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Merck

74540

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57652455
EC Number:
207-903-0
Beilstein/REAXYS Number:
2056826
MDL number:
MFCD00002206

Product Name

Nordihydroguaiaretic acid, ≥97.0% (HPLC)

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

SMILES string

CC(Cc1ccc(O)c(O)c1)C(C)Cc2ccc(O)c(O)c2

assay

≥97.0% (HPLC)

form

crystals

impurities

≤2% water

mp

184-186 °C (lit.)

Quality Level

100

Gene Information

mouse ... Alox12(11684)

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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.

General description

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

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6939
BCCM9340
BCCM6953
BCCJ6356
BCCG9593

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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)
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)
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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