laevo-leucine
4-methyl-L-norvaline
Identification
| Name | laevo-leucine |
| IUPAC | (2S)-2-amino-4-methylpentanoic acid |
| CAS Number | 61-90-5 |
| EINECS | 200-522-0 |
| FDA UNII | GMW67QNF9C |
| Molecular Formula | C6 H13 N O2 |
| Molecular Weight | 131.17501000 |
| MDL Number | MFCD00002617 |
| Nikkaji Number | J1.167C |
| Beilstein | 1721722 |
| CoE Number | 10482 |
| XlogP3 | -1.50 (est) |
Regulatory
| FDA/DG SANTE Petitions, Reviews, Notices | GRN 308 |
| JECFA Food Flavoring | 1423 L-leucine |
| DG SANTE Food Flavourings | 17.012 L-leucine |
| DG SANTE Food Additives | L-leucine |
| FEMA Number | 3297 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 61-90-5 ; L-LEUCINE |
| FDA Regulation | FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION |
Physical Properties
| Appearance | white crystalline powder (est) |
| Assay | 98.00 to 100.00 |
| Food Chemicals Codex Listed | Yes |
| Melting Point | 293.00 to 294.00 °C. @ 760.00 mm Hg |
| Boiling Point | 563.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.031000 mmHg @ 25.00 °C. (est) |
| Flash Point | > 230.00 °F. TCC ( > 110.00 °C. ) |
| logP (o/w) | 0.799 (est) |
| Soluble in | alcohol, slightly |
| Insoluble in | alcohol |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | antistatic agents |
Organoleptic Properties
| Odor Strength | none |
| Odor Description | at 100.00 %. |
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-rat LD50 5379 mg/kg |
| Dermal Toxicity | subcutaneous-rabbit LDLo 2620 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | special dietary and nutritional additives |
| Recommendation for laevo-leucine usage levels up to | not for fragrance use. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 12.00 (μg/capita/day) |
| baked goods | - |
| beverages(nonalcoholic) | - |
| beverages(alcoholic) | - |
| breakfast cereal | - |
| cheese | - |
| chewing gum | - |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | - |
| fruit ices | - |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | - |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | - |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | - |
| soft candy | - |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
BOC Sciences
Best of Chemicals Supplier
Quality supplier of research chemicals and biochemicals including inhibitors, building blocks, GMP Products, impurities and metabolites, APIs for Veterinary, Natural Compounds, ADCs, Stem Cell Molecul...
Charkit Chemical Corporation
The Specialty Chemical Specialists
Explore this website to discover the products and services that Charkit provides for your industry and please contact us directly to find out how we can be of service to you.
Glentham Life Sciences Ltd
The Chemical, Biochemical & Research Essentials Supplier
Glentham Life Sciences is a supplier of fine chemicals and raw materials with warehousing, laboratories and packaging facilities in the UK.
Jiangyin Healthway International Trade Co., Ltd
Independent Ingredients Supplier
We provide custom synthesis and contract manufacturing from milligrams to metric tonnes.
Penta International Corporation
Chemistry innovation
At Penta, our products and services help businesses do business better.
Sigma-Aldrich
Complete Supply Chain
The perfect blend of products and services that bring your creativity to life.
Qingdao Free Trade Zone United International Co Ltd
Quality Products
A partner in your supply chain solution.
