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

dextro,laevo-valine
DL-valine

Sponsors

Name:2-amino-3-methylbutanoic acid
CAS Number: 516-06-3Picture of molecule3D/inchi
Other:1105707-15-0
ECHA EINECS - REACH Pre-Reg:208-220-0
Nikkaji Web:J1.282C
Beilstein Number:0506689
MDL:MFCD00004267
CoE Number:17023
XlogP3:-2.30 (est)
Molecular Weight:117.14807000
Formula:C5 H11 N O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
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
JECFA Food Flavoring:1426 DL-valine
FLAVIS Number:17.023 (Old)
DG SANTE Food Flavourings:17.023 DL-valine
FEMA Number:3444 DL-valine
FDA Mainterm: DL-VALINE
 
Physical Properties:
Appearance:white crystalline powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 156.00 to 158.00 °C. @ 760.00 mm Hg
Boiling Point: 213.00 to 214.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.000000 mm/Hg @ 25.00 °C. (est)
Flash Point: 412.00 °F. TCC ( 211.20 °C. ) (est)
logP (o/w): -0.268 (est)
Soluble in:
 water, 184 parts in water at 24C
 water, 7.446e+004 mg/L @ 25 °C (est)
 water, 7.44E+04 mg/L @ 25 °C (exp)
 
Organoleptic Properties:
Odor Strength:none
Odor Description:at 100.00 %. odorless
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: antistatic agents
hair conditioning
masking agents
skin conditioning
 
Suppliers:
BOC Sciences
For experimental / research use only.
DL-Valine 99%
Glentham Life Sciences
DL-Valine
Penta International
DL-VALINE, Kosher
Sigma-Aldrich
DL-Valine, ≥97%
Certified Food Grade Products
TCI AMERICA
For experimental / research use only.
DL-Valine >98.0%(T)
 
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: special dietary and nutritional additives
Recommendation for dextro,laevo-valine usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 35.00 (μg/capita/day)
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 8. Update in publication number(s): 13
 average usual ppmaverage maximum ppm
baked goods: -300.00000
beverages(nonalcoholic): -15.00000
beverages(alcoholic): -0.90000
breakfast cereal: -0.90000
cheese: --
chewing gum: -200.00000
condiments / relishes: -300.00000
confectionery froastings: -300.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: -40.00000
fruit ices: -40.00000
gelatins / puddings: -80.00000
granulated sugar: --
gravies: --
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: -300.00000
milk products: -40.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: -300.00000
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --
 
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
Env. Mutagen Info. Center:Search
NLM Developmental and Reproductive Toxicity:Search
EPA Substance Registry Services (TSCA):516-06-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :1182
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
2-amino-3-methylbutanoic acid
Chemidplus:0000516063
 
References:
 2-amino-3-methylbutanoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:516-06-3
Pubchem (cid):1182
Pubchem (sid):134975915
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS):View
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
KEGG (GenomeNet):C16436
HMDB (The Human Metabolome Database):Search
FooDB:FDB012740
Export Tariff Code:2922.49.8000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
 antistatic agents
 
Occurrence (nature, food, other):note
 animal tissues
Search PMC Picture
 dairy products
Search PMC Picture
 fruits
Search PMC Picture
 milk
Search PMC Picture
 
Synonyms:
a-amino-2,3-dihydro-5-methyl-3-oxoisoxazolepropionic acid
2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)-propionic acid
2-amino-3-(3-hydroxy-5-methyl-isoxazol-4-yl)-propionic acid
(R,S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid
2-amino-3-(5-methyl-3-oxo-1,2-oxazol-4-yl)propanoic acid
2-amino-3-(5-methyl-3-oxo-2,3-dihydro-1,2-oxazol-4-yl)propanoic acid
2-amino-3-(5-methyl-3-oxo(2-hydroisoxazol-4-yl))propanoic acid
(RS)-a-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
a-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
DL-a-amino-3-hydroxy-5-methylisoxazole-4-propionic acid
dextro,laevo-2-amino-3-methyl butanoic acid
dextro,laevo-2-amino-3-methyl butyric acid
2-amino-3-methylbutanoic acid
DL-2-amino-3-methylbutanoic acid
DL-2-amino-3-methylbutyric acid
DL-alpha-aminoisovaleric acid
dextro,laevo-alpha-aminoisovaleric acid
2-ammonio-3-(3-hydroxy-5-methyl-1,2-oxazol-4-yl)propanoate
(R,S)-AMPA
(RS)-AMPA
 AMPA (RS)-
3-(3-hydroxy-5-methyl-1,2-oxazol-4-yl)alanine
3-(5-methyl-3-oxo-2,3-dihydro-1,2-oxazol-4-yl)alanine
DL-2-isopropyl glycine
dextro,laevo-2-isopropyl glycine
DL-valine
4-isoxazolepropanoic acid, a-amino-2,3-dihydro-5-methyl-3-oxo-
4-isoxazolepropanoic acid, a-amino-3-hydroxy-5-methyl-
 

