Nordihydroguaiaretic acid (Synonyms: NDGA)

Name: Nordihydroguaiaretic acid
Brand: MedChemExpress
SKU: HY-N0198
Rating: 5.0 (4 reviews)

Cat. No.: HY-N0198 Purity: 99.93%: FAQs
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Nordihydroguaiaretic acid is a 5-lipoxygenase (5LOX) (IC₅₀=8 μM) and tyrosine kinase inhibitor.

For research use only. We do not sell to patients.

Nordihydroguaiaretic acid Chemical Structure

CAS No. : 500-38-9

Size	Price	Stock	Quantity
Solid + Solvent (Highly Recommended)
10 mM * 1 mL in DMSO ready for reconstitution	USD 66	In-stock	Estimated Time of Arrival: December 31
Solution
10 mM * 1 mL in DMSO	USD 66	In-stock	Estimated Time of Arrival: December 31
Solid
100 mg	USD 60	In-stock	Estimated Time of Arrival: December 31
250 mg	USD 120	In-stock	Estimated Time of Arrival: December 31
500 mg		Get quote
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Based on 4 publication(s) in Google Scholar

Other Forms of Nordihydroguaiaretic acid:

Nordihydroguaiaretic acid (Standard) Get quote

4 Publications Citing Use of MCE Nordihydroguaiaretic acid

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Biological Activity
Protocol
Purity & Documentation
References
Customer Review

Description

Nordihydroguaiaretic acid is a 5-lipoxygenase (5LOX) (IC₅₀=8 μM) and tyrosine kinase inhibitor.

IC₅₀ & Target^[1]

5-LOX

8 μM (IC₅₀)

