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Merck

T4425

Sigma-Aldrich

(6R)-5,6,7,8-Tetrahydrobiopterin dihydrochloride

≥98% (HPLC), powder

Sinónimos:

(6R)-BH4

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About This Item

Fórmula empírica (notación de Hill):
C9H15N5O3 · 2HCl
Número de CAS:
Peso molecular:
314.17
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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Nombre del producto

(6R)-5,6,7,8-Tetrahydrobiopterin dihydrochloride,

Quality Level

solubility

water, oxygen free: soluble 19.60-20.40 mg/mL, clear to slightly hazy, colorless to faintly yellow

storage temp.

−20°C

SMILES string

Cl.Cl.C[C@H](O)[C@H](O)[C@H]1CNC2=C(N1)C(=O)NC(N)=N2

InChI

1S/C9H15N5O3.2ClH/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7;;/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17);2*1H/t3-,4+,6-;;/m0../s1

InChI key

RKSUYBCOVNCALL-NTVURLEBSA-N

Gene Information

human ... PAH(5053)

General description

Tetrahydrobiopterin is a natural cofactor for phenylalanine hydroxylase, tyrosine hydroxylase, tryptophan hydroxylase, nitric oxide synthase and alkylglycerol monooxygenase.[1]

Application

(6R)-BH4 has been used as a buffer component for assaying tyrosine hydroxylase enzyme activity in mouse brain tissues. (6R)-BH4 has also been identified as an activator compound from a LOPAC library screen using a fluorogenic α-glucosidase assay.

Biochem/physiol Actions

Lack of tetrahydrobiopterin may cause hyperphenylalaninemia. Diseases like, Parkinson′s, autism, depression and Alzheimer′s shows low concentration of tetrahydrobiopterin in the cerebrospinal fluid.[2] This coenzyme participates in dopamine (DA) synthesis.[3]

Features and Benefits

This compound is featured on the Dopamine, Norepinephrine and Epinephrine Synthesis and Nitric Oxide Synthases pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

(6R)-5,6,7,8-Tetrahydrobiopterin dihydrochloride ((6R)-BH4 ) is soluble in oxygen free water at 19.60 - 20.40 mg/ml and yields a clear to slightly hazy, colorless to faint yellow solution.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Visite la Librería de documentos

Ailing Fu et al.
Brain research, 1352, 208-213 (2010-07-06)
Glial-derived neurotrophic factor (GDNF) is a trophic factor for the nigra-striatal tract in experimental Parkinson's disease (PD). The neurotrophin must be administered by intra-cerebral injection, because GDNF does not cross the blood-brain barrier (BBB). In the present study, GDNF was
Keun-Sung Lee et al.
The Korean journal of physiology & pharmacology : official journal of the Korean Physiological Society and the Korean Society of Pharmacology, 17(1), 89-97 (2013-02-27)
Developing an animal model for a specific disease is very important in the understanding of the underlying mechanism of the disease and allows testing of newly developed new drugs before human application. However, which of the plethora of experimental animal
Translational Medicine Strategies in Drug Development for Mood Disorders
Handbook of Biologically Active Peptides (2019)
Kwon, N.S., et al.
The Journal of Biological Chemistry, 264, 20498-20498 (1989)
Pteridines
Colette DS, et al.
reference module in biomedical sciences (2018)

Artículos

Serotonin is stored in cells and metabolized by MAO, influencing CNS, GI, and platelet functions.

Serotonin is stored in cells and metabolized by MAO, influencing CNS, GI, and platelet functions.

Serotonin is stored in cells and metabolized by MAO, influencing CNS, GI, and platelet functions.

Serotonin is stored in cells and metabolized by MAO, influencing CNS, GI, and platelet functions.

Questions

1–2 of 2 Questions  
  1. Is the product T4425 (CAS 69056-38-8) soluble in distilled water?

    1 answer
    1. The product is advised to be dissolved in anoxic water. The use of distilled water is not recommended, as it can absorb more oxygen from the atmosphere.

      Helpful?

  2. How should a solution of (6R)-5,6,7,8-tetrahydrobiopterin (hydrochloride) be stored? How long is it good for?

    1 answer
    1. Tetrahydrobiopterin reacts with oxygen, particularly in neutral and alkaline solutions. The product should be reconstituted in oxygen-free water. Tetrahydrobiopterin solutions become yellow but are stable for several weeks at -20°C when prepared at 20-40 mg/mL in 0.1 N HCl.

      Please review the product data sheet for more information on this product:
      https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/277/129/t4425pis.pdf

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