Articles:

PubMed:Intermolecular vibrations in hydrophobic amino acid crystals: experiments and calculations.
PubMed:Development of a pilot-scale manufacturing process for protein-coated microcrystals (PCMC): mixing and precipitation - part I.
PubMed:Dipolar origin of water etching of amino acid surfaces.
PubMed:2₄-SEMA as a sensitive and offset compensated SLF sequence.
PubMed:Polynuclear manganese amino acid complexes.
PubMed:The first amino acid manganese cluster: a [Mn(IV)2Mn(III)3] DL-valine cage.
PubMed:Non-ionic surfactant modified ligand exchange chromatography using copper (II) complex of N,N-dimethyl-L-phenylalanine as the chiral additive for enantioselective amino acids separation.
PubMed:Effect of amino acids on tannase biosynthesis by Bacillus licheniformis KBR6.
PubMed:Inner-sphere oxidation of ternary iminodiacetatochromium(III) complexes involving DL-valine and L-arginine as secondary ligands. Isokinetic relationship for the oxidation of ternary iminodiacetato-chromium(III) complexes by periodate.
PubMed:Oligopeptides and copeptides of homochiral sequence, via beta-sheets, from mixtures of racemic alpha-amino acids, in a one-pot reaction in water; relevance to biochirogenesis.
PubMed:Formulation of the adenylate cyclase toxin of Bordetella pertussis as protein-coated microcrystals.
PubMed:Partial molar volumes of some alpha-amino acids in aqueous sodium acetate solutions at 308.15 K.
PubMed:Vibrational spectral analysis of DL-valine DL-valinium and DL-methionine DL-methioninium picrates.
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:Biosynthetic studies on a myxobacterial antibiotic, cystothiazole A: biosynthetic precursors of the carbon skeleton.
PubMed:Viscosity behavior of some alpha-amino acids and their groups in water-sodium acetate mixtures.
PubMed:Effect of amino acids and vitamins on laccase production by the bird's nest fungus Cyathus bulleri.
PubMed:Novel stachyflin derivatives from Stachybotrys sp. RF-7260. Fermentation, isolation, structure elucidation and biological activities.
PubMed:The stability constants of copper(II) complexes with some alpha-amino acids in dioxan-water mixtures.
PubMed:Effect of temperature on viscosity properties of some alpha-amino acids in aqueous urea solutions.
PubMed:One- and two-dimensional 13C-1H/15N- 1H dipolar correlation experiments under fast magic-angle spinning for determining the peptide dihedral angle phi.
PubMed:Direct thin layer chromatography enantioresolution of some basic DL-amino acids using a pharmaceutical industry waste as chiral impregnating reagent.
PubMed:Studies on the protonation constants and solvation of alpha-amino acids in dioxan-water mixtures.
PubMed:Hydroxyl radical-induced hydrogen/deuterium exchange in amino acid carbon-hydrogen bonds.
PubMed:[Thermodynamic and spectroscopic study of complex formation of dipeptides with dimethyl sulfoxide in their aqueous solutions].
PubMed:[The neurotropic and cardiotropic properties of new amino acid derivatives of isonicotinic acid].
PubMed:Mössbauer effect studies on some bioinorganic complexes of europium.
PubMed:Studies on asymmetric induction associated with the coupling of N-acylamino acids and N-benzyloxycarbonyldipeptides.
PubMed:Biochemical and ultrastructural studies induced by phanquone on Entamoeba histolytica NIH-200.
PubMed:Sensitivity of protein and RNA synthesis to antiamoebic drugs in axenic Entamoeba histolytica (NIH-200).
PubMed:[Studies on the stability of complexes of Cu(II), Ni(II), Zn(II) and Co(II) with DL-alanine and DL-valine].
PubMed:Sensitivity of protein and RNA synthesis to emetine in axenic Entamoeba histolytica.
PubMed:Thermal properties of water in myoglobin crystals and solutions at subzero temperatures.
PubMed:Models of molecular evolution. 2. Stereospecificity of dipeptide syntheses by means of cyanamides and carbodiimides.
PubMed:Milbemycins, a new family of macrolide antibiotics. Studies on the biosynthesis of milbemycins alpha 2, alpha 4 and D using 13C labeled precursors.
PubMed:Incorporation of 3H-2,3-DL-valine into pancreatic proteins of adrenalectomized rats stimulated with pancreozymin-CCK and secretin.
PubMed:Antitumor and antiinflammatory agents: N-benzoyl-protected cyanomethyl esters of amino acids.
PubMed:Carbon-11-labeled amino acids for the rectilinear and positron tomographic imaging of the human pancreas.
