92284-99-6

Basic information

• Product Name: (E)-ajoene
• Synonyms: (E)-ajoene;(E)-Form
• CAS NO: 92284-99-6
• Molecular Formula: C₉H₁₄OS₃
• Molecular Weight: 234.40186
• Mol File: 92284-99-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-ajoene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-ajoene(92284-99-6)
• EPA Substance Registry System: (E)-ajoene(92284-99-6)

Safety Data

• Hazardous Substances Data: 92284-99-6(Hazardous Substances Data)

Usage

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.

Upstream product

• 52713-51-6 toluene-4-thiosulfonic acid S-2-propen-1-yl ester 
• 2179-57-9 diallyl disulphide 
• 928838-16-8 1-allyl-2-(3-(allylthio)prop-1-en-1-yl)disulfane 
• 539-86-6 allicin 

Relevant articles and documents

Short Total Synthesis of Ajoene

We describe a short total synthesis of ajoene, a major biologically active constituent of garlic. The instability of allicin as the only other known alternative starting material has led to the development of a reliable procedure for the synthesis of ajoene from simple building blocks that is also suitable for upscale operations.

PROCESS FOR THE MANUFACTURE OF AJOENE DERIVATIVES

The present invention relates to the compound (E,Z)-ajoene of formula (1) for use in treatment of bacterial infections. Another aspect of the present invention is a composition comprising (E,Z)-ajoene of formula (1) and at least one antibiotic. Yet another aspect of the invention relates to a method for manufacturing (E,Z) ajoene of formula (1) wherein the conformation of the internal C=C- bond can be either E or Z or a mixture thereof, said method comprising reacting allicin of formula (3) with an acid in the presence of a solvent to provide (E,Z ajoene) of formula (1) as defined above. Yet another aspect of the invention is (E,Z)-ajoene of formula 1 obtainable by the method described above.

Substituted ajoenes as novel anti-cancer agents

A new synthesis of the ajoene pharmacophore core is presented involving the regioselective radical addition of a thiyl radical to a terminal alkyne as the key step. The synthesis allows structural variation of the two end groups on sulfur, and a range of novel derivatives varying the R1 group (sulfoxide end) has been prepared and tested against CT-1 transformed fibroblast cells for anti-cancer activity. The results indicate comparable or even improved activity compared to the parent natural product ajoene isomers. This opens up the way to systematically studying the biology of the ajoene core.