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SML0177

Sigma-Aldrich

AUDA

≥98% (HPLC)

Synonym(s):

12-[[(tricyclo[3.3.1.13,7]dec-1-ylamino)carbonyl]amino]-dodecanoic acid

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About This Item

Empirical Formula (Hill Notation):
C23H40N2O3
CAS Number:
479413-70-2
Molecular Weight:
392.58
MDL number:
MFCD12912267
UNSPSC Code:
12352200
PubChem Substance ID:
329825206
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: ≥10 mg/mL at warmed to 60 °C

storage temp.

−20°C

SMILES string

OC(=O)CCCCCCCCCCCNC(=O)NC12C[C@@H]3C[C@@H](C[C@@H](C3)C1)C2

InChI

1S/C23H40N2O3/c26-21(27)10-8-6-4-2-1-3-5-7-9-11-24-22(28)25-23-15-18-12-19(16-23)14-20(13-18)17-23/h18-20H,1-17H2,(H,26,27)(H2,24,25,28)/t18-,19+,20-,23-

InChI key

XLGSEOAVLVTJDH-UKBVAGSOSA-N

Application

AUDA has been used in the inhibition of epoxide hydrolase in human macrophages and in inhibition of tumor necrosis factor α (TNF-α)- induced phosphorylation in human aortic smooth muscle cells.
AUDA may be used in soluble epoxide hydrolase-mediated cell signaling studies.

Biochem/physiol Actions

Inhibition of soluble epoxide hydrolase by AUDA inhibits the metabolism of epoxyeicosatrienoic acids (EETs) and protects end-organs against the damaging effects of salt-sensitive hypertension. AUDA also renders protection against myocardial ischemia-reperfusion injury and cerebral ischemia.
AUDA is a potent inhibitor of soluble epoxide hydrolase

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jung Pyo Lee et al.
PloS one, 7(5), e37075-e37075 (2012-05-17)
Soluble epoxide hydrolase (sEH) in endothelial cells determines the plasma concentrations of epoxyeicosatrienoic acids (EETs), which may act as vasoactive agents to control vascular tone. We hypothesized that the regulation of sEH activity may have a therapeutic value in preventing
Jang Hoon Kim et al.
Biomolecules, 10(2) (2020-01-30)
: Three flavonoids derived from the leaves of Capsicum chinense Jacq. were identified as chrysoeriol (1), luteolin-7-O-glucopyranoside (2), and isorhamnetin-7-O-glucopyranoside (3). They had IC50 values of 11.6±2.9, 14.4±1.5, and 42.7±3.5 µg/mL against soluble epoxide hydrolase (sEH), respectively. The three inhibitors
In Sook Cho et al.
Molecules (Basel, Switzerland), 25(18) (2020-09-26)
Flavonoids and triterpenoids were revealed to be the potential inhibitors on soluble epoxide hydrolase (sEH). The aim of this study is to reveal sEH inhibitors from Fuji apples. A flavonoid and three triterpenoids derived from the fruit of Malus domestica
Soluble epoxide hydrolase inhibitor, 12-(3-adamantan-1-yl-ureido)-dodecanoic acid, represses human aortic smooth muscle cell proliferation and migration by regulating cell death pathways via the mTOR signaling
Li SH, et al.
International Journal of Clinical and Experimental Pathology, 10(8), 8434-8442 (2017)
Aylin Acun et al.
Acta biomaterialia, 94, 372-391 (2019-05-31)
Deaths attributed to ischemic heart disease increased by 41.7% from 1990 to 2013. This is primarily due to an increase in the aged population, however, research on cardiovascular disease (CVD) has been overlooking aging, a well-documented contributor to CVD. The
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