EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

biopterin
(L-erythro)-2-amino-6-(1,2-dihydroxypropyl)-4(3H)-pteridinon

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Name:2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1H-pteridin-4-one
CAS Number: 22150-76-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:244-807-8
FDA UNII: E54CTM794Y
Nikkaji Web:J313.857G
Beilstein Number:0087860
MDL:MFCD00036787
XlogP3-AA:-2.40 (est)
Molecular Weight:237.21927000
Formula:C9 H11 N5 O3
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:information only not used for fragrances or flavors
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 700 mg/L @ 20 °C (exp)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Biopterin > 95%
Odor: characteristic
Use: Biopterin is an oxidation product from the melanogenesis regulating cofactor (6R)5,6,7,8 tetrahydrobiopterin (6-BH4). It is an important cofactor in the production of many essential neurotransmitters, such as dopamine, seratonin and epinephrine,
Santa Cruz Biotechnology
For experimental / research use only.
L-Biopterin ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
6-Biopterin ≥97%
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
information only not used for fragrances or flavors
Recommendation for biopterin usage levels up to:
 not for fragrance use.
 
Recommendation for biopterin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :445040
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1H-pteridin-4-one
Chemidplus:0022150761
RTECS:UO3506000 for cas# 22150-76-1
 
References:
 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1H-pteridin-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):445040
Pubchem (cas):22150-76-1
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
KEGG (GenomeNet):C06313
HMDB (The Human Metabolome Database):HMDB00468
FooDB:FDB022060
Export Tariff Code:2933.90.8000
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
(S-(R*,S*))-2-amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-one
(L-erythro)-2-amino-6-(1,2-dihydroxypropyl)-4(3H)-pteridinon
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1H-pteridin-4-one
L-biopterin
4(1H)-pteridinone, 2-amino-6-(1,2-dihydroxypropyl)-, (S-(R*,S*))- (9CI)
 pterin H B2
 

Articles:

PubMed:Effect of Coffee in Lipopolysaccharide-Induced Indoleamine 2,3-Dioxygenase Activation and Depressive-like Behavior in Mice.
PubMed:Role of dihydrofolate reductase in tetrahydrobiopterin biosynthesis and lipid metabolism in the oleaginous fungus Mortierella alpina.
PubMed:Blood pressure-lowering effect of Korean red ginseng associated with decreased circulating Lp-PLA2 activity and lysophosphatidylcholines and increased dihydrobiopterin level in prehypertensive subjects.
PubMed:Mildly compromised tetrahydrobiopterin cofactor biosynthesis due to Pts variants leads to unusual body fat distribution and abdominal obesity in mice.
PubMed:Genetic predisposition in patients with hypertension and normal ejection fraction to oxidative stress.
PubMed:Brain catecholamine depletion and motor impairment in a Th knock-in mouse with type B tyrosine hydroxylase deficiency.
PubMed:Optimization of Expression Conditions Enhances Production of Sepiapterin, a Precursor for Tetrahydrobiopterin Biosynthesis, in Recombinant Escherichia coli.
PubMed:Disturbed biopterin and folate metabolism in the Qdpr-deficient mouse.
PubMed:Phenylketonuria Scientific Review Conference: state of the science and future research needs.
PubMed:Longitudinal quality of life analysis in a phenylketonuria cohort provided sapropterin dihydrochloride.
PubMed:Arginine and nitric oxide synthase: regulatory mechanisms and cardiovascular aspects.
PubMed:The effects of sapropterin on urinary monoamine metabolites in phenylketonuria.
PubMed:Structures and reaction mechanisms of GTP cyclohydrolases.
PubMed:Beneficial effects of the active principle component of Korean cabbage kimchi via increasing nitric oxide production and suppressing inflammation in the aorta of apoE knockout mice.
PubMed:Using change in plasma phenylalanine concentrations and ability to liberalize diet to classify responsiveness to tetrahydrobiopterin therapy in patients with phenylketonuria.
PubMed:Biochemical characterization of the tetrahydrobiopterin synthesis pathway in the oleaginous fungus Mortierella alpina.
PubMed:The effect of blood phenylalanine concentration on Kuvan™ response in phenylketonuria.
PubMed:BH(4) therapy impacts the nutrition status and intake in children with phenylketonuria: 2-year follow-up.
PubMed:Relative bioavailability of sapropterin from intact and dissolved sapropterin dihydrochloride tablets and the effects of food: a randomized, open-label, crossover study in healthy adults.
PubMed:Sapropterin: a new therapeutic agent for phenylketonuria.
PubMed:Tetrahydrobiopterin in intestinal lumen: its absorption and secretion in the small intestine and the elimination in the large intestine.
PubMed:First drug approved for treatment of phenylketonuria.
PubMed:Oral administration of both tetrahydrobiopterin and L-arginine prevents endothelial dysfunction in rats with chronic renal failure.
PubMed:Evaluation of electrospray-tandem mass spectrometry for the detection of phenylketonuria and other rare disorders.
PubMed:Dwarfism and low insulin-like growth factor-1 due to dopamine depletion in Pts-/- mice rescued by feeding neurotransmitter precursors and H4-biopterin.
PubMed:Applications of electron paramagnetic resonance spectroscopy to study interactions of iron proteins in cells with nitric oxide.
PubMed:Laboratory evaluation of the inflammatory myopathies.
PubMed:Food-derived heterocyclic amines, 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole and related amines, as inhibitors of monoamine metabolism.
PubMed:Aluminium administered in drinking water but not in the diet influences biopterin metabolism in the rodent.
PubMed:Reduction of enzymatic activity of tyrosine hydroxylase by a heterocyclic amine, 3-amino-1,4-dimethyl-5H-pyrido(4,3-b)indole (Trp-P-1), was due to reduced affinity to a cofactor biopterin.
PubMed:The influence of nutritional factors on biopterin excretion in laboratory animals.
PubMed:Biopterin and neopterin in various milks and infant formulas.
PubMed:Search for clues to the evolutionary meaning of ciliate phylogeny.
PubMed:[On the food of the queen cell in the honey bee. 4. Seasonal changes in the biopterin content of the food of the worker bee].
 
