Allicin

Base Information

• Chemical Name: Allicin
• CAS No.: 539-86-6
• Molecular Formula: C6H10OS2
• Molecular Weight: 162.277
• Hs Code.: 29329990
• European Community (EC) Number: 208-727-7
• NSC Number: 707388
• UNII: 3C39BY17Y6
• DSSTox Substance ID: DTXSID6043707
• Nikkaji Number: J71.032F,J816.011B
• Wikipedia: Allicin
• Wikidata: Q409641,Q105125581
• NCI Thesaurus Code: C68521
• Pharos Ligand ID: RYB4QSHURHCL,RYBBG8YPK9FL
• Metabolomics Workbench ID: 46312
• ChEMBL ID: CHEMBL359965
• Mol file: 539-86-6.mol

Synonyms:allicin;allimin;allylthiosulfinate;allylthiosulphinic acid allyl ester;diallyl disulfide-oxide;thio-2-propene-1-sulfinic acid S-allyl ester

Chemical Property of Allicin

Chemical Property:

• Appearance/Colour: Clear to slightly yellow liquid
• Vapor Pressure: 0.0379mmHg at 25°C
• Melting Point: 25°C
• Refractive Index: 1.567
• Boiling Point: 248.6 °C at 760 mmHg
• Flash Point: 104.2 °C
• PSA: 61.58000
• Density: 1.148 g/cm³
• LogP: 2.62100
• Water Solubility.: 24g/L(10 oC)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 162.01730729
• Heavy Atom Count: 9
• Complexity: 120

Purity/Quality:

100% Natural & No pollution ^*data from raw suppliers

Allicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCSS(=O)CC=C
• Description: Allicin is one of the major allergens in garlic (Allium sativum L.). It is responsible of the characteristical fiavour of the bulbs. Allicin is a natural product originally isolated from A. sativum that has wide-ranging biological effects including antioxidative, anticancer, antimicrobial, and antifungal activities. It inhibits the cysteine proteases cathepsin B and L, facipain 2, and rhodesain with Ki values of 8.6 and 9.3, 1.04, and 5.31 μM, respectively. It shows antiparasitic activity against P. falciparum (IC50 = 5.2 μM) and T. b. brucei (IC50 = 13.8 μM), the parasites that cause malaria and African sleeping sickness, respectively. Allicin (5-10 μM) dose-dependently inhibits cell adhesion, invasion, and migration in various lung adenocarcinoma cell lines. It also alters the balance of tissue inhibitors of matrix metalloproteinases (TIMPs) and matrix metalloproteinases (MMPs), decreases phosphorylation of Akt, and decreases PI3K/Akt signaling.
• Physical properties: Appearance: Light yellow powder or light yellow oily liquid, with strong irritating odor. Unstable and light, heat, and organic solvents will easily degrade it into a variety of sulfur-containing organic compounds. Solubility: Its solubility is about 2.5% in the 10?°C water. Soluble in ethanol, ether, benzene, and other organic solvents. Boiling point: 80–85?°C (0.2?kPa). Relative density of d20?=?1.112; refractive index nD 20 ?=?1.561.
• Uses: Allicin is naturally formed by the action of the enzyme allicinase on alliin when the tissue of the garlic bulb is disrupted. Allicin shows antibacterial activity.
• Indications: This product conforms to the national standards for chemical drugs. The current clinical used forms are allicin injection, garlic instant kelp capsule, etc. It is used clinically mainly for anti-pathogenic microbial infection, anti-tumor, and anti-dilation of blood vessels. It could also be used for the treatment of periodontitis and ulcerative colitis.
• Clinical Use: Allicin shows inhibitory effects on infections caused by bacteria, fungi, and virus. Clinical studies reported that allicin has cured 23 Candida albicans-infected patients . Combining allicin with surgery had cured ten patients with maxillary sinus aspergillosis. Good results for the treatment of chronic gastritis, peptic ulcer, chronic colitis, and fatty liver were achieved after allicin administration. Allicin is also capable of eliminating oxygen free radical ion. In addition, allicin can reduce the nitrite- and nitrate-reducing bacteria, and taking garlic could benefit chronic symptoms in stomach, such as stomach discomfort, fullness pain, acid reflux, heating, burning and loss of appetite, and so on.

Technology Process of Allicin

There total 19 articles about Allicin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

S‐allyl‐L‐cysteine sulfoxide (17795-27-6) → allicin (539-86-6)

Guidance literature:

With water extract of garlic; In water; at 20 ℃; Enzymatic reaction;

DOI:10.1021/jf4003818

Reference yield: 96.0%

diallyl disulphide (2179-57-9) → allicin (539-86-6)

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; at -50 - -20 ℃; for 0.75h; Product distribution / selectivity; Inert atmosphere;

Reference yield: 71.0%

C14H30OSSi → allicin (539-86-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 3h;

DOI:10.1021/acs.orglett.1c01149

upstream raw materials:

peracetic acid

diallyl disulphide

chloroform

Perbenzoic acid

Downstream raw materials:

3-vinyl-4H-<1,2>-dithiin

diallyl disulphide

diallyl trisulfide

2‐ethenyl‐4H‐1,3‐dithiine

Refernces

• 1、 Albrecht, Frank,Leontiev, Roman,Jacob, Claus,Slusarenko, Alan J.. "An optimized facile procedure to synthesize and purify allicin". . . Retrieved 2017.
• 2、 García Trejo, Ehécatl Miguel ángel,Buendía, Abraham Said Arellano,Reyes, Omegar Sánchez,Arroyo, Fernando Enrique García,García, Raúl Arguello,Mendoza, María Lilia Loredo,Tapia, Edilia,Lozada, Laura Gabriela Sánchez,Alonso, Horacio Osorio. "The beneficial effects of Allicin in chronic kidney disease are comparable to Losartan". . . Retrieved 2017.
• 3、 Freeman, Fillmore,Kodera, Yukihiro. "Garlic Chemistry: Stability of S-(2-Propenyl) 2-Propene-1-sulfinothioate (Allicin) in Blood, Solvents, and Simulated Physiological Fluids". . p. 2332 - 2338. Retrieved 1995.
• 4、 Coppi, Alida,Cabinian, Melissa,Mirelman, David,Sinnis, Photini. "Antimalarial activity of allicin, a biologically active compound from garlic cloves". . p. 1731 - 1737. Retrieved 2006.
• 5、 Vaidya, Vipraja,Ingold, Keith U.,Pratt, Derek A.. "Garlic: Source of the ultimate antioxidants - Sulfenic acids". . p. 157 - 160. Retrieved 2009.
• 6、 Li, Wen-Qing,Zhou, Hua,Zhou, Mei-Yun,Hu, Xing-Peng,Ou, Shi-Yi,Yan, Ri-An,Liao, Xiao-Jian,Huang, Xue-Song,Fu, Liang. "Characterization of phenolic constituents inhibiting the formation of sulfur-containing volatiles produced during garlic processing". . p. 787 - 794. Retrieved 2015.
• 7、 Janska, Petra,Knejzlík, Zdenek,Perumal, Ayyappasamy Sudalaiyadum,Jurok, Radek,Tokarova, Viola,Nicolau, Dan V.,Tepanek, FrantisekS,Kaspar, Ondrej. "Effect of physicochemical parameters on the stability and activity of garlic alliinase and its use for in-situ allicin synthesis". . . Retrieved 2021/03/26.
• 8、 -. "Tanshinol and H2 S/NO Donor binding, preparation method thereof and application in pharmacy (by machine translation)". Paragraph 0116-0118. . Retrieved 2020/08/18.