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S154

Sigma-Aldrich

Sepiapterin

solid

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

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Aidamalia Vargas-Lowman et al.
Proceedings of the National Academy of Sciences of the United States of America, 116(38), 19046-19054 (2019-09-06)
Naturalists have been fascinated for centuries by animal colors and color patterns. While widely studied at the adult stage, we know little about color patterns in the embryo. Here, we study a trait consisting of coloration that is specific to
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
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.
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)
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