INSM-18
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 201562

CAS#: 500-38-9

Description: INSM-18, also known as nordihydroguaiaretic acid, 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.


Price and Availability

Size
Price

1g
USD 300
Size
Price

5g
USD 780
Size
Price

INSM-18, 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#: 201562
Name: INSM-18
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: INSM18; INSM-18, INSM 18, 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:
Solid powder

Purity:
>98%

Certificate of Analysis:

Safety Data Sheet (MSDS):

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:
>5 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:
2934990300


Additional Information

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.
 


References

1: Díaz-Gerevini GT, Daín A, Pasqualini ME, López CB, Eynard AR, Repossi G. Diabetic encephalopathy: beneficial effects of supplementation with fatty acids ω3 and nordihydroguaiaretic acid in a spontaneous diabetes rat model. Lipids Health Dis. 2019 Feb 8;18(1):43. doi: 10.1186/s12944-018-0938-7. PubMed PMID: 30736810; PubMed Central PMCID: PMC6368734.

2: Awasthi S, Preethy R, Saraswathi NT. Nordihydroguaiaretic acid prevents glycation induced structural alterations and aggregation of albumin. Int J Biol Macromol. 2019 Feb 1;122:479-484. doi: 10.1016/j.ijbiomac.2018.10.173. Epub 2018 Oct 26. PubMed PMID: 30416092.

3: Nolte J, Pöttgen LA, Sperlich J, Grossert A, Kempa A, Teusch N, Schörken U. Glucansucrase catalyzed synthesis and functional characterization of nordihydroguaiaretic acid glucosides. Enzyme Microb Technol. 2019 Jan;120:69-76. doi: 10.1016/j.enzmictec.2018.10.002. Epub 2018 Oct 5. PubMed PMID: 30396401.

4: Singh M, Bittner S, Li Y, Bittner A, Han L, Cortez Y, Inayathullah M, Arif Z, Parthasarathi R, Rajadas J, Shen WJ, Nicolls MR, Kraemer FB, Azhar S. Anti-hyperlipidaemic effects of synthetic analogues of nordihydroguaiaretic acid in dyslipidaemic rats. Br J Pharmacol. 2019 Feb;176(3):369-385. doi: 10.1111/bph.14528. Epub 2018 Dec 10. PubMed PMID: 30374952; PubMed Central PMCID: PMC6329620.

5: Wang L, Li L, Quan MY, Wang D, Jia Z, Li ZF, Li B, Guo L, Tan GJ. Nordihydroguaiaretic acid can suppress progression of experimental autoimmune encephalomyelitis. IUBMB Life. 2018 May;70(5):432-436. doi: 10.1002/iub.1739. Epub 2018 Apr 10. PubMed PMID: 29637686.

6: Chan JKW, Bittner S, Bittner A, Atwal S, Shen WJ, Inayathullah M, Rajada J, Nicolls MR, Kraemer FB, Azhar S. Nordihydroguaiaretic Acid, a Lignan from Larrea tridentata (Creosote Bush), Protects Against American Lifestyle-Induced Obesity Syndrome Diet-Induced Metabolic Dysfunction in Mice. J Pharmacol Exp Ther. 2018 May;365(2):281-290. doi: 10.1124/jpet.117.243733. Epub 2018 Feb 22. PubMed PMID: 29472517; PubMed Central PMCID: PMC5878670.

7: Abbas MA, Badran D, Disi A. Effect of nordihydroguaiaretic acid on spermatogenesis and fertility in rats. Andrologia. 2018 Apr;50(3). doi: 10.1111/and.12916. Epub 2017 Nov 6. PubMed PMID: 29110321.

8: Bibikova MV, Spiridonova NA, Korystova AF, Kublik LN, Levitman MK, Shaposhnikova VV, Korystov YN. Lipoxygenase Inhibitors Nordihydroguaiaretic Acid and Fungus Lecanicillum lecanii Extract Induce Death of Lymphoid Leukemia Cells. Bull Exp Biol Med. 2017 Jul;163(3):330-333. doi: 10.1007/s10517-017-3796-9. Epub 2017 Jul 26. PubMed PMID: 28744653.

9: Merino-Ramos T, Jiménez de Oya N, Saiz JC, Martín-Acebes MA. Antiviral Activity of Nordihydroguaiaretic Acid and Its Derivative Tetra-O-Methyl Nordihydroguaiaretic Acid against West Nile Virus and Zika Virus. Antimicrob Agents Chemother. 2017 Jul 25;61(8). pii: e00376-17. doi: 10.1128/AAC.00376-17. Print 2017 Aug. PubMed PMID: 28507114; PubMed Central PMCID: PMC5527643.

