6-Biopterin

6-Biopterin Structure
CAS No.
22150-76-1
Chemical Name:
6-Biopterin
Synonyms
BIOPTERIN;L-BIOPTERIN;pterinhb2;NSC-339699;6-BIOPTERIN;6-Biopterin, ≥97%;D-erythro-Biopterin;L-erythro-Biopterin;(1'R,2'S)-BIOPTERIN;L-Biopterin(6-Biopterin)
CBNumber:
CB8691190
Molecular Formula:
C9H11N5O3
Molecular Weight:
237.22
MOL File:
22150-76-1.mol
MSDS File:
SDS
Modify Date:
2023/5/18 11:31:03

6-Biopterin Properties

Melting point >210°C dec.
alpha D24 -50° (c = 0.4 in 0.1N HCl); D24 -26° (c = 0.92 in 0.1N NaOH)
Boiling point 379.74°C (rough estimate)
Density 1.3472 (rough estimate)
refractive index 1.7610 (estimate)
storage temp. 2-8°C
solubility Aqueous Acid (Slightly, Heated, Sonicated)
form White to pale yellow powder.
pka 13.18±0.20(Predicted)
color White to Light Yellow
Merck 13,1229
BRN 87860
Stability Hygroscopic
CAS DataBase Reference 22150-76-1(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  3
RTECS  UO3506000
10-23
HS Code  29339900
Toxicity sln-par-dmg 10 mg/L MUREAV 128,147,84

6-Biopterin price More Price(3)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) B2517 6-Biopterin ≥97% 22150-76-1 5MG ₹8735.78 2022-06-14 Buy
Sigma-Aldrich(India) B2517 6-Biopterin ≥97% 22150-76-1 25MG ₹33211.1 2022-06-14 Buy
Sigma-Aldrich(India) B2517 6-Biopterin ≥97% 22150-76-1 50MG ₹59104.5 2022-06-14 Buy
Product number Packaging Price Buy
B2517 5MG ₹8735.78 Buy
B2517 25MG ₹33211.1 Buy
B2517 50MG ₹59104.5 Buy

6-Biopterin Chemical Properties,Uses,Production

Description

6-Biopterin (L-Biopterin) is the oxidized form of tetrahydro-L-biopterin (BH4), a nitric oxide synthase (NOS) cofactor. L-Biopterin can be reduced to BH4 via thioredoxin reductase followed by dihydropteridine reductase or reduced glutathione. It is extremely toxic to human melanocytes in culture (IC50 = 0.2 μM after 48 hrs). L-Biopterin is rarely found under physiological conditions except in the epidermis of patients with the depigmentation disorder Vitiligo.

Chemical Properties

Crystalline Solid

Uses

L-Biopterin is a pteridine widely distributed in nature; naturally occurring as the L-erythro-form. Considered as a growth factor for some insects. Fluoresces with a blue color in alkaline solution.

Definition

6-Biopterin is an enzymatic cofactor derived from pterin and involved in certain oxidation-reduction reactions. It is a biopterin in which the 1,2-dihydroxypropyl group has (1R,2S)-configuration; naturally occurring form. It is an enantiomer of a D-erythro-biopterin.

Application

6-Biopterin is an oxidation product from the melanogenesis regulating cofactor (6R)5,6,7,8 tetrahydrobiopterin (6-BH4). In vitro, 6-Biopterin is cytotoxic to melanocytes. However, in vivo, 6-Biopterin is rapidly and sequentially reduced back to 6-GH4 via q-BH2. Recent studies suggest that 6-Biopterin among other pteridines may be a useful non-invasive biomarker for cancer.

Preparation

Biopterin is synthesized by reacting 2,4,5-triamino-6-hydroxypyrimidine with 5-deoxy-L-arabinosone in aqueous solution at pH of about 7.5 to 10, acidifying and then recrystallizing by dissolving in basic solution and precipitating with acid. 5-deoxy-L-arabinosone is prepared by oxidizing S-deoxy-L-arabinose, which is prepared from L-rhamnose, using cupric acetate.
Process for the synthesis of biopterin

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx.

6-Biopterin Preparation Products And Raw materials

Raw materials

Preparation Products

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2-Amino-6-[(1S,2R)-1,2-dihydroxypropyl]pteridin-4(1H)-one 2-Amino-6-[(1S,2R)-1,2-dihydroxypropyl]pteridine-4(3H)-one D-erythro-Biopterin NSC-339699 2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4(1H)-pteridinone 2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]pteridin-4(3H)-one L-erythro-Biopterin 2-Amino-6-(1,2-dihydroxypropyl)- 4(1H)-pteridinone 6-Biopterin,(1’R,2’S)-Biopterin, 2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine, L-erythro-6-(1,2-Dihydroxypropyl)pterin L-Biopterin(NSC 339699,L-erythro-Biopterin) 2-amino-6-(1,2-dihydroxypropyl)-,(s-(r*,s*))-4(1h)-pteridinon 2-amino-6-(l-erythro-1,2-dihydroxypropyl)-4(3h)-pteridinon pterinhb2 L-ERYTHRO-6-(1,2-DIHYDROXYPROPYL)PTERIN 6-BIOPTERIN 2-AMINO-4-HYDROXY-6-[1,2-DIHYDROXYPROPYL]PTERIDINE (1'R,2'S)-BIOPTERIN [S-(R*,S*)]-2-amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-one L-Biopterin,2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine 2-amino-6-(1,2-dihydroxypropyl)-1H-pteridin-4-one (1R,2S)-Biopterin, 2-Amino-4-hydroxy-6-(1,2-dihydroxypropyl)pteridine, L-erythro-6-(1,2-Dihydroxypropyl)pterin 6-Biopterin, ≥97% Sapropterin Dihydrochloride Impurity C L-Biopterin [L-erythro-Biopterin] 4(1H)-Pteridinone, 2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]- 2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)pteridin-4(1H)-one L- BiopterinQ: What is L- Biopterin Q: What is the CAS Number of L- Biopterin Q: What is the storage condition of L- Biopterin Q: What are the applications of L- Biopterin L-Biopterin(6-Biopterin) BIOPTERIN L-BIOPTERIN Sapropterin Impurity 15 (Biopterin) 22150-76-1 Oxidation-Reduction Enzymes, Inhibitors, and Substrates Cofactors BioChemical Biochemicals and Reagents Fluorescent Labels & Indicators Bases & Related Reagents Chiral Reagents Heterocycles Nucleotides