Nordihydroguaiaretic acid
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 100552

CAS#: 500-38-9

Description: Nordihydroguaiaretic acid, also known as NDGA and masoprocol, is a naturally occurring antioxidant dicatechol originally derived from the creosote bush Larrea divaricatta with antipromoter, anti-inflammatory, and antineoplastic activities. NDGA directly inhibits activation of two receptor tyrosine kinases (RTKs), the insulin-like growth factor receptor (IGF-1R) and the c-erbB2/HER2/neu receptor, resulting in decreased proliferation of susceptible tumor cell populations. This agent may induce apoptosis in susceptible tumor cell populations as a result of disruption of the actin cytoskeleton in association with the activation of stress activated protein kinases (SAPKs). In addition, NDGA inhibits arachidonic acid 5-lipoxygenase (5LOX), resulting in diminished synthesis of inflammatory mediators such as prostaglandins and leukotrines; it may prevent leukocyte infiltration into tissues and the release of reactive oxygen species and, at higher concentrations, may also inhibit cyclooxygenase.


Price and Availability

Size
Price

500mg
USD 250
5g
USD 950
Size
Price

1g
USD 350
10g
USD 1750
Size
Price

2g
USD 550

Nordihydroguaiaretic acid, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100552
Name: Nordihydroguaiaretic acid
CAS#: 500-38-9
Chemical Formula: C18H22O4
Exact Mass: 302.15181
Molecular Weight: 302.36488
Elemental Analysis: C, 71.50; H, 7.33; O, 21.17.


Synonym: masoprocol, nordihydroguaiaretic acid, NDGA, actinex.

IUPAC/Chemical Name: 4,4'-((2R,3S)-2,3-dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)

InChi Key: HCZKYJDFEPMADG-TXEJJXNPSA-N

InChi Code: 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+

SMILES Code: C[C@@H](CC1=CC=C(O)C(O)=C1)[C@H](C)CC2=CC=C(O)C(O)=C2


Technical Data

Appearance:
white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Masoprocol is an antineoplastic drug used to treat skin growths caused by sun exposure. A form of nordihydroguaiaretic acid that is taken by mouth is being studied in the treatment of prostate cancer. Also called nordihydroguaiaretic acid, NDGA, and actinex.


References

1: Kim HY, Goo JH, Joo YA, Lee HY, Lee SM, Oh CT, Ahn SM, Kim NH, Hwang JS. 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. doi: 10.4062/biomolther.2012.20.5.463. PubMed PMID: 24009835; PubMed Central PMCID: PMC3762283.

2: Zúñiga-Toalá A, Zatarain-Barrón ZL, Hernández-Pando R, Negrette-Guzmán M, Huerta-Yepez S, Torres I, Pinzón E, Tapia E, Pedraza-Chaverri J. Nordihydroguaiaretic acid induces Nrf2 nuclear translocation in vivo and attenuates renal damage and apoptosis in the ischemia and reperfusion model. Phytomedicine. 2013 Jul 15;20(10):775-9. doi: 10.1016/j.phymed.2013.03.020. Epub 2013 Apr 30. PubMed PMID: 23643094.

3: Batallán G, Torre R, Flores F, Konigheim B, Ludueña-Almeida F, Tonn C, Contigiani M, Almirón W. 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. PubMed PMID: 23563831.

4: Guzmán-Beltrán S, Pedraza-Chaverri J, Gonzalez-Reyes S, Hernández-Sánchez F, Juarez-Figueroa UE, Gonzalez Y, Bobadilla K, Torres M. Nordihydroguaiaretic acid attenuates the oxidative stress-induced decrease of CD33 expression in human monocytes. Oxid Med Cell Longev. 2013;2013:375893. doi: 10.1155/2013/375893. Epub 2013 Feb 24. PubMed PMID: 23533689; PubMed Central PMCID: PMC3596923.

5: Li X, Jiang JH, Chen Q, Xiao SX, Li CH, Gu HW, Zhang H, Hu JL, Yao FH, Li QG. Synthesis of nordihydroguaiaretic acid derivatives and their bioactivities on S. pombe and K562 cell lines. Eur J Med Chem. 2013 Apr;62:605-13. doi: 10.1016/j.ejmech.2013.01.028. Epub 2013 Feb 4. PubMed PMID: 23434529.

6: Castro-Gamero AM, Borges KS, Moreno DA, Suazo VK, Fujinami MM, de Paula Gomes Queiroz R, de Oliveira HF, Carlotti CG Jr, Scrideli CA, Tone LG. Tetra-O-methyl nordihydroguaiaretic acid, an inhibitor of Sp1-mediated survivin transcription, induces apoptosis and acts synergistically with chemo-radiotherapy in glioblastoma cells. Invest New Drugs. 2013 Aug;31(4):858-70. doi: 10.1007/s10637-012-9917-4. Epub 2013 Jan 9. PubMed PMID: 23299390.

7: Zhang H, Shen WJ, Cortez Y, Kraemer FB, Azhar S. 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. doi: 10.1152/ajpgi.00328.2012. Epub 2012 Oct 25. PubMed PMID: 23104557; PubMed Central PMCID: PMC3543637.

8: Zhang Y, Xu S, Lin J, Yao G, Han Z, Liang B, Zou Z, Chen Z, Song Q, Dai Y, Gao T, Liu A, Bai X. 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. doi: 10.1007/s10549-012-2270-7. Epub 2012 Sep 29. PubMed PMID: 23053656.

9: Li YJ, Kukita A, Watanabe T, Takano T, Qu P, Sanematsu K, Ninomiya Y, Kukita T. Nordihydroguaiaretic acid inhibition of NFATc1 suppresses osteoclastogenesis and arthritis bone destruction in rats. Lab Invest. 2012 Dec;92(12):1777-87. doi: 10.1038/labinvest.2012.134. Epub 2012 Oct 8. PubMed PMID: 23044922.

10: Lodge-Ivey SL, Petersen J, Browne-Silva J. Effects of nordihydroguaiaretic acid on in vitro fermentation profiles of rumen bacteria. J Anim Sci. 2012 Nov;90(11):4118-25. doi: 10.2527/jas.2012-5339. Epub 2012 Aug 7. PubMed PMID: 22871941.