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Nordihydroguaiaretic Acid

Nordihydroguaiaretic Acid

Product ID N5669
Cas No. 500-38-9
Purity ≥99%
Product Unit SizeCostQuantityStock
500 mg $58.20 In stock
1 g $101.00 In stock
5 g $427.70 In stock
Bulk Quote

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  • Description
  • Product Info
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  • References
  • Description
  • Product Info
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Description

Nordihydroguaiaretic acid (NDGA) is a phenol found in the creosote bush that exhibits antioxidative, antiviral, anti-angiogenic, anti-metastatic, anti-inflammatory, anti-hyperlipidemic, anti-osteoporotic, anti-aging, neuromodulatory, anti-parasitic, antifungal, and anticancer chemotherapeutic activities. NDGA scavenges ROS, inhibits 5-lipoxygenase, and activates Nrf2. This compound inhibits dengue virus replication by preventing viral assembly; it also inhibits growth of Culex and Candida. In animal models, NDGA increases overall life span and inhibits acetylcholinesterase (AChE) and butylcholinesterase (BChE). In vivo, NDGA inhibits angiogenesis and suppresses invasion and proliferation of glioma cells. In various models, NDGA inhibits Ca2+ signaling and PAR2 activity, decreasing expression of IL-8, ICAM-1, IgE, and involucrin. In animal models, this compound increases expression of PPARα and decreases levels of serum triglycerides and liver weight. Additionally, NDGA inhibits osteoclastogenesis in vitro and decreases bone destruction in vivo. In cellular and animal models of breast cancer, NDGA inhibits mTORC1, decreases expression of VEGF, cyclin D1, and HIF-1α, and suppresses cellular proliferation and tumor growth.

Product Info

Cas No.

500-38-9

Purity

≥99%

Formula

C18H22O4

Formula Wt.

302.36

Chemical Name

4,4-(2,3-Dimethyl-1,4butanediyl)bis[1,2-benzenediol]

IUPAC Name

4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol

Synonym

NDGA, Dihydronorguaiaretic acid, Pyrocatechol, 4,4'-(2,3-dimethyltetramethylene)di-

Melting Point

184-186°C

Solubility

Soluble in ethanol, methanol, or hot water.

Appearance

White Solid Crystalline

Shipping and Storage

Store Temp

Ambient

Ship Temp

Ambient

Downloads

MSDS

N5669 MSDS PDF

Info Sheet

N5669 Info Sheet PDF

References

Hernández-Damián J, Andérica-Romero AC, Pedraza-Chaverri J. Paradoxical cellular effects and biological role of the multifaceted compound nordihydroguaiaretic Acid. Arch Pharm (Weinheim). 2014 Oct;347(10):685-97. PMID: 25100573.

Soto-Acosta R, Bautista-Carbajal P, Syed GH, et al. Nordihydroguaiaretic acid (NDGA) inhibits replication and viral morphogenesis of dengue virus. Antiviral Res. 2014 Sep;109:132-40. PMID: 25017471.

Harrison DE, Strong R, Allison DB, et al. Acarbose, 17-α-estradiol, and nordihydroguaiaretic acid extend mouse lifespan preferentially in males. Aging Cell. 2014 Apr;13(2):273-82. PMID: 24245565.

Yang X, Cui W, Yu S, et al. A synthetic dl-nordihydroguaiaretic acid (Nordy), inhibits angiogenesis, invasion and proliferation of glioma stem cells within a zebrafish xenotransplantation model. PLoS One. 2014 Jan 15;9(1):e85759. PMID: 24454929.

Szwajgier D. Anticholinesterase activity of phenolic acids and their derivatives. Z Naturforsch C. 2013 Mar-Apr;68(3-4):125-32. PMID: 23819308.

Batallán G, Torre R, Flores F, et al. Larvicidal activity of crude extracts from Larrea cuneifolia (Zygophyllaceae) and of its metabolite nordihydroguaiaretic acid against the vector Culex quinquefasciatus (Diptera: Culicidae). Rev Soc Bras Med Trop. 2013 Jan-Feb;46(1):84-7. PMID: 23563831.

Zhang H, Shen WJ, Cortez Y, et al. Nordihydroguaiaretic acid improves metabolic dysregulation and aberrant hepatic lipid metabolism in mice by both PPARα-dependent and -independent pathways. Am J Physiol Gastrointest Liver Physiol. 2013 Jan 1;304(1):G72-86. PMID: 23104557.

Martino RF, Davicino RC, Mattar MA, et al. Macrophages activation by a purified fraction, free of nordihydroguaiaretic acid (NDGA), from Larrea divaricata Cav. as a potential novel therapy against Candida albicans. Immunopharmacol Immunotoxicol. 2012 Dec;34(6):975-82. PMID: 22551492.

Li YJ, Kukita A, Watanabe T, et al. Nordihydroguaiaretic acid inhibition of NFATc1 suppresses osteoclastogenesis and arthritis bone destruction in rats. Lab Invest. 2012 Dec;92(12):1777-87. PMID: 23044922.

Zhang Y, Xu S, Lin J, et al. mTORC1 is a target of nordihydroguaiaretic acid to prevent breast tumor growth in vitro and in vivo. Breast Cancer Res Treat. 2012 Nov;136(2):379-88. PMID: 23053656.

Kim HY, Goo JH, Joo YA, et al. Impact on inflammation and recovery of skin barrier by nordihydroguaiaretic Acid as a protease-activated receptor 2 antagonist. Biomol Ther (Seoul). 2012 Sep;20(5):463-9. PMID: 24009835.

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