Nordihydroguaiaretic acid
Nordihydroguaiaretic acid structure
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Common Name | Nordihydroguaiaretic acid | ||
|---|---|---|---|---|
| CAS Number | 500-38-9 | Molecular Weight | 302.365 | |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 526.5±45.0 °C at 760 mmHg | |
| Molecular Formula | C18H22O4 | Melting Point | 184-189ºC | |
| MSDS | Chinese USA | Flash Point | 247.8±23.3 °C | |
| Symbol |
GHS07 |
Signal Word | Warning | |
Use of Nordihydroguaiaretic acidNordihydroguaiaretic acid is a 5-lipoxygenase (5LOX) (IC50=8±3 μM) and tyrosine kinase inhibitor. |
Summary: Nordihydroguaiaretic acid, Chinese name: 去甲二氢愈创木酸, CAS number: 500-38-9, molecular formula: C18H22O4, molecular weight: 302.365. Appearance: white to gray-white powder, melting point: 184-189°C, boiling point: 526.5±45.0 °C, density: 1.2±0.1 g/cm3. For use as an antioxidant, for research-use only, not for medical or clinical usage.
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | nordihydroguaiaretic acid |
|---|---|
| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| Description | Nordihydroguaiaretic acid is a 5-lipoxygenase (5LOX) (IC50=8±3 μM) and tyrosine kinase inhibitor. |
|---|---|
| Related Catalog | |
| Target |
IC50: 8±3 μM (5LOX)[1] |
| 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]. |
| 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]. |
| Cell Assay | 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]. |
| Animal Admin | 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. |
| References |
This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.
| Density | 1.2±0.1 g/cm3 |
|---|---|
| Boiling Point | 526.5±45.0 °C at 760 mmHg |
| Melting Point | 184-189ºC |
| Molecular Formula | C18H22O4 |
| Molecular Weight | 302.365 |
| Flash Point | 247.8±23.3 °C |
| Exact Mass | 302.151794 |
| PSA | 80.92000 |
| LogP | 3.71 |
| Vapour Pressure | 0.0±1.4 mmHg at 25°C |
| Index of Refraction | 1.627 |
| InChIKey | HCZKYJDFEPMADG-UHFFFAOYSA-N |
| SMILES | CC(Cc1ccc(O)c(O)c1)C(C)Cc1ccc(O)c(O)c1 |
| Storage condition | Freezer (-20°C) |
| Stability | Stable. Incompatible with oxidizing agents. |
| Water Solubility | slightly soluble |
This table provides MSDS information including hazard classification, first‑aid, fire‑fighting, spill handling, operation and storage instructions.
This table summarizes toxicological test data, acute & chronic toxicity and ecological hazard parameters for this chemical.
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATAACUTE TOXICITY DATA
MUTATION DATA
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This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.
| Symbol |
GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302-H315-H319-H335 |
| Precautionary Statements | P261-P305 + P351 + P338 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xn:Harmful; |
| Risk Phrases | R22;R36/37/38 |
| Safety Phrases | S26-S37/39 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | UX1750000 |
| HS Code | 2907299090 |
This table presents publicly reported synthetic routes, reaction conditions, reactants and product information of the compound.
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Nordihydroguaia... CAS#:500-38-9 |
| Literature: Palacio, Lorena; Cantero, Juan Jose; Cusido, Rosa; Goleniowski, Marta Process Biochemistry, 2011 , vol. 46, # 1 p. 418 - 422 |
This table lists upstream starting materials and downstream derivative products related to this chemical.
| Precursor 1 | |
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| DownStream 1 | |
CAS#:120-80-9This table shows customs‑related data including HS‑code, tariff and regulatory conditions for import and export.
| HS Code | 2907299090 |
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| Summary | 2907299090 polyphenols; phenol-alcohols。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:5.5%。general tariff:30.0% |
This table lists relevant public references with title, journal and publication metadata for this compound.
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Control of the pericentrosomal H2O2 level by peroxiredoxin I is critical for mitotic progression.
J. Cell Biol. 210 , 23-33, (2015) Proteins associated with the centrosome play key roles in mitotic progression in mammalian cells. The activity of Cdk1-opposing phosphatases at the centrosome must be inhibited during early mitosis to... |
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Inhibitors of the 5-lipoxygenase arachidonic acid pathway induce ATP release and ATP-dependent organic cation transport in macrophages
Biochim. Biophys. Acta 1838(7) , 1967-77, (2014) We have previously described that arachidonic acid (AA)-5-lipoxygenase (5-LO) metabolism inhibitors such as NDGA and MK886, inhibit cell death by apoptosis, but not by necrosis, induced by extracellul... |
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All-trans retinoic acid prevents oxidative stress-induced loss of renal tight junction proteins in type-1 diabetic model.
J. Nutr. Biochem. 26 , 441-54, (2015) We previously reported that diabetes decreased the expression of renal tight junction (TJ) proteins claudin-5 in glomerulus, and claudin-2 and occludin in proximal tubule through an oxidative stress d... |
This table contains target information, in‑vitro & in‑vivo assay data for this compound.
This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.
| meso-4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol |
| MFCD00002206 |
| 1,4-Bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane |
| Nordihydroguaiaretic acid |
| Nordihydroguaiaretic acid (meso-form) |
| MESO-NORDIHYDROGUAIARETIC ACID |
| Nordihydroguairaretic acid |
| 4,4'-(2,3-Dimethyltetramethylene)dipyrocatechol |
| Actinex |
| NDGA |
| 4-[(2R,3S)-4-(3,4-Dihydroxyphenyl)-2,3-dimethylbutyl]-1,2-benzenediol |
| b,g-Dimethyl-a,d-bis(3,4-dihydroxyphenyl)butane |
| Masoprocol |
| 4-[(2R,3S)-4-(3,4-Dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol |
| Nordihydro Guaiaretic Acid |
| EINECS 207-903-0 |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: What is the polar surface area (PSA) of nordihydroguaiaretic acid? |
| A: Polar surface area (PSA) of nordihydroguaiaretic acid is 80.92000. |
| Q: What is the CAS number of nordihydroguaiaretic acid? |
| A: CAS number of nordihydroguaiaretic acid is 500-38-9. |
| Q: What is the molecular weight of nordihydroguaiaretic acid? |
| A: Molecular weight of nordihydroguaiaretic acid is 302.365. |
| Q: What is the molecular formula of nordihydroguaiaretic acid? |
| A: Molecular formula of nordihydroguaiaretic acid is C18H22O4. |
| Q: What is the melting point of nordihydroguaiaretic acid? |
| A: Melting point of nordihydroguaiaretic acid is 184-189ºC. |
| Q: What is the English name of nordihydroguaiaretic acid? |
| A: The English name of nordihydroguaiaretic acid is nordihydroguaiaretic acid. |
| Q: What is the boiling point of nordihydroguaiaretic acid? |
| A: Boiling point of nordihydroguaiaretic acid is 526.5±45.0 °C at 760 mmHg. |
| Q: What are the storage conditions for nordihydroguaiaretic acid? |
| A: Storage conditions for nordihydroguaiaretic acid: Freezer (-20°C). |
| Q: What is the safety information for nordihydroguaiaretic acid? |
| A: Safety information for nordihydroguaiaretic acid: S26-S37/39. |
| Q: What are the upstream materials of nordihydroguaiaretic acid? |
| A: Related upstream materials(CAS) of nordihydroguaiaretic acid: 63-91-2. |
This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.
| Shanghai Nianxing Industrial Co., Ltd |
| Dayang Chem (Hangzhou) Co., Ltd. |
| naturewill |