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T4425

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

≥98% (HPLC), powder

Synonym(s):

(6R)-BH4

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About This Item

Empirical Formula (Hill Notation):
C9H15N5O3 · 2HCl
CAS Number:
Molecular Weight:
314.17
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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Product Name

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

Quality Segment

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.

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. This coenzyme participates in dopamine (DA) synthesis.

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.

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This Item
472804484235215921
Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

10-30°C

solubility

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

solubility

water: 50 mg/mL

solubility

methanol: soluble, water: soluble

solubility

methanol: 10 mg/mL, water: 50 mg/mL

Gene Information

human ... PAH(5053)

Gene Information

-

Gene Information

-

Gene Information

-


pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable



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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

      Helpful?

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