Potential Uses
Natural Occurrence
Synonyms
ajigras-leucine
ajipure leucine
(2S)-2-
amino-4-methyl pentanoic acid
(S)-2-
amino-4-methyl pentanoic acid
2-
amino-4-methyl pentanoic acid
laevo-(-)-2-
amino-4-methyl pentanoic acid
(S)-2-
amino-4-methyl valeric acid
2-
amino-4-methyl valeric acid
(2S)-2-
amino-4-methylpentanoic acid
(S)-2-
amino-4-methylpentanoic acid
L-(-)-2-
amino-4-methylpentanoic acid
(2S)-a-2-
amino-4-methylvaleric acid
(S)-2-
amino-4-methylvaleric acid
alpha-
aminoisocaproic acid
L-a-
aminoisocaproic acid
L-alpha-
aminoisocaproic acid
laevo-alpha-
aminoisocaproic acid
(2S)-a-
leucine
(S)-
leucine
(S)-(+)-
leucine
L-
leucine
L-(+)-
leucine
L-
leucine FCC
l-
leucine fcc; usp
L-
leucine natural
4-
methyl-L-norvaline
PubMed:
Amino acids and peptides activate at least five members of the human bitter taste receptor family.
PubMed:
Strategies to select yeast starters cultures for production of flavor compounds in cachaça fermentations.
PubMed:
An improved bioprocess for extracellular L-leucine amino peptidase production using Streptomyces gedanensis.
PubMed:
Kokumi-active glutamyl peptides in cheeses and their biogeneration by Penicillium roquefortii.
PubMed:
Molecular and sensory characterization of gamma-glutamyl peptides as key contributors to the kokumi taste of edible beans (Phaseolus vulgaris L.).
PubMed:
Improved production of isoamyl acetate by a sake yeast mutant resistant to an isoprenoid analog and its dependence on alcohol acetyltransferase activity, but not on isoamyl alcohol production.
PubMed:
Genetic and physiological analysis of branched-chain alcohols and isoamyl acetate production in Saccharomyces cerevisiae.
PubMed:
Conversion of L-leucine to isovaleric acid by Propionibacterium freudenreichii TL 34 and ITGP23.
PubMed:
ZnCl2-mediated practical protocol for the synthesis of Amadori ketoses.
PubMed:
Involvement of Val 315 located in the C-terminal region of thermolysin in its expression in Escherichia coli and its thermal stability.
PubMed:
Effects of conversion of the zinc-binding motif sequence of thermolysin, HEXXH, to that of dipeptidyl peptidase III, HEXXXH, on the activity and stability of thermolysin.
PubMed:
Hydrolysis of wheat gluten by combining peptidases of Flammulina velutipes and electrodialysis.
PubMed:
Measurements of substrate oxidation using (13)CO 2-breath testing reveals shifts in fuel mix during starvation.
PubMed:
Obesity-related metabolomic analysis of human subjects in black soybean peptide intervention study by ultraperformance liquid chromatography and quadrupole-time-of-flight mass spectrometry.
PubMed:
L-Leucine and L-isoleucine enhance growth of BBN-induced urothelial tumors in the rat bladder by modulating expression of amino acid transporters and tumorigenesis-associated genes.
PubMed:
Initial adhesion of Listeria monocytogenes to fine polished stainless steel under flow conditions is determined by prior growth conditions.
PubMed:
Effects of mutations of thermolysin, as N116 to asp and asp150 to glu, on salt-induced activation and stabilization.
PubMed:
A dipeptide and an amino acid present in whey protein hydrolysate increase translocation of GLUT-4 to the plasma membrane in Wistar rats.
PubMed:
Authentication of pure L-leucine products manufactured in China by discriminating between plant and animal sources using nitrogen stable isotope technique.
PubMed:
Amino acids and peptides activate at least five members of the human bitter taste receptor family.
PubMed:
Brainstem nutrient sensing in the nucleus of the solitary tract inhibits feeding.
PubMed:
A novel Fe(II)/α-ketoglutarate-dependent dioxygenase from Burkholderia ambifaria has β-hydroxylating activity of N-succinyl l-leucine.
PubMed:
Effects of "Bioactive" amino acids leucine, glutamate, arginine and tryptophan on feed intake and mRNA expression of relative neuropeptides in broiler chicks.
PubMed:
Long-term treatment with L-isoleucine or L-leucine in AIN-93G diet has promoting effects on rat bladder carcinogenesis.
PubMed:
Production, active staining and gas chromatography assay analysis of recombinant aminopeptidase P from Lactococcus lactis ssp. lactis DSM 20481.
