Nordihydroguaiaretic acid

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

Nordihydroguaiaretic acid
Names
IUPAC name
4,4'-(2,3-Dimethylbutane-1,4-diyl)dibenzene-1,2-diol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ECHA InfoCard 100.007.185
MeSH Nordihydroguaiaretic+acid
Properties
C18H22O4
Molar mass 302.370 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

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
  • Masoprocol, an antineoplastic drug used to treat skin growths caused by sun exposure.

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. 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. 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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