification, it can be promoted for clinical translation.
As a natural antioxidant and anti-inflammatory agent, allicin has potential applications in chronic inflammatory diseases, neurodegenerative diseases, and metabolic syndrome. Its excellent blood-brain barrier penetration provides the possibility for the treatment of neurological diseases.
Future research should focus on pharmacokinetic optimization, dosage form innovation, and clinical safety evaluation of allicin. At the same time, combining modern molecular biology and medicinal chemistry techniques, we will deeply analyze its multi-target mechanism of action, promote the design and development of allicin derivatives, and expand their clinical indications.
Allicin, as a natural product with rich biological activity, has shown extensive pharmacological potential in antifungal, anti-tumor, antioxidant, and hypoxia response regulation due to its unique chemical structure and multi-target mechanism of action. Its excellent pharmacological parameters and safety evaluation have laid a solid foundation for its clinical application. With the continuous elucidation of pharmacological mechanisms and the improvement of technological means, allicin is expected to become an important representative of natural product drug development, providing new strategies and choices for the treatment of various diseases. Future research needs to further strengthen its clinical translation and application promotion, and promote the widespread application of allicin in modern medicine.
