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Merck

SMB00376

CDDO Methyl Ester

≥98% (HPLC)

Synonym(s):

2-Cyano-3,12-dioxo-oleana-1,9(11)-dien-28-oic acid methyl ester, Bardoxolone Methyl, CDDO-Me

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About This Item

Empirical Formula (Hill Notation):
C32H43NO4
CAS Number:
218600-53-4
Molecular Weight:
505.69
NACRES:
NA.25
PubChem Substance ID:
329824977
UNSPSC Code:
12352205
MDL number:
MFCD11983137

Key Documents

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Product Name

CDDO Methyl Ester, ≥98% (HPLC)

InChI

1S/C32H43NO4/c1-27(2)11-13-32(26(36)37-8)14-12-31(7)24(20(32)17-27)21(34)15-23-29(5)16-19(18-33)25(35)28(3,4)22(29)9-10-30(23,31)6/h15-16,20,22,24H,9-14,17H2,1-8H3/t20-,22-,24-,29-,30+,31+,32-/m0/s1

SMILES string

CC1(C)CC[C@]2(C(OC)=O)CC[C@@]([C@@]3([H])[C@]2([H])C1)(C)[C@]4(C)CC[C@@]5([H])C(C)(C)C(C(C#N)=C[C@]5(C)C4=CC3=O)=O

InChI key

WPTTVJLTNAWYAO-KPOXMGGZSA-N

assay

≥98% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

Quality Level

200

Gene Information

human ... IKBKB(3551), KEAP1(9817), NFE2L2(4780), PPARG(5468)

Related Categories

Application

CDDO Methyl Ester has been used to test its effect on hepatocyte membrane transporters (HMTs) regulation and mitigation of cholestasis in hepatic ischemia-reperfusion injury (IRI). It has also been used activator of NF E2 Related Factor 2 (NRF2) to study its role in preventing cell death in melanoma cells.

Biochem/physiol Actions

CDDO-Me inhibits inflammatory mediators including interleukin-6 (IL-6), IL-10, and IL-12. It enhances apoptosis induced by TNF and chemotherapeutic agents. CDDO-Me exhibits anti-proliferative activity in osteosarcoma cells and enhances the effectiveness of chemotherapeutic agents by inducing an intrinsic mitochondrial-dependent apoptotic pathway. It can be used as an adjuvant treatment for advanced and fatal form of prostate cancer.

General description

CDDO-Me is a synthetic triterpenoid compound with anti-inflammatory, anti-tumor and cytoprotective properties. It is derived from the natural product oleanic acid.

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
0000482772
0000482772
0000368189
0000368190
0000361827

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The synthetic triterpenoid CDDO-methyl ester modulates microglial activities, inhibits TNF production, and provides dopaminergic neuroprotection
Tran T A, et al.
Journal of Neuroinflammation, 5(1), 1-1 (2008)
Sandhya Chipurupalli et al.
Frontiers in oncology, 10, 758-758 (2020-06-02)
Melanoma is the most aggressive type of skin cancer and resistance to the conventional chemotherapy is the major cause for its poor prognosis. Metabolic perturbations leading to increased production of reactive oxygen species activate NRF2-dependent anti-oxidative responses to survive oxidative
Joohyun Kim et al.
Transplantation direct, 6(8), e584-e584 (2020-08-09)
Cholestasis is a sign of hepatic ischemia-reperfusion injury (IRI), which is caused by the dysfunction of hepatocyte membrane transporters (HMTs). As transcriptional regulation of HMTs during oxidative stress is mediated by nuclear factor erythroid 2-related factor 2, we hypothesized that
A synthetic triterpenoid, CDDO-Me, inhibits IKBα kinase and enhances apoptosis induced by TNF and chemotherapeutic agents through down-regulation of expression of nuclear factor KB?regulated gene products in human leukemic cells.
Shishodia S, et al.
Clinical Cancer Research, 12(6), 1828-1838 (2006)
Differential regulation of innate immune cytokine production through pharmacological activation of Nuclear Factor-Erythroid-2-Related Factor 2 (NRF2) in burn patient immune cells and monocytes.
Eitas T K, et al.
PLoS ONE, 12(9), e0184164-e0184164 (2017)
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