Nordihydroguaiaretic acid

Nordihydroguaiaretic acid
Names
IUPAC name
4,4'-(2,3-Dimethylbutane-1,4-diyl)dibenzene-1,2-diol
Identifiers
500-38-9 YesY
ChEBI CHEBI:7625 N
ChEMBL ChEMBL52 N
4265
Jmol interactive 3D Image
MeSH Nordihydroguaiaretic+acid
PubChem 4534
Properties
C18H22O4
Molar mass 302.37 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Nordihydroguaiaretic acid (NDGA) is an antioxidant compound found in the creosote bush (Larrea tridentata).

The creosote plant has been used in herbal medicine, but its use is controversial. It was widely used during the 1950s as a food preservative and to preserve natural fibers, but was later banned after reports of toxicity during the early 1960s. Recently, it has been used as a nutritional supplement; however, renal toxicity and hepatotoxicity are reported for chronic use of creosote bush and NDGA.[1][2][3]

A 1986 study involved feeding female mosquitos NDGA to test the effect on their average life span. While the usual mosquito life span was 29 days, the NDGA-fed mosquitos lived an average of 45 days—an increase of 50 percent.[4] A 2008 study reported that nordihydroguaiaretic acid lengthened the lifespan of male mice, but not of female mice.[5]

See also

References

  1. ↑ Arteaga, S.; Andrade-Cetto, A.; Cárdenas, R. (2005). "Larrea tridentata (Creosote bush), an abundant plant of Mexican and US-American deserts and its metabolite nordihydroguaiaretic acid". Journal of Ethnopharmacology 98 (3): 231–239. doi:10.1016/j.jep.2005.02.002. PMID 15814253.
  2. ↑ Sahu, S. C.; Ruggles, D. I.; o’Donnell, M. W. (2006). "Prooxidant activity and toxicity of nordihydroguaiaretic acid in clone-9 rat hepatocyte cultures". Food and Chemical Toxicology 44 (10): 1751–7. doi:10.1016/j.fct.2006.05.016. PMID 16839654.
  3. ↑ Lambert, J. D.; Zhao, D; Meyers, R. O.; Kuester, R. K.; Timmermann, B. N.; Dorr, R. T. (2002). "Nordihydroguaiaretic acid: Hepatotoxicity and detoxification in the mouse". Toxicon : official journal of the International Society on Toxinology 40 (12): 1701–8. doi:10.1016/s0041-0101(02)00203-9. PMID 12457882.
  4. ↑ Richie Jr, J. P.; Mills, B. J.; Lang, C. A. (1986). "Dietary nordihydroguaiaretic acid increases the life span of the mosquito". Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine 183 (1): 81–85. doi:10.3181/00379727-183-42389. PMID 3749035.
  5. ↑ Strong, R.; Miller, R. A.; Astle, C. M.; Floyd, R. A.; Flurkey, K.; Hensley, K. L.; Javors, M. A.; Leeuwenburgh, C.; Nelson, J. F.; Ongini, E.; Nadon, N. L.; Warner, H. R.; Harrison, D. E. (2008). "Nordihydroguaiaretic acid and aspirin increase lifespan of genetically heterogeneous male mice". Aging Cell 7 (5): 641–650. doi:10.1111/j.1474-9726.2008.00414.x. PMC 2695675. PMID 18631321.
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