4-Aminobenzoic acid
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| 4-Aminobenzoic acid | |
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| General | |
| Systematic name | 4-Aminobenzoic acid |
| Other names | para-Aminobenzoic acid p-Aminobenzoic acid PABA Vitamin Bx Bacterial vitamin H1 |
| Molecular formula | C7H7NO2 |
| SMILES | C1=CC(=CC=C1C(=O)O)N |
| Molar mass | 137.136 g/mol |
| Appearance | white crystals |
| CAS number | [150-13-0] |
| Properties | |
| Density and phase | 1.374 g/ml, ? |
| Solubility in water | 1 g/170 ml (25 °C) 1 g/90 mL (90 °C) |
| Melting point | 187-189 °C |
| Boiling point | ? °C |
| Acidity (pKa) | 4.65 |
| Basicity (pKb) | 9.35 |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 | |
| Flash point | ? °C |
| R/S statement | R: ? S: ? |
| RTECS number | ? |
| Related compounds | |
| Related compounds | aniline benzoic acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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4-Aminobenzoic acid, para-aminobenzoic acid, or simply PABA, is an organic compound with 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.
PABA is an essential nutrient for some bacteria and is sometimes called Vitamin Bx. However, PABA is not essential for humans and it varies in its activity from other B vitamins. 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 bacteria synthesis of folate. Inhibition of PABA by sulfonamides will terminate bacterial synthesis.
Sulfonamides (sulfa drugs) are chemically similar to PABA, and their antibacterial activity is due to their ability to interfere with PABA utilization by bacteria.
In the past, PABA has been widely used as UV filter in sunscreen formulations. However, it has been determined that it increases the formation of a particular DNA defect in human cells, thus increasing the risk of skin cancer in people who lack the mechanisms to repair these cellular defects.[1] Currently, safer and more effective derivatives of PABA, such as octyl dimethyl PABA, are more commonly used.
The potassium salt is used as drug against fibrotic skin disorders.[2]
PABA also finds use in the manufacture of esters, folic acid, and azo dyes.
[edit] References
- ^ 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.
- ^ Compound Summary on PubChem. PubChem. National Institute of Health: National Library of Medicine (2006). Retrieved on 2006-04-05.