10: Zhao QW, Lin Y, Xu CR, Yao YL, Cui YH, Zhang X, Bian XW. NDGA-P21, a novel derivative of nordihydroguaiaretic acid, inhibits glioma cell proliferation and stemness. Lab Invest. 2017 Oct;97(10):1180-1187. doi: 10.1038/labinvest.2017.46. Epub 2017 May 15. PubMed PMID: 28504686.

11: Siddique YH, Ali F. Protective effect of nordihydroguaiaretic acid (NDGA) on the transgenic Drosophila model of Alzheimer's disease. Chem Biol Interact. 2017 May 1;269:59-66. doi: 10.1016/j.cbi.2017.04.005. Epub 2017 Apr 6. PubMed PMID: 28392391.

12: Dain A, Repossi G, Diaz-Gerevini GT, Vanamala J, Das UN, Eynard AR. Long chain polyunsaturated fatty acids (LCPUFAs) and nordihydroguaiaretic acid (NDGA) modulate metabolic and inflammatory markers in a spontaneous type 2 diabetes mellitus model (Stillman Salgado rats). Lipids Health Dis. 2016 Nov 25;15(1):205. PubMed PMID: 27884155; PubMed Central PMCID: PMC5123226.

13: Li X, Fan S, Pan X, Xiaokaiti Y, Duan J, Shi Y, Pan Y, Tie L, Wang X, Li Y, Li X. Nordihydroguaiaretic acid impairs prostate cancer cell migration and tumor metastasis by suppressing neuropilin 1. Oncotarget. 2016 Dec 27;7(52):86225-86238. doi: 10.18632/oncotarget.13368. PubMed PMID: 27863391; PubMed Central PMCID: PMC5349909.

14: Nusrat S, Zaidi N, Zaman M, Islam S, Ajmal MR, Siddiqi MK, Santra MK, Khan RH. Repositioning nordihydroguaiaretic acid as a potent inhibitor of systemic amyloidosis and associated cellular toxicity. Arch Biochem Biophys. 2016 Dec 15;612:78-90. doi: 10.1016/j.abb.2016.10.014. Epub 2016 Oct 24. PubMed PMID: 27789205.

15: Bergren DR, Valentine JL. Anti-anaphylactic action of nordihydroguaiaretic acid in antigen sensitized guinea pigs. Respir Physiol Neurobiol. 2016 Dec;234:26-31. doi: 10.1016/j.resp.2016.09.003. Epub 2016 Sep 3. PubMed PMID: 27595978.

16: Choi YS, Jung MY. Kinetic study on the singlet oxygen quenching activity of nordihydroguaiaretic acid (NDGA) using methylene blue sensitized photooxidation of α-terpinene. Food Sci Biotechnol. 2016 Oct 31;25(5):1333-1336. doi: 10.1007/s10068-016-0209-1. eCollection 2016. PubMed PMID: 30263413; PubMed Central PMCID: PMC6049261.

17: Leon D, Parada D, Vargas-Uribe M, Perez AA, Ojeda L, Zambrano A, Reyes AM, Salas M. Effect of nordihydroguaiaretic acid on cell viability and glucose transport in human leukemic cell lines. FEBS Open Bio. 2016 Aug 23;6(10):1000-1007. eCollection 2016 Oct. PubMed PMID: 27761359; PubMed Central PMCID: PMC5055036.

18: Nusrat S, Siddiqi MK, Zaman M, Zaidi N, Ajmal MR, Alam P, Qadeer A, Abdelhameed AS, Khan RH. Correction: A Comprehensive Spectroscopic and Computational Investigation to Probe the Interaction of Antineoplastic Drug Nordihydroguaiaretic Acid with Serum Albumins. PLoS One. 2016 Oct 13;11(10):e0164927. doi: 10.1371/journal.pone.0164927. eCollection 2016. PubMed PMID: 27736985; PubMed Central PMCID: PMC5063339.

19: Nusrat S, Siddiqi MK, Zaman M, Zaidi N, Ajmal MR, Alam P, Qadeer A, Abdelhameed AS, Khan RH. A Comprehensive Spectroscopic and Computational Investigation to Probe the Interaction of Antineoplastic Drug Nordihydroguaiaretic Acid with Serum Albumins. PLoS One. 2016 Jul 8;11(7):e0158833. doi: 10.1371/journal.pone.0158833. eCollection 2016. Erratum in: PLoS One. 2016 Oct 13;11(10 ):e0164927. PubMed PMID: 27391941; PubMed Central PMCID: PMC4938263.

20: Kimura K, Huang RC. Tetra-O-Methyl Nordihydroguaiaretic Acid Broadly Suppresses Cancer Metabolism and Synergistically Induces Strong Anticancer Activity in Combination with Etoposide, Rapamycin and UCN-01. PLoS One. 2016 Feb 17;11(2):e0148685. doi: 10.1371/journal.pone.0148685. eCollection 2016. PubMed PMID: 26886430; PubMed Central PMCID: PMC4757551.