19605-80-2

Basic information

• Product Name: taxusin
• Synonyms: taxusin;(1R)-5α,9α,10β,13α-Tetraacetoxy-taxa-4(20),11-diene;5α,9α,10β,13α-Tetraacetoxytaxa-4(20),11-diene;Taxa-4(20),11-diene-5α,9α,10β,13α-tetrol 5,9,10,13-tetraacetate;Taxa-4(20),11-diene-5α,9α,10β,13α-tetrol tetraacetate;TAXUSIN(P)
• CAS NO: 19605-80-2
• Molecular Formula: C28H40O8
• Molecular Weight: 504.616
• Mol File: 19605-80-2.mol

Chemical Properties

• Melting Point: 131～132℃
• Boiling Point: 537.3°Cat760mmHg
• Flash Point: 224.4°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 1.29E-11mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: taxusin(CAS DataBase Reference)
• NIST Chemistry Reference: taxusin(19605-80-2)
• EPA Substance Registry System: taxusin(19605-80-2)

Safety Data

• Hazardous Substances Data: 19605-80-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Taxusin is used as a pharmaceutical compound for its potential anticancer properties. It has been found to exhibit cytotoxic effects on various cancer cell lines, making it a promising candidate for the development of new cancer treatments.
Used in Drug Delivery Systems:
Similar to gallotannin, taxusin can also be incorporated into drug delivery systems to enhance its bioavailability and therapeutic outcomes. By using various organic and metallic nanoparticles as carriers, the delivery, efficacy, and targeting of taxusin to cancer cells can be improved.
Used in Traditional Medicine:
Taxusin, being a secondary metabolite of plants, has been used in traditional medicine for its potential therapeutic properties. It may be utilized in the formulation of herbal remedies and supplements, particularly those aimed at cancer treatment and prevention.
Used in Chemical Research:
As a taxane diterpenoid, taxusin is an important compound for chemical research and development. It can be used as a starting material for the synthesis of other bioactive compounds or as a reference compound in the study of the chemical properties and mechanisms of action of taxane diterpenoids.

InChI:InChI=1/C28H40O8/c1-14-21-12-20-13-23(34-17(4)30)15(2)24(27(20,7)8)25(35-18(5)31)26(36-19(6)32)28(21,9)11-10-22(14)33-16(3)29/h20-23,25-26H,1,10-13H2,2-9H3/t20-,21-,22+,23+,25-,26+,28-/m1/s1

