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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
Assay:
≥90% (HPLC)
Form:
crystalline

Key Documents

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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

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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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
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
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
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Global Trade Item Number

SKUGTIN
N5023-5G04061832785738
N5023-500MG04061832785721
N5023-1G04061826683743

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