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Atorvastatin

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Identification
Molecular formula
C33H35FN2O5
CAS number
134523-03-8
IUPAC name
(2S)-2-[[(3R)-8-hydroxy-3-methyl-1-oxo-isochromane-7-carbonyl]amino]-3-phenyl-propanoic acid
State
State

At room temperature, atorvastatin is solid.

Melting point (Celsius)
159.00
Melting point (Kelvin)
432.15
Boiling point (Celsius)
470.00
Boiling point (Kelvin)
743.15
General information
Molecular weight
558.65g/mol
Molar mass
558.6470g/mol
Density
1.2000g/cm3
Appearence

Atorvastatin is a white to off-white crystalline powder, which is practically insoluble in aqueous solutions of pH 4 and below. It is very slightly soluble in water, soluble in methanol, and freely soluble in alcohol.

Comment on solubility

Solubility Overview

The compound (2S)-2-[[(3R)-8-hydroxy-3-methyl-1-oxo-isochromane-7-carbonyl]amino]-3-phenyl-propanoic acid displays notable characteristics regarding its solubility, primarily influenced by its functional groups and structural complexity.

Factors Affecting Solubility

Several factors affect the solubility of this compound:

  • Polar Functional Groups: The presence of hydroxyl (-OH) and carboxylic acid (-COOH) groups often enhances solubility in water due to their ability to engage in hydrogen bonding.
  • Molecular Weight: The overall molecular weight can impact solubility; larger molecules may exhibit lower solubility compared to smaller ones.
  • Hydrophobic Elements: The phenyl group and iso-structural units may contribute to hydrophobic interactions, potentially decreasing solubility in polar solvents.

Solubility Characteristics

Considering these structural features, the solubility profile can be summarized as follows:

  • This compound is expected to have moderate solubility in polar solvents, particularly water, due to its ionic and polar functional groups.
  • In contrast, it may show limited solubility in non-polar solvents due to the presence of hydrophobic structural components.

In conclusion, while the unique structure of (2S)-2-[[(3R)-8-hydroxy-3-methyl-1-oxo-isochromane-7-carbonyl]amino]-3-phenyl-propanoic acid suggests a propensity for solubility in polar media, the intricate balance of hydrophilic and hydrophobic portions warrants careful consideration in various solvent systems.

Interesting facts

Interesting Facts about (2S)-2-[[(3R)-8-hydroxy-3-methyl-1-oxo-isochromane-7-carbonyl]amino]-3-phenyl-propanoic acid

This compound is a fascinating representative of the amino acid class, exhibiting unique structural features that contribute to its biochemical properties. Here are some engaging insights:

Key Characteristics:

  • Stereochemistry: The specific stereochemistry of the molecule, especially the (2S) and (3R) configurations, is crucial. Stereochemistry plays a significant role in biological activity, influencing how the molecule interacts with enzymes and receptors in biological systems.
  • Natural Product Derivative: The presence of an iso-chromane moiety in the structure suggests a potential link to naturally occurring compounds, many of which exhibit interesting pharmacological properties.
  • Hydroxyl Group: The hydroxyl group at the 8-position is significant for hydrogen bonding, which can affect the solubility and bioavailability of the compound in therapeutic applications.

Applications and Biological Relevance:

This compound is likely to be studied in the context of drug development due to its potential therapeutic effects. For instance:

  • Compounds with similar structures have been recognized for their actions as antioxidants and anti-inflammatory agents.
  • There is ongoing research regarding the influence of such structures on molecular signaling pathways, possibly leading to innovations in treating various diseases.

Research Insights:

As a chemist or a student, it’s exciting to note that the exploration of amino acid derivatives like this one not only furthers our understanding of organic chemistry but also opens doors to potential medicinal breakthroughs.
The minute details in the molecular structure can provide clues to the compound's biological activity, showcasing the elegant interface of chemistry and biology.

In summary, this compound represents the intricate relationship between molecular structure and function, exemplifying how studying such compounds can lead to important discoveries in science and medicine.

Synonyms
OCHRATOXIN B
4825-86-9
CCRIS 5094
HSDB 3438
UNII-ECJ5WS94N2
ECJ5WS94N2
BRN 1300160
OCHRATOXIN B [MI]
OCHRATOXIN B [HSDB]
L-Phenylalanine, N-((3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl)-, (R)-
DTXSID1075301
CHEBI:141524
Alanine, N-((8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenyl-, (-)-
Alanine, N-[(8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl]-3-phenyl-, (-)-
L-Phenylalanine, N-(((3R)-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl)-
L-Phenylalanine, N-[(3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl]-, (R)-
ALANINE, N-((8-HYDROXY-3-METHYL-1-OXO-7-ISOCHROMANYL)CARBONYL)-3-PHENYL-, L-
N-[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]-L-phenylalanine
N-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl]carbonyl}-L-phenylalanine
(2S)-2-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]amino}-3-phenylpropanoic acid
ALANINE, N-[(8-HYDROXY-3-METHYL-1-OXO-7-ISOCHROMANYL)CARBONYL]-3-PHENYL-, L-
N-((3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl)-L-phenylalanine
N-((8-Hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl)carbonyl)phenylalanine
N-[(8-Hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl)carbonyl]phenylalanine
(2S)-2-(((3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl)amino)-3-phenylpropanoic acid
(R)-N-((3,4-DIHYDRO-8-HYDROXY-3-METHYL-1-OXO-1H-2-BENZOPYRAN-7-YL)CARBOXYL)PHENYLALANINE
(R)-N-[(3,4-DIHYDRO-8-HYDROXY-3-METHYL-1-OXO-1H-2-BENZOPYRAN-7-YL)CARBOXYL]PHENYLALANINE
2-((hydroxy(8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)methylidene)amino)-3-phenylpropanoic acid
2-{[hydroxy(8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)methylidene]amino}-3-phenylpropanoic acid
L-Phenylalanine, N-[[(3R)-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]-
N-(((3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl)carbonyl)-L-phenylalanine
(2S)-2-(((3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl)amino)-3-phenylpropanoate
(2S)-2-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]amino}-3-phenylpropanoate
DTXCID1040613
2-((8-Hydroxy-3-methyl-1-oxoisochroman-7-carbonyl)amino)-3-phenylpropionic acid
2-[(8-Hydroxy-3-methyl-1-oxoisochroman-7-carbonyl)amino]-3-phenylpropionic acid
2-((8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)formamido)-3-phenylpropanoic acid
2-[(8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)formamido]-3-phenylpropanoic acid
(R)-N-
Alanine, N((8hydroxy3methyl1oxo7isochromanyl)carbonyl)3phenyl, ()
LPhenylalanine, N((3,4dihydro8hydroxy3methyl1oxo1H2benzopyran7yl)carbonyl), (R)
daeyivctqufntm-abaiwwiysa-n
un3462
(2S)-2-[[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl]amino]-3-phenylpropanoic acid
Ochratoxin B(OTB)
Ochratoxin B 10 microg/mL in Acetonitrile
SCHEMBL455061
MSK7231
N-[(8-Hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromen-7-yl)carbonyl]phenylalanine #
MSK7231-100A
AKOS030242138
DA-66300
NS00094943
Ochratoxin B Solution in Acetonitrile, 100ug/mL
Q3880769
OTB