125184-95-4

Basic information

• Product Name: dehydroartemisinyl alcohol
• Synonyms: dehydroartemisinyl alcohol
• CAS NO: 125184-95-4
• Molecular Weight: 220.355
• Mol File: 125184-95-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: dehydroartemisinyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: dehydroartemisinyl alcohol(125184-95-4)
• EPA Substance Registry System: dehydroartemisinyl alcohol(125184-95-4)

Safety Data

• Hazardous Substances Data: 125184-95-4(Hazardous Substances Data)

Usage

Description

Dehydroartemisinyl alcohol is a sesquiterpenoid precursor of artemisinin, which is a monocarboxylic acid derived from prop-2-en-1-ol acid. It is characterized by a 4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl group substitution at position 2 and exists as the 1S,4R,4aS,8aR diastereoisomer. dehydroartemisinyl alcohol is obtained from sweet wormwood, Artemisia annua, and plays a crucial role in the semi-synthesis of artemisinin.

Uses

1. Used in Pharmaceutical Industry:
Dehydroartemisinyl alcohol is used as a precursor for the semi-synthesis of artemisinin (A777500) for its potent antimalarial properties. Artemisinin is an effective agent used to treat malaria, a disease caused by parasites that infect red blood cells.
2. Used in Antimalarial Applications:
Dehydroartemisinyl alcohol is utilized as a key compound in the production of artemisinin, which serves as an antimalarial agent. It is particularly effective against Plasmodium parasites responsible for causing malaria, offering a vital treatment option for individuals suffering from this life-threatening disease.
3. Used in Drug Development:
As a precursor to artemisinin, dehydroartemisinyl alcohol is essential in the development of new drugs and therapies targeting malaria. Its role in the semi-synthesis of artemisinin highlights its importance in the pharmaceutical industry, where it contributes to the creation of innovative and effective treatments for this global health issue.

Upstream product

• 593-71-5 Chloroiodomethane 
• 917-54-4 methyllithium 
• 92692-39-2 (1R,4R,4aS,8aR)-4,7-dimethyl-1-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene 
• 76-05-1 trifluoroacetic acid 
• 64-17-5 ethanol 
• 916311-23-4 amorphadiene-11,12-epoxide 
• 186581-53-3 diazomethane 
• 80286-58-4 artemisinic acid 
• 82869-24-7 methyl artemisinate 

Downstream Products

• 80286-58-4 artemisinic acid 
• 125276-60-0 artemisinic aldehyde 

Relevant articles and documents

An enantioselective ambimodal cross-Diels–Alder reaction and applications in synthesis

Compared with the conventional Diels–Alder reaction, the development of selective cross-Diels–Alder reactions between two different conjugated dienes, especially in a catalytic asymmetric manner, has been neglected. We now report a peri- and enantioselective cross-Diels–Alder reaction of 3-alkoxycarbonyl-2-pyrones with unactivated conjugated dienes catalysed by a copper(II)–bis(oxazoline) complex, leading to formal inverse-electron-demand adducts with high enantioselectivity under mild reaction conditions. Computational studies showed that this reaction proceeds through an ambimodal transition state: post-transition-state bifurcation leads to [2+4] and [4+2] adducts with the same enantioselectivity, followed by a facile Cope rearrangement to provide a single observed thermodynamic [2+4] product. This reaction occurs with a wide variety of cyclopentadienes, fulvenes and cyclohexadienes, providing a highly efficient and enantioselective approach to densely functionalized cis-bicyclic scaffolds. The synthetic value of this reaction is demonstrated by the asymmetric synthesis of two biologically important natural products, artemisinic acid and coronafacic acid. [Figure not available: see fulltext.].

High-level semi-synthetic production of the potent antimalarial artemisinin

In 2010 there were more than 200 million cases of malaria, and at least 655,000 deaths. The World Health Organization has recommended artemisinin-based combination therapies (ACTs) for the treatment of uncomplicated malaria caused by the parasite Plasmodium falciparum. Artemisinin is a sesquiterpene endoperoxide with potent antimalarial properties, produced by the plant Artemisia annua. However, the supply of plant-derived artemisinin is unstable, resulting in shortages and price fluctuations, complicating production planning by ACT manufacturers. A stable source of affordable artemisinin is required. Here we use synthetic biology to develop strains of Saccharomyces cerevisiae (baker's yeast) for high-yielding biological production of artemisinic acid, a precursor of artemisinin. Previous attempts to produce commercially relevant concentrations of artemisinic acid were unsuccessful, allowing production of only 1.6 grams per litre of artemisinic acid. Here we demonstrate the complete biosynthetic pathway, including the discovery of a plant dehydrogenase and a second cytochrome that provide an efficient biosynthetic route to artemisinic acid, with fermentation titres of 25 grams per litre of artemisinic acid. Furthermore, we have developed a practical, efficient and scalable chemical process for the conversion of artemisinic acid to artemisinin using a chemical source of singlet oxygen, thus avoiding the need for specialized photochemical equipment. The strains and processes described here form the basis of a viable industrial process for the production of semi-synthetic artemisinin to stabilize the supply of artemisinin for derivatization into active pharmaceutical ingredients (for example, artesunate) for incorporation into ACTs. Because all intellectual property rights have been provided free of charge, this technology has the potential to increase provision of first-line antimalarial treatments to the developing world at a reduced average annual price.

CONVERSION OF AMORPHA-4,11-DIENE TO ARTEMISININ AND ARTEMISININ PRECURSORS

The present invention relates to methods for the conversion of amorpha-4,11-diene to artemisinin and various artemisinin precursors.