Notes:
Biopterin concentrations in cerebrospinal fluid from patients with Parkinson's disease, in which the nigrostriatal dopamine neurons degenerate, are lower than those from age-matched older controls. In hereditary progressive dystonia/DOPA-responsive dystonia, which is a dopamine deficiency caused by mutations in GTP cyclohydrolase I without neuronal cell death (Segawa's disease), biopterin in cerebrospinal fluid decrease in parallel owing to the decreased activity in GTP cyclohydrolase I (EC 3.5.4.16, is an enzyme that is part of the folate and biopterin biosynthesis pathways. It is responsible for the hydrolysis of guanosine triphosphate (GTP) to form 7,8-dihydroneopterin 3'-triphosphate. (Pteridines (1999), 10(1), 5-13.) Lowered levels of urinary biopterin concomitant with elevated serum phenylalanine concentration occur in a variant type of hyperphenylalaninemia caused by a deficiency of tetrahydrobiopterin (BH4), the obligatory cofactor for phenylalanine hydroxylase. The most frequent form of this cofactor deficiency is due to lack of 6-pyruvoyl-tetrahydropterin synthase (PTPS) activity, the second enzyme in the biosynthetic pathway for BH4. (PMID 8178819) The hepatic phenylalanine hydroxylating system consists of 3 essential components, phenylalanine hydroxylase, dihydropteridine reductase, and the nonprotein coenzyme, tetrahydrobiopterin. The reductase and the pterin coenzyme are also essential components of the tyrosine and tryptophan hydroxylating systems. There are 3 distinct forms of phenylketonuria or hyperphenylalaninemia, each caused by lack of 1 of these essential components. The variant forms of the disease that are caused by the lack of dihydropteridine reductase or tetrahydrobiopterin are characterized by severe neurol. deterioration, impaired functioning of tyrosine and tryptophan hydroxylases, and the resultant deficiency of tyrosine- and tryptophan-derived monoamine neurotransmitters in brain. (PMID 3930837) [HMDB]
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