T4425

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

• Synonym(s): (6R)-BH₄
• Empirical Formula (Hill Notation): C₉H₁₅N₅O₃ · 2HCl
• CAS Number: 69056-38-8
• Molecular Weight: 314.17
• MDL number: MFCD00891665
• UNSPSC Code: 12352200
• PubChem Substance ID: 24277922
• NACRES: NA.77

Properties

• Quality Level: 200
• 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)

Description

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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable