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S allyl l cysteine CAS 49621-03-6 is 99%+ pure substance. We get it with our technology of organic chemistry. S-neneneba Allyl-L-cysteine is a Natural product, which mainly exists in garlic. The Molecular formula is C6H11NO2S, CAS 49621-03-6, and the relative molecular weight is 161.23. It is a colorless to light yellow crystalline solid with a special odor and taste, often described as having a garlic aroma. It has a high solubility in water and is soluble in water and polar organic solvents such as methanol, ethanol, and ether solvents. The melting point is approximately 220-225 ° C. During the heating process, it gradually melts and becomes a colorless liquid. Combustible at high temperatures, but not easily combustible under normal circumstances. Relatively stable, able to be stored for a long time under conventional temperature and storage conditions. It is composed of cysteine molecule and Allyl group group, and its structure contains amide, sulfide and Allyl group functional groups. It is a natural organic sulfur compound extracted from garlic. It has been widely studied and is considered to have multiple important biological activities and potential medical applications.
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Chemical Formula |
C6H11NO2S |
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Exact Mass |
161.05 |
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Molecular Weight |
161.25 |
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m/z |
161.05 (100.0%), 162.05 (6.5%), 163.05 (4.5%) |
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Elemental Analysis |
C, 44.70; H, 6.88; N, 8.69; O, 19.85; S, 19.89 |
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S Allyl L Cysteine is a natural organic sulfur compound, which is extracted from garlic. Traditionally, garlic is widely used for both medicine and food, and S-Allyl group-L-cysteine is considered to be one of the main active ingredients of garlic. With the further study of S-Allyl group-L-cysteine, it has been found that S-allyl-L-cysteine has many important biological activities and potential medical applications.
1. Antioxidant effect:
S-Allyl group-L-cysteine has significant antioxidant activity, which can neutralize free radicals and reduce cell damage caused by oxidative stress. Oxidative stress is a common feature of many diseases, including cardiovascular disease, cancer, Degenerative disease and diabetes. By providing antioxidant protection, S-Allyl group-L-cysteine can help reduce the occurrence and development of these diseases.
2. Cardiovascular protection:
S-Allyl group-L-cysteine can reduce cholesterol levels, improve blood circulation, and protect the cardiovascular system from damage. It can reduce the oxidation of low density lipoprotein (LDL) cholesterol and increase the level of High-density lipoprotein (HDL) cholesterol, thus reducing the risk of Atherosclerosis and heart disease.
3. Immunomodulatory effects:
S-Allyl group-L-cysteine can regulate the function of the immune system and improve the body's ability to resist infection and disease. It can promote the response of cellular immunity and Humoral immunity, and enhance the activity of macrophages and Natural killer cell. In addition, it also has anti-inflammatory effects and can alleviate inflammatory reactions.
4. Antitumor effect:
Several studies have shown that S-Allyl group-L-cysteine has anti-tumor activity. It can inhibit the proliferation and invasion of tumor cells through various pathways, and promote tumor cell apoptosis. In addition, S-Allyl group-L-cysteine can also enhance the efficacy of chemotherapy drugs and reduce the damage to normal cells in vivo.
5. Liver protection:
S-Allyl group-L-cysteine has protective effect on liver. It can alleviate liver damage and inflammatory reactions, promote liver cell regeneration and repair. S-Allyl group-L-cysteine can also improve the activity of liver detoxification enzymes, help eliminate harmful substances in the body, and thus maintain the healthy function of the liver.
6. Blood glucose regulation effect:
S-Allyl group-L-cysteine can reduce blood glucose levels, increase insulin sensitivity, and improve insulin secretion. This is of great significance for the prevention and management of diabetes. In addition, S-Allyl group-L-cysteine can also reduce the risk of Complications of diabetes, such as cardiovascular disease and neuropathy.
7. Antibacterial effect:
S-Allyl group-L-cysteine has inhibitory effect on some bacteria and fungi. It can inhibit the growth and reproduction of bacteria and block their binding to host cells. This makes S-Allyl group-L-cysteine a potential natural antibacterial agent and food preservative.
8. Anti aging effect:
S-Allyl group-L-cysteine can slow down the aging process of the body. It enhances the antioxidant defense ability of cells, reduces the appearance of aging markers, and promotes health and longevity by providing antioxidant protection and regulating cellular signaling pathways.
