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176974

Sigma-Aldrich

2,4-Dihydroxypyridine

97%

Synonym(s):

2,4-Pyridinediol, 3-Deazauracil, 4-Hydroxy-2-pyridone

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About This Item

Empirical Formula (Hill Notation):
C5H5NO2
CAS Number:
626-03-9
Molecular Weight:
111.10
Beilstein:
108533
EC Number:
210-924-8
MDL number:
MFCD00006273
UNSPSC Code:
12352100
PubChem Substance ID:
24850611

Assay

97%

form

solid

mp

272-276 °C (lit.)

SMILES string

Oc1ccnc(O)c1

InChI

1S/C5H5NO2/c7-4-1-2-6-5(8)3-4/h1-3H,(H2,6,7,8)

InChI key

ZEZJPIDPVXJEME-UHFFFAOYSA-N

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General description

2,4-Dihydroxypyridine (3-deazauracil) is a potent inhibitor of dihydrouracil dehydrogenase.

Application

2,4-Dihydroxypyridine (3-deazauracil) was used in the synthesis of diazaphenoxathiin skeleton.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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F N Naguib et al.
Biochemical pharmacology, 38(9), 1471-1480 (1989-05-01)
One hundred and five nucleobase analogues were screened as inhibitors of dihydrouracil dehydrogenase (DHUDase, EC 1.3.1.2) from mouse liver. 5-Benzyloxybenzyluracil, 1-deazauracil (2,6-pyridinediol), 3-deazauracil (2,4-pyridinediol), 5-benzyluracil, 5-nitrobarbituric acid and 5,6-dioxyuracil (alloxan) were identified as potent inhibitors of this activity, with apparent
F P LaCreta et al.
Cancer research, 49(10), 2567-2573 (1989-05-15)
The breakdown of 5-fluoro-2'-deoxyuridine (FdUrd) to 5-fluorouracil (FUra) is catalyzed by the pyrimidine nucleoside phosphorylases, uridine phosphorylase and thymidine phosphorylase. The effects of nucleoside phosphorylase inhibitors on FdUrd and FUra elimination by the isolated perfused rat liver were investigated. The
M T Cocco et al.
European journal of medicinal chemistry, 35(5), 545-552 (2000-07-12)
4-hydroxy-2-pyridone derivatives 2 were prepared by reaction of 3-amino-3-dialkylaminopropenoates with bis(2,4, 6-trichlorophenyl)malonate. These compounds were further reacted with a set of aldehydes to give bis(pyridyl)methanes 3 and 4. The newly synthesized compounds 2, 3 and 4 were evaluated in vitro
M Kaneko et al.
Nucleic acids symposium series, (12)(12), 13-16 (1983-01-01)
New method for a synthesis of diazaphenoxathiin skeleton from 3-deazauracil derivatives is reported. It became possible to convert 3-deazauridine to 3-deazacytidine via an excellent intermediate "diazaphenoxathiin sulfoxide derivative".
Maria Teresa Cocco et al.
European journal of medicinal chemistry, 38(1), 37-47 (2003-02-21)
Bis(pyridyl)methane derivatives 5-40 were obtained from the reaction of 4-hydroxy-2-pyridones 3 and 4 with aldehydes. Compounds 5-40 were evaluated for cytotoxic activity against a panel of 60 human cancer cell lines by the National Cancer Institute and some of them
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