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17094-01-8

L-SEPIAPTERIN, a pteridine derivative, is a stable precursor of tetrahydrobiopterin (BH4). It is a yellow pigment found in the sepia mutant of Drosophila melanogaster and lemon Bombyx mori mutant (silkworm). As a yellow to orange powder, it serves as a substrate for BH4 synthesis via the pterin salvage pathway and has the ability to inhibit rat liver GTP cyclohydrolase.
Used in Pharmaceutical Industry:
L-SEPIAPTERIN is used as a precursor for BH4 synthesis, playing a crucial role in the pterin salvage pathway. Its ability to inhibit rat liver GTP cyclohydrolase with an IC50 value of approximately 25 μM makes it a valuable compound in the development of treatments for certain diseases and conditions.
Used in Diabetes Research and Treatment:
In the field of diabetes research and treatment, L-SEPIAPTERIN is used to improve endothelial dysfunction in subjects with Type I Diabetes, such as db/db mice, by decreasing oxidative stress. This application highlights its potential in managing and studying the complications associated with diabetes.
Used in DNA Research:
L-SEPIAPTERIN can also be used in DNA research to induce sequence-specific photolesions in double-stranded DNA. This property makes it a useful tool for studying DNA structure, function, and repair mechanisms, contributing to a broader understanding of genetic processes and potential therapeutic targets.
Used as a Research Tool:
Furthermore, L-SEPIAPTERIN can be used as a research tool to circumvent the inhibition of pterin biosynthesis by 2,4-diamino-6-hydroxy pyrimidine. This application is beneficial for scientists studying the effects of pterin pathway inhibition and the role of L-SEPIAPTERIN in various biological processes.

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  • 4(3H)-Pteridinone,2-amino-7,8-dihydro-6-[(2S)-2-hydroxy-1-oxopropyl]-

    Cas No: 17094-01-8

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  • 17094-01-8 Structure

  • Basic information

    1. Product Name: L-SEPIAPTERIN
    2. Synonyms: (S)-2-aMino-6-(2-hydroxypropanoyl)-7,8-dihydropteridin-4(1H)-one;(S)-2-AMino-6-(2-hydroxypropanoyl)-7,8-dihydropteridin-4(3H)-one;Sepiapterin solid;S(-)-2-AMINO-7,8-DIHYDRO-6-(2-HYDROXY-1-OXOPROPYL)-4(1H)-PTERIDINONE;SEPIAPTERIN;L-SEPIAPTERIN;L-SEPIAPTERIN DIHYDRATE;2-AMINO-7,8-DIHYDRO-6-(2S-HYDROXY-1-OXOPROPYL)-4(1H)-PTERIDINONE
    3. CAS NO:17094-01-8
    4. Molecular Formula: C9H11N5O3
    5. Molecular Weight: 237.22
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 17094-01-8.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 448.1 °C at 760 mmHg
    3. Flash Point: 224.8 °C
    4. Appearance: yellow/solid
    5. Density: 1.86 g/cm3
    6. Vapor Pressure: 6.54E-10mmHg at 25°C
    7. Refractive Index: 1.821
    8. Storage Temp.: −20°C
    9. Solubility: DMSO: 27 mg/mL
    10. PKA: 12.33±0.20(Predicted)
    11. Stability: Light Sensitive
    12. CAS DataBase Reference: L-SEPIAPTERIN(CAS DataBase Reference)
    13. NIST Chemistry Reference: L-SEPIAPTERIN(17094-01-8)
    14. EPA Substance Registry System: L-SEPIAPTERIN(17094-01-8)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 17094-01-8(Hazardous Substances Data)

17094-01-8 Usage

Biochem/physiol Actions

Cofactor of nitric oxide synthase; intracellularly converted to tetrahydro-biopterin leading to the stimulation of nitric oxide.

Check Digit Verification of cas no

The CAS Registry Mumber 17094-01-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,0,9 and 4 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 17094-01:
(7*1)+(6*7)+(5*0)+(4*9)+(3*4)+(2*0)+(1*1)=98
98 % 10 = 8
So 17094-01-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,15H,2H2,1H3,(H4,10,11,13,14,17)/t3-/m0/s1

17094-01-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail

  • Aldrich

  • (S154)  Sepiapterin  solid

  • 17094-01-8

  • S154-5MG

  • 1,731.60CNY

  • Detail

  • Aldrich

  • (S154)  Sepiapterin  solid

  • 17094-01-8

  • S154-25MG

  • 8,599.50CNY

  • Detail

17094-01-8Synthetic route

2-amino-6-(2S-2-hydroxypropionyl)-5,6,7,8-tetrahydro-3H-pteridin-4-one dihydrochloride

2-amino-6-(2S-2-hydroxypropionyl)-5,6,7,8-tetrahydro-3H-pteridin-4-one dihydrochloride

sepiapterin
17094-01-8

sepiapterin

Conditions
ConditionsYield
With dihydrogen peroxide In ethanol; water at -10℃; for 2h; Reagent/catalyst; Temperature; Solvent;89%
1-[4-tert-butoxycarbonyloxy-2-(N,N-di-tert-butoxycarbonyl)amino-7,8-dihydropteridin-6-yl]-2S-2-(tert-butyldimethylsilanyloxy)propan-1-one

