| Identification | Back Directory | [Name]
Terameprocol | [CAS]
24150-24-1 | [Synonyms]
M4N
TMNDGA
EM-1421
Terameprocol
TETRAMEPROCOL
TETRAMETHYL NDGA
tetra-O-methyl-NDGA
TETRAMETHYL NORDIHYDROGUAIARETIC ACID
Tetra-O-methyl nordihydroguaiaretic acid
Meso-tetra-o-methylnordihydroguaiaretic acid
2,3-Dimethyl-1,4-bis-(3,4-dimethoxyphenyl)butane
Butane, 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethyl-, meso-
Meso-tetramethoxy-4,4'-(2,3-dimethyltetramethylene)dipyrocatechol
4-[(2S,3R)-4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-1,2-dimethoxybenzene
rel-4-[(2R,3S)-4-(3,4-Dimethoxyphenyl)-2,3-dimethylbutyl]-1,2-dimethoxybenzene
Benzene, 4-[(2R,3S)-4-(3,4-diMethoxyphenyl)-2,3-diMethylbutyl]-1,2-diMethoxy-, rel- | [Molecular Formula]
C22H30O4 | [MDL Number]
MFCD11113155 | [MOL File]
24150-24-1.mol | [Molecular Weight]
358.47 |
| Chemical Properties | Back Directory | [Melting point ]
101-102 °C | [Boiling point ]
458.5±40.0 °C(Predicted) | [density ]
1.036±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMSO: ≥10mg/mL | [form ]
powder | [color ]
white to off-white | [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 | [SMILES]
COc1ccc(C[C@H](C)[C@H](C)Cc2ccc(OC)c(OC)c2)cc1OC |
| Safety Data | Back Directory | [Hazard Codes ]
N | [Risk Statements ]
50/53 | [Safety Statements ]
60-61 | [RIDADR ]
UN 3077 9 / PGIII | [WGK Germany ]
3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Aquatic Acute 1
Aquatic Chronic 1 |
| Hazard Information | Back Directory | [Uses]
Terameprocol is a synthetic derivative of NDGA and non-selective lipoxygenase inhibitor. | [Definition]
ChEBI: Terameprocol is a lignan. | [Biological Activity]
tetramethyl nordihydroguaiaretic acid (tmndga) is a synthetic derivative of ndga (nordihydroguaiaretic acid), a non-selective lipoxygenase inhibitor. tmndga showed the strongest anti-hiv activity. | [in vitro]
in vero cells, tmndga inhibited sp1 transcription factor binding at the hiv long terminal repeat promoter and at the α-icp4 promoter with ic50 values of 11 and 43.5 μm, respectively. the ic50 of tmndga varied between 11.7 and 4 μm in 10 passages of hsv-1 and 4 passages of hsv-2 [2]. tmndga inhibited sp1-dependent cdc2 gene expression. in m4n-treated transformed c3 cells, tmndga induced growth arrest and apoptosis by suppressing sp1-dependent cdc2 and survivin gene expression giving rise to its antitumorigenic activity [3]. tmndga treatment suppressed expression of the sp1-dependent survivin gene. in transiently and stably survivin-transfected c3 cells, tmndga reduced caspase-3 activation by 50% and 75%, respectively [3]. tmndga inhibited the growth of a number of tumor cell lines by inducing apoptosis in a non-schedule-dependent manner [4]. tmndga inhibited the synthesis of dna by melanoma cells and causes cell cycle arrest in g0/g1 and g2/m phases of the cell cycle [4]. | [in vivo]
tmndga effectively inhibited the growth of human tumors in nude mice [5]. tmndga inhibited the growth of both murine and human melanomas and human colon cancer without apparent hepatic or renal toxicity [4]. in nude (nu/nu) mice bearing xenografts of human tumor types (hep 3b, lncap, ht-29, mcf7, and k-562), treatment with tmndga (i.v. or i.p.) down-regulated cdc2 and survivin genes expression [5]. | [IC 50]
COX-2 | [storage]
Store at -20°C | [References]
[1] hwu j r, tseng w n, gnabre j, et al. antiviral activities of methylated nordihydroguaiaretic acids. 1. synthesis, structure identification, and inhibition of tat-regulated hiv transactivation[j]. journal of medicinal chemistry, 1998, 41(16): 2994-3000.
[2] chen h, teng l, li j n, et al. antiviral activities of methylated nordihydroguaiaretic acids. 2. targeting herpes simplex virus replication by the mutation insensitive transcription inhibitor tetra-o-methyl-ndga[j]. journal of medicinal chemistry, 1998, 41(16): 3001-3007.
[3] chang c c, heller j d, kuo j, et al. tetra-o-methyl nordihydroguaiaretic acid induces growth arrest and cellular apoptosis by inhibiting cdc2 and survivin expression[j]. proceedings of the national academy of sciences of the united states of america, 2004, 101(36): 13239-13244.
[4] lambert j d, meyers r o, timmermann b n, et al. tetra-o-methylnordihydroguaiaretic acid inhibits melanoma in vivo[j]. cancer letters, 2001, 171(1): 47-56.
[5] park r, chang c c, liang y c, et al. systemic treatment with tetra-o-methyl nordihydroguaiaretic acid suppresses the growth of human xenograft tumors[j]. clinical cancer research, 2005, 11(12): 4601-4609. |
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