PubMed:
Dietary L-leucine and L-alanine supplementation have similar acute effects in the prevention of high-fat diet-induced obesity.
PubMed:
Effect of central and peripheral leucine on energy metabolism in the Djungarian hamster (Phodopus sungorus).
PubMed:
Effects of site-directed mutagenesis of Asn116 in the β-hairpin of the N-terminal domain of thermolysin on its activity and stability.
PubMed:
Structural analysis of a new cytotoxic demethylated analogue of neo-N-methylsansalvamide with a different peptide sequence produced by Fusarium solani isolated from potato.
PubMed:
Prey digestion in the midgut of the predatory bug Podisus nigrispinus (Hemiptera: Pentatomidae).
PubMed:
Allocation of endogenous and dietary protein in the reconstitution of the gastrointestinal tract in migratory blackcaps at stopover sites.
PubMed:
Intracerebroventricular administration of metformin inhibits ghrelin-induced Hypothalamic AMP-kinase signalling and food intake.
PubMed:
Kinetic analysis for the degradation of glycyl-L-leucine and L-leucyl-glycine in subcritical water.
PubMed:
Effects of leucine and citrulline versus non-essential amino acids on muscle protein synthesis in fasted rat: a common activation pathway?
PubMed:
Growth of Esteya vermicola in media amended with nitrogen sources yields conidia with increased predacity and resistance to environmental stress.
PubMed:
Gelatin enhances 2-keto-L-gulonic acid production based on Ketogulonigenium vulgare genome annotation.
PubMed:
Olfactory sensitivity to amino acids in the blackspot sea bream (Pagellus bogaraveo): a comparison between olfactory receptor recording techniques in seawater.
PubMed:
Prolonged leucine supplementation does not augment muscle mass or affect glycemic control in elderly type 2 diabetic men.
PubMed:
Supplementation with a fish oil-enriched, high-protein medical food leads to rapid incorporation of EPA into white blood cells and modulates immune responses within one week in healthy men and women.
PubMed:
Technological characterization of lactococci isolated from traditional Chinese fermented milks.
PubMed:
Body weight and energy homeostasis was not affected in C57BL/6 mice fed high whey protein or leucine-supplemented low-fat diets.
PubMed:
Effects of site-directed mutagenesis of the loop residue of the N-terminal domain Gly117 of thermolysin on its catalytic activity.
PubMed:
Extrusion decreases the negative effects of kidney bean on enzyme and transport activities of the rat small intestine.
PubMed:
An improved bioprocess for extracellular L-leucine amino peptidase production using Streptomyces gedanensis.
PubMed:
Characterization of activity of a potential food-grade leucine aminopeptidase from kiwifruit.
PubMed:
Origin and Incidence of 2-Methoxy-3,5-dimethylpyrazine, a Compound with a "Fungal" and "Corky" Aroma Found in Cork Stoppers and Oak Chips in Contact with Wines.
PubMed:
Gellan gum as an immobilization matrix for the production of cyclosporin A.
PubMed:
Supplementing L-leucine to a low-protein diet increases tissue protein synthesis in weanling pigs.
PubMed:
Leucine supplementation favors liver protein status but does not reduce body fat in rats during 1 week of food restriction.
PubMed:
Dietary l-leucine supplementation of lactating rats results in a tendency to increase lean/fat ratio associated to lower orexigenic neuropeptide expression in hypothalamus.
PubMed:
Statistical optimization for improved production of cyclosporin a in solid-state fermentation.
PubMed:
Heating improves poor compliance with branched chain amino acid-rich supplementation in patients with liver cirrhosis: A before-after pilot study.
PubMed:
The mammalian target of rapamycin as novel central regulator of puberty onset via modulation of hypothalamic Kiss1 system.
PubMed:
Kokumi-active glutamyl peptides in cheeses and their biogeneration by Penicillium roquefortii.
