74540

Sigma-Aldrich

Nordihydroguaiaretic acid

≥97.0% (HPLC)

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:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥97.0% (HPLC)

impurities

≤2% water

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

Gene Information

mouse ... Alox12(11684)

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General description

Nordihydroguaiaretic acid (NDGA) is used as an antioxidant and potent scavenger of reactive oxygen species (ROS).

Application

Nordihydroguaiaretic acid can be used:
  • In the synthesis of nordihydroguaiaretic acid derivatives with potent HIV inhibition activity.
  • As a starting material in the synthesis of tetra-O-methylnordihydroguaiaretic acid.

Packaging

1, 5 g in glass bottle

Biochem/physiol Actions

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

Other Notes

Inhibitor of broad bean lipoxygenase

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Nordihydroguaiaretic acid is a potent in vitro scavenger of peroxynitrite, singlet oxygen, hydroxyl radical, superoxide anion and hypochlorous acid and prevents in vivo ozone-induced tyrosine nitration in lungs.
Floriano-Sanchez E, et al.
Free Radical Research, 40(5), 523-533 (2006)
Tetra-O-methylnordihydroguaiaretic acid inhibits melanoma in vivo
Lambert JD, et al.
Cancer Letters, 171(1), 47-56 (2001)
H.M. Al-Obaidy et al.
Journal of Food Science, 46, 597-597 (1981)
New nordihydroguaiaretic acid derivatives as anti-HIV agents.
Hwu JR, et al.
Bioorganic & Medicinal Chemistry Letters, 18(6), 1884-1888 (2008)
Silvia Arteaga et al.
Journal of ethnopharmacology, 98(3), 231-239 (2005-04-09)
Although controversial, Creosote bush, Larrea tridentata (Sesse and Moc. ex DC) Coville, is used to treat a variety of illnesses including infertility, rheumatism, arthritis, diabetes, gallbladder and kidney stones, pain and inflammation. Recently, it has been used as a nutritional...

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