dextro,laevo-serine

DL-2-amino-3-hydroxypropanoic acid

CAS: 302-84-1 C3 H7 N O3 MW: 105.09339000

Identification

Namedextro,laevo-serine
IUPAC2-amino-3-hydroxypropanoic acid
CAS Number302-84-1
EINECS206-130-6
FDA UNII00PAR1C66F
Molecular FormulaC3 H7 N O3
Molecular Weight105.09339000
MDL NumberMFCD00064223
Nikkaji NumberJ1.277G
Beilstein1721405
XlogP3-3.10 (est)

Regulatory

DG SANTE Food Flavourings17.020 DL-serine

Physical Properties

Appearance white powder (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 243.00 to 246.00 °C. @ 760.00 mm Hg
Boiling Point 394.82 °C. @ 760.00 mm Hg (est)
Flash Point 378.00 °F. TCC ( 192.22 °C. )
logP (o/w) -3.460
Soluble in alcohol

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesantistatic agents

No sensory data available

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-rat LD50 1890 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

Categoryspecial dietary and nutritional additives
Recommendation for dextro,laevo-serine usage levels up tonot for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU)0.61 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI)49000 (μg/person/day)
Threshold of Concern1800 (μg/person/day)
Structure ClassI
Dairy products, excluding products of category 02.0 (01.0)-
Fats and oils, and fat emulsions (type water-in-oil) (02.0)-
Edible ices, including sherbet and sorbet (03.0)-
Processed fruit (04.1)-
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2)-
Confectionery (05.0)-
Chewing gum (05.3)-
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0)-
Bakery wares (07.0)-
Meat and meat products, including poultry and game (08.0)-
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0)-
Eggs and egg products (10.0)-
Sweeteners, including honey (11.0)-
Salts, spices, soups, sauces, salads, protein products, etc. (12.0)-
Foodstuffs intended for particular nutritional uses (13.0)-
Non-alcoholic ("soft") beverages, excl. dairy products (14.1)150.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2)-
Ready-to-eat savouries (15.0)-
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0)-

