4-Aminobenzoic acid
| 4-Aminobenzoic acid | |
|---|---|
| File:4-Aminobenzoic acid.svg | |
| 4-Aminobenzoic acid | |
| Other names para-Aminobenzoic acid; p-Aminobenzoic acid; PABA; Vitamin Bx; Bacterial vitamin H1 | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 150-13-0 
|
| PubChem | 978 |
| ChemSpider | 953 |
| SMILES | Script error: No such module "collapsible list". |
| InChI | Script error: No such module "collapsible list". |
| InChI key | ALYNCZNDIQEVRV-UHFFFAOYAH |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C7H7NO2 |
| Molar mass | 137.14 g mol−1 |
| Appearance | White-grey 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) |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
4-Aminobenzoic acid (also known as para-aminobenzoic acid or PABA) is an organic compound with the formula H2NC6H4CO2H. PABA is a white grey crystalline substance that is only slightly soluble in water. It consists of a benzene ring substituted with an amino group and a carboxyl group.
Contents
Production and occurrence
In industry, PABA is mainly prepared by two routes: reduction of 4-nitrobenzoic acid and the Hoffman degradation of the monoamide derived from terephthalic acid.[1]
Food sources of PABA include liver, brewer's yeast (and unfiltered beer), kidney, molasses, and whole grains.[2]
Biology
Biochemistry
PABA is an intermediate in the bacterial synthesis of folate. It has been referred to as Vitamin Bx.[3] Some bacteria in the human intestinal tract such as E. coli[4] require PABA[5]. Humans require folate since we lack the enzymes to convert PABA to folate. Therefore, in humans, PABA is not a vitamin and is considered nonessential.[6]
Sulfonamide drugs are structurally similar to PABA, and their antibacterial activity is due to their ability to interfere with the conversion of PABA to folate by the enzyme dihydropteroate synthetase. Thus, bacterial growth is limited through folate deficiency without effect on human cells.
Medical use
The potassium salt is used as a drug against fibrotic skin disorders, such as Peyronie's disease, under the trade name Potaba.[7] PABA is also occasionally used in pill form by sufferers of irritable bowel syndrome to treat its associated gastrointestinal symptoms, and in nutritional epidemiological studies to assess the completeness of 24-hour urine collection for the determination of urinary sodium, potassium, or nitrogen levels.
Nutritional supplement
Despite the lack of any recognized syndromes of PABA deficiency in humans, many claims of benefit are made by commercial suppliers of PABA as a nutritional supplement. Benefit is claimed for fatigue, irritability, depression, weeping eczema (moist eczema), scleroderma (premature hardening of skin), patchy pigment loss in skin (vitiligo), and premature grey hair.[8]
Oral supplements of PABA can make the skin less sensitive to sun damage.
Commercial and industrial use
PABA mainly finds use in the biomedical sector. Other uses include its conversion to specialty azo dyes and crosslinking agents.
In the past, PABA was widely used in sunscreens as a UV filter. It is a UVB absorber, meaning that it can absorb wavelengths between 290-320 nm. Cite error: Invalid <ref> tag;
invalid names, e.g. too many Patented in 1943, PABA was one of the first active ingredients to be used in sunscreen. [9] The first in vivo studies on mice showed that PABA reduced UV damage. In addition, PABA was shown to protect against skin tumors in rodents. [10]
Animal and in vitro studies in the early 1980's suggested PABA might increase the risk of cellular UV damage.[11] On the basis of these studies as well as problems with allergies and clothing discoloration, PABA fell out of favor as a sunscreen. However, water-insoluble PABA derivatives such as octyl dimethyl PABA (padimate O) are currently used in some products.
Safety considerations
PABA is largely nontoxic, the median lethal dose of PABA in dogs (oral) is 2 g/kg.[1] Allergic reactions to PABA can occur. PABA is formed in the metabolism of certain ester local anesthetics, and many allergic reactions to local anesthetics are the result of reactions to PABA.[12]
References
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cs:Kyselina 4-aminobenzoováde:P-Aminobenzoesäure et:P-aminobensoehape es:Ácido 4-aminobenzoico fr:Acide 4-amino-benzoïque it:Acido 4-amminobenzoico ja:4-アミノ安息香酸 no:PABA pl:Kwas p-aminobenzoesowy pt:Ácido 4-aminobenzoico
zh:对氨基苯甲酸- ↑ 1.0 1.1 Takao Maki and Kazuo Takeda "Benzoic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_555
- ↑ Nutritional Health Resource
- ↑ "Para-aminobenzoic acid poisoning". National Institute of Health: National Library of Medicine. 2007. Retrieved 2007-06-19.
- ↑ Folate Synthesis (Abstract)
- ↑ In vivo Folate Production
- ↑ [1]
- ↑ "Compound Summary on PubChem". PubChem. National Institute of Health: National Library of Medicine. 2006. Retrieved 2006-04-05.
- ↑ Health Library (Supplements) PABA
- ↑ F. P.; Mitchnick, M.; Nash, J. F. A Review of Sunscreen Safety and Efficacy Photochem. Photobiol. 1998, 68, 243 <last_page> 256.
- ↑ H.; Thune, P.; Eeg Larsen, T. The inhibiting effect of PABA on photocarcinogenesis Arch. Dermatol. Res. 1990, 282, 38 <last_page> 41
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ http://emedicine.medscape.com/article/819628-overview
