EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

dextro,laevo-serine
DL-2-amino-3-hydroxypropanoic acid

Supplier Sponsors

Name:2-amino-3-hydroxypropanoic acid
CAS Number: 302-84-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:206-130-6
FDA UNII: 00PAR1C66F
Nikkaji Web:J1.277G
Beilstein Number:1721405
MDL:MFCD00064223
XlogP3:-3.10 (est)
Molecular Weight:105.09339000
Formula:C3 H7 N O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
EFSA/JECFA Comments:
Register name to be changed to DL-Serine (racemate) (EFSA, 2006b)
Category:special dietary and nutritional additives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
DG SANTE Food Flavourings:17.020 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
 water, 39800 mg/L @ 20 °C (exp)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: antistatic agents
fragrance
hair conditioning
skin conditioning
 
Suppliers:
BASF
Micropatch™ moisturizing marin
BOC Sciences
For experimental / research use only.
DL-2-Amino-3-hydroxypropionic Acid
EMD Millipore
For experimental / research use only.
DL-Serine
sds
Glentham Life Sciences
DL-Serine
sds
Matrix Scientific
For experimental / research use only.
DL-Serine, 95+%
sds
Penta International
DL-SERINE
Sigma-Aldrich: Sigma
For experimental / research use only.
DL-Serine ≥98% (TLC)
sds
TCI AMERICA
For experimental / research use only.
DL-Serine >98.0%(T)
sds
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 22 - Do not breath dust.
S 24/25 - Avoid contact with skin and eyes.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 1890 mg/kg
Yakugaku Zasshi. Journal of Pharmacy. Vol. 89, Pg. 1138, 1969.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
special dietary and nutritional additives
Recommendation for dextro,laevo-serine usage levels up to:
 not 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 Concern:1800 (μg/person/day)
Structure Class: I
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
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): --
 
Safety References:
European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Amino acids from chemical group 34 Flavouring Group Evaluation 26, Revision 1 - Scientific opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 29 (FGE29)[1] - Substance from the priority list: Vinylbenzene from chemical group 31 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 79, (FGE.79)[1] - Consideration of amino acids and related substances evaluated by JECFA (63rd meeting) structurally related to amino acids from chemical group 34 evaluated by EFSA in FGE.26Rev1 (2008)
View page or View pdf

Scientific Report of EFSA on the risk assessment of salts of authorised acids, phenols or alcohols for use in food contact materials [1]
View page or View pdf

Scientific Opinion on the safety and efficacy of the use of amino acids (chemical group 34) when used as flavourings for all animal species
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 49, Revision 1 (FGE.49Rev1): xanthine alkaloids from the priority list
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):302-84-1
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :617
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
2-amino-3-hydroxypropanoic acid
Chemidplus:0000302841
 
References:
 2-amino-3-hydroxypropanoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:302-84-1
Pubchem (cid):617
Pubchem (sid):135024463
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C00716
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2922.50.5000
FDA Listing of Food Additive Status:View
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
flavor, food and pharmaceutical grades; usp and fcc grades
 
Potential Blenders and core components note
None Found
 
Potential Uses:
 antistatic agents
 hair conditioning
 skin conditioning
 
Occurrence (nature, food, other):note
 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-
 

Articles:

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.
 
Notes:
None found
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