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Potential Uses

antistatic agents hair conditioning skin conditioning

Natural Occurrence

not found in nature

Synonyms

2- amino-3-hydroxy-propionicacid 2- amino-3-hydroxypropanoic acid DL-2- amino-3-hydroxypropanoic acid (±)-2- amino-3-hydroxypropionic acid 2- amino-3-hydroxypropionic acid DL-2- amino-3-hydroxypropionic acid H-DL-Ser-OH 3- hydroxy-alanine serine (±)- serine dextro,laevo- serine DL- serine serine DL-form serine, DL- PubMed: Effects of prolonged selective serotonin reuptake inhibition on the development and expression of L-DOPA-induced dyskinesia in hemi-parkinsonian rats. PubMed: Electron densities by the maximum entropy method (MEM) for various types of prior densities: a case study on three amino acids and a tripeptide. PubMed: Semi-maleate salts of L- and DL-serinium: the first example of chiral and racemic serinium salts with the same composition and stoichiometry. PubMed: [Development of unprotected syntheses in aqueous media]. PubMed: Effect of pressure on crystalline L- and DL-serine: revisited by a combined single-crystal X-ray diffraction at a laboratory source and polarized Raman spectroscopy study. PubMed: Understanding non-enzymatic aminophospholipid glycation and its inhibition. Polar head features affect the kinetics of Schiff base formation. PubMed: Enantioselective synthesis induced by chiral crystal composed of DL-serine in conjunction with asymmetric autocatalysis. PubMed: Degradability of poly(L-lysine) and poly(DL-aminoserinate) complexed with a polyanion under conditions modelling physico-chemical characteristics of body fluids. PubMed: Isotope fractionation of mercury during its photochemical reduction by low-molecular-weight organic compounds. PubMed: Discrimination of chiral solids: a terahertz spectroscopic investigation of L- and DL-serine. PubMed: Effect of amino acids on tannase biosynthesis by Bacillus licheniformis KBR6. PubMed: Cell cycle synchronization of Escherichia coli using the stringent response, with fluorescence labeling assays for DNA content and replication. PubMed: Purification and gene cloning of alpha-methylserine aldolase from Ralstonia sp. strain AJ110405 and application of the enzyme in the synthesis of alpha-methyl-L-serine. PubMed: Crystal and molecular structure of DL-serine hydrochloride studied by X-ray diffraction, low-temperature Fourier transform infrared spectroscopy and DFT(B3LYP) calculations. PubMed: Difference in the dynamic properties of chiral and racemic crystals of serine studied by Raman spectroscopy at 3-295 K. PubMed: Different dynamics of chiral and racemic (L- and DL-) serine crystals: evidenced by incoherent inelastic neutron and Raman scattering. PubMed: Enantioseparation and stacking of Cyanobenz[f]isoindole-amino acids by reverse polarity capillary electrophoresis and sulfated beta-cyclodextrin. PubMed: Global gene expression during stringent response in Corynebacterium glutamicum in presence and absence of the rel gene encoding (p)ppGpp synthase. PubMed: Significantly contrasting solid state dynamics of the racemic and enantiomerically pure crystalline forms of an amino acid. PubMed: Bis(glycinium) oxalate: evidence of strong hydrogen bonding. PubMed: [Interrelation between thrombin structure and its stability]. PubMed: Spontaneous resolution of binary copper(II) complexes with racemic dipeptides: crystal structures of glycyl-L-alpha-amino-n-butyrato copper(II) monohydrate, glycyl-D-valinato copper(II) hemihydrate, and glycyl-L-valinato copper(II) hemihydrate. PubMed: A correlation between the proton stretching vibration red shift and the hydrogen bond length in polycrystalline amino acids and peptides. PubMed: Influence of dipeptidyl peptidase inhibitors on growth, peptidase activity, and ammonia production by ruminal microorganisms. PubMed: Potential protease inhibitors based on a functionalized cyclic sulfamide scaffold. PubMed: Evaluation of in vitro antimicrobial and in vivo cytotoxic properties of some novel titanium-based coordination complexes. PubMed: Role of aspartate-133 and histidine-458 in the mechanism of tryptophan indole-lyase from Proteus vulgaris. PubMed: Kinetic and biochemical analysis of the mechanism of action of lysine 5,6-aminomutase. PubMed: Synthesis and fungicidal activity of lipophylic N- and O-acyl derivatives of beta-hydroxy DL-alpha-amino acids. PubMed: Accumulation of anthranilic acid and N-glucosylanthranilic acid by a Corynebacterium glutamicum mutant resistant to DL-serine hydroxamate. PubMed: lcd from Streptococcus anginosus