Synonym: 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
CAS Number: 24150-24-1
Empirical Formula (Hill Notation): C22H30O4
Molecular Weight: 358.47
MDL Number: MFCD11113155
Linear Formula: C22H30O4
Product Type: Chemical
| assay |
≥98% (HPLC) |
| color |
white to off-white |
| form |
powder |
| 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+ |
| InChI key |
ORQFDHFZSMXRLM-IYBDPMFKSA-N |
| Quality Level |
100  |
| SMILES string |
COc1ccc(C[C@H](C)[C@H](C)Cc2ccc(OC)c(OC)c2)cc1OC |
| solubility |
DMSO: ≥10 mg/mL |
| storage temp. |
−20°C |
| 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. |
| Biochem/physiol Actions: |
Terameprocol is known to reduce angiogenesis1. |
| Packaging: |
10, 50 mg in glass bottle |
| Preparation Note: |
Terameprocol is soluble in DMSO at a concentration that is greater than or equal to 10 mg/ml. |
| Symbol |
 GHS09 |
| Signal word |
Warning |
| Hazard statements |
H410 |
| Precautionary statements |
P273 - P501 |
| Hazard Codes |
N |
| Risk Statements |
50/53 |
| Safety Statements |
60-61 |
| RIDADR |
UN 3077 9 / PGIII |
| WGK Germany |
WGK 3 |
| Flash Point(F) |
Not applicable |
| Flash Point(C) |
Not applicable |
| Purity |
≥98% (HPLC) |
| Storage Temp. |
−20°C |
| UNSPSC |
12352200 |