Cellular Effect

Cell Line	Type	Value	Description	References
A-375	IC₅₀	54.3 μM Compound: NDGA	Cytotoxicity against human A375 cells after 5 days by MTT assay Cytotoxicity against human A375 cells after 5 days by MTT assay	[PMID: 19615898]
BGC-823	IC₅₀	> 60 μM Compound: NDGA	Antiproliferative activity against human BGC823 cells after 72 hrs by MTT assay Antiproliferative activity against human BGC823 cells after 72 hrs by MTT assay	[PMID: 27829519]
HEK293	EC₅₀	35 μM Compound: NDGA	Agonist activity at human TRPA1 expressed in HEK293 cells assessed as increase in calcium influx by Fluo-4-AM dye based fluorescence assay Agonist activity at human TRPA1 expressed in HEK293 cells assessed as increase in calcium influx by Fluo-4-AM dye based fluorescence assay	[PMID: 30878828]
HEK293	EC₅₀	4.9 μM Compound: NDGA	Agonist activity at human TRPA1 expressed in HEK293 cells assessed as increase in calcium influx by Calcium-5 dye based fluorescence assay Agonist activity at human TRPA1 expressed in HEK293 cells assessed as increase in calcium influx by Calcium-5 dye based fluorescence assay	[PMID: 30878828]
HeLa	IC₅₀	0.08 μg/mL Compound: NDGA	Antiallergic activity in Ca(2+)-stimulated differentiated human HeLa cells assessed as inhibition of cys-leukotriene release after 6 days by ELISA Antiallergic activity in Ca(2+)-stimulated differentiated human HeLa cells assessed as inhibition of cys-leukotriene release after 6 days by ELISA	[PMID: 19942440]
Hepatocyte	IC₅₀	3 x 10⁴ nM Compound: Nordihydroguaiaretic acid	Antimicrobial activity against Plasmodium yoelii 265 liver infected in mammalian hepatocytes after 48 hrs Antimicrobial activity against Plasmodium yoelii 265 liver infected in mammalian hepatocytes after 48 hrs	[PMID: 18212104]
HepG2	IC₅₀	54.1 μM Compound: NDGA	Cytotoxicity against human HepG2 cells after 5 days by MTT assay Cytotoxicity against human HepG2 cells after 5 days by MTT assay	[PMID: 19615898]
HL-60	IC₅₀	12.2 μM Compound: NDGA	Cytotoxicity against human HL60 cells by XTT assay Cytotoxicity against human HL60 cells by XTT assay	[PMID: 16562834]
HL-60	IC₅₀	2.3 μM Compound: NDGA	Antioxidant activity in human HL60 cells assessed as inhibition of TPA-stimulated hydrogen peroxide induced DCFH-DA oxidation by fluorometric microplate assay Antioxidant activity in human HL60 cells assessed as inhibition of TPA-stimulated hydrogen peroxide induced DCFH-DA oxidation by fluorometric microplate assay	[PMID: 16562834]
HT-29	IC₅₀	51.3 μM Compound: NDGA	Cytotoxicity against human HT-29 cells after 5 days by MTT assay Cytotoxicity against human HT-29 cells after 5 days by MTT assay	[PMID: 19615898]
L929	EC₅₀	19 μM Compound: nordihydroguaiaretic acid	Inhibition of recombinant human TNF-alpha-induced cytotoxicity of mouse L929 cells assessed as survivality preincubated for 15 mins before TNFalpha addition measured after 24 hrs by [methyl-3H]thymidine incorporation assay Inhibition of recombinant human TNF-alpha-induced cytotoxicity of mouse L929 cells assessed as survivality preincubated for 15 mins before TNFalpha addition measured after 24 hrs by [methyl-3H]thymidine incorporation assay	[PMID: 9287415]
L929	EC₅₀	28 μM Compound: nordihydroguaiaretic acid	Inhibition of recombinant human TNF-alpha-induced cytotoxicity of mouse L929 cells assessed as survivality preincubated for 15 mins before TNFalpha addition measured after 24 hrs by crystal violet staining Inhibition of recombinant human TNF-alpha-induced cytotoxicity of mouse L929 cells assessed as survivality preincubated for 15 mins before TNFalpha addition measured after 24 hrs by crystal violet staining	[PMID: 9287415]
LNCaP	IC₅₀	38.8 μM Compound: 4, ZINC00012342, Nordihydroguaiaretic acid	Transcriptional activity at human androgen receptor BF3 site stably transfected in eGFP-expressing human LNCAP cells after 5 days by fluorometric analysis Transcriptional activity at human androgen receptor BF3 site stably transfected in eGFP-expressing human LNCAP cells after 5 days by fluorometric analysis	[PMID: 22047606]
Macrophage	IC₅₀	6 μM Compound: NDGA	Antiinflammatory activity in NMRI mouse macrophages assessed as inhibition of A23187-induced LTC4 release by Ellman's method Antiinflammatory activity in NMRI mouse macrophages assessed as inhibition of A23187-induced LTC4 release by Ellman's method	[PMID: 8988605]
MCF7	IC₅₀	8.5 μM Compound: NDGA	Cytotoxicity against human MCF7 cells after 5 days by MTT assay Cytotoxicity against human MCF7 cells after 5 days by MTT assay	[PMID: 19615898]
MGC-803	IC₅₀	45.8 μM Compound: NDGA	Antiproliferative activity against human MGC803 cells after 72 hrs by MTT assay Antiproliferative activity against human MGC803 cells after 72 hrs by MTT assay	[PMID: 27829519]
RBL-1	IC₅₀	0.12 μM Compound: NDGA	Inhibition of 5-lipoxygenase by measuring 5-HETE levels in RBL-1 cell-free supernatant Inhibition of 5-lipoxygenase by measuring 5-HETE levels in RBL-1 cell-free supernatant	[PMID: 8568814]
RBL-1	IC₅₀	0.15 μM Compound: NDGA (Nordihydroguaiaretic aid)	Ability to inhibit 5-lipoxygenase by using a crude preparation of the cytosolic enzyme from the rat basophilic leukemia (RBL-1) cell line Ability to inhibit 5-lipoxygenase by using a crude preparation of the cytosolic enzyme from the rat basophilic leukemia (RBL-1) cell line	[PMID: 2104936]
SGC-7901	IC₅₀	> 60 μM Compound: NDGA	Antiproliferative activity against human SGC7901 cells after 72 hrs by MTT assay Antiproliferative activity against human SGC7901 cells after 72 hrs by MTT assay	[PMID: 27829519]

