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4-Aminobenzoic acid



4-Aminobenzoic acid
IUPAC name 4-aminobenzoic acid
Other names para-Aminobenzoic acid
p-Aminobenzoic acid
PABA
Vitamin Bx
Bacterial vitamin H1
Identifiers
CAS number 150-13-0
PubChem 978
SMILES C1=CC(=CC=C1C(=O)O)N
Properties
Molecular formula C7H7NO2
Molar mass 137.136
Appearance white crystals
Density 1.374 g/mL
Melting point

187-189 °C

Solubility in water 1 g/170 mL (25 °C)
1 g/90 mL (90 °C)
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

4-Aminobenzoic acid (also known as para-aminobenzoic acid or PABA) is an organic compound with the molecular formula C7H7NO2. PABA is a white crystalline substance that is only slightly soluble in water. It consists of a benzene ring substituted with an amino group and a carboxylic acid.

Additional recommended knowledge

Contents

Functions

Organic

PABA is an essential nutrient for some bacteria and is sometimes called Vitamin Bx[1]. However, PABA is not essential to human health, and is therefore not officially classified as a vitamin. Although humans lack the ability to synthesize folate from PABA, it is sometimes marketed as an essential nutrient under the premise that it can stimulate intestinal bacteria.

PABA is an intermediate in bacterial synthesis of folate. Sulfonamides are chemically similar to PABA, and their antibacterial activity is due to their ability to interfere with conversion of PABA to folate by dihydropteroate synthetase, and subsequent utilization, by bacteria.

Industrial

In the past, PABA has been widely used as a UV filter in sunscreen formulations. However, there have been inconclusive studies on whether it increases the formation of a particular DNA defect in human cells, thus increasing the risk of skin cancer.[2] Currently, safer and more effective derivatives of PABA, such as octyl dimethyl PABA, are more commonly used.

The potassium salt is used as a drug against fibrotic skin disorders under the trade name POTABA.[3] PABA is also occasionally used in pill form by sufferers of Irritable bowel syndrome to treat the associated gastrointestinal symptoms.

PABA also finds use in the manufacture of esters, folic acid, and azo dyes.

See also

  • Aminomethylbenzoic acid

References

  1. ^ Para-aminobenzoic acid poisoning. National Institute of Health: National Library of Medicine (2007). Retrieved on 2007-06-19.
  2. ^ P. J. Osgood; S. H. Moss, D. J. Davies (1982). "The sensitization of near-ultraviolet radiation killing of mammalian cells by the sunscreen agent para-aminobenzoic acid". Journal of Investigative Dermatology 79 (6): 354-357.
  3. ^ Compound Summary on PubChem. PubChem. National Institute of Health: National Library of Medicine (2006). Retrieved on 2006-04-05.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "4-Aminobenzoic_acid". A list of authors is available in Wikipedia.
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