dextro,laevo-homocysteine

DL-2-amino-4-mercaptobutyric acid

CAS: 454-29-5 C4 H9 N O2 S MW: 135.18613000

Identification

Namedextro,laevo-homocysteine
IUPAC2-amino-4-sulfanylbutanoic acid
CAS Number454-29-5
EINECS207-222-9
FDA UNIIS7IJP4A89K
Molecular FormulaC4 H9 N O2 S
Molecular Weight135.18613000
MDL NumberMFCD00004898
Nikkaji NumberJ1.203C
Beilstein5493225
XlogP3-3.40 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 299.70 °C. @ 760.00 mm Hg (est)
Flash Point > 230.00 °F. TCC ( > 110.00 °C. )
logP (o/w) 0.220 (est)
Soluble in water, 1.136e+005 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 500 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryinformation only not used for fragrances or flavors
Recommendation for dextro,laevo-homocysteine usage levels up tonot for fragrance use.
Recommendation for dextro,laevo-homocysteine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

spinach plant

Synonyms

2- amino-4-mercapto-butanoic acid 2- amino-4-mercapto-butyric acid 2- amino-4-mercapto-DL-butyric acid 2- amino-4-mercaptobutanoic acid 2- Amino-4-mercaptobutyric acid DL-2- amino-4-mercaptobutyric acid 2- amino-4-sulfanylbutanoic acid butanoic acid, 2-amino-4-mercapto- butyric acid, 2-amino-4-mercapto- butyric acid, 2-amino-4-mercapto-, DL- (9CI) D,L-homo cysteine DL-homo cysteine PubMed: Contribution of Weak S-H...O Hydrogen Bonds to the Side-Chain Motions in DL-Homocysteine on Cooling. PubMed: [Homocysteine peroxidase activity in rat blood plasma: stoichiometry and enzymatic character of the reaction]. PubMed: Effects of DL-homocysteine thiolactone on cardiac contractility, coronary flow, and oxidative stress markers in the isolated rat heart: the role of different gasotransmitters. PubMed: Homocysteine is a novel risk factor for suboptimal response of blood platelets to acetylsalicylic acid in coronary artery disease: a randomized multicenter study. PubMed: Endoplasmic reticulum redox state is not perturbed by pharmacological or pathological endoplasmic reticulum stress in live pancreatic β-cells. PubMed: Optimal conditions for the direct RP-HPLC determination of underivatized amino acids with online multiple detection. PubMed: Anticonvulsive effect of folic acid in homocysteine thiolactone-induced seizures. PubMed: Chronic homocysteine exposure upregulates endothelial adhesion molecules and mediates leukocyte: endothelial cell interactions under flow conditions. PubMed: Cloning and characterisation of a cystathionine β/γ-lyase from two Oenococcus oeni oenological strains. PubMed: Dietary intake of S-(alpha-carboxybutyl)-DL-homocysteine induces hyperhomocysteinemia in rats. PubMed: [Effect of thiolactone homocysteine loading on adenosine metabolism in rats: relationship with platelet hyper-reactivity, correction of this metabolism disorders by vitamin-microelement complex]. PubMed: Adult rats are more sensitive to the vascular effects induced by hyperhomocysteinemia than young rats. PubMed: Nucleophilic reactivity of thiolate, hydroxide and phenolate ions towards a model O-arylated diazeniumdiolate prodrug in aqueous and cationic surfactant media. PubMed: Hydrogen sulfide production from cysteine and homocysteine by periodontal and oral bacteria. PubMed: Role of NMDA receptor in homocysteine-induced activation of mitogen-activated protein kinase and phosphatidyl inositol 3-kinase pathways in cultured human vascular smooth muscle cells. PubMed: Hyperhomocysteinemia induced by feeding rats diets rich in DL-homocysteine thiolactone promotes alterations on carotid reactivity independent of arterial structure. PubMed: Dose- and Glucose-Dependent Effects of Amino Acids on Insulin Secretion from Isolated Mouse Islets and Clonal INS-1E Beta-Cells. PubMed: Effects of C-reactive Protein and Homocysteine on Cytokine Production: Modulation by Pravastatin. PubMed: HYPERHOMOCYSTEINAEMIA-INDUCED CARDIOVASCULAR CHANGES IN RATS. PubMed: Two-dimensionally well-ordered multilayer structures in thin films of a brush polypeptide. PubMed: Discovery of amide (peptide) bond synthetic activity in Acyl-CoA synthetase. PubMed: [A study on health behavior in people at risk for a cerebrovascular accident]. PubMed: Homocysteine induces connective tissue growth factor expression in vascular smooth muscle cells. PubMed: Immobilization of Prussian Blue nanoparticles onto thiol SAM modified Au electrodes for electroanalytical or biosensor applications. PubMed: [Renal tubular epithelocytic changes in hypercysteinemia and experimental chronic renal failure]. PubMed: Homocysteine thiolactone-induced