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Terameprocol

Product Name
Terameprocol
CAS No.
24150-24-1
Chemical Name
Terameprocol
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
CBNumber
CB22456380
Molecular Formula
C22H30O4
Formula Weight
358.47
MOL File
24150-24-1.mol
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Terameprocol Property

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
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Safety

Hazard Codes 
N
Risk Statements 
50/53
Safety Statements 
60-61
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T3455
Product name
Terameprocol
Purity
≥98% (HPLC)
Packaging
10mg
Price
$90
Updated
2024/03/01
Sigma-Aldrich
Product number
T3455
Product name
Terameprocol
Purity
≥98% (HPLC)
Packaging
50mg
Price
$354
Updated
2024/03/01
Cayman Chemical
Product number
70302
Product name
tetramethyl Nordihydroguaiaretic Acid
Purity
≥95%
Packaging
50mg
Price
$16
Updated
2024/03/01
Cayman Chemical
Product number
70302
Product name
tetramethyl Nordihydroguaiaretic Acid
Purity
≥95%
Packaging
1g
Price
$188
Updated
2024/03/01
Cayman Chemical
Product number
70302
Product name
tetramethyl Nordihydroguaiaretic Acid
Purity
≥95%
Packaging
100mg
Price
$28
Updated
2024/03/01
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Terameprocol Chemical Properties,Usage,Production

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].

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.

Terameprocol Preparation Products And Raw materials

Raw materials

Preparation Products

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Terameprocol Suppliers

TargetMol Chemicals Inc.
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+1-781-999-5354 +1-00000000000
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marketing@targetmol.com
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United States
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ApexBio Technology
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sales@apexbt.com
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BOC Sciences
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16314854226
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info@bocsci.com
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United States
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Cayman Chemical Company
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cayman@caymanchem.com
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United States
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6213
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Riedel-de Haen AG
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United States
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6773
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24150-24-1, TerameprocolRelated Search:


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  • M4N
  • TETRAMEPROCOL
  • TETRAMETHYL NDGA
  • TETRAMETHYL NORDIHYDROGUAIARETIC ACID
  • TMNDGA
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  • Meso-tetramethoxy-4,4'-(2,3-dimethyltetramethylene)dipyrocatechol
  • Meso-tetra-o-methylnordihydroguaiaretic acid
  • Benzene, 4-[(2R,3S)-4-(3,4-diMethoxyphenyl)-2,3-diMethylbutyl]-1,2-diMethoxy-, rel-
  • 2,3-Dimethyl-1,4-bis-(3,4-dimethoxyphenyl)butane
  • rel-4-[(2R,3S)-4-(3,4-Dimethoxyphenyl)-2,3-dimethylbutyl]-1,2-dimethoxybenzene
  • Tetra-O-methyl nordihydroguaiaretic acid
  • tetra-O-methyl-NDGA
  • 4-[(2S,3R)-4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-1,2-dimethoxybenzene
  • Terameprocol
  • inhibit,LOX,EM1421,EM 1421,Inhibitor,Lipoxygenase,Terameprocol
  • 24150-24-1