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H9377

Sigma-Aldrich

Hypoxanthine

≥99.0%

Synonym(s):

6-Hydroxypurine

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About This Item

Empirical Formula (Hill Notation):
C5H4N4O
CAS Number:
68-94-0
Molecular Weight:
136.11
Beilstein/REAXYS Number:
5811
EC Number:
200-697-3
MDL number:
MFCD00005725
UNSPSC Code:
41106305
PubChem Substance ID:
24895850
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

300

assay

≥99.0%

form

powder

mp

>300 °C (lit.)

solubility

formic acid: water (2:1): 50 mg/mL, clear to slightly hazy, colorless to yellow

SMILES string

O=C1NC=Nc2nc[nH]c12

InChI

1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)

InChI key

FDGQSTZJBFJUBT-UHFFFAOYSA-N

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Application

Hypoxanthine is a nutrient additive for a variety of cell culture applications involving bacterial, parasite (Plasmodium falciparum) and animal cells. Hypoxanthine is a component of selection media used in hybridoma technologies.
Hypoxanthine has been used:
  • to gavage mice and to evaluate the activity of xanthine oxidase (XO) in pasteurized whole milk in vivo in potassium oxonate (PO) -induced mouse model of hyperuricemia
  • as a supplement in Iscove′s modified Dulbecco′s medium (IMDM) medium to cultivate in-vitro cell line (EL-1 cells)
  • as a pure standard for the quantification of hypoxanthine in vitreous fluid sample using high-performance liquid chromatography-ultra-violet (HPLC-UV) for the estimation of post-mortem interval

Biochem/physiol Actions

Hypoxanthine acts as an intermediate in purine metabolism. It elicits a vital role as a 5′-base of the anticodon in a few transfer-RNAs. Though similar to guanine (Gua), it is devoid of the exocyclic amino group at C(2) position. It may be used as a substrate to study the specificity and kinetics of hypoxanthine-guanine phosphoribosyl transferases.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Different processed milk with residual xanthine oxidase activity and risk of increasing serum uric acid level
Sha W, et al.
Food Bioscience (2021)
Influence of the nature of death in biochemical analysis of the vitreous humour for the estimation of post-mortem interval
Perez-Martinez C, et al.
Australian journal of public health (2020)
John V W Becker et al.
Malaria journal, 10, 295-295 (2011-10-12)
Anti-malarial drug resistance threatens to undermine efforts to eliminate this deadly disease. The resulting omnipresent requirement for drugs with novel modes of action prompted a national consortium initiative to discover new anti-plasmodial agents from South African medicinal plants. One of
Abdulazeez T Lawal et al.
Food chemistry, 135(4), 2982-2987 (2012-09-18)
A potentiometric enzyme electrode for detection of hypoxanthine (Hx) in fish meat is described. The sensor was developed by entrapment of xanthine oxidase (XOD) and ferrocene carboxylic acid (Fc) into polypyrrole (PPy) film during galvanostatic polymerisation film formation. The responses
Tomáš Tichý et al.
European journal of medicinal chemistry, 55, 307-314 (2012-08-04)
Hexadecyloxypropyl esters of acyclic nucleoside phosphonates containing guanine (G) or hypoxanthine (Hx) and a (S)-[3-hydroxy-2-(phosphonomethoxy)propyl] [(S)-HPMP] or 2-(2-phosphonoethoxy)ethyl (PEE) acyclic moiety have been prepared. The activity of the prodrugs was evaluated in vitro against different virus families. Whereas ester derivatives of
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