1-[4-tert-butoxycarbonyloxy-2-(N,N-di-tert-butoxycarbonyl)amino-7,8-dihydropteridin-6-yl]-2S-2-(tert-butyldimethylsilanyloxy)propan-1-one

sepiapterin
17094-01-8

sepiapterin

Conditions
ConditionsYield
Stage #1: 1-[4-tert-butoxycarbonyloxy-2-(N,N-di-tert-butoxycarbonyl)amino-7,8-dihydropteridin-6-yl]-2S-2-(tert-butyldimethylsilanyloxy)propan-1-one With hydrogenchloride In water; acetonitrile at 50℃; for 3h;
Stage #2: With sodium hydroxide In water; acetonitrile pH=7;		88%
1-(2-amino-4-cyclohexyloxy-7,8-dihydropteridin-6-yl)-2S-2-(methoxyethoxymethoxy)propan-1-one

1-(2-amino-4-cyclohexyloxy-7,8-dihydropteridin-6-yl)-2S-2-(methoxyethoxymethoxy)propan-1-one

sepiapterin
17094-01-8

sepiapterin

Conditions
ConditionsYield
Stage #1: 1-(2-amino-4-cyclohexyloxy-7,8-dihydropteridin-6-yl)-2S-2-(methoxyethoxymethoxy)propan-1-one With hydrogenchloride; ascorbic acid In methanol; water at 50℃; for 6h; Darkness;
Stage #2: With ammonia In methanol; water pH=7;		86%
S-lactoylpterin

S-lactoylpterin

sepiapterin
17094-01-8

sepiapterin

Conditions
ConditionsYield
With Pd/C (Ph2S); hydrogen; triethylamine In methanol; water at 40℃; for 3h; Reagent/catalyst; Solvent; Temperature;59%
1-(2-amino-4-cyclohexyloxypteridin-6-yl)-2S-2-(methoxymethoxy)propan-1-one

1-(2-amino-4-cyclohexyloxypteridin-6-yl)-2S-2-(methoxymethoxy)propan-1-one

sepiapterin
17094-01-8

sepiapterin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride / methanol; water / 3 h / 50 °C
1.2: pH 7
2.1: hydrogen; Pd/C (Ph2S); triethylamine / methanol; water / 3 h / 40 °C
View Scheme
Multi-step reaction with 2 steps
1.1: hydrogen; potassium carbonate; palladium 10% on activated carbon / ethyl acetate / 3 h / 50 °C
2.1: hydrogenchloride / water / Heating
2.2: pH 6 - 7
View Scheme
1-(2-amino-4-cyclohexyloxypteridin-6-yl)-1R,2S-1-hydroxy-2-(methoxymethoxy)propan
1104608-07-2

1-(2-amino-4-cyclohexyloxypteridin-6-yl)-1R,2S-1-hydroxy-2-(methoxymethoxy)propan

sepiapterin
17094-01-8

sepiapterin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 1 h / 60 °C / Inert atmosphere; Molecular sieve
2.1: hydrogenchloride / methanol; water / 3 h / 50 °C
2.2: pH 7
3.1: hydrogen; Pd/C (Ph2S); triethylamine / methanol; water / 3 h / 40 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 1 h / 60 °C / Inert atmosphere; Molecular sieve
2.1: hydrogen; potassium carbonate; palladium 10% on activated carbon / ethyl acetate / 3 h / 50 °C
3.1: hydrogenchloride / water / Heating
3.2: pH 6 - 7
View Scheme
1-(2-amino-4-cyclohexyloxy-7,8-dihydropteridin-6-yl)-2S-2-(methoxymethoxy)propan-1-one

1-(2-amino-4-cyclohexyloxy-7,8-dihydropteridin-6-yl)-2S-2-(methoxymethoxy)propan-1-one

sepiapterin
17094-01-8

sepiapterin

Conditions
ConditionsYield
Stage #1: 1-(2-amino-4-cyclohexyloxy-7,8-dihydropteridin-6-yl)-2S-2-(methoxymethoxy)propan-1-one With hydrogenchloride In water Heating;
Stage #2: With sodium hydroxide In water pH=6 - 7;
1-(2-amino-4-cyclohexyloxypteridin-6-yl)-2S-2-(methoxyethoxymethoxy)propan-1-one

1-(2-amino-4-cyclohexyloxypteridin-6-yl)-2S-2-(methoxyethoxymethoxy)propan-1-one

sepiapterin
17094-01-8

sepiapterin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide; ascorbic acid; sodium dithionite / methanol; water / 1 h / 20 °C
2.1: hydrogenchloride; ascorbic acid / methanol; water / 6 h / 50 °C / Darkness
2.2: pH 7
View Scheme
sepiapterin
17094-01-8

sepiapterin

S-sepiapterin hydrochloride

S-sepiapterin hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 0℃; for 0.5h;91%

17094-01-8Downstream Products

17094-01-8Relevant articles and documents

METHOD FOR PRODUCING SEPIAPTERIN AND TETRAHYDROLACTOYLPTERIN

-

Paragraph 0140-0141, (2015/03/28)

To provide a method for producing sepiapterin, lactoylpterin or tetrahydrolactoylpterin. Sepiapterin, lactoylpterin and tetrahydrolactoylpterin are produced at high yield through the following reaction scheme.

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