Skip to Content
Merck
All Photos(1)

Documents

SML2416

Sigma-Aldrich

HET0016

≥95% (HPLC)

Synonym(s):

HET 0016, HET-0016, N′-(4-Butyl-2-methylphenyl)-N-hydroxymethanimidamide, N-(4-Butyl-2-methylphenyl)-N′-hydroxyformamidine, N-(4-Butyl-2-methylphenyl)-N′-hydroxymethanimidamide, N-Hydroxy-N′-(4-n-butyl-2-methylphenyl)formamidine

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C12H18N2O
CAS Number:
339068-25-6
Molecular Weight:
206.28
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

CCCCC1=CC=C(C(C)=C1)/N=C/NO

InChI

1S/C12H18N2O/c1-3-4-5-11-6-7-12(10(2)8-11)13-9-14-15/h6-9,15H,3-5H2,1-2H3,(H,13,14)

InChI key

LYNOGBKNFIHKLE-UHFFFAOYSA-N

Biochem/physiol Actions

HET0016 is a potent and selective inhibitor against cytochrome P450 (CYP450) ω-hydroxylases (human CYP4A11/4A22/4F2/4F3, rat CYP4A1/4A2/4A3/4A8)-mediated 20-hydroxyeicosatetraenoic acid (20-HETE) biosynthesis (IC50 = 8.9/35 nM using human/rat renal microsomes), exhibiting much reduced potency against epoxyeicosatrienoic acids (EETs) biosynthesis (IC50 = 2.8 μM/rat microsome) or the enzyme activities of CYP2C9/2D6/3A4 and COX (IC50 = 3.3/83.9/71 μM and 2.3 μM). HET0016 is widely employed both in cultures (1-10 μM) and in aminals in vivo (1-10 mg/kg via i.v., i.m., i.p. or s.c.) for probing 20-HETE-dependent physiological and pathological processes.

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

M Sato et al.
Bioorganic & medicinal chemistry letters, 11(23), 2993-2995 (2001-11-21)
N-(4-Butyl-2-methylphenyl)-N'-hydroxyformamidine (HET0016) was evaluated as the first potent and selective inhibitor of 20-hydroxy-5,8,11,14-eicosatetraenoic acid (20-HETE) synthase. The IC(50) value of HET0016 for the production of 20-HETE from arachidonic acid (AA) by human renal microsomes was 8.9+/-2.7 nM, with over 200
Guangrui Lai et al.
Prostaglandins & other lipid mediators, 134, 123-130 (2017-08-16)
We previously found that 20-hydroxyeicosatetraeonic acid (20-HETE) showed an effect on proteasome activity in cytochrome P450 F2 (CYP4F2) transgenic mice. Proteasome subunit β5 (PSMB5) is a primary subunit of the proteasome. In the current study, we examine whether 20-HETE has
Fan Fan et al.
Frontiers in bioscience (Landmark edition), 21, 1427-1463 (2016-04-23)
Cytochrome P450s enzymes catalyze the metabolism of arachidonic acid to epoxyeicosatrienoic acids (EETs), dihydroxyeicosatetraenoic acid and hydroxyeicosatetraeonic acid (HETEs). 20-HETE is a vasoconstrictor that depolarizes vascular smooth muscle cells by blocking K+ channels. EETs serve as endothelial derived hyperpolarizing factors.
N Miyata et al.
British journal of pharmacology, 133(3), 325-329 (2001-05-26)
The present study examined the inhibitory effects of N-hydroxy-N'-(4-butyl-2-methylphenyl)-formamidine (HET0016) on the renal metabolism of arachidonic acid by cytochrome P450 (CYP) enzymes. HET0016 exhibited a high degree of selectivity in inhibiting the formation of 20-hydroxy-5,8,11,14-eicosatetraenoic acid (20-HETE) in rat renal
Matthew G McDonald et al.
Drug metabolism and disposition: the biological fate of chemicals, 45(12), 1364-1371 (2017-10-12)
CYP4Z1 is an "orphan" cytochrome P450 (P450) enzyme that has provoked interest because of its hypothesized role in breast cancer through formation of the signaling molecule 20-hydroxyeicosatetraenoic acid (20-HETE). We expressed human CYP4Z1 in Saccharomyces cerevisiae and evaluated its catalytic
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service