encodes a C-S lyase with alpha,beta-elimination activity that degrades L-cysteine. PubMed: Effects of salts on the conformation and catalytic properties of d-amino acid aminotransferase. PubMed: Copper(II)- cis, cis-1,3,5-triaminocyclohexane complex-promoted hydrolysis of dipeptides: kinetic, speciation and structural studies. PubMed: Improved polygalacturonase production from Bacillus sp. MG-cp-2 under submerged (SmF) and solid state (SSF) fermentation. PubMed: Motility-regulated mucin association of Serpulina pilosicoli, the agent of colonic spirochetosis of humans and animals. PubMed: A novel NADP(+)-dependent serine dehydrogenase from Agrobacterium tumefaciens. PubMed: 3-Hydroxyisobutyrate dehydrogenase from Pseudomonas putida E23: purification and characterization. PubMed: Characterization of the aegA locus of Escherichia coli: control of gene expression in response to anaerobiosis and nitrate. PubMed: pH-metric studies on ternary metal complexes of some amino acids and benzimidazole. PubMed: Evidence for indirect utilization of glycine for production of N-bases of glycerophospholipids and sphingolipids in mouse neuroblastoma cells by using 15N-labeled glycine. PubMed: Yeast seryl-tRNA synthetase expressed in Escherichia coli recognizes bacterial serine-specific tRNAs in vivo. PubMed: Oxido-reductive functions of Entamoeba histolytica in relation to virulence. PubMed: Possible application to medium-term organ bioassays for renal carcinogenesis modifiers in rats treated with N-ethyl-N-hydroxyethylnitrosamine and unilateral nephrectomy. PubMed: Phosphatidylserine reverses the age-dependent decrease in cortical acetylcholine release: a microdialysis study. PubMed: Linear dichroism studies of tryptophanase and its quasisubstrate complexes oriented in polyacrylamide gel. PubMed: Thermostable S-alkylcysteine alpha, beta-lyase from a thermophile: purification and properties. PubMed: Enzymatic production of L-tryptophan from DL-serine and indole by a coupled reaction of tryptophan synthase and amino acid racemase. PubMed: [Study of coenzyme reorientation in the active center of tryptophanase by linear dichroism method]. PubMed: Conformational changes in the active site of tryptophanase revealed by the circular dichroism method. PubMed: [Interaction of tryptophanase with substrate analogs]. PubMed: Stereoselective formation of a 2'(3')-aminoacyl ester of a nucleotide. PubMed: Experimental study of chronic ambulatory peritoneal dialysis. I. Inhibition of protein and amino acid losses by single amino acids. PubMed: DL-Serine: promoting activity on renal tumorigenesis by N-ethyl-N-hydroxyethylnitrosamine in rats. PubMed: Phosphorus 31 nuclear magnetic resonance study of tryptophanase. Pyridoxal phosphate-binding site. PubMed: Absence of accumulation of ppGpp and RNA during amino acid starvation in Rhizobium meliloti. PubMed: Membrane mutants: a yeast mutant with a lesion in phosphatidylserine biosynthesis. PubMed: Synthesis of vitamin B6 by a mutant of Escherichia coli K12 and the action of 4'-deoxypyridoxine. PubMed: Serine-borate complex as a transition-state inhibitor of gamma-glutamyl transpeptidase. PubMed: Production and chemical studies of protease from Bacillus subtilis (SH-6) Egyptian strain. PubMed: [Comparative studies on wholebody retention of iron(II)-sulfate and a combination of iron(II)-sulfate and DL-serine]. PubMed: [Ultrastructural studies on an animal model of epiphyseolysis. Cells and matrix in the proximal growth plate of the rat tibia after administration of DL-serine(3,4,5-trihydroxybenzyl)-hydrazide] (author's transl) PubMed: [Special developmental derangements of the rat skeleton after administration of DL-serine-(2,3,4-trihydroxybenzyl)-hydrazide (author's transl)]. PubMed: Microbial metabolism of amino alcohols. 1-Aminopropan-2-ol and ethanolamine metabolism via propionaldehyde and acetaldehyde in a species of Pseudomonas. PubMed: New kinetic method for determination of ultramicro quantities of organic substances. Determination of amino acids (glycine, DL-serine, DL-phenylalanine, DL-glutamic acid, and L-arginine). PubMed: Influence of nutrition on the morphology of a strain of Bifidobacterium bifidum. PubMed: [Selective, rapid cleavage of peptide bonds in glycyl-DL-alanyl-DL-serine and glycyl-DL-alanyl-DL-alanine in pure water]. PubMed: [Effects of dietary surcharges of DL-methionine and DL-serine adminisitered alone or in combination on the development of mono and binucleated rat pancreas cells]. PubMed: [Effect of tyramine and cheese on the blood pressure and their modification by