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INSM-18

Alias: INSM-18, INSM 18, masoprocol, nordihydroguaiaretic acid, NDGA, actinex.; INSM18
Cat No.:V22133 Purity: ≥98%
Nordihydroguaiaretic acid is a 5-lipoxygenase (5LOX) (IC50=8 μM) and tyrosine kinase inhibitor (TKI).
INSM-18
INSM-18 Chemical Structure CAS No.: 500-38-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
250mg
Other Sizes

Other Forms of INSM-18:

  • Masoprocol
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Nordihydroguaiaretic acid is a 5-lipoxygenase (5LOX) (IC50=8 μM) and tyrosine kinase inhibitor (TKI).
Biological Activity I Assay Protocols (From Reference)
ln Vitro
The natural bisphenol nordihydroguaiaretic acid (NDGA) derived from the Zygophyllaceae family of plants, specifically the creosote plant, functions as a selective 5LOX inhibitor. Naturally occurring bisphenol nordihydroguaiaretic acid is a highly strong, non-toxic antagonist of TNFα-stimulated asteroid cell activation; it inhibits 5LOX. In vitro, nordihydroguaiaretic acid has an IC50 value of 8±3 μM and no toxicity at 100 μM, making it about six times more powerful than minocycline. At 800 nM nordihydroguaiaretic acid, a significant NO2-inhibition was seen. Both natural and synthesized nordihydroguaiaretic acid, as well as its toluenyl ester, showed comparable potency. With an IC50 of 841 nM, nordihydroguaiaretic acid also suppresses the synthesis of PGE 2 in TNFα-stimulated EOC-20 cells [1]. Effects of nordihydroguaiaretic acid (NDGA) and firesin E1 on cancer cell lines' proliferation. Different dosages of an individual chemical and the sophisticated compound 8-anilino-1-ethanesulfonate (ANS) were administered to the HepG2 cell line. Check cell viability using the MTT test after a 24-hour treatment. With an estimated IC50 of 25.888 μM, ANS demonstrated dose-dependent inhibition at 0, 10, 30, 50, 80, 100, 120, and 150 μM. The detection IC50 of nordihydroguaiaretic acid and scaffoldin E1 at various doses of 0, 30, 60, 80, 100, 120, and 140 μM were 45.646 μM and 41.223 μM, respectively [2].
ln Vivo
The high-dose nordihydroguaiaretic acid (NDGA) diet group began to lose weight significantly at 9 weeks, while the low-dose group started to lose weight at 12 weeks, in comparison to the postgraduate ob/ob diet group. Treatment with nordihydroguaiaretic acid raises the ob/ob body weight (rectal) temperature, particularly when the dose of the acid is high [3].
References

[1]. The arachidonic acid 5-lipoxygenase inhibitor Nordihydroguaiaretic acid inhibits tumor necrosis factor alpha activation of microglia and extends survival of G93A-SOD1 transgenic mice. J Neurochem. 2004 Oct;91(1):133-43.

[2]. Virtual Screening for Potential Allosteric Inhibitors of Cyclin-Dependent Kinase 2 from Traditional Chinese Medicine. Molecules. 2016 Sep 21;21(9). pii: E1259.

[3]. 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.

Additional Infomation
Nordihydroguaiaretic acid is a tetrol that is butane which is substituted at positions 2 and 3 by 3,4-dihydroxybenzyl groups. Masoprocol, the meso-form found in the leaves of the creosote bush (Larrea divaricata), is a potent lipoxygenase inhibitor. It has a role as an antioxidant, a plant metabolite, a ferroptosis inhibitor and a geroprotector. It is a member of catechols, a tetrol and a lignan.
Nordihydroguaiaretic acid has been reported in Arabidopsis thaliana, Magnolia sinica, and other organisms with data available.
A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.
See also: Masoprocol (annotation moved to).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H22O4
Molecular Weight
302.36488
Exact Mass
302.151
CAS #
500-38-9
Related CAS #
500-38-9 (stereoisomers);27686-84-6 (RS-isomer);500-38-9 (NGDA);180634-64-4 (pivalate);
PubChem CID
4534
Appearance
White to yellow solid powder
Density
1.2±0.1 g/cm3
Boiling Point
526.5±45.0 °C at 760 mmHg
Melting Point
184-189ºC
Flash Point
247.8±23.3 °C
Vapour Pressure
0.0±1.4 mmHg at 25°C
Index of Refraction
1.627
LogP
3.71
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
5
Heavy Atom Count
22
Complexity
303
Defined Atom Stereocenter Count
0
InChi Key
HCZKYJDFEPMADG-UHFFFAOYSA-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
Chemical Name
4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
Synonyms
INSM-18, INSM 18, masoprocol, nordihydroguaiaretic acid, NDGA, actinex.; INSM18
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~250 mg/mL (~826.83 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.88 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (6.88 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (6.88 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.3073 mL 16.5366 mL 33.0732 mL
5 mM 0.6615 mL 3.3073 mL 6.6146 mL
10 mM 0.3307 mL 1.6537 mL 3.3073 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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