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SMB00978

Sigma-Aldrich

L-Hercynine

≥95% (HPLC)

Synonym(s):

α-N,N,N-Trimethylhistidine, N-α-trimethyl histidine, Histidine-betaine

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About This Item

Empirical Formula (Hill Notation):
C9H15N3O2
CAS Number:
534-30-5
Molecular Weight:
197.23
NACRES:
NA.26

Quality Level

200

assay

≥95% (HPLC)

form

solid

storage temp.

2-8°C

SMILES string

C[N+](C)(C)[C@H](C([O-])=O)CC1=CN=CN1

InChI

1S/C9H15N3O2/c1-12(2,3)8(9(13)14)4-7-5-10-6-11-7/h5-6,8H,4H2,1-3H3,(H-,10,11,13,14)/t8-/m0/s1

InChI key

GPPYTCRVKHULJH-QMMMGPOBSA-N

General description

Hercynine is the precursor and redox metabolite of ergothioneine, which regulates microbial physiology and enables the survival of microbes under stressful conditions encountered in their natural environments. Ergothioneine is primarily present as a thione physiological pH, which makes it resistant to autoxidation. Ergothioneine enables pathogenic microbes, such as Mycobacterium tuberculosis (Mtb) to withstand hostile environments within the host to establish infection.

Application

Hercynine is a versatile molecule and it finds application in biochemical and metabolomics research.

Features and Benefits

  • Can be used in Metabolomics and Biochemical research
  • High-quality compound suitable for multiple research applications

Other Notes

For additional information on our range of Biochemicals, please complete this form.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000368919
0000347004
0000368919
0000210652
0000256902

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Tomoyuki Kamide et al.
Journal of agricultural and food chemistry, 68(23), 6390-6394 (2020-05-22)
We previously constructed a heterologous production system for ergothioneine (ERG) in Escherichia coli using five ERG biosynthesis genes (egtABCDE) from Mycobacterium smegmatis. However, significant amounts of hercynine (HER), an intermediate of ERG, as ERG were accumulated, suggesting that the reaction
Salvatore Sotgia et al.
Antioxidants (Basel, Switzerland), 9(9) (2020-09-17)
The dependence of a stallion's spermatozoa on oxidative phosphorylation for energy requirements results in an unconventional relationship between reactive oxygen species (ROS) production and fertility. In such a scenario, antioxidant activity must be finely controlled and not affect the essential
Katarina Valachova et al.
Polymers, 13(1) (2021-01-02)
A high-molecular weight hyaluronan is oxidatively degraded by Cu(II) ions and ascorbate-the so called Weissberger biogenic oxidative system-which is one of the most potent generators of reactive oxygen species, namely •OH radicals. Ergothioneine, hercynine, or histidine were loaded into chitosan/hyaluronan

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