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37343

Sigma-Aldrich

7,8-Dihydroneopterin

≥97.0% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C9H13N5O4
CAS Number:
1218-98-0
Molecular Weight:
255.23
Beilstein:
1133875
MDL number:
MFCD00049358
UNSPSC Code:
12352106
PubChem Substance ID:
57649718
NACRES:
NA.25

Quality Level

100

Assay

≥97.0% (HPLC)

form

solid

storage temp.

−20°C

SMILES string

NC1=NC(=O)C2=C(NCC(=N2)[C@H](O)[C@H](O)CO)N1

InChI

1S/C9H13N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h4,6,15-17H,1-2H2,(H4,10,11,13,14,18)/t4-,6+/m1/s1

InChI key

YQIFAMYNGGOTFB-XINAWCOVSA-N

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)

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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Renate Horejsi et al.
Biochimica et biophysica acta, 1571(2), 124-130 (2002-06-07)
7,8-Dihydroneopterin and neopterin are secreted by human and primate macrophages after activation by interferon-gamma in a ratio of 2:1. 7,8-Dihydroneopterin is known to suppress radical-mediated processes, but it is also able in the presence of iron ions to generate superoxide
S P Gieseg et al.
British journal of pharmacology, 153(4), 627-635 (2007-08-19)
The rise in plasma neopterin observed with increasing severity of vascular disease is a strong indicator of the inflammatory nature of atherosclerosis. Plasma neopterin originates as the oxidation product of 7,8-dihydroneopterin secreted by gamma-interferon stimulated macrophages within atherosclerotic plaques. Neopterin
Christiane Enzinger et al.
European journal of cell biology, 81(4), 197-202 (2002-05-23)
Activated cell-mediated immunity is known to be accompanied by elevated concentrations of 7,8-dihydroneopterin which in high concentrations was found to interfere with the oxidant-antioxidant balance. In this study we investigated whether 7,8-dihydroneopterin mediates apoptosis of Jurkat T-lymphocytes via a CrmA-
Carole A Firth et al.
Clinical biochemistry, 41(13), 1078-1083 (2008-07-16)
Plasma neopterin is a clinical marker of inflammation. Interferon-gamma triggers 7,8-dihydroneopterin and its oxidation product, neopterin, to be released from macrophages. 7,8-dihydroneopterin is a potent antioxidant which can protect macrophages from oxidative damage in vitro. This study examined whether 7,8-dihydroneopterin/neopterin
Sarah K Baird et al.
Biochimica et biophysica acta, 1745(3), 361-369 (2005-08-09)
The atherosclerotic plaque is an inflammatory site where macrophage cells are exposed to cytotoxic oxidised low density lipoprotein (oxLDL). Interferon-gamma released from T-cells results in macrophage synthesis of 7,8-dihydroneopterin which has antioxidant and cytoprotective activity. Using the human derived monocyte-like
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