4-[(2R,3S)-3-[(3,4-dimethoxyphenyl)methyl]-2-methylbutyl]-1,2-dimethoxybenzene

• ChemBase ID: 153218
• Molecular Formular: C22H30O4
• Molecular Mass: 358.4712
• Monoisotopic Mass: 358.21440944
• SMILES: C[C@H](Cc1ccc(c(c1)OC)OC)[C@@H](C)Cc1ccc(c(c1)OC)OC
• Canonical SMILES: COc1cc(ccc1OC)C[C@H]([C@H](Cc1ccc(c(c1)OC)OC)C)C
• InChI: InChI=1S/C22H30O4/c1-15(11-17-7-9-19(23-3)21(13-17)25-5)16(2)12-18-8-10-20(24-4)22(14-18)26-6/h7-10,13-16H,11-12H2,1-6H3/t15-,16+
• InChIKey: ORQFDHFZSMXRLM-IYBDPMFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2R,3S)-3-[(3,4-dimethoxyphenyl)methyl]-2-methylbutyl]-1,2-dimethoxybenzene
• IUPAC Traditional name: 4-[(2R,3S)-3-[(3,4-dimethoxyphenyl)methyl]-2-methylbutyl]-1,2-dimethoxybenzene
• Synonyms: 2,3-Dimethyl-1,4-bis-(3,4-dimethoxyphenyl)butane; EM-1421; M4N; TMNDGA; Tetra-O-methyl nordihydroguaiaretic acid; rel-4-[(2R,3S)-4-(3,4-Dimethoxyphenyl)-2,3-dimethylbutyl]-1,2-dimethoxybenzene; tetra-O-methyl-NDGA; tetramethyl NDGA; tetramethyl Nordihydroguaiaretic Acid; Terameprocol

Database IDs

• CAS Number: 24150-24-1
• MDL Number: MFCD11113155
• PubChem SID: 162247357
• PubChem CID: 476861

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 5.342099
• LogD (pH = 7.4): 5.342099
• Log P: 5.342099
• Molar Refractivity: 104.5482 cm^3
• Polarizability: 40.89223 Å^3
• Polar Surface Area: 36.92 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Nature polluting (N)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H410
• GHS Precautionary statements: P273-P501
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H30O4

DETAILS

Sigma Aldrich - T3455

Biochem/physiol Actions
Terameprocol is a synthetic derivative of NDGA, a non-selective lipoxygenase inhibitor. It inhibits Sp1 transcription factor binding at the HIV long terminal repeat promoter and at the α-ICP4 promoter, a gene essential for HSV replication, with IC50 values of 11 and 43.5 μM respectively. TMNDGA induces growth arrest and apoptosis by suppressing Sp1-dependent Cdc2 and survivin gene expression giving rise to its antitumorigenic activity. The in vivo growth of xenografts in numerous human tumor types was suppressed upon treatment with TMNDGA It also inhibits the growth of murine and human melanomas and human colon cancer in vivo without causing other tissue toxicity.