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74540

Sigma-Aldrich

Nordihydroguaiaretic acid

≥97.0% (HPLC)

Synonym(s):

1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane, 4,4′-(2,3-Dimethyltetramethylene)dipyrocatechol, Masoprocol, NDGA

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About This Item

Linear Formula:
[-CH(CH3)CH2C6H3-1,2-(OH)2]2
CAS Number:
500-38-9
Molecular Weight:
302.36
Beilstein/REAXYS Number:
2056826
EC Number:
207-903-0
MDL number:
MFCD00002206
UNSPSC Code:
12352100
PubChem Substance ID:
57652455
NACRES:
NA.22

assay

≥97.0% (HPLC)

form

crystals

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.

Biochem/physiol Actions

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

Other Notes

Inhibitor of broad bean lipoxygenase

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
New nordihydroguaiaretic acid derivatives as anti-HIV agents.
Hwu JR, et al.
Bioorganic & Medicinal Chemistry Letters, 18(6), 1884-1888 (2008)
H.M. Al-Obaidy et al.
Journal of Food Science, 46, 597-597 (1981)
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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