H4628

Sigma-Aldrich

DL-Homocysteine

≥95% (titration)

Synonym(s):
2-Amino-4-mercaptobutyric acid
Linear Formula:
HSCH2CH2CH(NH2)COOH
CAS Number:
Molecular Weight:
135.18
Beilstein/REAXYS Number:
1721683
EC Number:
MDL number:
eCl@ss:
42021308
PubChem Substance ID:
NACRES:
NA.26
Pricing and availability is not currently available.

Quality Level

assay

≥95% (titration)

form

powder

application(s)

cell analysis: suitable
peptide synthesis: suitable

mp

232-233 °C (lit.)

solubility

H2O: soluble

storage temp.

−20°C

SMILES string

NC(CCS)C(O)=O

InChI

1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)

InChI key

FFFHZYDWPBMWHY-UHFFFAOYSA-N

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Application

DL-Homocysteine has been used to induce hyperhomocysteinemia in Sprague–Dawley rats. It has also been used to study the effects of hyperhomocysteinemia on atherosclerosis in apolipoprotein E-deficient mice.

Packaging

10 mg in autosample vial
1, 5, 25 g in poly bottle

Biochem/physiol Actions

Homocysteine is a sulfhydryl-containing amino acid, synthesized from methionine. It is a non-essential, non-proteinogenic amino acid. It is an important determinant of the methylation cycle and is present in the plasma in four forms. An abnormally high level of homocysteine leads to hyperhomocysteinemia and also promotes atherosclerosis.
Increased plasma homocysteine is a risk factor for coronary heart disease and carcinogenesis; may be a marker for tumor cell growth.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H4628.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

The Molecular and Cellular Effect of Homocysteine Metabolism Imbalance on Human Health
Henrieta S
International Journal of Molecular Sciences, 17(10), 1733-1733 (2016)
Homocysteine: role and implications in atherosclerosis.
Guthikonda S and Haynes WG
Current Atherosclerosis Reports, 8(2), 100-106 (2006)
Hyperhomocysteinemia decreases bone blood flow
Neetu Tyagi
Vascular Health, 7, 31-35 (2011)
Effects of vitamin supplementation and hyperhomocysteinemia on atherosclerosis in apoE-deficient mice
Ji Zhou
Atherosclerosis, 168(2), 255-262 (2003)
Wolfgang C Winkelmayer et al.
Journal of the American Society of Nephrology : JASN, 16(1), 255-260 (2004-11-26)
Homocysteine is implicated to be an atherogenic amino acid and has been associated with increased risk of adverse cardiovascular outcomes. The prognostic significance of plasma total homocysteine (tHcy) levels for mortality and allograft loss in kidney transplant recipients has not...
Articles
Inborn errors of metabolism are caused by changes in specific enzymatic reactions and hundreds of different such alterations, which affect about 1 of every 5000 newborns, have been characterized.
Read More

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