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SMB00388

Sigma-Aldrich

2,4,3′,5′-tetramethoxystilbene

≥98% (HPLC)

Synonym(s):

2,4,3′,5′-tetramethoxystilbene, 1-[(1E)-2-(3,5-dimethoxyphenyl)ethenyl]-2,4-dimethoxy-benzene, 2,3′,4,5′-Tetramethoxystilbene

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About This Item

Empirical Formula (Hill Notation):
C18H20O4
CAS Number:
24144-92-1
Molecular Weight:
300.35
MDL number:
MFCD03428621
UNSPSC Code:
85151701
PubChem Substance ID:
329824983
NACRES:
NA.79

Quality Level

200

Assay

≥98% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

white to yellow

storage temp.

−20°C

SMILES string

COC1=CC(OC)=CC=C1/C=C/C2=CC(OC)=CC(OC)=C2

InChI

1S/C18H20O4/c1-19-15-8-7-14(18(12-15)22-4)6-5-13-9-16(20-2)11-17(10-13)21-3/h5-12H,1-4H3/b6-5+

InChI key

JDBCWSHYEQUBLW-AATRIKPKSA-N

Biochem/physiol Actions

2,3′,4,5′-Tetramethoxystilbene, also known as TMS, is a selective and competitive inhibitor of cytochrome P450 1B. It is a synthetic trans-stilbene analog. TMS is an analog of resveratrol and is an anti-cancer agent. TMS is cytotoxic to gefitinib-resistant (G-R) non-small-cell lung cancer (NSCLC) cells. It binds to sarco/endoplasmic reticulum Ca2+-ATPase (SERCA) and promotes apoptosis and autophagy. TMS is also a selective inhibitor of CYP1B1.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Modulation of human cytochrome P450 1B1 expression by 2, 4, 3?, 5?-tetramethoxystilbene
Chun YJ, et al.
Drug Metabolism and Disposition, 33(12), 1771-1776 (2005)
A new selective and potent inhibitor of human cytochrome P450 1B1 and its application to antimutagenesis
Chun YJ, et al.
Cancer Research, 61(22), 8164-8170 (2001)
(Z) 3, 4, 5, 4?-trans-tetramethoxystilbene, a new analogue of resveratrol, inhibits gefitinb-resistant non-small cell lung cancer via selectively elevating intracellular calcium level
Fan XX, et al.
Scientific Reports, 5, 16348-16348 (2015)
The resveratrol analogue, 2, 3?, 4, 5?-tetramethoxystilbene, does not inhibit CYP gene expression, enzyme activity and benzo [a] pyrene-DNA adduct formation in MCF-7 cells exposed to benzo [a] pyrene
Einem Lindeman T, et al.
Mutagenesis, 26(5), 629-635 (2011)
Inik Chang et al.
Oncotarget, 8(24), 39087-39100 (2017-04-08)
Cytochrome P450 1B1 (CYP1B1) is recognized as a universal tumor biomarker and a feasible therapeutic target due to its specific overexpression in cancer tissues. Despite its up-regulation in prostate cancer (PCa), biological significance and clinicopathological features of CYP1B1 are still
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