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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
Molecular Weight:
358.47
MDL Number:
MFCD11113155
MOL File:
24150-24-1.mol
Last updated:2023-09-20 16:43:00

Terameprocol Properties

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
NCI Dictionary of Cancer Terms EM-1421; tetra-O-methyl NDGA; tetra-O-methyl nordihydroguaiaretic acid
FDA UNII 53YET703F2

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
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  3

Terameprocol price More Price(13)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich T3455 Terameprocol ≥98% (HPLC) 24150-24-1 10mg $90 2024-03-01 Buy
Sigma-Aldrich T3455 Terameprocol ≥98% (HPLC) 24150-24-1 50mg $354 2024-03-01 Buy
Cayman Chemical 70302 tetramethyl Nordihydroguaiaretic Acid ≥95% 24150-24-1 50mg $16 2024-03-01 Buy
Cayman Chemical 70302 tetramethyl Nordihydroguaiaretic Acid ≥95% 24150-24-1 1g $188 2024-03-01 Buy
Cayman Chemical 70302 tetramethyl Nordihydroguaiaretic Acid ≥95% 24150-24-1 100mg $28 2024-03-01 Buy
Product number Packaging Price Buy
T3455 10mg $90 Buy
T3455 50mg $354 Buy
70302 50mg $16 Buy
70302 1g $188 Buy
70302 100mg $28 Buy

Terameprocol Chemical Properties,Uses,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

Global( 18)Suppliers
Supplier Tel Email Country ProdList Advantage
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 19892 58
Shanghai Fuhe Chemistry Technology Co., Ltd. 0086-21-67651709 cfx759@hotmail.com China 410 57
NCE Biomedical Co.,Ltd. 4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988 China 1494 55
LETOPHARM LIMITED +86-21-5821 5861 sales@letopharm.com China 2384 58
SPIRO PHARMA eric_feng1954@126.com China 9254 55
ChemeGen(Shanghai) Biotechnology Co.,Ltd. 18818260767 sales@chemegen.com China 11289 58
Energy Chemical 021-58432009 400-005-6266 marketing@energy-chemical.com China 44941 58
Henan Kehong Biological Technology Co. LTD 0371-55969461 info@kehobio.com China 725 58
Changzhou Bojia Biomedical Technology Co., Ltd. 2122619822 czbjpharma@126.com China 18488 58
TargetMol Chemicals Inc. 4008200310 marketing@tsbiochem.com China 24131 58

Terameprocol Spectrum

EM-1421 M4N TETRAMEPROCOL TETRAMETHYL NDGA TETRAMETHYL NORDIHYDROGUAIARETIC ACID TMNDGA Butane, 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethyl-, meso- 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