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Merck
CN

479975

NDGA

A cell-permeable antioxidant and a selective lipoxygenase (LOX) inhibitor (IC50 = 200 nM, 30 µM, and 30 µM for 5-LOX, 12-LOX, and 15-LOX, respectively) over cyclooxygenase (IC50 = 100 µM).

Synonym(s):

NDGA, Nordihydroguaiaretic Acid

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About This Item

Empirical Formula (Hill Notation):
C18H22O4
CAS Number:
500-38-9
Molecular Weight:
302.36
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00002206

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Product Name

NDGA, A cell-permeable antioxidant and a selective lipoxygenase (LOX) inhibitor (IC50 = 200 nM, 30 µM, and 30 µM for 5-LOX, 12-LOX, and 15-LOX, respectively) over cyclooxygenase (IC50 = 100 µM).

SMILES string

Oc1c(ccc(c1)C[C@H]([C@H](Cc2cc(c(cc2)O)O)C)C)O

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/t11-,12+

InChI key

HCZKYJDFEPMADG-TXEJJXNPSA-N

description

Merck USA index - 14, 6693

assay

≥90% (HPLC)

form

crystalline solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

solubility

DMSO: 10 mg/mL
ethanol: soluble

shipped in

ambient

storage temp.

10-30°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Cell permeable: yes
Primary Target
LOX-5
Product does not compete with ATP.
Reversible: no
Target IC50: 200 nM, 30 µM, and 30 µM for 5-LOX, 12-LOX, and 15-LOX, respectively

Disclaimer

Toxicity: Harmful (C)

General description

A cell-permeable antioxidant and a selective lipoxygenase (LOX) inhibitor (IC50 = 200 nM, 30 µM, and 30 µM for 5-LOX, 12-LOX, and 15-LOX, respectively) over cyclooxygenase (IC50 = 100 µM). Also shown to inhibit platelet-derived growth factor (PDGF)-stimulated DNA synthesis in Swiss/3T3 cells. A powerful hydroxy radical quencher.
A cell-permeable, antioxidant and a selective lipoxygenase (LO) inhibitor (IC50 = 200 nM, 30 µM, and 30 µM for 5-LO, 12-LO, and 15-LO, respectively) over cyclooxygenase (IC50 = 100 µM). Also shown to inhibit platelet-derived growth factor (PDGF)-stimulated DNA synthesis in Swiss 3T3 cells.

Other Notes

Domin, J., et al. 1994. J. Biol. Chem. 269, 8260.
Goodman, Y., et al. 1994. Brain Res. 654, 171.
Kozubik, A., et al. 1993. Exp. Hematol. 21, 138.
Salari, H., et al. 1984. Prostagland. Leuk. Med. 13, 53.
Hope, W.C., et al. 1983. Biochem. Pharmacol. 32, 367.

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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