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Merck

O9890

5Z-7-Oxozeaenol

≥98% (HPLC), powder, TAK1 inhibitor

Synonym(s):

C 292, F 152, FR148083, L 783279, LL-Z1640-2

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About This Item

Empirical Formula (Hill Notation):
C19H22O7
CAS Number:
253863-19-3
Molecular Weight:
362.37
UNSPSC Code:
12352200
PubChem Substance ID:
329818946
NACRES:
NA.77
MDL number:
MFCD12912700

Key Documents

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Product Name

5Z-7-Oxozeaenol, ≥98% (HPLC)

SMILES string

COc1cc(O)c2C(=O)O[C@@H](C)CC=CC(=O)[C@@H](O)[C@@H](O)C\C=C\c2c1

InChI key

NEQZWEXWOFPKOT-BYRRXHGESA-N

InChI

1S/C19H22O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,15,18,21-23H,5,8H2,1-2H3/b6-4+,7-3-/t11-,15-,18+/m0/s1

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

Quality Level

100

Related Categories

Application

5Z-7-Oxozeaenol has been used:
  • as transforming growth factor β-activated kinase 1 (TAK1) inhibitor to treat human colon cancer cells
  • as TAK1-specific inhibitor to provide intraperitoneal injection to mice for aortic banding
  • as TAK1 inhibitor to treat cells for luciferase reporter assay
  • to test growth and differentiation factor 2 (GDF2)-mediated anoikis

Biochem/physiol Actions

5Z-7-oxozeaenol is a potent ATP-competitive irreversible inhibitor of ERK2 (IC50 = 80 nM), TAK1 (MEKK7), MKK7, and MEK1, which all contain a common cysteine residue in the ATP-binding site. 5Z-7-oxozeaenol has no activity against other MAP kinases. 5Z-7-oxozeaenol is also anti-inflammatory.
The anti-inflammatory effects of 5Z-7-oxozeaenol may affect cardiac hypertrophy.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the MAPKKKs and MAPKs pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000354257
0000354257
0000229260
0000218541
0000229260

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Li Bo et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 84, 917-924 (2016-10-21)
Resistance to taxol represents a major obstacle for long-term remission in ovarian cancer. Transforming Growth Factor-β-Activated Kinase 1 (TAK1) is a critical component in immune response pathway. However, the role of TAK1 in the development of chemoresistance in ovarian cancer
Cytosolic Internalization of Anti-DNA Antibodies by Human Monocytes Induces Production of Pro-Inflammatory Cytokines Independently of the Tripartite Motif-Containing 21 (TRIM21)-Mediated Pathway
Park H, et al.
Frontiers in Immunology, 9 (2018)
Gang Wang et al.
Journal of cellular and molecular medicine, 25(14), 6584-6601 (2021-06-03)
Gastric cancer (GC) is the most frequent digestive system malignant tumour and the second most common cause of cancer death globally. Cancer stem cell (CSC) is a small percentage of cancer cells in solid tumours that have differentiation, self-renewal and
Dual-specificity phosphatase 14 protects the heart from aortic banding-induced cardiac hypertrophy and dysfunction through inactivation of TAK1-P38MAPK/-JNK1/2 signaling pathway
Li CY, et al.
Basic Research in Cardiology, 111(2), 19-19 (2016)
Epigenetic regulation of GDF2 suppresses anoikis in ovarian and breast epithelia
Varadaraj A, et al.
Neoplasia, 17(11), 826-838 (2015)
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