N1144

Sigma-Aldrich

Nordihydroguaiaretic acid

≥90% (HPLC), from Larrea divaricata (creosote bush)

Synonym(s):
Masoprocol, 4,4′-(2,3-Dimethyltetramethylene)dipyrocatechol, NDGA, 1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane
Linear Formula:
[-CH(CH3)CH2C6H3-1,2-(OH)2]2
CAS Number:
Molecular Weight:
302.36
Beilstein/REAXYS Number:
2056826
EC Number:
MDL number:

biological source

Larrea divaricata (creosote bush)

assay

≥90% (HPLC)

mp

184-186 °C (lit.)

SMILES string

CC(Cc1ccc(O)c(O)c1)C(C)Cc2ccc(O)c(O)c2

InChI

1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3

InChI key

HCZKYJDFEPMADG-UHFFFAOYSA-N

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Biochem/physiol Actions

Lipoxygenase inhibitor; polyphenol-bearing o-dihydroxy (catechol) structure.

Certificate of Analysis

Certificate of Origin

Joseph E Blecha et al.
Bioorganic & medicinal chemistry letters, 17(14), 4026-4029 (2007-05-16)
Herein, we pursue the hypothesis that the structure of nordihydroguaiaretic acid (NDGA) can be refined for selective potency against the insulin-like growth factor 1 receptor (IGF-1R) as a potential therapeutic target for breast cancer while diminishing its action against other...
David S Weinstein et al.
Bioorganic & medicinal chemistry letters, 15(5), 1435-1440 (2005-02-17)
A series of inhibitors of mammalian 15-lipoxygenase based on tryptamine and homotryptamine scaffolds is described. Compounds with aryl substituents at C-2 of the indole core of tryptamine and homotryptamine sulfonamides (e.g., 37a-p) proved to be potent inhibitors of the isolated...
Jennifer L Billinsky et al.
Journal of natural products, 71(9), 1612-1615 (2008-08-05)
The lignan meso-nordihydroguaiaretic acid is known to undergo spontaneous oxidation in alkaline solution. In the presence of the trapping agent glutathione, the major oxidation products are consistent with the formation of a meso-nordihydroguaiaretic acid ortho-quinone. In the absence of a...
Yesseny Vasquez-Martinez et al.
Bioorganic & medicinal chemistry, 15(23), 7408-7425 (2007-09-18)
Human lipoxygenase (hLO) isozymes have been implicated in a number of disease states and have attracted much attention with respect to their inhibition. One class of inhibitors, the flavonoids, have been shown to be potent lipoxygenase inhibitors but their study...
Michael Scholz et al.
European journal of medicinal chemistry, 43(6), 1152-1159 (2007-11-03)
The aim of this study was to investigate 4,5-diaryl isoselenazoles as multiple target non-steroidal anti-inflammatory drugs (MTNSAIDs) which can intervene into the inflammatory processes via different mechanisms of action creating a new class of compounds. Here we describe the synthesis...

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