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4-(Carboxymethylamino)-2-hydroxybenzoic acid

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Identification
Molecular formula
C8H9NO4
CAS number
119-31-5
IUPAC name
4-[amino(carboxy)methyl]-2-hydroxy-benzoic acid
State
State
At room temperature, this compound is typically in a solid state. It is often stored in airtight containers to prevent absorption of moisture from the air.
Melting point (Celsius)
238.00
Melting point (Kelvin)
511.15
Boiling point (Celsius)
500.00
Boiling point (Kelvin)
773.15
General information
Molecular weight
181.16g/mol
Molar mass
181.1570g/mol
Density
1.6142g/cm3
Appearence

4-(Carboxymethylamino)-2-hydroxybenzoic acid typically appears as a white to off-white crystalline powder. It may sometimes be slightly hygroscopic, depending on the degree of purity and specific crystal structure.

Comment on solubility

Solubility of 4-[amino(carboxy)methyl]-2-hydroxy-benzoic acid

The solubility of 4-[amino(carboxy)methyl]-2-hydroxy-benzoic acid (C8H9NO4) is influenced by its functional groups and overall polarity. This compound contains both an amino group and a carboxylic acid, which can engage in hydrogen bonding with water, enhancing its solubility in aqueous solutions.

Key Factors Affecting Solubility:

  • Polarity: The presence of the –NH2 and –COOH groups increases the polarity, allowing for greater interaction with polar solvents like water.
  • Hydrogen Bonding: The ability to form hydrogen bonds plays a significant role in solubility. The –OH and –COOH groups can donate and accept hydrogen bonds, facilitating solvation.
  • pH Dependence: The solubility may vary with pH due to the ionization of the carboxylic acid group, which can become deprotonated in basic solutions, further increasing solubility.

As a result, one can expect that 4-[amino(carboxy)methyl]-2-hydroxy-benzoic acid will have considerable solubility in water, especially under neutral to alkaline conditions, where the ionization enhances its ability to dissolve. The intricate balance of functional groups and their interactions with different solvents leads to its complex solubility behavior, making it a compound of interest in various chemical formulations.

Interesting facts

4-[Amino(carboxy)methyl]-2-hydroxy-benzoic acid

4-[Amino(carboxy)methyl]-2-hydroxy-benzoic acid, commonly known as p-aminobenzoic acid (PABA), is a fascinating compound that holds a unique position in both biochemistry and industrial applications. Here are some intriguing aspects:

  • Biological Importance: PABA is a natural substance found in various foods and is a para-aminobenzoic acid derivative. It plays a critical role as a precursor in the biosynthesis of folate (vitamin B9), which is vital for cell growth and metabolism.
  • Sun Protection: One of the most popular uses of PABA has been in sunscreens, where it acts as a sunscreen agent by absorbing UV light. This makes it particularly useful in protecting the skin from sunburn.
  • Historical Context: PABA has been extensively studied in the mid-20th century for its potential benefits in treating certain skin conditions and enhancing the therapeutic effectiveness of some medications.
  • Functions in the Body: Aside from its role in folate synthesis, PABA is also known to contribute to the formation of red blood cells and can have a role in the health of the digestive system.
  • Cosmetic Applications: In addition to its use in sunscreens, PABA is also used in various cosmetic formulations for its moisturizing properties and skin conditioning effects.

Despite some controversies regarding its safety, particularly when used in high concentrations in sunscreens, the importance of PABA in both biological systems and commercial products cannot be overstated. As a chemistry student or scientist, exploring the diverse roles of this compound opens up exciting avenues for research and application.

Synonyms
134052-66-7
(RS)-4-Carboxy-3-hydroxyphenylglycine
4-[amino(carboxy)methyl]-2-hydroxybenzoic acid
(RS)-4C3HPG
Benzeneacetic acid, a-amino-4-carboxy-3-hydroxy-
CHEMBL444589
4-(Amino(carboxy)methyl)-2-hydroxybenzoic acid
M725GQ103A
4-Chpgly
(RS)-4C3H-PG
4-Carboxy-3-hydroxyphenylglycine
UNII-M725GQ103A
alpha-Amino-4-carboxy-3-hydroxybenzeneacetic acid
(+-)-alpha-Amino-4-carboxy-3-hydroxybenzeneacetic acid
Benzeneacetic acid, alpha-amino-4-carboxy-3-hydroxy-
SCHEMBL12648353
CHEBI:93904
DTXSID60928397
Benzeneacetic acid, alpha-amino-4-carboxy-3-hydroxy-, (+-)-
HMS3266G05
HMS3266G09
HMS3411E05
HMS3675E05
BDBM50030628
AKOS024457427
HY-100840A
(+/-)-4-carboxy-3-hydroxyphenylglycine
4-(Amino(carboxy)methyl)-2-hydroxybenzoicacid
4-(Amino-carboxy-methyl)-2-hydroxy-benzoic acid
L000843
SR-01000597631
4-CARBOXY-3-HYDROXYPHENYLGLYCINE, (+/-)-
SR-01000597631-1
BRD-A80383043-001-01-7
BRD-A80383043-001-03-3
Q27165658
4-(Amino-carboxy-methyl)-2-hydroxy-benzoic acid(S-4C3HPG)
BENZENEACETIC ACID, .ALPHA.-AMINO-4-CARBOXY-3-HYDROXY-
BENZENEACETIC ACID, .ALPHA.-AMINO-4-CARBOXY-3-HYDROXY-, (+/-)-