In Vitro

The natural dicatechol Nordihydroguaiaretic acid (NDGA) is a selective 5LOX inhibitor from the creosote plant (Larrea tridentata: Zygophyllaceae). The 5LOX-inhibiting natural dicatechol Nordihydroguaiaretic acid is a very effective, non-toxic antagonist of TNFα-stimulated microglial activation. Nordihydroguaiaretic acid is approximately six times more potent than Minocycline in vitro, with an IC₅₀ value of 8±3 μM and no toxicity at 100 μM. Significant NO₂^- suppression is observed at 800 nM Nordihydroguaiaretic acid. Similar efficacy is observed for natural and synthetic Nordihydroguaiaretic acid, as well as for the acetyl ester of Nordihydroguaiaretic acid. Nordihydroguaiaretic acid also suppresses TNFα-stimulated PGE₂ production by EOC-20 cells with an IC₅₀ of 841 nM^[1].To test the proliferation effect of prostaglandin E1 and Nordihydroguaiaretic acid (NDGA) on cancer cell lines, HepG2 cell lines are treated with various doses of the two compounds and the positive compounds 8-anilino-1-naphtalene sulfonate (ANS), respectively, for 24 h and cell viability is examined by the MTT assay. ANS displays a dose-dependent inhibition (0, 10, 30, 50, 80, 100, 120, and 150 μM) with the estimated IC₅₀ being 25.888 μM. The tested IC₅₀ of prostaglandin E1 is 41.223 μM and Nordihydroguaiaretic acid is 45.646 μM, respectively, at different concentrations of 0, 30, 60, 80, 100, 120, and 140 μM^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Compared with the control ob/ob chow diet group, there is a significant reduction of body weight starting from 9 wk treatment in the high-dose Nordihydroguaiaretic acid (NDGA) diet group, and from 12 wk in the low-dose group. Nordihydroguaiaretic acid treatment results in higher body (rectal) temperatures of ob/ob mice, especially with the high dose of Nordihydroguaiaretic acid^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Clinical Trial

Molecular Weight

302.36

Formula

C₁₈H₂₂O₄

CAS No.

500-38-9

Appearance

Solid

Color

White to yellow

SMILES

CC(CC1=CC=C(O)C(O)=C1)C(C)CC2=CC=C(O)C(O)=C2

Structure Classification

Initial Source

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Store at room temperature 3 years

In solvent	-80°C	2 years
	-20°C	1 year

Solvent & Solubility

In Vitro:

DMSO : 250 mg/mL (826.83 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions

Concentration Solvent Mass	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

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Molarity Calculator
Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

Concentration _(start)

Volume _(start)

Concentration _(final)

Volume _(final)

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.08 mg/mL (6.88 mM); Clear solution

This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.08 mg/mL (6.88 mM); Clear solution

This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil
Solubility: ≥ 2.08 mg/mL (6.88 mM); Clear solution

This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

DMSO +

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Saline

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Calculation results:

Working solution concentration: mg/mL

Method for preparing stock solution: mg drug dissolved in μL DMSO (Stock solution concentration: mg/mL).

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).

Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.

If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.