hyperhomocysteinemia does not alter concentrations of cholesterol and SREBP-2 target gene mRNAS in rats. PubMed: Inhibition of sulfur compounds and antioxidants on MMP-2 and -9 at the activity level found during neonatal hypoxia-reoxygenation. PubMed: Hyperhomocysteinemia increases arterial permeability and stiffness in mice. PubMed: Effect of L-arginine on asymmetric dimethylarginine (ADMA) or homocysteine-accelerated endothelial cell aging. PubMed: Inhibition of betaine-homocysteine S-methyltransferase causes hyperhomocysteinemia in mice. PubMed: Homocysteine at pathophysiologic concentrations activates human monocyte and induces cytokine expression and inhibits macrophage migration inhibitory factor expression. PubMed: Cleavage of disulfide-linked fetuin-bisphosphonate conjugates with three physiological thiols. PubMed: Homocysteine, a risk factor for atherosclerosis, biphasically changes the endothelial production of kynurenic acid. PubMed: Are STATS arginine-methylated? PubMed: Sulfur-containing amino acids block stretch-dependent K+ channels and nitrergic responses in the murine colon. PubMed: Dual effect of DL-homocysteine and S-adenosylhomocysteine on brain synthesis of the glutamate receptor antagonist, kynurenic acid. PubMed: Effect of NaCN on currents evoked by uremic retention solutes in dissociated mouse neurons. PubMed: Homocysteine increases the expression of vascular endothelial growth factor by a mechanism involving endoplasmic reticulum stress and transcription factor ATF4. PubMed: Identification and characterization of two isoenzymes of methionine gamma-lyase from Entamoeba histolytica: a key enzyme of sulfur-amino acid degradation in an anaerobic parasitic protist that lacks forward and reverse trans-sulfuration pathways. PubMed: Definitive identification of cysteine and glutathione complexes of bismuth by mass spectrometry: assessing the biochemical fate of bismuth pharmaceutical agents. PubMed: Chemical and biomechanical characterization of hyperhomocysteinemic bone disease in an animal model. PubMed: Organelle specific enzyme markers as indicators of methylmercury neurotoxicity and antidotal efficacy in mice. PubMed: Kinetics and mechanism for reduction of the anticancer prodrug trans,trans,trans-[PtCl2(OH)2(c-C6H11NH2)(NH3)] (JM335) by thiols. PubMed: lcd from Streptococcus anginosus encodes a C-S lyase with alpha,beta-elimination activity that degrades L-cysteine. PubMed: A study of micturition inducing sites in the periaqueductal gray of the mesencephalon. PubMed: Fibrillin-2 defects impair elastic fiber assembly in a homocysteinemic chick model. PubMed: Homocysteine upregulates vascular cell adhesion molecule-1 expression in cultured human aortic endothelial cells and enhances monocyte adhesion. PubMed: Homocysteine impairs the nitric oxide synthase pathway: role of asymmetric dimethylarginine. PubMed: Overexpression of cellular glutathione peroxidase rescues homocyst(e)ine-induced endothelial dysfunction. PubMed: Homocysteine induces expression and secretion of monocyte chemoattractant protein-1 and interleukin-8 in human aortic endothelial cells: implications for vascular disease. PubMed: Quantification of L-ascorbic acid and total ascorbic acid in fruits and spinach by capillary zone electrophoresis. PubMed: [Effect of activities of vagi and sympathetic nervous system on heart rate variability]. PubMed: L-cysteine and sodium hydrosulphide inhibit spontaneous contractility in isolated pregnant rat uterine strips in vitro. PubMed: Occurrence of transsulfuration in synthesis of L-homocysteine in an extremely thermophilic bacterium, Thermus thermophilus HB8. PubMed: The direct electrochemistry of myoglobin at a DL-homocysteine self-assembled gold electrode. PubMed: Mechanisms for the formation of protein-bound homocysteine in human plasma. PubMed: Biochemical characterization of cystine lyase from broccoli (Brassica oleracea var. italica). PubMed: Sulfur-containing amino acids decrease cisplatin cytotoxicity and uptake in renal tubule epithelial cell lines. PubMed: Accelerated volatilization rates of selenium from different soils. PubMed: A novel endogenous antimalarial: Fe(II)-protoporphyrin IX alpha (heme) inhibits hematin polymerization to beta-hematin (malaria pigment) and kills malaria parasites. PubMed: Determination of L-ascorbic acid and total ascorbic acid in vascular and nonvascular plants by capillary zone electrophoresis. PubMed: Restoration of methylmercury inhibited adenosine triphosphatases during vitamin and monothiol therapy. PubMed: Activation