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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

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Certificates of Analysis (COA)

Lot/Batch Number
017K7020
107H7052
040K7040
099H7002
052K7033

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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
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
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
Irina Daurkin et al.
Cancer research, 71(20), 6400-6409 (2011-09-09)
Renal cell carcinoma (RCC), the most common human kidney cancer, is frequently infiltrated with tumor-associated macrophages (TAM) that can promote malignant progression. Here, we show that TAMs isolated from human RCC produce substantial amounts of the proinflammatory chemokine CCL2 and
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
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