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Substance Name: Nordihydroguaiaretic acid
RN: 500-38-9
InChIKey: HCZKYJDFEPMADG-UHFFFAOYSA-N

Note

  • A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.

Molecular Formula

  • C18-H22-O4

Molecular Weight

  • 302.368
 

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antioxidants
  • Cyclooxygenase Inhibitors
  • Enzyme Inhibitors
  • Lipoxygenase Inhibitors
  • Mutation Data
  • Peripheral Nervous System Agents
  • Protective Agents
  • Sensory System Agents
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Names and Synonyms

Results Name

  • Nordihydroguaiaretic acid

Name of Substance

  • 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-
  • 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis-1,2-benzenediol
  • Nordihydroguaiaretic acid
  • Nordihydroguaiaretic acid (unspecified)

MeSH Heading

  • Nordihydroguaiaretic acid

Synonyms

  • 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-
  • 2,3-Bis(3,4-dihydroxyphenylmethyl)butane
  • 2,3-Dimethyl-1,4-bis(3,4-dihydroxyphenyl)butane
  • 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(1,2-benzenediol)
  • 4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol)
  • 4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol
  • AI3-23059
  • beta,gamma-Dimethyl-alpha,delta-bis(3,4-dihydroxyphenyl)butane
  • Butane, 1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethyl-
  • CCRIS 1399
  • Dihydronorguaiaretic acid
  • Dinorguaiaretic acid, dihydro-
  • EINECS 207-903-0
  • NDGA
  • Nordihydroguaiaretic acid
  • Nordihydroguairaretic acid
  • Norguaiaretic acid, dihydro
  • Norguaiaretic acid, dihydro-
  • Norhydroguaiaretic acid
  • NSC 4291
  • NSC 682984
  • Pyrocatechol, 4,4'-(2,3-dimethyltetramethylene)di-

Systematic Names

  • 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-
  • 4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol
  • Nordihydroguaiaretic acid
  • Pyrocatechol, 4,4'-(2,3-dimethyltetramethylene)di-

Superlist Name

  • Nordihydroguaiaretic acid

Registry Numbers

CAS Registry Number

  • 500-38-9

Other Registry Number

  • 1413-68-9

System Generated Number

  • 0000500389

Structure Descriptors

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

c1(ccc(O)c(c1)O)C[C@@H]([C@@H](Cc1cc(c(cc1)O)O)C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 830mg/kg (830mg/kg)   Advances in Food Research. Vol. 3, Pg. 197, 1951.
mouse LD50 intraperitoneal 550mg/kg (550mg/kg)   Advances in Food Research. Vol. 3, Pg. 197, 1951.
mouse LD50 oral 2gm/kg (2000mg/kg)   Journal of the American Oil Chemists' Society. Vol. 54, Pg. 239, 1977.
rat LD50 oral 2gm/kg (2000mg/kg)   Journal of the American Oil Chemists' Society. Vol. 54, Pg. 239, 1977.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 185.5 deg C   EXP
log P (octanol-water) 4.640 (none)   EST
Atmospheric OH Rate Constant 1.23E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.