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Merck
CN

N5023

Nordihydroguaiaretic acid

≥90% (HPLC), from Larrea divaricata (creosote bush)

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:
12352200
NACRES:
NA.77
PubChem Substance ID:
57654453
EC Number:
207-903-0
Beilstein/REAXYS Number:
2056826
MDL number:
MFCD00002206

Key Documents

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Product Name

Nordihydroguaiaretic acid, ≥90% (HPLC), from Larrea divaricata (creosote bush)

InChI key

HCZKYJDFEPMADG-UHFFFAOYSA-N

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

SMILES string

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

biological source

Larrea divaricata (creosote bush)

assay

≥90% (HPLC)

form

crystalline

mp

184-186 °C (lit.)

solubility

ethanol: 50 mg/mL, clear to slightly hazy

Gene Information

human ... ALOX15(246), PTGS1(5742), PTGS2(5743)
mouse ... Alox12(11684)

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Biochem/physiol Actions

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

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
017K7020
104K7037
076H7160
074K7008
063K7027

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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
Lorena Palacio et al.
Plant science : an international journal of experimental plant biology, 193-194, 1-7 (2012-07-17)
The lignan nordihydroguaiaretic acid (NDGA) and its derivatives existing in Larrea divaricata species show a wide range of pharmacological activities which makes this genus an interesting target to consider the plant in vitro cultivation systems as a feasible alternative source
Victor Kenyon et al.
Journal of medicinal chemistry, 54(15), 5485-5497 (2011-07-12)
We report the discovery of novel small molecule inhibitors of platelet-type 12-human lipoxygenase, which display nanomolar activity against the purified enzyme, using a quantitative high-throughput screen (qHTS) on a library of 153607 compounds. These compounds also exhibit excellent specificity, >50-fold
Ana I Rojo et al.
Free radical biology & medicine, 52(2), 473-487 (2011-12-07)
Defense against oxidative stress is executed by an antioxidant program that is tightly controlled by the transcription factor Nrf2. The stability of Nrf2 involves the interaction of two degradation domains, designated Neh2 and Neh6, with the E3 ubiquitin ligase adaptors
Malcolm J Daniels et al.
Scientific reports, 9(1), 2937-2937 (2019-03-01)
Growing evidence implicates α-synuclein aggregation as a key driver of neurodegeneration in Parkinson's disease (PD) and other neurodegenerative disorders. Herein, the molecular and structural mechanisms of inhibiting α-synuclein aggregation by novel analogs of nordihydroguaiaretic acid (NDGA), a phenolic dibenzenediol lignan
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