6-Biopterin

Base Information

• Chemical Name: 6-Biopterin
• CAS No.: 22150-76-1
• Molecular Formula: C9H11N5O3
• Molecular Weight: 237.218
• Hs Code.: 29339900
• Mol file: 22150-76-1.mol

Synonyms:4(1H)-Pteridinone,2-amino-6-(1,2-dihydroxypropyl)-, [S-(R*,S*)]-;4(3H)-Pteridinone,2-amino-6-(L-erythro-1,2-dihydroxypropyl)- (7CI,8CI);(-)-Biopterin;Biopterin;L-Biopterin;L-erythro-Biopterin;NSC 339699;Pterin HB2;

Chemical Property of 6-Biopterin

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 1.4E-13mmHg at 25°C
• Melting Point: >210 °C dec.
• Refractive Index: 1.821
• Boiling Point: 590.2 °C at 760 mmHg
• PKA: 13.18±0.20(Predicted)
• Flash Point: 310.7 °C
• PSA: 138.01000
• Density: 1.86 g/cm³
• LogP: -0.70930
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Acid (Slightly, Heated, Sonicated)

Purity/Quality:

99% ^*data from raw suppliers

6-Biopterin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• 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.
• 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.

Technology Process of 6-Biopterin

There total 56 articles about 6-Biopterin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

4-amino-L-biopterin → biopterin (22150-76-1)

Guidance literature:

With water; sodium hydroxide; at 78 ℃; for 3h;

Reference yield: 92.0%

1',2'-O-diacetyl-L-biopterin (62933-57-7) → biopterin (22150-76-1)

Guidance literature:

With water; tetraethylammonium hydroxide; at 25 ℃; pH=Ca. 11.5;

Reference yield: 84.0%

(3S,8S,9S,10R,13S,14S,17S)-3-Acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid (1S,2R)-2-(2-amino-4-butoxy-pteridin-6-yl)-2-hydroxy-1-methyl-ethyl ester (141191-98-2,141271-04-7) → biopterin (22150-76-1)

Guidance literature:

With potassium hydroxide; In methanol; at 100 ℃; for 1h;

DOI:10.1055/s-1992-26097

upstream raw materials:

5-deoxy-L-arabinose

2,5,6-triaminopyrimidin-4(3H)-one dihydrochloride

5-deoxy-L-arabinose phenylhydrazone

(2S,3S,4S)-1-(Phenyl-hydrazono)-pentane-2,3,4-triol

Downstream raw materials:

Sapropterin dihydrochloride

6-formylpterin

pterine-6-carboxylic acid

6-formyl-7,8-dihydropterin

Refernces

• 1、 Vignoni, Mariana,Cabrerizo, Franco M.,Lorente, Carolina,Claparols, Catherine,Oliveros, Esther,Thomas, Andres H.. "Photochemistry of dihydrobiopterin in aqueous solution". . p. 800 - 810. Retrieved 2010.
• 2、 -. "Preparation method of L-erythro biopterin compound". . . Retrieved 2021/02/24.
• 3、 -. "Preparation method of sapropterin dihydrochloride". Paragraph 0027-0028. . Retrieved 2019/06/07.