Skip to Content
Merck
CN

S154

Sepiapterin

solid

Synonym(s):

S-(−)-2-Amino-7,8-dihydro-6-(2-hydroxy-1-oxopropyl)-4(1H)-pteridinone, L-Sepiapterin

Sign In to View Organizational & Contract Pricing

Select a Size

About This Item

Empirical Formula (Hill Notation):
C9H11N5O3
CAS Number:
17094-01-8
Molecular Weight:
237.22
MDL number:
MFCD00210214
UNSPSC Code:
12352005
PubChem Substance ID:
57654606
NACRES:
NA.22

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

form

solid

color

yellow

solubility

DMSO: 27 mg/mL
0.1 M NaOH: 9.8 mg/mL

εmax

6170 at 409 nm in 0.1 M HCl
7410 at 271 nm in 0.1 M HCl at 1%

storage temp.

−20°C

SMILES string

C[C@H](O)C(=O)C1=NC2=C(NC1)NC(N)=NC2=O

InChI

1S/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

InChI key

VPVOXUSPXFPWBN-VKHMYHEASA-N

Gene Information

human ... NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846)

General description

Sepiapterin, a pteridine derivative, is a stable precursor of tetrahydrobiopterin (BH4). It is a yellow pigment found in sepia mutant of Drosophila melanogaster and lemon Bombyx mori mutant (silkworm).

Application

Sepiapterin can be used to induce sequence-specific photolesions in double-stranded DNA.

Biochem/physiol Actions

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCBZ1798
BCBV0960
BCBT6239
BCBS8664V
BCBS8664

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

S S Gross et al.
The Journal of biological chemistry, 267(36), 25722-25729 (1992-12-25)
Nitric oxide (NO) synthesis is induced in vascular smooth muscle cells by lipopolysaccharide (LPS) where it appears to mediate a variety of vascular dysfunctions. In some cell types tetrahydrobiopterin (BH4) synthesis has also been found to be induced by cytokines.
Matthieu Legrand et al.
Journal of cardiovascular pharmacology, 58(2), 192-198 (2011-05-13)
Acute kidney injury (AKI) can occur after aortic clamping due to microvascular dysfunction leading to renal hypoxia. In this rat study, we have tested the hypothesis that the administration of the precursor of the nitric oxide synthase essential cofactor tetrahydrobiopterin
Isolation, purification, and identification of an important pigment, sepiapterin, from integument of the lemon mutant of the silkworm, Bombyx mori."
JunShan G, et al.
Journal of Insect Science, 13(118) (2013)
Photoinduced hydroxylation of deoxyguanosine in DNA by pterins: sequence specificity and mechanism.
Ito K and Kawanishi S
Biochemistry, 36(7), 1774-1781 (1997)
Soo Hyeon Kim et al.
Archives of pharmacal research, 34(9), 1571-1577 (2011-10-07)
Tetrahydrobiopterin (BH(4)) has been known to be an essential cofactor for the activities of nitric oxide (NO) synthase and aromatic amino acid hydroxylases, which are involved in physiological and pathological processes. In the present study, we report that sepiapterin, the
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service