Nordihydroguaiaretic acid

Nordihydroguaiaretic acid
IUPAC name 4,4'-(2,3-dimethylbutane-1,4-diyl)dibenzene-1,2-diol
Identifiers
CAS number	500-38-9 Y
PubChem	4534
MeSH	Nordihydroguaiaretic+acid
ChEMBL	CHEMBL52 N
Jmol-3D images	Image 1
SMILES Oc2ccc(CC(C)C(C)Cc1ccc(O)c(O)c1)cc2O
Properties
Molecular formula	C18H22O4
Molar mass	302.36 g mol−1
N acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 ^[1] 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. ^[2]

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. ^[3]

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. ^ Strong R, Miller RA, Astle CM, Floyd RA, Flurkey K, Hensley KL, Javors MA, Leeuwenburgh C, Nelson JF, Ongini E, Nadon NL, Warner HR, Harrison DE. “Nordihydroguaiaretic acid and aspirin increase lifespan of genetically heterogeneous mice.” Aging Cell. 2008 Oct; 7(5):641-50.
3. ^ 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