PubMed:
Protein properties of mackerel viscera extracted by supercritical carbon dioxide.
PubMed:
The effects of age on uptake, serum half-life and bioavailability of mouse [D-Leu-4]OB3, a synthetic peptide amide with leptin-like activity, in male C57BL/6J mice.
PubMed:
Effects of introducing negative charges into the molecular surface of thermolysin by site-directed mutagenesis on its activity and stability.
PubMed:
Anti-peptide antibody production elicited by in vitro immunization of human peripheral blood mononuclear cells.
PubMed:
Inhibitory effect of aroma on the bitterness of branched-chain amino acid solutions.
PubMed:
Production of L-leucine aminopeptidase by selected Streptomyces isolates.
PubMed:
Metabolic and digestive response to food ingestion in a binge-feeding lizard, the Gila monster (Heloderma suspectum).
PubMed:
Improving the activity and stability of thermolysin by site-directed mutagenesis.
PubMed:
Enantioselective separation of all-E-astaxanthin and its determination in microbial sources.
PubMed:
Molecular and sensory characterization of gamma-glutamyl peptides as key contributors to the kokumi taste of edible beans (Phaseolus vulgaris L.).
PubMed:
Effects of leucine and phenylalanine supplementation during intermittent periods of food restriction and refeeding in adult rats.
PubMed:
Effects of site-directed mutagenesis of the surface residues Gln128 and Gln225 of thermolysin on its catalytic activity.
PubMed:
Kinetic analysis of the activation-and-inhibition dual effects of cobalt ion on thermolysin activity.
PubMed:
Molecular mechanism of the inhibitory effect of cobalt ion on thermolysin activity and the suppressive effect of calcium ion on the cobalt ion-dependent inactivation of thermolysin.
PubMed:
Kinetics of plasma apolipoprotein C-III as a determinant of diet-induced changes in plasma triglyceride levels.
PubMed:
Suppression of myofibrillar proteolysis in chick skeletal muscles by alpha-ketoisocaproate.
PubMed:
Lactoferricin-related peptides with inhibitory effects on ACE-dependent vasoconstriction.
PubMed:
Purification and characterization of a halotolerant intracellular protease from Bacillus subtilis strain FP-133.
PubMed:
Protease and esterase activity of staphylococci.
PubMed:
Effects of leucine supplementation on the body composition and protein status of rats submitted to food restriction.
PubMed:
Sequence diversity of the peptaibol antibiotic suzukacillin-A from the mold Trichoderma viride.
PubMed:
Effect of individual amino acids and glucose on activation and germination of Rhizopus oligosporus sporangiospores in tempe starter.
PubMed:
Characterization of Gly-D-Phe, Gly-L-Leu, and D-Phe as affinity ligands to thermolysin.
PubMed:
Extracellular production of recombinant thermolysin expressed in Escherichia coli, and its purification and enzymatic characterization.
PubMed:
Asp578 in LEU4p is one of the key residues for leucine feedback inhibition release in sake yeast.
PubMed:
Clinical comparison of branched-chain amino acid (l-Leucine, l-Isoleucine, l-Valine) granules and oral nutrition for hepatic insufficiency in patients with decompensated liver cirrhosis (LIV-EN study).
PubMed:
Lipid-lowering efficacy of 3,4-di(OH)-phenylpropionic L-leucine in high-cholesterol fed rats.
PubMed:
Leptin secretion and protein kinase A activity.
PubMed:
Direct spectrophotometric measurement of angiotensin I-converting enzyme inhibitory activity for screening bioactive peptides.
PubMed:
Atmospheric oxygen and other conditions affecting the production of cereulide by Bacillus cereus in food.
PubMed:
Prolonged oral treatment with an essential amino acid L-leucine does not affect female reproductive function and embryo-fetal development in rats.
PubMed:
Tissue-specific regulation of 4E-BP1 and S6K1 phosphorylation by alpha-ketoisocaproate.
