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Cinnamic acid, p-hydroxycyano-

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Identification
Molecular formula
C10H7NO3
CAS number
14246-50-7
IUPAC name
2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
State
State

At room temperature, 2-Cyano-3-(4-hydroxyphenyl)prop-2-enoic acid exists in a solid state.

Melting point (Celsius)
222.00
Melting point (Kelvin)
495.15
Boiling point (Celsius)
433.20
Boiling point (Kelvin)
706.35
General information
Molecular weight
189.17g/mol
Molar mass
189.1840g/mol
Density
1.3820g/cm3
Appearence

2-Cyano-3-(4-hydroxyphenyl)prop-2-enoic acid appears as a crystalline solid, which can range in color from a yellowish to brownish hue depending on the purity and exact conditions. These crystals may exhibit a needle-like or powder form under microscopic examination.

Comment on solubility

Solubility of 2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid (C10H7NO3)

The solubility of 2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid is influenced by its unique molecular structure.

Factors Affecting Solubility

  • Polarity: The presence of both cyano and hydroxy functional groups contributes to certain polar characteristics, which typically enhance solubility in polar solvents.
  • Hydrogen Bonding: The hydroxyl group can engage in hydrogen bonding, increasing solubility in protic solvents, such as water and alcohols.
  • pH Dependency: As a carboxylic acid, its solubility can be affected by the pH of the solution; increased acidity can enhance solvation of the anionic form.

It is important to note that while 2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid exhibits some solubility in polar solvents, it may show limited solubility in nonpolar solvents due to its polar nature. As a result, this compound generally demonstrates a higher affinity for aqueous environments:

  • Soluble in water at moderate levels
  • Significantly less soluble in organic solvents such as hexane and toluene

In conclusion, the solubility of 2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid is relatively favorable in polar solvents due to its polar functional groups and ability to participate in hydrogen bonding. Understanding its solubility profile is crucial for applications in various chemical and biological contexts.

Interesting facts

Interesting Facts about 2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid

2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid, commonly known for its structural features and functional applications, is a fascinating compound in the realm of organic chemistry.

Chemical Properties

This compound demonstrates unique chemical properties that can be attributed to its:

  • Cyano group: The presence of the cyano (–C≡N) group contributes to the compound's reactivity, allowing it to participate in various chemical reactions, such as nucleophilic substitutions.
  • Hydroxyl group: The hydroxyl (–OH) group is instrumental in the compound's ability to form hydrogen bonds, which enhances its solubility and biological activity.
  • Conjugated system: The double bond in its structure creates a conjugated system, leading to interesting electronic properties that can be exploited in photochemical applications.

Biological Significance

In addition to its chemical attributes, 2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid has garnered attention for its potential biological activities. Key areas of interest include:

  • Antioxidant properties: Compounds like this often exhibit antioxidant activity, neutralizing free radicals and contributing to health benefits.
  • Potential pharmaceutical applications: Research suggests this compound may be useful in the development of new drugs, especially in treating conditions related to oxidative stress.
  • Role in organic synthesis: This compound serves as an intermediate in synthesizing various organic molecules, thus playing a critical role in chemical research and industrial applications.

Applications

2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid is of particular interest in:

  • Material science: Due to its unique electronic and optical properties, it can be utilized in the development of advanced materials.
  • Synthetic chemistry: It serves as a precursor for various derivatives that find use in agrochemicals and pharmaceuticals.
  • Chemical sensors: Its ability to interact with specific ions and molecules offers potential applications in the field of biosensors.

Overall, the exploration and study of 2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid offer exciting possibilities for future research, enhancing our understanding of organic compounds and their multifaceted applications in science and industry.

Synonyms
28166-41-8
alpha-Cyano-4-hydroxycinnamate
2-cyano-4-hydroxycinnamate
4-hydroxy-alpha-cyanocinnamate
NSC 173138
2-Cyano-3-(4-hydroxyphenyl)acrylic acid
EINECS 248-879-1
NL5EEM9E2G
a-Cyano-4-hydroxycinnamic acid
2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
Spectrum_001499
2-Propenoic acid, 2-cyano-3-(4-hydroxyphenyl)-
4-CIN
NSC-173138
2-Cyano-3-(4-hydroxyphenyl)-2-propenoic Acid; 4-Hydroxy-alpha-cyanocinnamic Acid; NSC 173138; alpha-Cyano-4-hydroxycinnamic Acid;
CHC
Spectrum2_001947
Spectrum3_000730
Spectrum4_000334
UNII-NL5EEM9E2G
KBioGR_000707
KBioSS_001979
DivK1c_000219
SPBio_002013
alpha-cyano4-hydroxycinnamic acid
GTPL11300
KBio1_000219
KBio2_001979
KBio2_004547
KBio2_007115
KBio3_001480
NINDS_000219
4-hydroxy-alpha-cyanocinnamic acid
DTXSID501018295
HMS3741O15
HMS3867D03
AKOS028110673
2-cyano-3-(4-hydroxyphenyl) acrylic acid
DB-047349
2-Cyano-3-(4-hydroxy-phenyl)-acrylic acid
C1768
NS00015227