92285-00-2

Basic information

• Product Name: (Z)-ajoene
• Synonyms: Z-AJOENE
• CAS NO: 92285-00-2
• Molecular Formula: C₉H₁₄OS₃
• Molecular Weight: 234.40186
• Mol File: 92285-00-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 376.0±42.0 °C(Predicted)
• Appearance: /
• Density: 1.181±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (Z)-ajoene(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-ajoene(92285-00-2)
• EPA Substance Registry System: (Z)-ajoene(92285-00-2)

Safety Data

• Hazardous Substances Data: 92285-00-2(Hazardous Substances Data)

Usage

General Description

(Z)-Ajoene is a natural organosulfur compound derived from garlic that has been found to possess various medicinal properties. It is known for its anti-fungal, anti-bacterial, and anti-inflammatory properties, making it a potential candidate for the treatment of various infections and inflammatory conditions. (Z)-Ajoene has been investigated for its potential in treating conditions such as athlete's foot, ringworm, and other fungal infections, as well as its ability to inhibit the growth of bacteria and reduce inflammation. Additionally, it has shown potential for use in cancer treatment due to its ability to induce apoptosis in cancer cells. Overall, (Z)-Ajoene has demonstrated promising therapeutic potential and continues to be of interest for further research and development in the medical field.

Upstream product

• 52713-51-6 toluene-4-thiosulfonic acid S-2-propen-1-yl ester 
• 2179-57-9 diallyl disulphide 
• 89027-60-1 allyl(prop-2-yn-1-yl)sulfane 
• 928838-16-8 1-allyl-2-(3-(allylthio)prop-1-en-1-yl)disulfane 
• 539-86-6 allicin 

Relevant articles and documents

Ajoene, A stable garlic by-product, inhibits high fat diet-induced hepatic steatosis and oxidative injury through LKB1-dependent AMPK activation

Hepatic steatosis, a hepatic component of metabolic syndrome, is common and may progress to steatohepatitis and cirrhosis. The liver X receptor-α (LXRα)-sterol regulatory element binding protein-1c (SREBP-1c) pathway plays a key role in hepatic steatosis. This study investigated the potential of ajoene, a stable garlic by-product, to inhibit high fat diet (HFD)-induced hepatic steatosis and the underlying mechanism. Ajoene treatment attenuated fat accumulation and induction of lipogenic genes in the liver of HFD-fed mice. Blood biochemical analyses and histopathologic examinations showed that ajoene prevented liver injury with the inhibition of oxidative stress, as evidenced by thiobarbituric acid reactive substances formation and nitrotyrosinylation. Moreover, ajoene treatment inhibited LXRα agonist (T0901317)-mediated SREBP-1c activation, and transactivation of the lipogenic target genes in hepatocytes. Ajoene was found to activate AMP-activated protein kinase (AMPK) via LKB1, responsible for the inhibition of p70 ribosomal S6 kinase-1 (S6K1). The ability of ajoene to repress T0901317-induced SREBP-1c expression was antagonized by inhibition of AMPK or activation of S6K1, supporting the role of these kinases in the antisteatotic effect. Our results demonstrate that ajoene has an effect of activating AMPK through LKB1 and inhibit S6K1 activity, contributing to the prevention of SREBP-1c-mediated hepatic lipogenesis via the inhibition of LXRα activity.

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 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.