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

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

Uses

Used in Antimicrobial Applications:
(E)-Ajoene is used as an antimicrobial agent for its effectiveness against a wide range of bacteria and fungi, with minimum inhibitory concentrations (MICs) ranging from 10-500 μg/ml.
Used in Anticancer Applications:
(E)-Ajoene is used as an anticancer agent for its ability to inhibit the proliferation of various cancer cells, including MDA-MB-231 breast, HeLa cervical, and WHCO1 esophageal cancer cells, with IC50s ranging from 18.6 to 61 μM.
Used in Enzyme Inhibition:
(E)-Ajoene is used as an enzyme inhibitor for its capacity to inhibit human glutathione reductase and T. cruzi trypanothione reductase at a concentration of 200 μM.
Used in Neuroprotection:
(E)-Ajoene is used as a neuroprotective agent in animal models of ischemia-reperfusion injury, demonstrating its potential to reduce reactive astrocytosis and microgliosis in the hippocampal CA1 region at a dosage of 25 mg/kg.
Used in Antioxidant Applications:
(E)-Ajoene is used as an antioxidant for its ability to inhibit the release of superoxide, which can help protect cells from oxidative damage.
Used in Antithrombotic Applications:
(E)-Ajoene is used as an antithrombotic agent for its anti-clotting properties, which can help prevent platelets in the blood from forming blood clots, potentially reducing the risk of heart disease and stroke in humans.

Upstream product

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

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.

Novel Ajoene derivatives, preparation method thereof, and pharmaceutical composition for use in preventing or treating cancer containing the same as an active ingredient

The present invention relates to novel ajoene derivatives, to a preparation method thereof, and to a pharmaceutical composition for preventing or treating cancer containing the same as active ingredients, wherein the novel ajoene derivatives according to the present invention were confirmed to inhibit proliferation of human renal cancer cell line (ACHN), breast cancer cell line (MDA-MB-231), colorectal cancer cell line (HCT-15), prostate cancer cell line (PC-3), stomach cancer cell line (NUGC-3) and lung cancer cell line (NCI-H23) to be usefully used as a pharmaceutical composition for preventing or treating cancer containing the same as the active ingredients.COPYRIGHT KIPO 2018

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.

PROCESS FOR THE PREPARATION OF AJOENE

The present invention is directed to a process for the preparation of ajoene, and to ajoene having a relatively high purity which may be obtained by the process. The invention also relates to processes for the preparation of allicin, to a process for freeze concentrating allicin.

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.

(E,Z)-Ajoene: A potent antithrombotic agent from garlic

A report is presented of the structural characterization and simple synthesis of (E,Z)-ajoene.