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Paclitaxel

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Identification
Molecular formula
C47H51NO14
CAS number
33069-62-4
IUPAC name
[(1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,16S,17R,18R,19S,22S,23S,25R)-16,17-diacetoxy-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-13-[(2R)-2-methylbutanoyl]oxy-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-22-yl] (2S)-2-hydroxy-2-methyl-butanoate
State
State
Paclitaxel is in solid state at room temperature, appearing as a white crystalline powder.
Melting point (Celsius)
213.00
Melting point (Kelvin)
486.15
Boiling point (Celsius)
196.00
Boiling point (Kelvin)
469.15
General information
Molecular weight
853.91g/mol
Molar mass
853.9080g/mol
Density
1.3502g/cm3
Appearence

Paclitaxel appears as a white to off-white crystalline powder. It is insoluble in water but widely soluble in organic solvents such as ethanol, methanol, and DMSO.

Comment on solubility

Solubility of the Compound

The solubility characteristics of the compound named [(1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,16S,17R,18R,19S,22S,23S,25R)-16,17-diacetoxy-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-13-[(2R)-2-methylbutanoyl]oxy-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-22-yl] (2S)-2-hydroxy-2-methyl-butanoate is quite intriguing due to its complex structure.

In general, the solubility of a compound can be influenced by several factors, including:

  • Polarity: The presence of hydroxyl groups typically enhances solubility in polar solvents like water.
  • Hydroxyl Groups: This compound has multiple hydroxyl (-OH) functionalities that suggest potential for good solubility in aqueous solutions.
  • Functional Groups: The presence of ester and acyl groups may influence both solubility and stability, possibly allowing it to dissolve better in organic solvents.
  • Molecular Structure: Its large and complex structure may limit solubility in common solvents, particularly at higher concentrations.

As a general rule, compounds that can engage in hydrogen bonding, like this one, tend to exhibit better solubility in water. However, due to the intricate nature of this molecule, its solubility may vary significantly with changes in temperature, solvent choice, and concentration.

In conclusion, while the expectation is for a degree of solubility due to its multiple functional groups, the extent will require empirical validation to determine the exact solubility profile. Such a nuanced balance makes it a subject of great interest for further exploration.

Interesting facts

Interesting Facts About the Compound

The compound known as (1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,16S,17R,18R,19S,22S,23S,25R)-16,17-diacetoxy-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-13-[(2R)-2-methylbutanoyl]oxy-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-22-yl] (2S)-2-hydroxy-2-methyl-butanoate is a fascinating example of complexity in organic chemistry. Here are several intriguing aspects:

  • Structural Complexity: This molecule represents a remarkable level of structural complexity, featuring multiple stereogenic centers and a rigid multicyle framework. Such structures can be challenging in both synthesis and analysis.
  • Natural Products: Many compounds with similar structural characteristics are often derived from natural sources, particularly plants. They might play crucial roles in biological activities like signaling pathways or defense mechanisms.
  • Bioactivity Potential: Compounds with extensive hydroxyl and acetoxy groups may exhibit interesting bioactivities. Research often explores their potential for antimicrobial, anti-inflammatory, or other pharmacological effects.
  • Syntheses and Applications: The intricate synthesis of such compounds may involve various synthetic strategies including multi-step processes and possibly asymmetric syntheses, showcasing the ingenuity required in modern organic chemistry labs.
  • Future Research: With the ever-growing field of medicinal chemistry, compounds like this one can pave the way for developing new therapeutic agents by modulating their functional groups and exploring derivatives.

As scientists and chemistry students delve into the world of complex compounds, such examples remind us of the incredible diversity found in chemical structures and their potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

