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Cinnamic acid

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Identification
Molecular formula
C9H8O2
CAS number
140-10-3
IUPAC name
3-phenylprop-2-enoic acid
State
State

Cinnamic acid is typically found as a solid at room temperature. It crystallizes easily and maintains a stable solid form under standard conditions.

Melting point (Celsius)
133.00
Melting point (Kelvin)
406.00
Boiling point (Celsius)
300.00
Boiling point (Kelvin)
573.00
General information
Molecular weight
148.16g/mol
Molar mass
148.1580g/mol
Density
1.2470g/cm3
Appearence

Cinnamic acid appears as white crystalline powder or colorless crystals. It may also be encountered in a slightly yellowish form. It has a characteristic odor and is sparingly soluble in water but readily soluble in many organic solvents.

Comment on solubility

Solubility of 3-phenylprop-2-enoic acid

3-phenylprop-2-enoic acid, also known as cinnamic acid, exhibits interesting solubility properties that are influenced by its structure. This compound is generally characterized by its:

  • Moderate solubility in water: Due to its carboxylic acid group, 3-phenylprop-2-enoic acid can form hydrogen bonds with water molecules, which allows for limited solubility.
  • Solubility in organic solvents: It is highly soluble in non-polar solvents such as ether, acetone, and ethanol. This is largely attributed to its phenyl ring, which enhances its hydrophobic characteristics.
  • Dependence on pH: The solubility of 3-phenylprop-2-enoic acid can significantly increase in alkaline conditions where it dissociates to form the cinnamate ion, making it more soluble in water.

In summary, while 3-phenylprop-2-enoic acid has limited solubility in water, its solubility dramatically improves in organic solvents and under certain pH conditions. As a result, understanding these solubility dynamics is crucial for its applications in various fields.

Interesting facts

Interesting Facts about 3-Phenylprop-2-enoic Acid

3-Phenylprop-2-enoic acid, commonly known as cinnamic acid, is a fascinating organic compound that plays a vital role in both nature and industry. Here are some intriguing aspects of this compound:

  • Natural Occurrence: Cinnamic acid is primarily found in the natural world, particularly in the bark of cinnamon trees, from which it derives its name. It contributes to the characteristic flavor and fragrance of cinnamon.
  • Usage in Flavoring and Fragrance: This compound is widely used as a flavoring agent in food products and as a fragrance in cosmetics and perfumes due to its sweet and warming scent.
  • Chemical Properties: Cinnamic acid is a key precursor in the synthesis of various compounds including polymers and pharmaceuticals, illustrating its significance in organic chemistry.
  • Biological Role: The compound has been studied for its potential health benefits, including antimicrobial and anti-inflammatory properties. Some research suggests it may have the ability to inhibit the growth of certain pathogens.
  • Industrial Importance: Cinnamic acid serves as a building block in the manufacture of plastics, resins, and dyes, showcasing its versatility beyond culinary applications.
  • Synthetic Reactions: It is often synthesized using the Knoevenagel condensation, demonstrating the efficient methods by which chemical compounds can be created in the lab.

Overall, 3-phenylprop-2-enoic acid is more than just a simple compound; its multifaceted nature and applications highlight the intricate connections between chemistry, nature, and industry. As a chemistry student or scientist exploring this compound, one cannot help but appreciate its role in both traditional uses and modern advancements.

Synonyms
2-Propenoic acid, 3-phenyl-
3-Phenyl-2-propenoic acid
Heparin, lithium salt
Cinnamylic acid
Kyselina skoricove
Acidum cinnamylicum
(2Z)-3-phenylprop-2-enoic acid
NSC 9189
Benzenepropenoic acid
Benzylideneacetic acid
Cinnamic acid (natural)
.beta.-Phenylacrylic acid
3-Phenylacrylic acid; beta-Phenylacrylic acid
DTXSID40110056
cinnamoic acid
EINECS 210-708-3
cinnamoyl alcohol
NSC 623441
BRN 0507757
3-Phenyl-2-propenoic Acid; 3-Phenylacrylic Acid; NSC 623441; NSC 9189; Phenylacrylic Acid; ss-Phenylacrylic Acid
AI3-00891
Zimtsaeure [German]
(E/Z)-cinnamic acid
Styrene Carboxylic Acid
Kyselina skoricove [Czech]
SCHEMBL5814771
AAA10294
AKOS016890705
DB-003617
Q57826855