Ajoene

Base Information

• Chemical Name: Ajoene
• CAS No.: 92284-99-6
• Molecular Formula: C9H14OS3
• Molecular Weight: 234.408
• NSC Number: 614554
• UNII: W36UK64JYA
• DSSTox Substance ID: DTXSID501318485
• Nikkaji Number: J468.837F,J248.063H
• Wikipedia: Ajoene
• Wikidata: Q338762
• NCI Thesaurus Code: C68526
• ChEMBL ID: CHEMBL122890
• Mol file: 92284-99-6.mol

Synonyms:4,5,9-trithiadodeca-1,6,11-triene 9-oxide;ajoene

Chemical Property of Ajoene

Chemical Property:

• Boiling Point: 376.0±42.0 °C (760 mmHg)
• PSA: 86.88000
• Density: 1.181±0.06 g/cm3 (20 °C, 760 mmHg)
• LogP: 3.86790
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 234.02067859
• Heavy Atom Count: 13
• Complexity: 199

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCSSC=CCS(=O)CC=C
• Isomeric SMILES: C=CCSS/C=C/CS(=O)CC=C
• Description: (E)-Ajoene is a disulfide that has been found in A. sativum and has diverse biological activities. It is active against Gram-positive and Gram-negative bacteria (MICs = 10-250 and 150->500 μg/ml, respectively) and fungi (MICs = 15-50 μg/ml). (E)-Ajoene inhibits proliferation of a variety of cancer cells, including MDA-MB-231 breast, HeLa cervical, and WHCO1 esophageal cancer cells (IC50s = 18.6, 61, and 39.2 μM, respectively). It also inhibits human glutathione reductase and T. cruzi trypanothione reductase when used at a concentration of 200 μM. (E)-Ajoene (25 mg/kg) is neuroprotective in a gerbil model of ischemia-reperfusion injury, reducing reactive astrocytosis and microgliosis in the hippocampal CA1 region.
• Uses: E/Z Ajoene functions as an antioxidant, by inhibiting the release of superoxide. Ajoene also has antithrombotic (anti-clotting) properties, which helps prevent platelets in the blood from forming blood clots, potentially reducing the risk of heart disease and stroke in humans.

Technology Process of Ajoene

There total 7 articles about Ajoene 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:

allicin (539-86-6) → (Z)-ajoene (92285-00-2) + (E)-ajoene (92284-99-6)

Guidance literature:

In water; acetone; at 63 - 64 ℃; for 4h; Mechanism; Product distribution; Heating; in water-benzene, 37 deg C, 48 h;

DOI:10.1021/ja00282a033

Reference yield:

1-allyl-2-(3-(allylthio)prop-1-en-1-yl)disulfane (928838-16-8) → (Z)-ajoene (92285-00-2) + (E)-ajoene (92284-99-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2008.08.056

Reference yield:

diallyl disulphide (2179-57-9) → (Z)-ajoene (92285-00-2) + (E)-ajoene (92284-99-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 3,3-dimethyldioxirane / acetone / 0.75 h / -50 - -20 °C / Inert atmosphere

2: acetic acid / benzene; water / 48 h / 37 °C

With 3,3-dimethyldioxirane; acetic acid; In water; acetone; benzene;

upstream raw materials:

allicin

1-allyl-2-(3-(allylthio)prop-1-en-1-yl)disulfane

diallyl disulphide

toluene-4-thiosulfonic acid S-2-propen-1-yl ester

Refernces

• 1、 Silva, Filipa,Khokhar, Shaista S.,Williams, Danielle M.,Saunders, Robert,Evans, Gareth J. S.,Graz, Michael,Wirth, Thomas. "Short Total Synthesis of Ajoene". supporting information. p. 12290 - 12293. Retrieved 2018/09/18.
• 2、 -. "PROCESS FOR THE PREPARATION OF AJOENE". Page/Page column 23-24. . Retrieved 2010/09/18.