155588-14-0 Usage
Chemical compound
A precursor to paclitaxel, a widely used chemotherapy drug.
Source
Derived from the Pacific yew tree (Taxus brevifolia).
Research focus
Extensive research due to its potential anti-cancer properties.
Chemical structure
Unique structure that makes it valuable in the synthesis of paclitaxel and other taxane-based drugs.
Cancer cell inhibition
Ability to inhibit the growth of cancer cells.
Low toxicity
Makes it a promising candidate for the development of new cancer treatments.
Medical applications
Studied for potential use in treating other medical conditions, such as cardiovascular diseases.
Taxol production
Serves as a key intermediate in the semi-synthesis of Taxol (paclitaxel).
Taxane family
Belongs to the taxane family of natural products, which are known for their potent anti-cancer activity.
Biosynthesis
Produced in the needles, bark, and wood of the Pacific yew tree.
Extraction method
Obtained through a complex extraction process from the yew tree, which is both time-consuming and resource-intensive.
Semi-synthesis
Can be converted into paclitaxel through a series of chemical reactions, making it a more sustainable and efficient source for drug production.
Structural features
Contains a complex tetracyclic ring system with multiple functional groups, including hydroxyl and acetate moieties.
Stereochemistry
Exhibits multiple stereocenters, which contribute to its biological activity and make its synthesis challenging.
Patent protection
The initial patent for the use of 13-deoxybaccatin III in the synthesis of paclitaxel has expired, allowing for further research and development by other organizations.
Check Digit Verification of cas no
The CAS Registry Mumber 155588-14-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,5,5,8 and 8 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 155588-14:
(8*1)+(7*5)+(6*5)+(5*5)+(4*8)+(3*8)+(2*1)+(1*4)=160
160 % 10 = 0
So 155588-14-0 is a valid CAS Registry Number.
155588-14-0Relevant articles and documents
Formal total synthesis of (-)-taxol through Pd-catalyzed eight-membered carbocyclic ring formation
Hirai, Sho,Utsugi, Masayuki,Iwamoto, Mitsuhiro,Nakada, Masahisa
, p. 355 - 359 (2015/02/19)
A formal total synthesis of (-)-taxol by a convergent approach utilizing Pd-catalyzed intramolecular alkenylation is described. Formation of the eight-membered carbocyclic ring has been a problem in the convergent total synthesis of taxol but it was solved by the Pd-catalyzed intramolecular alkenylation of a methyl ketone affording the cyclized product in excellent yield (97 %), indicating the high efficiency of the Pd-catalyzed intramolecular alkenylation. Rearrangement of the epoxy benzyl ether through a 1,5-hydride shift, generating the C3 stereogenic center and subsequently forming the C1-C2 benzylidene, was discovered and utilized in the preparation of a substrate for the Pd-catalyzed reaction.
METHOD FOR SEPARATION AND PURIFICATION OF 13-DEHYDROXYBACCATIN III AND 10-DEACETYLPACLITAXEL FROM TAXANS-CONTAINING MATERIALS
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Page/Page column 6, (2008/06/13)
This invention is directed to a method for efficiently separating and purifying 13-dehydroxybaccatin III and 10-deacetylpaclitaxel with a high purity of 90% or higher purity, preferably 99.5% or higher purity, from taxane-containing materials such as Taxus species, and the thusly obtained highly pure 13-dehydroxybaccatin III and 10-deacetylpaclitaxel can be used as semi-synthetic precursors of paclitaxel and/or docetaxel that are anticancer agents.
Novel chemistry of taxol: Retrosynthetic and synthetic studies
Nicolaou,Nantermet,Ueno,Guy
, p. 295 - 296 (2007/10/02)
10-Deacetyl baccatin III was used in the synthesis of compounds, all of which were converted to Taxol via efficient synthetic pathways