Reaction of Amino Groups
Acylation reaction
Under acidic conditions, the α - amino group of SAC can react with acyl chlorides or anhydrides
Example: Reacts with acetic anhydride (pH 4-5) to produce N-acetyl-S-allyl-L-cysteine.
Alkylation reaction
Introducing alkyl groups through reductive amination reaction
Product: S allyl l cysteine (with enhanced lipophilicity).
Reaction of carboxylic acid groups
Esterification reaction
Reaction with alcohols catalyzed by concentrated sulfuric acid
Example: Reacts with methanol to produce S-allyl-L-cysteine methyl ester (with membrane permeability).
Acylation reaction
Generate amides through DCC condensation with amines
Product: S-Allyl-L-cysteine Benzamide (biologically stable).
Reaction of Allyl
Double Bond Addition Reaction
Epoxidation: Reacts with m-CPBA to produce epichlorohydrin derivatives
Hydroxylation: Under the catalysis of osmium tetroxide, diol compounds are generated.
Sulfide oxidation
Allyl sulfide can be oxidized by hydrogen peroxide to sulfoxide or sulfone
Product: S-Allyl-L-cysteine sulfoxide (with higher polarity).
Potential reactions at thiol sites
Although thiol groups are protected by allyl groups, they can still undergo substitution under the action of strong electrophilic reagents such as iodomethane
Product: S - (allyl) - S-methyl-L-cysteine (disulfide structure).
A common method of synthesizing S-Allyl-L-Cysteine is as follows:
Step 1:
First, L-cysteine is reacted with allyl aldehyde to generate the raw material intermediate S-neneneba allyl-L-cysteine ester. The reaction is usually carried out in an anhydrous environment with the addition of an acid catalyst. The reaction temperature and time vary depending on specific reaction conditions.
Step 2:
The next step is to hydrogenate S-Allyl group-L-cysteine ester to S-Allyl group-L-cysteine. Usually, platinum catalysts (such as platinum black) are used for hydrogenation reactions, which are carried out in appropriate solvents at appropriate temperatures and pressures.
Step 3:
Finally, remove the S-allyl group protective group through the deprotection reaction to obtain pure S-allyl group-L-cysteine. The common deprotection method is to use alkaline conditions, such as sodium hydroxide solution.
A common method to synthesize S-Allyl group-L-cysteine is as follows:
Step 1:
Prepare L-cysteine sulfate. React L-cysteine with excessive sulfuric acid to produce L-cysteine sulfate. This reaction is usually carried out at room temperature and it is necessary to ensure that the reactants are thoroughly mixed.
Step 2:
Synthesize Allyl group bromide. Allyl alcohol reacts with dilute hydrochloric acid and Copper(I) bromide solution to produce Allyl group bromide. This reaction needs to be carried out in an inert atmosphere (such as nitrogen), and the reaction temperature and time should be controlled.
Step 3:
Synthesis of S Allyl L Cysteine. The sulfate of L-cysteine obtained in step 1 is reacted with Allyl group bromide prepared in step 2 under alkaline conditions. Use appropriate alkali (such as sodium hydroxide) and solvent, add the two reactants to the reaction system, and control the reaction temperature and time.
Step 4:
Purification and separation of the product. Purify and separate the reaction mixture through appropriate purification techniques. Common purification methods include crystallization, solvent extraction, chromatography, etc.
It should be noted that this is only one of the laboratory synthesis methods, and the specific experimental conditions and steps may vary depending on Laboratory equipment and needs. In practical operation, please refer to relevant research literature and professional opinions to ensure the accuracy and feasibility of the synthesis method. In addition, when conducting laboratory synthesis, it is essential to comply with laboratory safety regulations and chemical waste disposal requirements.
Early discovery: Tracing from garlic to active components
The discovery of SAC is closely related to the chemical research on garlic. As a traditional medicinal plant, garlic (Allium sativum) has been utilized by humans for thousands of years for its antibacterial, anti-inflammatory, and other properties. In the early 20th century, scientists began to analyze the chemical components of garlic and found that the sulfur-containing compounds were the main source of its activity. In 1944, Cavallito and Bailey were the first to isolate "allicin", an antibacterial active substance, from garlic. However, allicin is unstable and easily decomposes into various sulfur-containing organic substances, including the precursor substance of SAC.