PubMed:
Suppression of the bitterness of enteral nutrients using increased particle sizes of branched-chain amino acids (BCAAs) and various flavours: a taste sensor study.
PubMed:
Diversity of L-leucine catabolism in various microorganisms involved in dairy fermentations, and identification of the rate-controlling step in the formation of the potent flavour component 3-methylbutanal.
PubMed:
Purification and some properties of cathepsin H from rabbit skeletal muscle.
PubMed:
Isolation and characterization of aminopeptidase (Jc-peptidase) from Japanese cedar pollen (Cryptomeria japonica).
PubMed:
Oral administration of leucine stimulates phosphorylation of 4E-bP1 and S6K 1 in skeletal muscle but not in liver of diabetic rats.
PubMed:
Contribution of insulin to the translational control of protein synthesis in skeletal muscle by leucine.
PubMed:
Time course of leucine-induced 4E-BP1 and S6K1 phosphorylation in the liver and skeletal muscle of rats.
PubMed:
Effects of cobalt-substitution of the active zinc ion in thermolysin on its activity and active-site microenvironment.
PubMed:
Whole-body L-leucine oxidation in patients with variant form of maple syrup urine disease.
PubMed:
Native and acid-denatured L-lactate dehydrogenase are different in the lysosomal proteinases involving in their overall degradation.
PubMed:
Effect of amino acids on the composition and properties of extruded mixtures of wheat flour and glucose.
PubMed:
Screen-printed amperometric biosensors for the rapid measurement of L- and D-amino acids.
PubMed:
Olfactory discrimination of amino acids in brown bullhead catfish.
PubMed:
Growth hormone effects on essential amino acid absorption, muscle amino acid profile, N-retention and nutritional requirements of striped bass hybrids.
PubMed:
Reproducibility of the separation of astaxanthin stereoisomers on Pirkle covalent L-leucine and D-phenylglycine columns.
PubMed:
The naturally occurring furanones: formation and function from pheromone to food.
PubMed:
Digestive responses during food restriction and realimentation in nestling house sparrows (Passer domesticus).
PubMed:
Formation of amino acid (L-leucine, L-phenylalanine) derived volatile flavour compounds by Moraxella phenylpyruvica and Staphylococcus xylosus in cured meat model systems.
PubMed:
Effects of pH, temperature, and alcohols on the remarkable activation of thermolysin by salts.
PubMed:
Visual and chemical release of feeding behavior in adult rainbow trout.
PubMed:
Changes in blood-brain barrier nutrient transport in the offspring of iodine-deficient rats and their preventability.
PubMed:
Effects of leucine on whole body leucine, valine, and threonine metabolism in humans.
PubMed:
Response of rainbow trout (Oncorhynchus mykiss) to supplements of individual essential amino acids in a semipurified diet, including an estimate of the maintenance requirement for essential amino acids.
PubMed:
Rapid liquid chromatographic method to distinguish wild salmon from aquacultured salmon fed synthetic astaxanthin.
PubMed:
Is diet shifting facilitated by modulation of intestinal nutrient uptake? Test of an adaptational hypothesis in yellow-rumped warblers.
PubMed:
Purification of aminopeptidase from Australian classified barley flour.
PubMed:
Production of egg proteins, enriched with L-leucine-13C1, for the study of protein assimilation in humans using the breath test technique.
PubMed:
Effect of amino acid residues at the cleavable site of substrates on the remarkable activation of thermolysin by salts.
PubMed:
Lipoprotein that selectively inhibits taste nerve responses to bitter substances.
PubMed:
Influence of leucine on intestinal baclofen absorption as a model compound of neutral alpha-aminoacids.
PubMed:
In vitro adsorption of amino acids onto isolated rat erythrocyte membranes.
PubMed:
Enhanced formation of isoamyl alcohol in Zygosaccharomyces rouxii due to elimination of feedback inhibition of alpha-isopropylmalate synthase.
