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N5023

Sigma-Aldrich

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

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

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

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
Nassira Mahmoudi et al.
Antimicrobial agents and chemotherapy, 52(4), 1215-1220 (2008-01-24)
We conducted a quantitative structure-activity relationship (QSAR) study based on a database of 127 compounds previously tested against the liver stage of Plasmodium yoelii in order to develop a model capable of predicting the in vitro antimalarial activities of new
Judith Sylvester et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 30(3), 563-574 (2012-07-27)
We investigated the unknown molecular mechanisms of Interleukin-1 (IL-1β)-induced cartilage aggrecan degeneration by aggrecanase (ADAMTS-A Disintegrin And Metalloproteinase with ThromboSpondin motifs) in human articular chondrocytes, a model mimicking human arthritis. Chondrocytes were pretreated with various pharmacological inhibitors and then stimulated
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