From the 1950s to the 1960s, Japanese scholars conducted research on the fermentation process of garlic and discovered that ordinary garlic, after being fermented under high temperature and high humidity, would produce a black substance (i.e., black garlic), with significant changes in its sulfur-containing components. In 1972, the team led by Japanese scientist Akira Okawa isolated a stable sulfur-containing amino acid from black garlic and determined its structure to be S-allyl-L-cysteine (SAC). This discovery revealed the chemical basis for the unique flavor and health benefits of black garlic, laying the foundation for subsequent research.
Structure Confirmation and Preliminary Exploration of Biological Activity
The chemical structure of SAC is that the thiol group (-SH) of L-cysteine is replaced by an allyl group (CH₂=CH-CH₂-). Its molecular formula is C₆H₁₁NO₂S. In the early stage of its discovery, scientists gradually confirmed its biological activity through the following studies:
Antioxidant and Anti-Cancer Activity
In the 1980s, Japanese scholars discovered that SAC could inhibit the occurrence of gastric cancer in mice induced by chemical carcinogens and reduce the proliferation of tumor cells. Further studies showed that SAC exerted antioxidant effects by eliminating free radicals and inhibiting lipid peroxidation, thereby indirectly inhibiting carcinogenesis.
Neuroprotective Effect
In 2003, a team from Kyoto University in Japan published a study in "Neuroscience" proving that SAC could protect neurons from cell death induced by β-amyloid protein (Aβ) and reduce the intracellular reactive oxygen species (ROS) level. This discovery drew attention to the potential of SAC in treating neurodegenerative diseases such as Alzheimer's disease.
Anti-Inflammatory and Immune Regulation
After 2010, multiple studies confirmed that SAC exerted anti-inflammatory effects by inhibiting the NF-κB pathway and reducing the release of inflammatory factors (such as TNF-α, IL-6). For example, a 2018 report in "Biochimica et Biophysica Acta" stated that SAC could inhibit tumor necrosis factor (TNF-α)-induced skeletal muscle atrophy by regulating the expression of genes related to protein catabolism.
The Rise of Functional Foods and Clinical Research
With the clarification of SAC's biological activity, its application has expanded from the laboratory to functional foods and clinical research:
Functionalization development of black garlic
Japanese enterprises were the first to promote black garlic as a health food, marking the SAC content as the quality indicator. Studies have shown that consuming 2mg of SAC (equivalent to 1-2 cloves of black garlic) daily can significantly improve sleep quality and relieve fatigue. For example, in 2022, the Japanese Functional Food Association approved a black garlic extract containing SAC for use in "reducing work-related mental fatigue".
International market expansion
The US market combines SAC with components such as South African passion fruit and GABA to develop sleep-aid candies; Chinese research teams are exploring its potential to improve cognitive impairment, and relevant clinical trials are underway.
Breakthroughs in synthesis technology and industrialization
The natural extraction cost of SAC is high, prompting scientists to develop chemical synthesis methods:
Cysteine reacts with allylating reagents
By reacting L-cysteine with allyl bromide (or allyl thiol) under alkaline conditions, SAC can be efficiently synthesized. This method can achieve a yield of over 80%, but the control of side reactions (such as double allylation) is required.
Biocatalytic method
Using enzymatic reactions (such as cysteine sulfination enzyme) to combine cysteine with allyl compounds has advantages such as high stereoselectivity and environmental friendliness, but it is still at the laboratory stage.
Future prospects: From molecular mechanisms to precise health
Current research is deeply analyzing the target sites and signaling pathways of SAC:
Neuroprotection field: The discovery of SAC enables regulation of autophagy-related proteins (such as LC3, p62), providing a new direction for the treatment of Alzheimer's disease.
Metabolic syndrome intervention: Animal experiments have shown that SAC can improve insulin resistance and lower blood lipids, potentially becoming a new intervention method for metabolic diseases.
Personalized nutrition: Based on individual genomic differences, exploring the optimal dosage and efficacy of SAC in different populations, promoting precise health management.
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