DL-serine-N2-isopropylhydrazide (Ro 4-1038) on awake intact dogs]. PubMed: Structure of DL-serine phosphate monohydrate: an intermediate phosphate bonding system exhibiting very short hydrogen bonds. PubMed: "Dysgonic" strains of mycobacterium tuberculosis on Ogawa's egg medium isolated as pathogens from patients suffering from lung tuberculosis. II. Growth-inhibitory effects of D-asparagine, D-aspartic acid, Dl-serine, or L-serine against "dysgonic". PubMed: Microbial metabolism of amino ketones. L-1-aminopropan-2-ol dehydrogenase and L-threonine dehydrogenase in Escherichia coli. PubMed: Amino Acid and vitamin requirements of several bacteroides strains. PubMed: Role of methionine in cephalosporin synthesis. PubMed: [New methods of splitting DL-serine into its optical antipodes]. PubMed: DL-Serine bis(2-chloropropyl)carbamate ester (CB-3210; NSC-37023) for treatment of cancer patients. Preliminary results. PubMed: ELECTRON MICROSCOPY OF RENAL COAGULATIVE NECROSIS DUE TO DL-SERINE, WITH SPECIAL REFERENCE TO MITOCHONDRIAL PYKNOSIS. PubMed: [ANTIHYPERTENSIVE PROPERTIES OF A MONOAMINE OXIDASE INHIBITOR (DL-SERINE-N2-ISOPROPYLHYDRAZIDE: RO 4-1038). CLINICAL RESULTS AND EFFECT ON RENAL FUNCTION]. PubMed: EFFECT OF N-DICHLOROACETYL-DL-SERINE ON REGENERATION IN THE FORELIMB OF DIEMICTYLUS VIRIDESCENS. PubMed: EFFECT OF O-METHYL-DL-THREONINE AND O-METHYL-DL-SERINE ON GROWTH AND PROTEIN SYNTHESIS IN ESCHERICHIA COLI. PubMed: MECHANISM OF O,N-ACYL SHIFT IN O-ACETYL-DL-SERINE. PubMed: CLINICAL EXPERIENCE WITH THE MONOAMINE OXIDASE INHIBITOR, DL-SERINE-N-ISOPROPYLHYDRAZIDE (RO 4-1038), IN THE TREATMENT OF HYPERTENSION. PubMed: SYNTHESES OF POLY-DL-SERINE DERIVATIVES CONTAINING CYTOTOXIC GROUPS. PubMed: Observations pertinent to antihypertensive mechanisms of MAO inhibitors using DL-serine isopropylhydrazine. PubMed: INCORPORATION OF RADIOACTIVITY OF D-GLUCOSAMINE-1-C14,D-GLUCOSE-1-C14,D-GALACTOSE-1-C14, AND DL-SERINE-3-C14 INTO RAT BRAIN GLYCOLIPIDS. PubMed: Amino acid cross resistance in Agrobacterium tumefaciens. PubMed: Hemodynamic studies of a monoamine oxidase inhibitor, DL-serine-N2-isopropylhydrazide (RO 4-1038). Mechanism of hypotensive action. PubMed: [N,N-bis(2-chloroethyl)carbamoyl]-DL-serine studied on the Allium test: demonstration of a latency period]. PubMed: [Syntheses in the vitamin B12 group. IX. On the synthesis of cobyrinyl-abcdeg-hexamide-f-N-DL-serine phosphate and cobyrinyl-abcdeg-f-N-DL-threonine phosphate and the biosynthetic evaluation of some cobinamide analogs]. PubMed: [On the treatment of arterial hypertension with a drug inhibiting monoamine oxidase (DL-serine-N2-isopropylhydrazide)]. PubMed: Effect of single dose of DL-serine on lipide phosphorylation in kidney of rats. PubMed: Serine derivative with antitumor activity. PubMed: Acyl N to O shift in poly-DL-serine. PubMed: A synthesis and resolution of DL-serine. PubMed: [DL-Serine isopropyl hydrazide (Ro4-1038) in depressive syndromes]. PubMed: The formation of glycine and serine; the influence of the administration of glycine, DL-serine and other compounds on levels of tissue glycine and serine. PubMed: A comparative study of enzymatic staining reactions in the rat kidney with necrobiosis induced by ischemia and nephrotoxic agents (mercuhydrin and DL-serine). PubMed: [Comparative study of the adaptation of Escherichia coli to chloromycetin and to dl-serine]. PubMed: Antagonisms in the utilization of D-amino acids by lactic acid bacteria. II. Influence of DL-serine and glycine on the utilization of D-alanine. PubMed: Toxic effects of dl serine on virulent human tubercle bacilli. PubMed: Conversion of dl-serine into inactive cystine. PubMed: A new synthesis of dl-serine. PubMed: Studies on the nephrotoxic action of dl-serine in the rat; the influence of experimental hydronephrosis. PubMed: Influence of dl-methionine and other substances on the nephrotoxic action of dl-serine. PubMed: The nephrotoxic action of dl-serine as related to certain dietary factors. PubMed: The Nephrotoxic Action of DL-Serine as Related to Certain Dietary Factors. PubMed: Variations of some constituents in the urine of rats receiving dl-serine and dl-alanine. PubMed: The relative toxicity of l- and dl-serine in rats. PubMed: TOLERANCE TO AMINO ACID MIXTURES AND CASEIN DIGESTS GIVEN INTRAVENOUSLY : GLUTAMIC ACID RESPONSIBLE FOR REACTIONS. PubMed: THE CHANGES IN RAT KIDNEY COCARBOXYLASE ASSOCIATED WITH THE INJURIOUS EFFECTS OF dl-SERINE. PubMed: Factors influencing bacterial deamination: Factors influencing the activity of dl-serine deaminase in Bacterium coli.