nordihydroguaiaretic acid (CHEBI:7625)

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ChEBI Name	nordihydroguaiaretic acid

ChEBI ID	CHEBI:7625

Definition	A tetrol that is butane which is substituted at positions 2 and 3 by 3,4-dihydroxybenzyl groups. Masoprocol, the meso-form found in the leaves of the creosote bush (Larrea divaricata), is a potent lipoxygenase inhibitor.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C18H22O4

Net Charge

Average Mass

302.36490

Monoisotopic Mass

302.15181

InChI

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

InChIKey

HCZKYJDFEPMADG-UHFFFAOYSA-N

SMILES

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

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.

Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. ferroptosis inhibitor Any substance that inhibits the process of ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.

Application(s):	geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

ChEBI Ontology
Outgoing	nordihydroguaiaretic acid (CHEBI:7625) has role antioxidant (CHEBI:22586) nordihydroguaiaretic acid (CHEBI:7625) has role ferroptosis inhibitor (CHEBI:173084) nordihydroguaiaretic acid (CHEBI:7625) has role geroprotector (CHEBI:176497) nordihydroguaiaretic acid (CHEBI:7625) has role plant metabolite (CHEBI:76924) nordihydroguaiaretic acid (CHEBI:7625) is a catechols (CHEBI:33566) nordihydroguaiaretic acid (CHEBI:7625) is a lignan (CHEBI:25036) nordihydroguaiaretic acid (CHEBI:7625) is a tetrol (CHEBI:33573)

Incoming	masoprocol (CHEBI:73468) is a nordihydroguaiaretic acid (CHEBI:7625)

IUPAC Name

4,4'-(2,3-dimethylbutane-1,4-diyl)dibenzene-1,2-diol

Synonyms	Sources
1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane	NIST Chemistry WebBook
2,3-bis(3,4-dihydroxyphenylmethyl)butane	NIST Chemistry WebBook
4,4'-(2,3-dimethyl-1,4-butanediyl)bis(pyrocatechol)	NIST Chemistry WebBook
4,4'-(2,3-dimethyltetramethylene)dipyrocatechol	NIST Chemistry WebBook
β,γ-dimethyl-α,δ-bis(3,4-dihydroxyphenyl)butane	ChemIDplus
NDGA	ChemIDplus
nordihydroguaiaretic acid	ChemIDplus
nordihydroguaiaretic acid (unspecified)	ChemIDplus
norhydroguaiaretic acid	ChemIDplus
NSC 4291	NIST Chemistry WebBook

Last Modified

20 September 2021

General Comment
2013-05-02	For configuration of the naturally occurring form, see Perry, C.W., et al., J. Org. Chem., 1972, v37, 4371.