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Key Documents

E4267

Sigma-Aldrich

9-Ethylguanine

Synonym(s):

2-Amino-9-ethyl-6-hydroxypurine, 6-Amino-9-ethyl-2-hydroxypurine, 9-EtG

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About This Item

Empirical Formula (Hill Notation):
C7H9N5O
CAS Number:
Molecular Weight:
179.18
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

Assay

≥98%

Quality Level

form

powder

solubility

1 M NaOH: 9.80-10.20 mg/mL, clear, colorless to faintly yellow

storage temp.

2-8°C

SMILES string

CCn1cnc2C(=O)N=C(N)Nc12

InChI

1S/C7H9N5O/c1-2-12-3-9-4-5(12)10-7(8)11-6(4)13/h3H,2H2,1H3,(H3,8,10,11,13)

InChI key

WDOYBEPLTCFIRQ-UHFFFAOYSA-N

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Application

9-Ethylguanine (9-EtG) is used as a DNA model base for a variety of physical chemical studies of organometallic complexes.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Anna C G Hotze et al.
Inorganic chemistry, 43(16), 4935-4943 (2004-08-03)
The striking difference in cytotoxic activity between the inactive cis-[Ru(bpy)(2)Cl(2)] and the recently reported highly cytotoxic alpha-[Ru(azpy)(2)Cl(2)] (alpha indicating the isomer in which the coordinating Cl atoms, pyridine nitrogens, and azo nitrogens are in mutual cis, trans, cis orientation) encouraged
Haimei Chen et al.
Proceedings of the National Academy of Sciences of the United States of America, 100(25), 14623-14628 (2003-12-06)
Organometallic chemistry offers novel concepts in structural diversity and molecular recognition that can be used in drug design. Here, we consider DNA recognition by eta 6-arene Ru(II) anticancer complexes by an induced-fit mechanism. The stereochemistry of the dinuclear complex [((eta
José Ruiz et al.
Inorganic chemistry, 50(18), 9164-9171 (2011-08-13)
The novel steroidal conjugate 17-α-[2-phenylpyridyl-4-ethynyl]-19-nortestosterone (LEV-ppy) (1) and the steroid-C,N-chelate ruthenium(II) conjugate [Ru(η(6)-p-cymene)(LEV-ppy)Cl] (2) have been prepared. At 48 h incubation time, complex 2 is more active than cisplatin (about 8-fold) in T47D (breast cancer) and also shows an improved
Anna F A Peacock et al.
Journal of the American Chemical Society, 129(11), 3348-3357 (2007-02-27)
Potential biological and medical applications of organometallic complexes are hampered by a lack of knowledge of their aqueous solution chemistry. We show that the hydrolytic and aqueous solution chemistry of half-sandwich OsII arene complexes of the type [(eta6-arene)Os(XY)Cl] can be
Zhe Liu et al.
Inorganic chemistry, 50(12), 5777-5783 (2011-05-31)
Replacing the N,N-chelating ligand 2,2'-bipyridine (bpy) in the Ir(III) pentamethylcyclopentadienyl (Cp*) complex [(η(5)-C(5)Me(5))Ir(bpy)Cl](+) (1) with the C,N-chelating ligand 2-phenylpyridine (phpy) to give [(η(5)-C(5)Me(5))Ir(phpy)Cl] (2) switches on cytotoxicity toward A2780 human ovarian cancer cells (IC(50) values of >100 μM for 1

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