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Prephenic acid

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Identification
Molecular formula
C10H8O6
CAS number
126-49-8
IUPAC name
(3R,4R)-3-(1-carboxyvinyloxy)-4-hydroxy-cyclohexa-1,5-diene-1-carboxylic acid
State
State

Prephenic acid is typically solid at room temperature.

Melting point (Celsius)
200.00
Melting point (Kelvin)
473.15
Boiling point (Celsius)
-1.00
Boiling point (Kelvin)
-1.00
General information
Molecular weight
196.17g/mol
Molar mass
196.1490g/mol
Density
1.5000g/cm3
Appearence

Prephenic acid typically appears as a white, crystalline powder.

Comment on solubility

Solubility of (3R,4R)-3-(1-carboxyvinyloxy)-4-hydroxy-cyclohexa-1,5-diene-1-carboxylic acid

Understanding the solubility properties of (3R,4R)-3-(1-carboxyvinyloxy)-4-hydroxy-cyclohexa-1,5-diene-1-carboxylic acid is crucial for its application in various chemical and biological systems.

This compound contains multiple functional groups that significantly influence its solubility:

  • Carboxylic Acids: The presence of carboxylic acid groups generally enhances solubility in polar solvents, especially water, due to the ability to form hydrogen bonds.
  • Hydroxyl Groups: The hydroxy group also contributes to increased solubility in polar environments, aiding in solvation and enhancing interactions with water molecules.
  • Polarity: The overall polarity of the molecule suggests a favorable solubility profile in aqueous solutions.

However, the presence of additional structural features may introduce complexities. For instance:

  • The molecular structure could lead to intramolecular interactions, potentially limiting the degree to which it can interact with solvent molecules.
  • The stability of the compounds in solution may vary based on pH and temperature, which can affect dissociation and ionization.

In summary, the solubility of (3R,4R)-3-(1-carboxyvinyloxy)-4-hydroxy-cyclohexa-1,5-diene-1-carboxylic acid is likely to be high in polar solvents, particularly water, owing to its hydrophilic functional groups, yet the specific dynamics can change depending on environmental conditions.

Interesting facts

Interesting Facts about (3R,4R)-3-(1-carboxyvinyloxy)-4-hydroxy-cyclohexa-1,5-diene-1-carboxylic acid

The compound (3R,4R)-3-(1-carboxyvinyloxy)-4-hydroxy-cyclohexa-1,5-diene-1-carboxylic acid is a fascinating member of the chemical landscape, particularly known for its biological significance. Here are some intriguing points about this compound:

  • Structural Complexity: This compound features a unique cyclic structure that emphasizes the importance of stereochemistry, shown in the (3R,4R) designation, indicating its chiral centers. This highlights how the spatial arrangement of atoms can profoundly influence a compound's chemical behavior.
  • Biological Relevance: Compounds like this often play crucial roles in various biological pathways, including metabolism. Understanding its structure can shed light on its functionality in biological systems.
  • Synthesis: The ability to synthesize such compounds in the lab showcases the innovative techniques chemists use, including organic synthesis pathways that can include coupling reactions and functional group transformations.
  • Historical Context: Compounds similar to this one may have historical significance in pharmacology, potentially serving as precursors or analogs to drugs that treat various ailments.
  • Environmental Impact: Studying compounds like this can also help in understanding their potential roles in ecological systems and their impact on the environment.

In summary, the multifaceted nature of (3R,4R)-3-(1-carboxyvinyloxy)-4-hydroxy-cyclohexa-1,5-diene-1-carboxylic acid encapsulates the very essence of chemistry—where structure meets function, and intricate interactions pave the way for biological processes. As a representative of complex organic molecules, it inspires ongoing research and discovery in both academic and industrial settings.

Synonyms
chorismic acid
617-12-9
Acid, Chorismic
GI1BLY82Y1
(3R,4R)-3-(1-carboxyethenoxy)-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
CHORISMIC ACID [MI]
CHEBI:17333
DTXSID50210697
(3R,4R)-3-[(1-carboxyethenyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
1,5-Cyclohexadiene-1-carboxylic acid, 3-((1-carboxyethenyl)oxy)-4-hydroxy-, (3R-trans)-
(3R,4R)-3-((1-CARBOXYETHENYL)OXY)-4-HYDROXY-1,5-CYCLOHEXADIENE-1-CARBOXYLIC ACID
(3R,4R)-3-[(1-carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
(3R-trans)-3-((1-carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid
(3R,4R)-3-((1-carboxyethenyl)oxy)-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
(3R,4R)-3-((1-carboxyvinyl)oxy)-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
1,5-Cyclohexadiene-1-carboxylic acid, 3-[(1-carboxyethenyl)oxy]-4-hydroxy-, (3R-trans)-
DTXCID80133188
chorismate
Chorismic acid from Enterobacter aerogenes
UNII-GI1BLY82Y1
Chorisminsaure
ISJ
trans-3-([1-Carboxyethenyl]oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid
55508-12-8
bmse000075
bmse000998
SCHEMBL812019
HY-N10479
C00251
G91244
Q423531
Chorismic acid from Enterobacter aerogenes, >=80%
197FEC28-FF63-4FD2-8A56-AA36745A2338
(3R,4R)-3-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
(3R,4R)-3-[(1-Carboxyethenyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylate
1,5-Cyclohexadiene-1-carboxylic acid, 3-[(1-carboxyethenyl)oxy]-4-hydroxy-, (3R,4R)-
1,5-Cyclohexadiene-1-carboxylic acid, 3-[(1-carboxyvinyl)oxy]-4-hydroxy-, (3R-trans)-
1,5-Cyclohexadiene-1-carboxylic acid,3- [(1-carboxyethenyl)oxy]-4-hydroxy-,(3R,4R)-
(-)-Chorismic acid (3R-trans)-3-(1-Carboxyvinyloxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid