laevo-proline
L-proline
Identification
| Name | laevo-proline |
| IUPAC | (2S)-pyrrolidine-2-carboxylic acid |
| CAS Number | 147-85-3 |
| EINECS | 205-702-2 |
| FDA UNII | 9DLQ4CIU6V |
| Molecular Formula | C5 H9 N O2 |
| Molecular Weight | 115.13213000 |
| MDL Number | MFCD00064318 |
| Nikkaji Number | J9.117K |
| Beilstein | 0080810 |
| CoE Number | 10490 |
| XlogP3 | -2.50 (est) |
Regulatory
| JECFA Food Flavoring | 1425 L-proline |
| DG SANTE Food Flavourings | 17.019 L-proline |
| FEMA Number | 3319 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 147-85-3 ; L-PROLINE |
| 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 | 220.00 to 222.00 °C. @ 760.00 mm Hg |
| Boiling Point | 252.19 °C. @ 760.00 mm Hg (est) |
| Vapor Pressure | 0.006000 mmHg @ 25.00 °C. (est) |
| Flash Point | > 230.00 °F. TCC ( > 110.00 °C. ) |
| logP (o/w) | -2.540 |
| Soluble in | alcohol |
| Insoluble in | ether |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | hair conditioning |
Organoleptic Properties
| Odor Strength | none |
| Odor Description | at 100.00 %. |
| Taste Description | slightly sweet |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| 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-proline usage levels up to | not for fragrance use. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 41.00 (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 | - |
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Potential Uses
Natural Occurrence
Synonyms
ajipure proline
3,4-
dihydro-L-proline
L-
prolin
(-)-(S)-
proline
(L)-
proline
(S)-
proline
(S)-(-)-
proline
L-
proline
L-(-)-
proline
L-
proline FCC; USP
L-
proline natural
L-
proline synthetic
proline, L-
2-
pyrrolidine caboxylic acid
(-)-2-
pyrrolidine carboxylic acid
(S)-2-
pyrrolidine carboxylic acid
L-alpha-
pyrrolidine carboxylic acid
laevo-alpha-
pyrrolidine carboxylic acid
(2S)-
pyrrolidine-2-carboxylic acid
(S)-
pyrrolidine-2-carboxylic acid
(S)-(-)-
pyrrolidine-2-carboxylic acid
L-
pyrrolidine-2-carboxylic acid
laevo-
pyrrolidine-2-carboxylic acid
(-)-2-
pyrrolidinecarboxylic acid
(S)-2-
pyrrolidinecarboxylic acid
L-a-
pyrrolidinecarboxylic acid
2-
pyrrolidinecarboxylic acid, (S)-
Info:
Proline
PubMed:
Study to elucidate formation pathways of selected roast-smelling odorants upon extrusion cooking.
PubMed:
Olfactory perception of 6 amino acids by human subjects.
PubMed:
Formation of strecker aldehydes from polyphenol-derived quinones and alpha-amino acids in a nonenzymic model system.
PubMed:
Detailed investigation of the production of the bread flavor component 6-acetyl-1,2,3,4-tetrahydropyridine in proline/1,3-dihydroxyacetone model systems.
PubMed:
Quantitative model studies on the efficiency of precursors in the formation of cooling-active 1-pyrrolidinyl-2-cyclopenten-1-ones and bitter-tasting cyclopenta-[b]azepin-8(1H)-ones.
PubMed:
Grape-seed procyanidins modulate cellular membrane potential and nutrient-induced GLP-1 secretion in STC-1 cells.
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:
Study to elucidate formation pathways of selected roast-smelling odorants upon extrusion cooking.
PubMed:
Metabolic profiling of Chinese tobacco leaf of different geographical origins by GC-MS.
PubMed:
Antioxidant capacities of fractionated barley hordein hydrolysates in relation to peptide structures.
PubMed:
Edwardsiella piscicida sp. nov., a novel species pathogenic to fish.
PubMed:
Production, active staining and gas chromatography assay analysis of recombinant aminopeptidase P from Lactococcus lactis ssp. lactis DSM 20481.
PubMed:
Global gene expression of Listeria monocytogenes to salt stress.
PubMed:
Lactobacillus brantae sp. nov., isolated from faeces of Canada geese (Branta canadensis).
PubMed:
Gelatin enhances 2-keto-L-gulonic acid production based on Ketogulonigenium vulgare genome annotation.
PubMed:
Betaines in fruits of Citrus genus plants.
PubMed:
Asymmetric response of carbon metabolism at high and low salt stress in Vibrio sp. DSM14379.
PubMed:
Olfactory sensitivity to amino acids in the blackspot sea bream (Pagellus bogaraveo): a comparison between olfactory receptor recording techniques in seawater.
PubMed:
Proline derivatives in fruits of bergamot (Citrus bergamia Risso et Poit): presence of N-methyl-L-proline and 4-hydroxy-L-prolinebetaine.
PubMed:
Thermodynamics of grape and wine tannin interaction with polyproline: implications for red wine astringency.
PubMed:
Watermelon profilin: characterization of a major allergen as a model for plant-derived food profilins.
PubMed:
Toxicological evaluation of L-proline in a 90-day feeding study with Fischer 344 rats.
PubMed:
Lead and other elemental content of normal and Erwinia carotovora infected Amorphallus konjac corms.
PubMed:
Olfactory perception of 6 amino acids by human subjects.
PubMed:
Expression, purification, crystallization and preliminary crystallographic analysis of an endo-1,5-alpha-L-arabinanase from hyperthermophilic Thermotoga petrophila.
PubMed:
Identification of genetic and phenotypic differences associated with prevalent and non-prevalent Salmonella Enteritidis phage types: analysis of variation in amino acid transport.
PubMed:
A novel prodrug of 4'-geranyloxy-ferulic acid suppresses colitis-related colon carcinogenesis in mice.
PubMed:
Localization of post-proline cleaving peptidases in Tenebrio molitor larval midgut.
PubMed:
Allelic variation of the Tas1r3 taste receptor gene selectively affects taste responses to sweeteners: evidence from 129.B6-Tas1r3 congenic mice.
PubMed:
Metabolic and digestive response to food ingestion in a binge-feeding lizard, the Gila monster (Heloderma suspectum).
PubMed:
Dietary oxalate and calcium oxalate nephrolithiasis.
PubMed:
Interactions between flavan-3-ols and poly(L-proline) studied by isothermal titration calorimetry: effect of the tannin structure.
PubMed:
Linear solvation energy correlation of the solvatochromic response of amino acid functionalized chromophores.
PubMed:
Delta1-pyrroline-5-carboxylic acid formed by proline dehydrogenase from the Bacillus subtilis ssp. natto expressed in Escherichia coli as a precursor for 2-acetyl-1-pyrroline.
PubMed:
Characterization of recombinant Mal d 4 and its application for component-resolved diagnosis of apple allergy.
PubMed:
Epicatechin gallate, a component of green tea, reduces halotolerance in Staphylococcus aureus.
PubMed:
Transepithelial flux of early and advanced glycation compounds across Caco-2 cell monolayers and their interaction with intestinal amino acid and peptide transport systems.
PubMed:
Formation of strecker aldehydes from polyphenol-derived quinones and alpha-amino acids in a nonenzymic model system.
PubMed:
Studies of the toxicological potential of tripeptides (L-valyl-L-prolyl-L-proline and L-isoleucyl-L-prolyl-L-proline): VI. Effects of Lactobacillus helveticus-fermented milk powder on fertility and reproductive performance of rats.
PubMed:
Studies of the toxicological potential of tripeptides (L-valyl-L-prolyl-L-proline and L-isoleucyl-L-prolyl-L-proline): V. A 13-week toxicity study of tripeptides-containing casein hydrolysate in male and female rats.
PubMed:
Studies of the toxicological potential of tripeptides (L-valyl-L-prolyl-L-proline and L-isoleucyl-L-prolyl-L-proline): IV. Assessment of the repeated-dose toxicological potential of synthesized L-valyl-L-prolyl-L-proline in male and female rats and dogs.
PubMed:
Studies of the toxicological potential of tripeptides (L-valyl-L-prolyl-L-proline and L-isoleucyl-L-prolyl-L-proline): III. Single- and/or repeated-dose toxicity of tripeptides-containing Lactobacillus helveticus-fermented milk powder and casein hydrolysate in rats.
PubMed:
Studies of the toxicological potential of tripeptides (L-valyl-L-prolyl-L-proline and L-isoleucyl-L-prolyI-L-proline): II. Introduction.
PubMed:
Effect of individual amino acids and glucose on activation and germination of Rhizopus oligosporus sporangiospores in tempe starter.
PubMed:
Allergenic reactivity of the melon profilin Cuc m 2 and its identification as major allergen.
PubMed:
[Study on N-nitroso compound in food and its relevant risk factors for esophageal cancer].
PubMed:
Effects of luminal deoxynivalenol and L-proline on electrophysiological parameters in the jejunums of laying hens.
PubMed:
Pho d 2, a major allergen from date palm pollen, is a profilin: cloning, sequencing, and immunoglobulin E cross-reactivity with other profilins.
PubMed:
Detailed investigation of the production of the bread flavor component 6-acetyl-1,2,3,4-tetrahydropyridine in proline/1,3-dihydroxyacetone model systems.
PubMed:
Application of stepwise discriminant analysis to classify commercial orange juices using chiral micellar electrokinetic chromatography-laser induced fluorescence data of amino acids.
PubMed:
Purification and characterization of a novel prolyl aminopeptidase from Maitake (Grifola frondosa).
PubMed:
Influence of blending on the content of different compounds in the biological aging of sherry dry wines.
PubMed:
Tomato profilin Lyc e 1: IgE cross-reactivity and allergenic potency.
PubMed:
A porcine model of calcium oxalate kidney stone disease.
PubMed:
Antioxidizing potency of phenol compounds in olive oil mill wastewater.
PubMed:
Pseudoalteromonas sagamiensis sp. nov., a marine bacterium that produces protease inhibitors.
PubMed:
Alkaloidal components in the poisonous plant, Ipomoea carnea (Convolvulaceae).
PubMed:
Design of chiral monochloro-s-triazine reagents for the liquid chromatographic separation of amino acid enantiomers.
PubMed:
Quantitative model studies on the efficiency of precursors in the formation of cooling-active 1-pyrrolidinyl-2-cyclopenten-1-ones and bitter-tasting cyclopenta-[b]azepin-8(1H)-ones.
PubMed:
IgE reactivity to profilin in pollen-sensitized subjects with adverse reactions to banana and pineapple.
PubMed:
Cross-reactivities between date palm (Phoenix dactylifera L.) polypeptides and foods implicated in the oral allergy syndrome.
PubMed:
Temperature-dependent binding of monoclonal antibodies to C hordein.
PubMed:
Studies on the inhibition of tumor cell growth and microtubule assembly by 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3-cyclopentene-1,2-dione, an intensively coloured Maillard reaction product.
PubMed:
Sweetener preference of C57BL/6ByJ and 129P3/J mice.
PubMed:
Effect of food shortage on the physiology and competitive abilities of sand martin (Riparia riparia) nestlings.
PubMed:
Influence of aeration on the physiological activity of flor yeasts.
PubMed:
Changes in nitrogen compounds in must and wine during fermentation and biological aging by flor yeasts.
PubMed:
Cross-reactivity within the profilin panallergen family investigated by comparison of recombinant profilins from pear (Pyr c 4), cherry (Pru av 4) and celery (Api g 4) with birch pollen profilin Bet v 2.
PubMed:
Patient-tailored cloning of allergens by phage display: peanut (Arachis hypogaea) profilin, a food allergen derived from a rare mRNA.
PubMed:
Characterization of natural "cooling" compounds formed from glucose and l-proline in dark malt by application of taste dilution analysis.
PubMed:
New and Convenient Syntheses of the Important Roasty, Popcorn-like Smelling Food Aroma Compounds 2-Acetyl-1-pyrroline and 2-Acetyltetrahydropyridine from Their Corresponding Cyclic alpha-Amino Acids.
PubMed:
Effects of food shortage and oversupply on energy utilization, histology, and function of the gut in nestling song thrushes (Turdus philomelos).
PubMed:
Cloning of the minor allergen Api g 4 profilin from celery (Apium graveolens) and its cross-reactivity with birch pollen profilin Bet v 2.
PubMed:
Olfactory discrimination of amino acids in brown bullhead catfish.
PubMed:
Influence of L-cysteine on the formation of bitter-tasting aminohexose reductones from glucose and L-proline: identification of a novel furo[2,3-b]thiazine.
PubMed:
Cloning and high level expression of Cynodon dactylon (Bermuda grass) pollen profilin (Cyn d 12) in Escherichia coli: purification and characterization of the allergen.
PubMed:
Visual and chemical release of feeding behavior in adult rainbow trout.
PubMed:
Oxyntomodulin stimulates intestinal glucose uptake in rats.
PubMed:
Recombinant DNA technology in allergology: cloning and expression of plant profilins.
PubMed:
Evaluation of D-amino acid levels in rat by gas chromatography-selected ion monitoring mass spectrometry: no evidence for subacute toxicity of orally fed D-proline and D-aspartic acid.
PubMed:
Antihypertensive peptides are present in aorta after oral administration of sour milk containing these peptides to spontaneously hypertensive rats.
PubMed:
Dietary L-arginine in renal disease.
PubMed:
Fourier transform IR spectroscopic study of hydration-induced structure changes in the solid state of omega-gliadins.
PubMed:
Adaptations of intestinal nutrient transport to chronic caloric restriction in mice.
PubMed:
Mitigating the effects of halofuginone on skin strength by feeding L-proline to broiler chickens.
PubMed:
An ATP-dependent L-carnitine transporter in Listeria monocytogenes Scott A is involved in osmoprotection.
PubMed:
Gustatory control of feeding behavior in goldfish.
PubMed:
Proteolytic and lipolytic activities of Micrococcus roseus (65), Halomonas elongata (16) and Vibrio sp. (168) isolated from Danish bacon curing brines.
PubMed:
Consummatory feeding behavior to amino acids in intact and anosmic channel catfish Ictalurus punctatus.
PubMed:
Chemical and visual control of feeding and escape behaviors in the channel catfish Ictalurus punctatus.
PubMed:
Nutritional profile and antimicrobial spectrum of the spice Aframomum danielli K. Schum.
PubMed:
Effects of fruit juices, processed vegetable juice, orange peel and green tea on endogenous formation of N-nitrosoproline in subjects from a high-risk area for gastric cancer in Moping County, China.
PubMed:
Influence of fruit and vegetable juices on the endogenous formation of N-nitrosoproline and N-nitrosothiazolidine-4-carboxylic acid in humans on controlled diets.
PubMed:
Toxicity studies of the non-sulfhydryl angiotensin converting enzyme inhibitor N-[8-amino-1(S)-carboxyoctyl]-L-alanyl-L-proline in rats.
PubMed:
N-nitrosoproline excretion by rural Nebraskans drinking water of varied nitrate content.
PubMed:
Synthesis and biological activity of CCK heptapeptide analogues. Effects of conformational constraints and standard modifications on receptor subtype selectivity, functional activity in vitro, and appetite suppression in vivo.
PubMed:
Hypotensive effect of a phosphorus-containing novel angiotensin converting enzyme inhibitor, (S)-1-[6-amino-2[[hydroxy(4-phenylbutyl)phosphinyl] oxy]-1-oxohexyl]-L-proline (SQ 29,852) in conscious hypertensive dogs.
PubMed:
Profilin is a cross-reactive allergen in pollen and vegetable foods.
PubMed:
Pharmacology of a phosphorus-containing novel angiotensin converting enzyme inhibitor, SQ 29 852 in anesthetized dogs.
PubMed:
Quantitative relationship between oral nitrate-reducing activity and the endogenous formation of N-nitrosoamino acids in humans.
PubMed:
Nutrient extraction by cold-exposed mice: a test of digestive safety margins.
PubMed:
Some behavioural effects of captopril in rats.
PubMed:
Nutritional toxicology: on the mechanisms of inhibition of formation of potent carcinogens during cooking.
PubMed:
Effects of thyrotropin-releasing hormone and its analogue L-6-ketopiperidine-2-carbonyl-leucyl-L-prolin-amide on behaviour and electroencephalogram.
PubMed:
Relationship between ascorbic acid dose and N-nitrosoproline excretion in humans on controlled diets.
PubMed:
Increased excretion of histidyl-L-proline diketopiperazine by infants receiving Pregestimil and Nutramigen formulas.
PubMed:
Effect of food on the bioavailability of lisinopril, a nonsulfhydryl angiotensin-converting enzyme inhibitor.
PubMed:
Urinary excretion of N-nitrosamino acids and nitrate by inhabitants of high- and low-risk areas for esophageal cancer in Northern China: endogenous formation of nitrosoproline and its inhibition by vitamin C.
PubMed:
Lung collagen and elastin after ozone exposure in vitamin B-6-deficient rats.
PubMed:
Behavioral study of chemoreception in the sea star Marthasterias glacialis: structure-activity relationships of lactic acid, amino acids, and acetylcholine.
PubMed:
What transport adaptations enable mammals to absorb sugars and amino acids faster than reptiles?
PubMed:
Amino acid suppression of taurine-sensitive chemosensory neurons.
PubMed:
Synthesis of three N-nitroso dipeptides N-terminal in proline and a method for their determination in food.
PubMed:
Azetidine-2-carboxylic acid contaminated dietary proline as a cause of urinary excretion of 4-amino-2-(S-cysteinyl)butyric acid in patients on oral treatment with a synthetic diet.
PubMed:
Studies on the nutritional roles of L-proline. 1. Influence of dietary proline deletion to amino acid pool of rat organs.
PubMed:
Neonatal iminoglycinuria: evidence that the prolinuria originates in selective deficiency of transport activity in the proximal nephron.