of H-ras oncogenes in male B6C3F1 mouse liver tumors induced by vinthionine or 2-chloroethyl-methyl sulfide. PubMed: Physical properties of hemoglobin vesicles as red cell substitutes. PubMed: Glycogen phosphorylase activity in the cerebral cortex of rats during development: effect of homocysteine-induced seizures. PubMed: Tyrosinase inhibition due to interaction of homocyst(e)ine with copper: the mechanism for reversible hypopigmentation in homocystinuria due to cystathionine beta-synthase deficiency. PubMed: Vitamins and monothiols efficacy in the restoration of adenosine nucleotide degradation enzymes altered during methylmercury intoxication. PubMed: Coagulation protein function. II. Influence of thiols upon acetaldehyde effects. PubMed: Fluctuation of trace elements during methylmercury toxication and chelation therapy. PubMed: The uptake and metabolism of cysteine by Giardia lamblia trophozoites. PubMed: Liver distribution of 99mTc-DL-homocysteine in experimental hepatitis rats. PubMed: Study of growth requirements other than cysteine of naturally occurring Escherichia coli and Klebsiella spp. auxotrophic for cysteine. PubMed: Determination of total vitamin C in fruits by capillary zone electrophoresis. PubMed: Acetylcholinesterase fluctuations in central nervous system of rat during methylmercury intoxication and chelation therapy. PubMed: Conformational changes of the alpha 1-proteinase inhibitor affecting its cholesterol binding ability. PubMed: Homocysteine-induced modulation of tissue plasminogen activator binding to its endothelial cell membrane receptor. PubMed: Ameliorative capacities of vitamins and monothiols administered alone or in combinations in methylmercury mobilisation in nervous and non-nervous tissues of mice. PubMed: Cerebral energy state of neonatal rats during seizures induced by homocysteine. PubMed: Cerebral energy state of neonatal rats during seizures induced by homocysteine. PubMed: Inhibition by thiols of copper(II)-induced oxidation of oxyhemoglobin. PubMed: Synthesis and biological activity of novel folic acid analogues: pteroyl-S-alkylhomocysteine sulfoximines. PubMed: S-adenosylhomocysteine hydrolase activity in human myocardium. PubMed: Homocysteine-induced alterations in extracellular amino acids in rat hippocampus. PubMed: Therapeutic abilities of thiol compounds in the restoration of methylmercury-inhibited cholesterol and triglycerides of the rat's central nervous system. PubMed: Inability of thiol compounds to restore CNS arylsulfatases inhibited by methyl mercury. PubMed: Role of serum albumin as a carrier of 99mTc-complex to tumor tissue. PubMed: Effect of dietary homocysteine on copper status in rats. PubMed: Effects of radical scavengers on the development of experimental diabetes. PubMed: Tumor accumulation mechanism of 99mTc-DL-homocysteine, a model compound for the development of tumor-imaging radiopharmaceuticals. PubMed: Dose and duration related methylmercury deposition, glycosidases inhibition, myelin degeneration and chelation therapy. PubMed: Elucidation of the mechanism by which homocysteine potentiates the anti-vaccinia virus effects of the S-adenosylhomocysteine hydrolase inhibitor 9-(trans-2',trans-3'-dihydroxycyclopent-4'-enyl)-adenine. PubMed: Confirmation of a ping-pong mechanism for S-adenosyl-L-methionine:magnesium protoporphyrin methyltransferase of etiolated wheat by an exchange reaction. PubMed: Beta-DL-methylene-aspartate, an inhibitor of aspartate aminotransferase, potently inhibits L-glutamate uptake into astrocytes. PubMed: A therapeutic profile of metal chelators in the detoxication of methylmercury chloride inhibited acid and alkaline phosphatases in different areas of the central nervous system of rats. PubMed: Intensification of tumor affinity of 99mTc-DL-homocysteine by cooperative use of SH-containing compounds. PubMed: Chemical form of tumor-tropic 99mTc-DL-homocysteine. PubMed: Chemical properties of technetium-99m-DL-homocysteine, a possible tumor-imaging agent. PubMed: Mechanism of tumor transport of 99mTc-DL-homocysteine, a possible tumor-imaging agent. PubMed: Na-Stimulated Transport of l-Methionine in Brevibacterium linens CNRZ 918. PubMed: A highly sensitive high-performance liquid chromatography method for the estimation of ascorbic and dehydroascorbic acid in tissues, biological fluids, and foods. PubMed: Site-specific antibodies to human erythropoietin: immunoaffinity purification of urinary and recombinant hormone. PubMed: Methylmercury chloride-induced and antagonist-reverted succinic dehydrogenase