Synonyms
protoveratrine A
Protoveratrin
Protalba
Protoveratrine
Protofecaterine A
Puroverine
143-57-7
NSC 7526
EINECS 205-602-9
XP343X1HJU
NSC 23865
NSC-23865
BRN 0077415
NSC-7526
NSC23865
PROTOVERATRINE A [MI]
CHEBI:8594
PROTOVERATRINE A [WHO-DD]
4-21-00-06845 (Beilstein Handbook Reference)
Cevane-3,4,6,7,14,15,16,20-octol, 4,9-epoxy-, 6,7-diacetate 3-(2-hydroxy-2-methylbutanoate) 15-(2-methylbutanoate), (3beta(S),4alpha,6alpha,7alpha,15alpha(R),16beta)-
Cevane-3-beta,4-beta,6-alpha,7-alpha,14,15-alpha-16-beta,20-octol, 4,9-epoxy-, 6,7-diacetate 3-((+)-2-hydroxy-2-methylbutyrate) 15-((-)-2-methylbutyrate)
(3beta(S),4alpha,6alpha,7alpha,15alpha(R),16beta)-4,9-Epoxycevane-3,4,6,7,14,15,16,20-octol 6,7-diacetate 3-(2-hydroxy-2-methylbutyrate) 15-(2-methylbutyrate)
Cevane-3beta,4beta,6alpha,7alpha,14,15alpha,16beta,20-octol, 4,9-epoxy-, 6,7-diacetate 3-((+)-2-hydroxy-2-methylbutyrate) 15-((-)-2-methylbutyrate)
(3.BETA.(S),4.ALPHA.,6.ALPHA.,7.ALPHA.,15.ALPHA.(R),16.BETA.)-4,9-EPOXYCEVANE-3,4,6,7,14,15,16,20-OCTOL 6,7-DIACETATE 3-(2-HYDROXY-2-METHYLBUTANOATE) 15-(2-METHYLBUTANOATE)
[(1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,16S,17R,18R,19S,22S,23S,25R)-16,17-diacetyloxy-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-13-[(2R)-2-methylbutanoyl]oxy-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-22-yl] (2S)-2-hydroxy-2-methylbutanoate
CEVANE-3,4,6,7,14,15,16,20-OCTOL, 4,9-EPOXY-, 6,7-DIACETATE 3-((2S)-2-HYDROXY-2-METHYLBUTANOATE) 15-((2R)-2-METHYLBUTANOATE), (3.BETA.,4.ALPHA.,6.ALPHA.,7.ALPHA.,15.ALPHA.,16.BETA.)-
Cevane-3,4,6,7,14,15,16,20-octol, 4,9-epoxy-, 6,7-diacetate 3-(2-hydroxy-2-methylbutanoate) 15-(2-methylbutanoate), (3.beta.(S),4.alpha.,6.alpha.,7.alpha.,15.alpha.(R),16.beta.)-
Cevane-3beta,4beta,6alpha,7alpha,14,15alpha,16beta,20-octol, 4,9-epoxy-, 6,7-diacetate 3-((+)-2-hydroxy-2-methylbutyrate) 15-((-)-2-methylbutyrate) (8CI)
PROTOVERINE 3-((+)-(2S)-2-HYDROXY-2-METHYLBUTYRATE) 6,7-DIACETATE 15-((-)-(2R)-2-METHYLBUTYRATE)
UNII-XP343X1HJU
DTXSID301009391
bmse000853
CHEMBL2105769
DTXCID801436222
Cevane-3,6,7,14,15,16,20-octol, 4,9-epoxy-, 6,7-diacetate 3-(2-hydroxy-2-methylbutanoate) 15-(2-methylbutanoate), [3.beta.(S),4.alpha.,6.alpha.,7.alpha.,15.alpha.(R),16.beta.]-
Cevane-3.beta.,6.alpha.,7.alpha.,14,15.alpha.,16.beta.,20-octol, 4,9-epoxy-, 6,7-diacetate 3-((+)-2-hydroxy-2-methylbutyrate) 15-((-)-2-methylbutyrate)
Cevane-3.beta.,6.alpha.,7.alpha.,14,15.alpha.,16.beta.,20-octol, 4,9-epoxy-, 6,7-diacetate, 3-((+)-2-hydroxy-2-methylbutyrate) 15-((-)-2-methylbutyrate)
WLN: T5 L6 J6 I6 G566 3CFG AO LNTJ BQ COVYQ2&1 F1 N1 RQ R1 TQ UOVY2&1 VQ A&OV1 B&OV1
MFCD00135586
FP76725
DA-57168
HY-105697
NS00008506
Q27108102
(3BETA(S),4ALPHA,6ALPHA,7ALPHA,15ALPHA(R),16BETA)-4,9-EPOXYCEVANE-3,4,6,7,14,15,16,20-OCTOL 6,7-DIACETATE 3-(2-HYDROXY-2-METHYLBUTANOATE) 15-(2-METHYLBUTANOATE)
(3S,4S,4AR,5R,6S,6aS,6bR,8R,8aR,9S,9aS,12S,15aS,15bS,16aR,16bS)-5,6-bis(acetyloxy)-4,6b,8,9-tetrahydroxy-9,12,16b-trimethyl-7-{[(2S)-2-methylbutanoyl]oxy}docosahydro-2H-4,16a-epoxybenzo[4,5]indeno[1,2-h]pyrido[1,2-b]isoquinolin-3-yl (2S)-2-hydroxy-2-m...
[diacetoxy-tetrahydroxy-trimethyl-[(2R)-2-methylbutanoyl]oxy-[?]yl] (2S)-2-hydroxy-2-methyl-butanoate
CEVANE-3,4,6,7,14,15,16,20-OCTOL, 4,9-EPOXY-, 6,7-DIACETATE 3-((2S)-2-HYDROXY-2-METHYLBUTANOATE) 15-((2R)-2-METHYLBUTANOATE), (3BETA,4ALPHA,6ALPHA,7ALPHA,15ALPHA,16BETA)-
Cevane-3,4,6,7,14,15,16,20-octol, 4,9-epoxy-, 6,7-diacetate 3-(2-hydroxy-2-methylbutanoate) 15-(2-methylbutanoate), (3beta(S),4alpha,6alpha,7alpha,15alpha(R),16beta)- (9CI)
Cevane-3,4,6,7,14,15,16,20-octol, 4,9-epoxy-, 6,7-diacetate 3-(2-hydroxy-2-methylbutanoate) 15-(2-methylbutanoate), (3beta(S),4alpha,6alpha,7alpha,15alpha(R),16beta)-(9CI)
Cevane-3,4,6,7,14,15,16,20-octol,4,9-epoxy-,6,7-diacetate 3-[(2S)-2-hydroxy-2-methylbutanoate]15-[(2R)-2-methylbutanoate],(3b,4a,6a,7a,15a,16b)-