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Merck

37272

7,8-Dihydro-L-biopterin

≥94% (HPLC)

Synonym(s):

2-amino-6-(1,2-dihydroxypropyl)-7,8-dihydro-3H-pteridin-4-one

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About This Item

Empirical Formula (Hill Notation):
C9H13N5O3
CAS Number:
6779-87-9
Molecular Weight:
239.23
UNSPSC Code:
12352116
NACRES:
NA.25
PubChem Substance ID:
57649709
MDL number:
MFCD00049357
Beilstein/REAXYS Number:
536551

Key Documents

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InChI

1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,6,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,6-/m1/s1

SMILES string

C[C@@H](O)[C@@H](O)C1=NC2=C(NC1)N=C(N)NC2=O

InChI key

FEMXZDUTFRTWPE-AWFVSMACSA-N

assay

≥94% (HPLC)

storage temp.

−20°C

Quality Level

100

Application


  • A Landscape of Metabonomics for Intermingled Phlegm and Blood Stasis and Its Concurrent Syndromes in Stable Angina Pectoris of Coronary Heart Disease.: This study by Zheng et al. (2022) explores the metabolic profiles associated with phlegm and blood stasis syndromes in patients with stable angina pectoris. The research highlights the role of various metabolites, including 7,8-Dihydro-ʟ-biopterin, in the pathophysiology of these syndromes, suggesting potential diagnostic and therapeutic targets (Zheng et al., 2022).

  • Three-dimensional structure of human tryptophan hydroxylase and its implications for the biosynthesis of the neurotransmitters serotonin and melatonin.: Wang et al. (2002) present the crystal structure of human tryptophan hydroxylase, providing detailed insights into the enzyme′s interaction with cofactors such as 7,8-Dihydro-ʟ-biopterin. This structural information is crucial for developing drugs targeting neurotransmitter biosynthesis pathways (Wang et al., 2002).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

37272-VAR: + 37272-BULK: + 37272-10MG: + 37272-50MG:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6700
BCCL9357
BCCK4430
BCCH8100
BCCF1599

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Saptarshi Kar et al.
Free radical biology & medicine, 51(7), 1411-1427 (2011-07-12)
Endothelial dysfunction is associated with increase in oxidative stress and low NO bioavailability. The endothelial NO synthase (eNOS) uncoupling is considered an important factor in endothelial cell oxidative stress. Under increased oxidative stress, the eNOS cofactor tetrahydrobiopterin (BH(4)) is oxidized
An L Moens et al.
Journal of molecular and cellular cardiology, 51(4), 564-569 (2011-06-08)
The exogenous administration of tetrahydrobiopterin (BH4), an essential cofactor of nitric oxide synthase (NOS), has been shown to reduce left ventricular hypertrophy, fibrosis, and cardiac dysfunction in mice with pre-established heart disease induced by pressure-overload. In this setting, BH4 re-coupled
Angela Weinmann et al.
Pediatric research, 69(4), 325-329 (2010-12-24)
Breast milk reduces the incidence of necrotizing enterocolitis (NEC). BH4 is a cofactor for endothelial NOS (eNOS). Reduced BH4 levels, or its oxidation to dihydrobiopterin (BH2), uncouple eNOS resulting in formation of reactive oxygen species (ROS) that have been implicated
Stephen Wedgwood et al.
American journal of physiology. Lung cellular and molecular physiology, 302(6), L616-L626 (2011-12-27)
NADPH oxidase is a major source of superoxide anions in the pulmonary arteries (PA). We previously reported that intratracheal SOD improves oxygenation and restores endothelial nitric oxide (NO) synthase (eNOS) function in lambs with persistent pulmonary hypertension of the newborn
Livius V d'Uscio et al.
American journal of physiology. Heart and circulatory physiology, 301(6), H2227-H2234 (2011-10-04)
In the present study, we used the hph-1 mouse, which displays GTP-cyclohydrolase I (GTPCH I) deficiency, to test the hypothesis that loss of tetrahydrobiopterin (BH(4)) in conduit and small arteries activates compensatory mechanisms designed to protect vascular wall from oxidative
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