163594-75-0

Usage

Uses

Used in Pharmaceutical Industry:
Taxa-4,11-diene is used as a pharmaceutical compound for its potential anti-inflammatory, anti-cancer, and antimicrobial effects. Its unique chemical structure and biological activities make it a promising candidate for the development of new drugs and treatments.
Used in Medicinal Applications:
Taxa-4,11-diene is used as a medicinal agent for its potential therapeutic benefits. Its anti-inflammatory properties can help alleviate inflammation and pain, while its anti-cancer effects may contribute to the development of novel cancer treatments. Additionally, its antimicrobial properties can be utilized in the development of new antibiotics or antifungal agents.
Used in Aromatherapy:
Taxa-4,11-diene, being a major component of essential oils, is used in aromatherapy for its potential calming and soothing effects. Its unique aroma can help promote relaxation and stress relief, making it a valuable addition to various aromatherapy practices.
Used in Cosmetic Industry:
Due to its potential anti-inflammatory and antimicrobial properties, taxa-4,11-diene can be used in the cosmetic industry as an ingredient in skincare products. It may help improve skin health by reducing inflammation and combating harmful microorganisms, contributing to the development of natural and effective cosmetic formulations.
Used in Agricultural Applications:
Taxa-4,11-diene's antimicrobial properties can also be applied in agriculture, particularly in the development of natural pesticides or fungicides. Its potential to combat harmful microorganisms can help protect crops and promote sustainable agricultural practices.

Upstream product

• 358-71-4 isopentyl pyrophosphate 
• 87262-14-4 8β-Hydroxy-4aβ-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 
• 1350704-23-2 C₂₂H₃₄O₂ 
• 1350704-21-0 ( 4aS,6R,12aS)-9,12a,13,13-tetramethyl-5-oxo-1,2,4a,5,6,7,8,11,12,12a-decahydro-6,10-methanobenzo[10]annulene-4-yl trifluoromethanesulfonate 
• 1442555-84-1 C₂₀H₃₂O₂ 

Downstream Products

• 357436-25-0 taxa-4(20),11(12)-diene-5α,13α-diol 
• 178888-02-3 taxa-4(20),11(12)-dien-5-ol 

Relevant academic research and scientific papers

Studies on the Biosynthesis of Taxol: Total Synthesis of Taxa-4(20),11(12)-diene and Taxa-4(5),11(12)-diene. The First Committed Biosynthetic Intermediate

The total synthesis of taxa-4(20),11(12)-diene and taxa-4(5),11(12)-diene is described.

Engineering Escherichia coli for the synthesis of taxadiene, a key intermediate in the biosynthesis of taxol

Taxadiene, the key inte mediate of paclitaxel (Taxol) biosynthesis, has been prepared enzymatically from isopentenyl diphosphate in cell-free extracts of Escherichi coli by ove expressing genes encoding isopentenyl diphosphate isomerase, geranylgeranyl diphosphate synthase and taxadiene synthase. In addition, by the expression of three genes encoding four enzymes on the terpene biosynthetic pathway in a single strain of E. coli, taxadiene can be conveniently synthesized in vivo, at the unoptimized yield of 1.3 mg per liter of cell culture. The success of both in vitro and in vivo synthesis of taxadiene bodes well for the future production of taxoids by non-paclitaxel producing organisms through pathway engineering. Copyright

Total synthesis of taxane terpenes: Cyclase phase Dedicated to Professor Melanie S. Sanford on the occasion of her receipt of the Tetrahedron Young Investigator Award

A full account of synthetic efforts toward a lowly oxidized taxane framework is presented. A non-natural taxane, dubbed 'taxadienone', was synthesized as our first entry into the taxane family of diterpenes. The final synthetic sequence illustrates a seven-step, gram-scale, and enantioselective route to this tricyclic compound in 18% overall yield. This product was then modified further to give (+)-taxadiene, the lowest oxidized member of the taxane family of natural products.

Scalable enantioselective total synthesis of taxanes

Taxanes form a large family of terpenes comprising over 350 members, the most famous of which is Taxol (paclitaxel), a billion-dollar anticancer drug. Here, we describe the first practical and scalable synthetic entry to these natural products via a concise preparation of (+)-taxa-4(5),11(12)-dien-2-one, which has a suitable functional handle with which to access more oxidized members of its family. This route enables a gram-scale preparation of the 'parent' taxane-taxadiene-which is the largest quantity of this naturally occurring terpene ever isolated or prepared in pure form. The characteristic 6-8-6 tricyclic system of the taxane family, containing a bridgehead alkene, is forged via a vicinal difunctionalization/Diels-Alder strategy. Asymmetry is introduced by means of an enantioselective conjugate addition that forms an all-carbon quaternary centre, from which all other stereocentres are fixed through substrate control. This study lays a critical foundation for a planned access to minimally oxidized taxane analogues and a scalable laboratory preparation of Taxol itself.

Stereochemistry of the macrocyclization and elimination steps in taxadiene biosynthesis through deuterium labeling

Taxadiene synthase catalyzes the cyclization of (E,E,E)-geranylgeranyl diphosphate (GGPP) to taxa-4(5),11(12)-diene (Scheme 1, 5 → 2) as the first committed step of Taxol biosynthesis. Deuterated GGPPs labeled stereospecifically at C-1, C-4, and C-16 were