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Naproxen

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Identification
Molecular formula
C14H14O3
CAS number
22204-53-1
IUPAC name
2-ethyl-2-(1-naphthyl)butanoic acid
State
State

Naproxen is in a solid state at room temperature.

Melting point (Celsius)
153.00
Melting point (Kelvin)
426.00
Boiling point (Celsius)
215.00
Boiling point (Kelvin)
488.00
General information
Molecular weight
230.26g/mol
Molar mass
230.2620g/mol
Density
1.1810g/cm3
Appearence

Naproxen appears as a white or almost white, crystalline powder. It is practically insoluble in water, soluble in alcohol and in methylene chloride. It is a tasteless and odorless substance that typically forms as fine crystalline particles.

Comment on solubility

Solubility of 2-ethyl-2-(1-naphthyl)butanoic acid

2-ethyl-2-(1-naphthyl)butanoic acid, a compound with a complex structure, exhibits notable solubility characteristics. Its solubility can be influenced by multiple factors, including:

  • Polarity: The presence of the carboxylic acid functional group provides some polarity, allowing the compound to engage in hydrogen bonding with solvents.
  • Hydrophobic Nature: The naphthyl group contributes to the overall hydrophobic character of the molecule, potentially reducing solubility in polar solvents like water.
  • Solvent Interaction: It has been observed that 2-ethyl-2-(1-naphthyl)butanoic acid is more soluble in organic solvents such as ethanol, ether, and other non-polar or slightly polar solvents.

Due to its unique structure:

  • In water: The compound exhibits low solubility, which can be attributed to its hydrophobic portions that resist interaction with water molecules.
  • In non-polar solvents: It tends to dissolve much better, displaying an affinity for solvents that complement its hydrophobic regions.

In summary, while 2-ethyl-2-(1-naphthyl)butanoic acid is not highly soluble in water, it shows a significant degree of solubility in organic solvents. This characteristic is vital for its applications in pharmaceuticals and organic chemistry, enabling it to effectively participate in various chemical processes.

Interesting facts

Interesting Facts about 2-ethyl-2-(1-naphthyl)butanoic Acid

2-ethyl-2-(1-naphthyl)butanoic acid, also known as Nabumetone, is a fascinating compound with a variety of applications in medicinal chemistry.

Medicinal Uses

This compound is primarily recognized for its role as a non-steroidal anti-inflammatory drug (NSAID). Some key points include:

  • Pain Relief: It is used to alleviate pain and inflammation, especially useful for conditions like arthritis.
  • Mechanism of Action: Nabumetone works by inhibiting the enzyme cyclooxygenase (COX), which is pivotal in the synthesis of prostaglandins—molecules that promote inflammation.
  • Prodrug: It is classified as a prodrug, meaning that the compound itself is inactive but gets converted into an active form within the body.

Chemical Characteristics

The compound features a unique structural design that contributes to its effectiveness:

  • Steric Hindrance: The bulky 1-naphthyl group provides steric hindrance that enhances selectivity for COX enzymes.
  • Acidity: The carboxylic acid functional group is crucial for its pharmacological activity.

Safety and Side Effects

While Nabumetone is effective, it's important to note:

  • Gastrointestinal Risks: Similar to other NSAIDs, it may cause gastrointestinal irritation, ulcers, or bleeding.
  • Cardiovascular Concerns: Prolonged use may be associated with cardiovascular risks; thus, monitoring is recommended.

Cultural Impact

The compound has achieved recognition beyond the lab:

  • Brand Names: It is marketed under various brand names, highlighting its widespread acceptance in clinical practice.
  • Research Interest: Ongoing studies focus on optimizing its properties and exploring potential new therapeutic applications.

In conclusion, 2-ethyl-2-(1-naphthyl)butanoic acid stands as an important compound in the pharmaceutical realm, symbolizing the intersection of chemistry and healthcare. Its intricate design reflects how molecular structure uplifts pharmacological efficacy, making it a compelling subject for both seasoned chemists and curious minds alike.

Synonyms
Nafcaproic acid
1085-91-2
Nafcapronsaeure
Acido nafcaproico
Acide nafcaproique
Nafcaproic acid [INN]
Acidum nafcaproicum
DA 808
alpha,alpha-Diethyl-1-naphthaleneacetic acid
Acide nafcaproique [INN-French]
Acido nafcaproico [INN-Spanish]
Acidum nafcaproicum [INN-Latin]
Ethyl 2-(1-naphtyl)buttersaeure
DA-808
UNII-0FI451I3D5
BRN 2582415
alpha,alpha-Diethyl-1-naphthalinessigsaeure
0FI451I3D5
Acido alpha,alpha-dietil-1-naftilacetico [Italian]
Acido alpha,alpha-dietil-1-naftilacetico
DTXSID40148576
1-NAPHTHALENEACETIC ACID, alpha,alpha-DIETHYL-
.ALPHA.,.ALPHA.-DIETHYL-1-NAPHTHALENEACETIC ACID
Acide nafcaproique (INN-French)
Acido nafcaproico (INN-Spanish)
Acidum nafcaproicum (INN-Latin)
Nafcaproate
DTXCID8071067
2-ethyl-2-(naphthalen-1-yl)butanoic acid
2-ethyl-2-naphthalen-1-ylbutanoic acid
2-Ethyl-2-(naphthalen-1-yl)butanoicacid
SCHEMBL2109457
CHEMBL2106771
AKOS016009303
DB-365075
NS00123825
Q27236716