tetra-O-methyl nordihydroguaiaretic acid

Base Information

• Chemical Name: tetra-O-methyl nordihydroguaiaretic acid
• CAS No.: 5701-82-6
• Molecular Formula: C22H30 O4
• Molecular Weight: 358.478
• NSC Number: 136955
• DSSTox Substance ID: DTXSID10972502
• Nikkaji Number: J490.487G
• Wikidata: Q72509556
• ChEMBL ID: CHEMBL492149
• Mol file: 5701-82-6.mol

Synonyms:4,4'-(2,3-dimethyl-1,4-butanediyl)bis-1,2-dimethoxybenzene;FW 358.2;FW-358.2;terameprocol;tetra-O-methyl-NDGA;tetra-O-methylnordihydroguaiaretic acid;tetramethoxynordihydroguaiaretic acid;TMNDGA

Chemical Property of tetra-O-methyl nordihydroguaiaretic acid

Chemical Property:

• Vapor Pressure: 3.15E-11mmHg at 25°C
• Boiling Point: 458.5°Cat760mmHg
• Flash Point: 108.8°C
• PSA: 36.92000
• Density: 1.036g/cm³
• LogP: 4.77840
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 358.21440943
• Heavy Atom Count: 26
• Complexity: 352

Purity/Quality:

99% ^*data from raw suppliers

Terameprocol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC(=C(C=C1)OC)OC)C(C)CC2=CC(=C(C=C2)OC)OC
• Recent ClinicalTrials: A Pilot Study of EM-1421 for the Treatment of Cervical Intraepithelial Neoplasia

Technology Process of tetra-O-methyl nordihydroguaiaretic acid

There total 33 articles about tetra-O-methyl 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: 100.0%

C22H28O4 (278808-07-4) → 2,3-bis[(3,4-dimethoxyphenyl)methyl]butane (5701-82-6,24150-24-1,68930-18-7,119182-23-9)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethyl acetate; for 1h;

DOI:10.1016/S0040-4039(01)01182-0

Reference yield: 88.25%

1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethyl-2,3-butanediol (335327-93-0) → 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane (5701-82-6)

Guidance literature:

With trifluoroacetic acid; HSiPh₃; In dichloromethane; at 20 ℃; for 48.5h; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield:

ethanol (64-17-5) + 1,4-bis(3,4-dimethoxyphenyl),2,3-dimethylbutane-1,4-dione (4440-92-0) → 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane (5701-82-6)

Guidance literature:

at 150 - 160 ℃; under 147102 Torr; Hydrogenation;

DOI:10.1021/ja01181a020

upstream raw materials:

diazomethane

nordihydroguaiaretic acid

dimethylsulfone

4-(4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl)benzene-1,2-diol

Downstream raw materials:

nordihydroguaiaretic acid

C₁₈H₂₂O₄

Refernces

• 1、 Nakayama,Hori,Osawa,Kawakishi. "Suppression of hydrogen peroxide-induced mammalian cytotoxicity by nordihydroguaiaretic acid.". . p. 1162 - 1163. Retrieved 1992.
• 2、 Gezginci, Mikail H,Timmermann, Barbara N. "A short synthetic route to nordihydroguaiaretic acid (NDGA) and its stereoisomer using Ti-induced carbonyl-coupling reaction". . p. 6083 - 6085. Retrieved 2007/10/03.