PubMed:
Effects of excess dietary leucine and leucine catabolites on growth and immune responses in weanling pigs.
PubMed:
The influence of net water absorption on the permeability of antipyrine and levodopa in the human jejunum.
PubMed:
[The effect of the isolated or group housing of rat pups weaned at different times from the lactating female on the development of a spectrum of digestive enzymes in the small intestine].
PubMed:
Nutritional profile and antimicrobial spectrum of the spice Aframomum danielli K. Schum.
PubMed:
Leucine and glucose turnover in chronic alcoholics during early abstinence and after an ethanol load.
PubMed:
Requirement of thiol compounds as reducing agents for IL-2-mediated induction of LAK activity and proliferation of human NK cells.
PubMed:
On the 13C CP/MAS spectra of leucine.
PubMed:
Isoleucine requirements of the chicken: the effect of excess leucine and valine on the response to isoleucine.
PubMed:
Influence of subchronic exposure to low dietary deoxynivalenol, a trichothecene mycotoxin, on intestinal absorption of nutrients in mice.
PubMed:
Measurement of very low density and low density lipoprotein apolipoprotein (Apo) B-100 and high density lipoprotein Apo A-I production in human subjects using deuterated leucine. Effect of fasting and feeding.
PubMed:
Effects of valine on 15N incorporation into serum and tissue protein and non-protein fractions following 15N-L-leucine administration to normal and liver-injured rats.
PubMed:
Insulin secretion in the isolated islets of single-, regular-fasted and fed rats.
PubMed:
[Effect on uptake of D-glucose, L-leucine and L-leucylglycine into intestinal brush border membrane vesicles isolated from rats fed either oligopeptide or amino acid elemental diet].
PubMed:
[Effect of feeding a small-peptide elemental diet on amino acid absorption and its mechanism--study by measuring the transmural potential difference in guinea-pig small intestine].
PubMed:
L-leucine and its analogue: specific inhibitors for S-benzyl-L-cysteine-p-nitroanilide-hydrolyzing enzyme in Escherichia coli B.
PubMed:
Comparative effects of individual amino acid excesses when added to a corn-soybean meal diet: effects on growth and dietary choice in the chick.
PubMed:
Amino acid excesses for young pigs: effects of excess methionine, tryptophan, threonine or leucine.
PubMed:
Effect of L-leucine on oral melphalan kinetics in patients.
PubMed:
Behavioral study of chemoreception in the sea star Marthasterias glacialis: structure-activity relationships of lactic acid, amino acids, and acetylcholine.
PubMed:
Amino acid and dipeptide absorption in rats fed chemically defined diets of differing fiber composition.
PubMed:
[Absorption of 14C-leucine and 15N-leucine in rats after feeding a fish meal diet in comparison with a gelatin diet].
PubMed:
The control of food mobilization in seeds of Cucumis sativus L. : III. The control of protein degradation.
PubMed:
Production of oxytetracycline by Streptomyces rimosus 12,907 as an animal feed supplement.
PubMed:
Peptidase activity in Tetrahymena.
PubMed:
Hyperphagia following intraventricular p-chlorophenylalanine-, leucine- or tryptophan-methyl esters: lack of correlation with whole brain serotonin levels.
PubMed:
The effect of a high level of dietary leucine on the niacin status of chicks and rats.
PubMed:
The branched-chain amino acid antagonism in chicks.
PubMed:
Chemosensory tracking of scent trails by the planktonic shrimp Acetes sibogae australis.
PubMed:
[Resorption and incorporation of radioactive-labeled amino acids during the administration of various protein carriers in rats. 2. Uptake of radioactivity by tissues of the gastrointestinal tract after intragastric administration of 14C-L-U-leucine and 3H-glycine].
PubMed:
Effects of mercury on spermatogenesis studied by velocity sedimentation cell separation and serial mating.
PubMed:
The effect of pregnancy and lactation on food intake, gastrointestinal anatomy and the absorptive capacity of the small intestine in the albino rat.