Upstream product

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• 208044-30-8 (3S,4aR,6R,9Z,11R,12R,12aR)-1,3,4,4a,5,6,7,11,12,12a-decahydro-11,12-(isopropylidenedioxy)-3-(methoxymethoxy)-12a,13,13-trimethyl-4-methylene-6,10-methanobenzocyclodecen-8(2H)-one 
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• 208044-20-6 (3S,4aR,6R,9Z,11R,12R,12aR)-1,3,4,4a,5,6,7,11,12,12a-decahydro-11,12-(isopropylidenedioxy)-3-(methoxymethoxy)-9,12a,13,13-tetramethyl-4-methylene-6,10-methanobenzocyclodecen-8(2H)-one 
• 208044-42-2 (3S,4aR,6R,9S,10R,11S,12R,12aR)-ddoecahydro-9,10-dihydroxy-11,12-(isopropylidenedioxy)-3-(methoxymethoxy)-12a,13,13-trimethyl-4-methylene-6,10-methanobenzocyclodecen-8(2H)-one 
• 208044-48-8 (3S,4aR,6R,9S,10R,11S,12R,12aR)-dodecahydro-9,10-dihydroxy-11,12-(isopropylidenedioxy)-3-(methoxymethoxy)-9,12a,13,13-tetramethyl-4-methylene-6,10-methanobenzocyclodecen-8(2H)-one 
• 208044-47-7 (3S,4aR,6R,8R,9R,10R,11S,12R,12aR)-dodecahydro-11,12-(isopropylidenedioxy)-3-(methoxymethoxy)-9,12a,13,13-tetramethyl-4-methylene-8-{[2-(trimethylsilyl)ethoxy]methoxy}-6,10-methanobenzocyclodecene-9,10(2H)-diol 
• 208044-44-4 (3S,4aR,6R,9R,10S,11S,12R,12aR)-tetradecahydro-11,12-(isopropylidenedioxy)-9,10-[(R)-(p-methoxybenzylidene)dioxy]-3-(methoxymethoxy)-12a,13,13-trimethyl-4-methylene-6,10-methanobenzocyclodecen-8-ol 
• 208044-29-5 (3S,4aR,6S,7S,9Z,11R,12R,12aR)-1,3,4,4a,5,6,7,11,12,12a-decahydro-7-hydroxy-11,12-(isopropylidenedioxy)-3-(methoxymethoxy)-12a,13,13-trimethyl-4-methylene-6,10-methanobenzocyclodecen-8(2H)-one benzoate 
• 208044-43-3 (3S,4aR,6R,9S,10R,11S,12R,12aR)-dodecahydro-11,12-(isopropylidenedioxy)-9,10-[(R)-(p-methoxybenzylidene)dioxy]-3-(methoxymethoxy)-12a,13,13-trimethyl-4-methylene-6,10-methanobenzocyclodecen-8(2H)-one 
• 208044-54-6 trimethyl-{2-[({(3S,4aR,6R,8R,9R,10S,11S,12R,12aR)-tetradecahydro-11,12-(isopropylidenedioxy)-9,10-[(R)-(p-methoxybenzylidene)dioxy]-3-(methoxymethoxy)-12a,13,13-trimethyl-4-methylene-6,10-methanobenzocyclodecen-8-yl}oxy)methoxy]ethyl}silane 
• 208044-45-5 (3S,4aR,6R,8R,9R,10S,11S,12R,12aR)-dodecahydro-11,12-(isopropylidenedioxy)-3-(methoxymethoxy)-12a,13,13-trimethyl-4-methylene-8-{[2-(trimethylsilyl)ethoxy]methoxy}-6,10-methanobenzocyclodecene-9,10(2H)-diol 

Related news

Stereoselective synthesis of an advanced taxusin (cas 19605-80-2) intermediate: an application of the type 2 intramolecular Diels–Alder reaction☆08/25/2019

Stereoselective synthesis of an advanced taxusin intermediate is described. The key step is the successful application of the type 2 intramolecular Diels–Alder (IMDA) reaction for the assembly of the tricyclic core of this natural product.detailed

Relevant articles and documents

Enantioselective total synthesis of (+)-taxusin

For the total synthesis of (+)-taxusin, the AC-ring fragment 8 was prepared from an optically active 2-bromo-3-siloxycyclohexenecarbacetal 5 via 4 steps and was converted to the dienol silyl ether 13. The thus-obtained 13 underwent B-ring cyclization in the presence of Me2AlOTf to produce the ABC endo-tricarbocycle 14 having C9α, C10β-substituents, which was converted to the cyclopropyl ketone 21a. Introduction of C19 methyl via reductive cleavage of the cyclopropane ring under Birch conditions and successive in situ treatment of the resulting enol with methanol gave the C3α-protonated ketone 24. Next, 24 was converted to the allylsilane 29, which was then oxidized with m-CPBA to produce the fully functionalized taxusin carbon skeleton. Finally, removal of the silyl protecting groups followed by acetylation completed the total synthesis of (+)-taxusin.

Enantiospecific total synthesis of natural (+)-taxusin. 2. Functionalization of the A-ring and arrival at the target

A total synthesis of (+)-taxusin (1) has been realized by virtue of the development of a practical route for complete functionalization of the A ring. To achieve this goal, it proved necessary to devise a strategy that would enable chemical transformation