Purity & Documentation

Purity: 99.93%

Select Batch:

Data Sheet (290 KB) SDS (392 KB)

COA (244 KB) HNMR (263 KB) RP-HPLC (243 KB) LCMS (251 KB)

Handling Instructions (2659 KB)

References

[1]. West M, et al. 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. [Content Brief]

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

[3]. Zhang H, 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. [Content Brief]

Cell Assay ^[2]	MTT assay is used to measure cell growth-inhibitory activity of the selected most promising compounds in HepG2 cell lines. Cells are cultured in 96-well culture plate at 1×10⁴ cells/well. After 24 h cultured at 37 °C in the atmosphere of 5% CO₂, cells are adhered and treated with different concentrations of the targeted compounds (e.g., Nordihydroguaiaretic acid, 0, 30, 60, 80, 100, 120, and 140 μM) and incubated for 24 h. Then, the supernatants are discarded and MTT (0.5 mg/mL) is added to each well and incubated at 37°C in 5% CO₂ for an additional 4 h. Following, the MTT is removed and 150 μL of formazan in DMSO is added to terminate response and then plates are set to the table shaker for 5 min at low speed. Cell proliferation is evaluated by measuring the absorbance at 570 nm using ELISA Plate Reader. The IC₅₀ values are calculated by SPSS statistics 17.0^[2]. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Animal Administration ^[3]	Mice^[3] *Seven-week-old male control C57BL/6J mice, male leptin-deficient (ob/ob) mice, and male Pparα-deficient mutant mice (B6.129S4-Pparatm1Gonz/J)* are used. These mice are fed a standard chow diet for 1 wk to allow them to acclimatize to a controlled new environment (25±2°C, 55±5% relative humidity with a 12-h light-dark cycle). Subsequently, one group of ob/ob mice is switched to a chow diet supplemented with either low- (0.83 g/kg chow diet) or high-dose (2.5 g/kg chow diet) Nordihydroguaiaretic acid and maintained on this diet for 16 wk. The other groups of ob/ob mice and control mice continue to be fed a normal chow diet for 16 wk. In another set of studies, C57BL/6J mice and Pparα-deficient mutant mice are fed either a high-fat diet (~60% of total calories come from fat), or the same high-fat diet supplemented with a high dose of Nordihydroguaiaretic acid (2.5 g/kg diet). Food intake and body weights are measured once a week throughout the experiment. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
References	[1]. West M, et al. 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. [Content Brief] [2]. Lu F, et al. Virtual Screening for Potential Allosteric Inhibitors of Cyclin-Dependent Kinase 2 from Traditional Chinese Medicine. Molecules. 2016 Sep 21;21(9). pii: E1259. [Content Brief] [3]. Zhang H, 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. [Content Brief]

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

DMSO	1 mM	3.3073 mL	16.5366 mL	33.0732 mL	82.6829 mL
	5 mM	0.6615 mL	3.3073 mL	6.6146 mL	16.5366 mL
	10 mM	0.3307 mL	1.6537 mL	3.3073 mL	8.2683 mL
	15 mM	0.2205 mL	1.1024 mL	2.2049 mL	5.5122 mL
	20 mM	0.1654 mL	0.8268 mL	1.6537 mL	4.1341 mL
	25 mM	0.1323 mL	0.6615 mL	1.3229 mL	3.3073 mL
	30 mM	0.1102 mL	0.5512 mL	1.1024 mL	2.7561 mL
	40 mM	0.0827 mL	0.4134 mL	0.8268 mL	2.0671 mL
	50 mM	0.0661 mL	0.3307 mL	0.6615 mL	1.6537 mL
	60 mM	0.0551 mL	0.2756 mL	0.5512 mL	1.3780 mL
	80 mM	0.0413 mL	0.2067 mL	0.4134 mL	1.0335 mL
	100 mM	0.0331 mL	0.1654 mL	0.3307 mL	0.8268 mL

Nordihydroguaiaretic acid Related Classifications

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Nordihydroguaiaretic acid (Synonyms: NDGA)

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4 Publications Citing Use of MCE Nordihydroguaiaretic acid

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Complete Stock Solution Preparation Table

Nordihydroguaiaretic acid Related Classifications

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