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H9633

Sigma-Aldrich

L-Homocysteic acid

≥95%

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Synonym(s):
L-2-Amino-4-sulfobutyric acid
Empirical Formula (Hill Notation):
C4H9NO5S
CAS Number:
Molecular Weight:
183.18
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥95%
≥98% (TLC)

form

powder

color

white to off-white

application(s)

cell analysis

SMILES string

N[C@@H](CCS(O)(=O)=O)C(O)=O

InChI

1S/C4H9NO5S/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H,8,9,10)/t3-/m0/s1

InChI key

VBOQYPQEPHKASR-VKHMYHEASA-N

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1 of 4

This Item
H6503H4628M1126
vibrant-m

H9633

L-Homocysteic acid

vibrant-m

H4628

DL-Homocysteine

vibrant-m

M1126

L-Methionine sulfoxide

assay

≥95%, ≥98% (TLC)

assay

≥98% (TLC)

assay

≥95% (titration)

assay

≥98% (TLC)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

color

white to off-white

color

white

color

-

color

white to off-white

application(s)

cell analysis

application(s)

detection
peptide synthesis

application(s)

cell analysis
peptide synthesis

application(s)

detection
peptide synthesis

Application

L-Homocysteic acid has been used to study hydrogen peroxide-mediated changes in physiological and pathological conditions in the nervous system.

Biochem/physiol Actions

L-Homocysteic acid (L-HCA) is an endogenous neurotransmitter ligand of NMDA (N-methyl-D-aspartate) receptors. It is an analog of glutamate and competitively suppresses glutamate-cystine (xc-) antiporter function in neurons, causing decrease in cysteine uptake.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Hari H Subramanian et al.
The Journal of comparative neurology, 526(2), 229-242 (2017-09-07)
The nucleus retroambiguus (NRA) is a neuronal cell group in the medullary ventrolateral tegmentum, rostrocaudally between the obex and the first cervical spinal segment. NRA neurons are premotor interneurons with direct projections to the motoneurons of soft palate, pharynx, and
M Piraud et al.
Rapid communications in mass spectrometry : RCM, 19(22), 3287-3297 (2005-10-20)
Seventy-six compounds of biological interest for the diagnosis of inherited disorders of amino acids (AA) metabolism have previously been demonstrated to be detectable in positive mode electrospray ionisation tandem mass spectrometry (ESI-MS/MS), after separation by ion-pairing reversed-phase liquid chromatography (RPLC).
R Gurke et al.
Journal of pharmaceutical and biomedical analysis, 174, 578-587 (2019-07-02)
The role of homocysteic acid (HCA) in severe diseases like Alzheimer's disease is under discussion and some recent studies correlate elevated HCA concentrations with the diagnosis of Alzheimer's. However, non-selective and insufficiently sensitive methods have been used to quantitate HCA
J W Olney et al.
Brain research bulletin, 19(5), 597-602 (1987-11-01)
L-Homocysteic acid (L-HCA) has been proposed as a natural transmitter at the N-methyl-D-aspartate (NMDA) subtype of excitatory amino acid receptor based on recent evidence that L-HCA occurs L-HCA occurs naturally in the mammalian CNS, is released from K+ stimulated brain
T Knöpfel et al.
Neuroscience letters, 81(1-2), 188-192 (1987-10-16)
The effects of ionophoretically applied L-homocysteate (L-HCA), L-glutamate (L-Glu) and N-methyl-D-aspartate (NMDA) were compared in rat neocortical neurons recorded intracellularly in vitro. The firing pattern and the time course of membrane depolarization induced by L-HCA resembled those of NMDA responses.

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