PubMed:[Alkylating derivatives of 2-amino-2-desoxy-1,3,4,6-tetraacetyl-D-glucopyranose (synthesis and experimental study)].
PubMed:Synthesis and biological activity of tuftsin and of [O = C Thr1]-tuftsin. A novel synthetic route to peptides containing N-terminal L -O = C Thr and L - O = C Ser residues.
PubMed:Mapping of the locus involved in the catabolic oxidation of D-amino acids in Pseudomonas aeruginosa PAO.
PubMed:Anti-inflammatory activity of DL-valine.
PubMed:Influence of pregnancy and postpartum period in vitro incorporation of dl-valine-1-14C into oviducal and uterine protein.
PubMed:Free radicals produced by gamma irradiation in a single crystal of N-acetyl-DL-valine at 77 K and after heat treatment.
PubMed:[1-11C] DL-valine, a potential pancreas-imaging agent.
PubMed:Production and chemical studies of protease from Bacillus subtilis (SH-6) Egyptian strain.
PubMed:[Study of 14 denitrifying soil bacteria of the "pseudomonas stutzeri" group isolated by enrichment culture in the presence of nitrous oxide (author's transl)].
PubMed:Effect of different concentrations of dl-isoleucine, dl-valine, and dl-alanine on growth and sporulation in Fusarium oxysporum f. udum (Butl.) Sn. et H.
PubMed:Paramagnetic centres formed by photolysis in a single crystal of N-acetyl-DL-valine at room temperature.
PubMed:Conformation of poly(DL-valine) obtained by the polymerization of the N-carboxy anhydride.
PubMed:Influence of amino acids on the growth of Bacteroides melaninogenicus.
PubMed:Leucine imbalance in corn-soybean meal diets for laying hens.
PubMed:Incorporation of double-labeled L-cystine and DL-valine in penicillin.
PubMed:Vitamin B12 nutrition and metabolism in the baboon (Papio cynocephalus).
PubMed:Electron-spin resonance of an X-irradiated single crystal of N-acetyl-DL-valine.
PubMed:Detection of a cephalosporin C acetyl esterase in the carbamate cephalosporin antibiotic-producing culture, Streptomyces clavuligerus.
PubMed:Studies on physiology and biochemistry of the fallopian tube: in vitro uptake of dl-valine-1-C 14 by different parts of the rabbit Fallopian tube during early pregnancy.
PubMed:In vivo incorporation of 3 H-2,3-DL-valine in cholate-induced acute pancreatitis in rats.
PubMed:[Effect of DL-methionine and DL-valine on elaboration and extinction of a conditioned avoidance reaction (avoidance conditioning)].
PubMed:Biochemical characterization of a mutant isoleucyl-transfer ribonucleic acid synthetase from Escherichia coli K-12.
PubMed:[Reaction kinetics of radiation-induced free radicals of glycyl-DL-valine and DL-valyl-glycine during heat treatment and UV-irradiation].
PubMed:[Electron spin resonance spectroscopy of some radiation-induced free radicals of DL-valine, N-acetyl-DL-valine and glycyl-DL-valine].
PubMed:Effect of a contraceptive suture on incorporation of dl-valine-1-14C in the uterine fluid protein of rats.
PubMed:[Studies on the dependency upon radiation dose of microwaves saturation in electron spin resonance radiation-induced free radicals of DL-valine and DL-leucine].
PubMed:Alteration of the microwave saturation behaviour after heat treatment in electron spin resonance studies of free radicals produced in DL-valine by x-irradiation.
PubMed:Oxidation of D-amino acids by a particulate enzyme from Pseudomonas aeruginosa.
PubMed:Gluconeogenesis in the kidney and liver slices of a lizard, Uromastix hardwickii.
PubMed:Amino Acid and vitamin requirements of several bacteroides strains.
PubMed:Alanine and aspartate formation during growth on valine-C14 by Pseudomonas aeruginosa.
PubMed:Oxidation of D- and L-valine by enzymes of Pseudomonas aeruginosa.
PubMed:UPTAKE OF VALINE AND GLYCYLVALINE BY LEUCONOSTOC MESENTEROIDES.
PubMed:Amino acids as gustatory stimuli in the rat.
PubMed:Physiological studies of the rumen protozoan Ophryoscolex caudatus Eberlein.
PubMed:[Toxic effects of DL-valine].
PubMed:Biosynthesis of penicillins; utilization of deuterophenylacetyl-N15-dl-valine in penicillin biosynthesis.
PubMed:PLASMA PROTEIN PRODUCTION INFLUENCED BY AMINO ACID MIXTURES AND LACK OF ESSENTIAL AMINO ACIDS : A DEFICIENCY STATE RELATED TO UNKNOWN FACTORS.
PubMed:TOLERANCE TO AMINO ACID MIXTURES AND CASEIN DIGESTS GIVEN INTRAVENOUSLY : GLUTAMIC ACID RESPONSIBLE FOR REACTIONS.
PubMed:AMINO ACID MIXTURES EFFECTIVE PARENTERALLY FOR LONG CONTINUED PLASMA PROTEIN PRODUCTION. CASEIN DIGESTS COMPARED.
 
