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Nordihydroguaiaretic acid

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Nordihydroguaiaretic acid
Names
IUPAC name 4,4'-(2,3-dimethylbutane-1,4-diyl)dibenzene-1,2-diol
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.007.185 Edit this at Wikidata
MeSH Nordihydroguaiaretic+acid
PubChem CID
CompTox Dashboard (EPA)
SMILES
  • Oc2ccc(CC(C)C(C)Cc1ccc(O)c(O)c1)cc2O
Properties
Chemical formula C18H22O4
Molar mass 302.365
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Nordihydroguaiaretic acid (NDGA) is a potent antioxidant compound found in the long-lived creosote bush. It is believed that NDGA reduces cell damage by free radicals, so under the free-radical theory of aging, could be responsible for the bush's long life. 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. Nordihydroguaiaretic acid is also published as lengthening the lifespan of mice

The plant has been used to treat a variety of illnesses including infertility, rheumatism, arthritis, diabetes, gallbladder and kidney stones, pain and inflammation 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 and hepatotoxicity are reported for chronic use of creosote bush and NDGA.

References

  1. Richie JP Jr, Mills BJ, Lang CA. "Dietary nordihydroguaiaretic acid increases the life span of the mosquito." Proc Soc Exp Biol Med. 1986 Oct;183(1):81-5
  2. Adapted from Arteaga S, Andrade-Cetto A, Cardenas R. "Larrea tridentata (Creosote bush), an abundant plant of Mexican and US-American deserts and its metabolite nordihydroguaiaretic acid." J Ethnopharmacol. 2005 Apr 26;98(3):231-9
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