changes in the brain and trigeminal ganglia of the rat. PubMed: Effect of N-acetyl-DL-homocysteine thiolactone and 2,3-dimercaptosuccinic acid on the restoration of alkaline phosphatase in the nervous system of rat during methylmercury toxication. PubMed: Effect of L-homocysteine and derivatives on the high-affinity uptake of taurine and GABA into synaptosomes and cultured neurons and astrocytes. PubMed: DL-S-(2-[N-3-(2-oxo-tetrahydrothienyl)acetamido])-thioglycolic acid: a novel mucolytic agent of the class of homocysteine thiolactone derivatives. PubMed: Effects of cysteine and structurally related compounds on ochratoxin production by Aspergillus ochraceus. PubMed: Enzymatic oxidation of L-homocysteine. PubMed: Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 10. Base- and amino acid modified analogues of S-aristeromycinyl-L-homocysteine. PubMed: 99mTc-DL-Homocysteine, a potential tumor imaging agent. PubMed: Impairment of insulin release by methylation inhibitors. PubMed: Tumor detection with some 99mTc-labeled S-containing amino acids. PubMed: Oxidation of cysteine to cystine by membrane fractions of Chlorella fusca. PubMed: Phospholipid methylation in pancreatic islets. PubMed: Evidence for direct methyl transfer in betaine: homocysteine S-methyl-transferase. PubMed: The inhibitory effect of L-cysteine and its derivatives on glycolysis in Ehrlich ascites tumour cells. PubMed: Chemotherapeutic potential of methionine analogue inhibitors of tumor-derived methionine adenosyltransferases. PubMed: Experimental homocysteinemia in pigs: comparison with studies in sixteen homocystinuric patients. PubMed: Methionine regulation of N-5-methyltetrahydrofolate: homocysteine methyltransferase and its influence on the growth and protein synthesis in normal, neoplastic, and transformed cells in culture. PubMed: S-Adenosylhomocysteine hydrolase from rat liver. Purification and some properties. PubMed: Effect of nutritional and enzymatic methionine deprivation upon human normal and malignant cells in tissue culture. PubMed: Structural requirements for the sequestration of metabolically generated acetaldehyde. PubMed: Cerebral metabolic and circulatory changes in the rat during sustained seizures induced by DL-homocysteine. PubMed: Preparation of the bifunctional enzyme ribonuclease-deoxyribonuclease by cross-linkage. PubMed: Synthetic sulfur-containing amino acids. Inhibition of transport systems in S37 ascites tumor cells. PubMed: Methionine requirement and replacement by homocysteine in tissue cultures of selected rodent and human malignant and normal cells. PubMed: Factors affecting methionine toxicity and its alleviation in the chick. PubMed: Rat liver cysteine dioxygenase (cysteine oxidase). Further purification, characterization, and analysis of the activation and inactivation. PubMed: Effect of DL-homocysteine on some hepatic folate enzymes and folate concentration in cobalamin-deficient rats. PubMed: Adenosylhomocysteinase from yellow lupin seeds. Purification and properties. PubMed: The mode of action of homocysteine on mouse brain glutamic decarboxylase and gamma-aminobutyrate aminotransferase. PubMed: The effect of N-acetylated DL-penicillamine and DL-homocysteine thiolactone on the mercury distribution in adult rats, rat foetuses and macaca monkeys after exposure to methyl mercuric chloride. PubMed: Search for new treatment approaches in schizophrenia: in vitro studies of potential N-methyltransferase inhibitors. PubMed: Partial purification and properties of adenosine nucleosidase from leaves of spinach beet (Beta vulgaris L.). PubMed: Protection against acute toxicity of acetaldehyde in mice. PubMed: Formation of methyl mercury by bacteria. PubMed: [Some physical and chemical properties of serinesulfhydrase from chicken liver]. PubMed: Effects of several unusual sulfur-containing amino acids on rat liver cystathionine-gamma-lyase. PubMed: Lysine-methionine-threonine interactions in growth and development of Mimulus cardinalis seedlings. PubMed: Methionine, DL-homocysteine thiolactone and n-acetyl-DL-methionine for ruminants. PubMed: THE REACTION OF INSULIN WITH N-ACETYL-DL-HOMOCYSTEINE THIOLACTONE: SOME CHEMICAL AND BIOLOGICAL PROPERTIES OF THE PRODUCTS. PubMed: L-CYSTINE REQUIREMENT FOR PRODUCTION OF COXSACKIE B3 VIRUS IN CULTURED MONKEY HEART CELLS. PubMed: [Inhibition of enzymatic decarboxylation of amino acids by DL-penicillamine, L-cysteine and DL-homocysteine]. PubMed: Chemical derivatives of alpha-chymotrypsinogen. III. Reaction with N-acetyl-Dl-homocysteine thiolactone.