Notes:
Flavouring ingredient Branched chain amino acids (BCAA) are essential amino acids whose carbon structure is marked by a branch point. These three amino acids are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. "BCAA" denotes valine, isoleucine and leucine which are branched chain essential amino acids. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats and isoleucine to both. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors.; Many types of inborn errors of BCAA metabolism exist, and are marked by various abnormalities. The most common form is the maple syrup urine disease, marked by a characteristic urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary restriction of BCAA and at least one form is correctable by supplementation with 10 mg of biotin daily. BCAA are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia or portacaval shunt; Valine (abbreviated as Val or V) is an ?-amino acid with the chemical formula HO2CCH(NH2)CH(CH3)2. L-Valine is one of 20 proteinogenic amino acids. Its codons are GUU, GUC, GUA, and GUG. This essential amino acid is classified as nonpolar. Along with leucine and isoleucine, valine is a branched-chain amino acid. It is named after the plant valerian. In sickle-cell disease, valine substitutes for the hydrophilic amino acid glutamic acid in hemoglobin. Because valine is hydrophobic, the hemoglobin does not fold correctly.; Valine is an essential amino acid, hence it must be ingested, usually as a component of proteins. And will flow bood engorged pumps to the penile region. It is synthesized in plants via several steps starting from pyruvic acid. The initial part of the pathway also leads to leucine. The intermediate ?-ketovalerate undergoes reductive amination with glutamate. Enzymes involved in this biosynthesis include:; aromatic amino acids (AAA)-tyrosine, tryptophan and phenylalanine, as well as methionine-are increased in these conditions. Valine in particular, has been established as a useful supplemental therapy to the ailing liver. All the BCAA probably compete with AAA for absorption into the brain. Supplemental BCAA with vitamin B6 and zinc help normalize the BCAA:AAA ratio. (http://www.dcnutrition.com)
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