Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

S154

Sigma-Aldrich

Sepiapterin

solid

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

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

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
R Lelchuk et al.
The Journal of pharmacology and experimental therapeutics, 262(3), 1220-1224 (1992-09-01)
Human megakaryoblastic cells (Meg-01) were found to possess constitutive and express inducible nitric oxide (NO) synthase activities. The constitutive NO synthase was Ca+(+)- and NADPH-dependent, as is the NO synthase found previously in human platelets. Stimulation of Meg-01 cells by
Surawee Chuaiphichai et al.
British journal of pharmacology, 174(8), 657-671 (2017-01-28)
The cofactor tetrahydrobiopterin (BH4) is a critical regulator of endothelial NOS (eNOS) function, eNOS-derived NO and ROS signalling in vascular physiology. To determine the physiological requirement for de novo endothelial cell BH4 synthesis for the vasomotor function of resistance arteries
G Schoedon et al.
European journal of biochemistry, 213(2), 833-839 (1993-04-15)
Nitric oxide is a recently discovered biomolecule with a broad range of actions. The present study investigated the regulation of nitric oxide synthase activity by dexamethasone and the cofactor tetrahydrobiopterin in murine macrophages. The influence of the tetrahydrobiopterin biosynthesis inhibitors
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