Nordihydroguaiaretic acid

Base Information

• Chemical Name: Nordihydroguaiaretic acid
• CAS No.: 500-38-9
• Deprecated CAS: 1413-68-9
• Molecular Formula: C18H22O4
• Molecular Weight: 302.37
• Hs Code.: 29072990
• European Community (EC) Number: 207-903-0
• NSC Number: 682984,4291
• DSSTox Substance ID: DTXSID5022437
• Nikkaji Number: J9.195B
• Wikipedia: Nordihydroguaiaretic_acid
• Wikidata: Q7050774
• Pharos Ligand ID: NPKH9YCZS449
• Metabolomics Workbench ID: 141905
• ChEMBL ID: CHEMBL52
• Mol file: 500-38-9.mol

Synonyms:(R*,S*)-4,4'-(2,3-Dimethylbutane-1,4-diyl)bispyrocatechol;Acid, meso-Nordihydroguaiaretic;Actinex;Dihydronorguaiaretic Acid;Masoprocol;meso Nordihydroguaiaretic Acid;meso-Nordihydroguaiaretic Acid;Nordihydroguaiaretic Acid;Nordihydroguaiaretic Acid, (R*,S*)-Isomer

Chemical Property of Nordihydroguaiaretic acid

Chemical Property:

• Appearance/Colour: light yellow crystalline solid
• Vapor Pressure: 1.06E-11mmHg at 25°C
• Melting Point: 182-187 °C
• Refractive Index: 1.626
• Boiling Point: 526.5 °C at 760 mmHg
• PKA: 9.56±0.10(Predicted)
• Flash Point: 247.8 °C
• PSA: 80.92000
• Density: 1.241 g/cm³
• LogP: 3.56640
• Storage Temp.: Freezer (-20°C)
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: slightly soluble
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 302.15180918
• Heavy Atom Count: 22
• Complexity: 303

Purity/Quality:

99% ^*data from raw suppliers

NordihydroGuaiareticAcid(mixtureofdiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37-37/39-24/25-22

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CC(CC1=CC(=C(C=C1)O)O)C(C)CC2=CC(=C(C=C2)O)O
• Recent ClinicalTrials: Pharmacokinetic and Efficacy Study of Nordihydroguaiaretic Acid (NDGA) in Non Metastatic Recurrent Prostate Cancer
• Description: Nordihydroguaiaretic acid (NDGA) is a grayish-white crystalline compound that was widely used as an antioxidant in animal fats in the 1950s and 1960s. It possesses phenolic properties similar to gallates, including their advantages and disadvantages. Besides the isolation of natural material (resinous exudate of creosote bush), NDGA has also been chemically synthesized. As the result of unfavorable toxicological findings, NDGA is prohibited from use in the US. More specifically, NDGA is a potent lipoxygenase inhibitor which interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carbox- ylesterase,and,to a lesser extent, cyclooxygenase.
• Uses: Nordihydroguaiaretic acid is used in the treatment of multiple diseases, including cardiovascular diseases, neurological disorders and cancers. It is also used as an antioxidant.

Technology Process of Nordihydroguaiaretic acid

There total 5 articles about Nordihydroguaiaretic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.26%

1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane (5701-82-6) → nordihydroguaiaretic acid (500-38-9,27686-84-6,741285-10-9)

Guidance literature:

With hydrogen bromide; In water; at 126 ℃; for 10h; Reagent/catalyst; Inert atmosphere;

Reference yield:

→ nordihydroguaiaretic acid (500-38-9,27686-84-6,741285-10-9)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/ja01198a513

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → para-coumaric acid (7400-08-0,50940-26-6) + nordihydroguaiaretic acid (500-38-9,27686-84-6,741285-10-9)

Guidance literature:

With Larrea divaricata Cav_. callus cells; In ethanol; Enzymatic reaction;

DOI:10.1016/j.procbio.2010.08.029

upstream raw materials:

L-phenylalanine

1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane

3,4-dimethoxyphenylacetone

Downstream raw materials:

1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane

benzene-1,2-diol

Refernces

• 1、 Palacio, Lorena,Cantero, Juan José,Cusidó, Rosa,Goleniowski, Marta. "Phenolic compound production by Larrea divaricata Cav. plant cell cultures and effect of precursor feeding". experimental part. p. 418 - 422. Retrieved 2011/09/20.