CHEBI:7625 - nordihydroguaiaretic acid

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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 0
Average Mass 302.36490
Monoisotopic Mass 302.152
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.
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ChEBI Ontology
Outgoing nordihydroguaiaretic acid (CHEBI:7625) has role antioxidant (CHEBI:22586)
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
Manual Xrefs Databases
C10719 KEGG COMPOUND
CPD-7661 MetaCyc
HMDB0012270 HMDB
LSM-6507 LINCS
Nordihydroguaiaretic_acid Wikipedia
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Registry Numbers Types Sources
500-38-9 CAS Registry Number KEGG COMPOUND
500-38-9 CAS Registry Number NIST Chemistry WebBook
500-38-9 CAS Registry Number ChemIDplus
9803564 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
25 February 2016
General Comment
2013-05-02 For configuration of the naturally occurring form, see Perry, C.W., et al., J. Org. Chem., 1972, v37, 4371.