anserine
b-alanyl-N(pi)-methyl-L-histidine
 
Notes:
This dipeptide is normally absent from human tissues and body fluids, and its appearance there is an artifact of diet (Proc Soc Pediatr Res 134, 1967.) and serum carnosinase deficiency. (OMIM 212200) Anserine is present in the skeletal muscle of birds and certain species of mammals, notably the rabbit, rat, and whale, contains anserine. (Proc Soc Pediatr Res 134, 1967) The methyl group of anserine is added to carnosine by the enzyme S-adenosylmethionine: carnosine N-methyltransferase. (J Biol Chem 237:1207, 1962.) [HMDB]
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(2S)-2-(3-aminopropanoylamino)-3-(3-methylimidazol-4-yl)propanoic acid (Click)
CAS Number: 584-85-0Picture of molecule
Other: 1145-43-3
ECHA EINECS - REACH Pre-Reg: 209-545-0
FDA UNII: HDQ4N37UGV
Nikkaji Web: J28.566H
Beilstein Number: 089932
XlogP3-AA: -4.00 (est)
Molecular Weight: 240.26312000
Formula: C10 H16 N4 O3
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: antioxidant, humectant agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 611.30 °C. @ 760.00 mm Hg (est)
Flash Point: 614.00 °F. TCC ( 323.50 °C. ) (est)
logP (o/w): -2.220 (est)
Soluble in:
 water, 1.575e+004 mg/L @ 25 °C (est)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antioxidants
humectants
skin conditioning
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Suppliers:
 None found
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Safety Information:
 
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
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Safety in Use Information:
Category: antioxidant, humectant agents
Recommendation for anserine usage levels up to:
 not for fragrance use.
 
Recommendation for anserine flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 112072
National Institute of Allergy and Infectious Diseases: Data
 (2S)-2-(3-aminopropanoylamino)-3-(3-methylimidazol-4-yl)propanoic acid
Chemidplus: 0000584850
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References:
 (2S)-2-(3-aminopropanoylamino)-3-(3-methylimidazol-4-yl)propanoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 112072
Pubchem (sid): 134978654
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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
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C01262
HMDB (The Human Metabolome Database): HMDB00194
FooDB: FDB021903
YMDB (Yeast Metabolome Database): YMDB01565
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 found in nature
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Synonyms:
b-alanyl-3-methyl-L-histidine
N-b-alanyl-3-methyl-L-histidine
b-alanyl-N(pai)-methyl-L-histidine
b-alanyl-N(pi)-methyl-L-histidine
(S)-2-(3-aminopropanamido)-3-(1-methyl-1H-imidazol-4-yl)propanoic acid
(2S)-2-(3-aminopropanoylamino)-3-(1-methylimidazol-5-yl)propanoic acid
(2S)-2-(3-aminopropanoylamino)-3-(3-methylimidazol-4-yl)propanoic acid
L-anserine
L-histidine, b-alanyl-3-methyl-
L-histidine, beta-alanyl-3-methyl-
L-histidine, N-b-alanyl-3-methyl-
3-methyl-N,a-(b-alanyl)-L-histidine
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Articles:
PubMed: Long-term consumption of dried bonito dashi (a traditional Japanese fish stock) reduces anxiety and modifies central amino acid levels in rats.
PubMed: Genetic parameters for carnitine, creatine, creatinine, carnosine, and anserine concentration in longissimus muscle and their association with palatability traits in Angus cattle.
PubMed: Bioactivities of chicken essence.
PubMed: Interaction of soluble peptides and proteins from skeletal muscle with volatile compounds in model systems as affected by curing agents.
PubMed: Interactions of soluble peptides and proteins from skeletal muscle on the release of volatile compounds.
PubMed: Effects of chicken-liver hydrolysates on lipid metabolism in a high-fat diet.
PubMed: Long-term consumption of dried bonito dashi (a traditional Japanese fish stock) reduces anxiety and modifies central amino acid levels in rats.
PubMed: Biological functions of histidine-dipeptides and metabolic syndrome.
PubMed: Effects of chicken essence on recovery from mental fatigue in healthy males.
PubMed: ¹H NMR and multivariate data analysis of the relationship between the age and quality of duck meat.
PubMed: Variability in the contents of pork meat nutrients and how it may affect food composition databases.
PubMed: Effect of a dipeptide-enriched diet in an adult Drosophila melanogaster laboratory strain.
PubMed: L-carnosine modulates respiratory burst and reactive oxygen species production in neutrophil biochemistry and function: may oral dosage form of non-hydrolized dipeptide L-carnosine complement anti-infective anti-influenza flu treatment, prevention and self-care as an alternative to the conventional vaccination?
PubMed: Nutritional pork meat compounds as affected by ham dry-curing.
PubMed: Bioactivities of chicken essence.
PubMed: How much chicken is food? Questioning the definition of food by analyzing amino acid composition of modern convenience products.
PubMed: Composition and some quality characteristics of the longissimus muscle of reindeer in Norway compared to farmed New Zealand red deer.
PubMed: A NMR-based metabolomic approach for differentiation of hagfish dental and somatic skeletal muscles.
PubMed: High-Resolution (1)H Magic Angle Spinning NMR Spectroscopy of Intact Arctic Char (Salvelinus Alpinus) Muscle. Quantitative Analysis of n-3 Fatty Acids, EPA and DHA.
PubMed: Effect of anserine ingestion on hyperglycemia and the autonomic nerves in rats and humans.
PubMed: Quality characteristics and composition of the longissimus muscle in the short-loin from male and female farmed red deer in New Zealand.
PubMed: Effect of anserine ingestion on the hyperglycemia and autonomic nerves in rats and humans.
PubMed: Sensory-guided identification of N-(1-methyl-4-oxoimidazolidin-2-ylidene)-alpha-amino acids as contributors to the thick-sour and mouth-drying orosensation of stewed beef juice.
PubMed: The bioactive dipeptide anserine is transported by human proton-coupled peptide transporters.
PubMed: Profiling histidine dipeptides in plasma and urine after ingesting beef, chicken or chicken broth in humans.
PubMed: Intestinal absorption and blood clearance of L-histidine-related compounds after ingestion of anserine in humans and comparison to anserine-containing diets.
PubMed: Antioxidant combination inhibits reactive oxygen species mediated damage.
PubMed: Creatine supplementation augments skeletal muscle carnosine content in senescence-accelerated mice (SAMP8).
PubMed: Food restriction and refeeding in lambs influence muscle antioxidant status.
PubMed: Anserine and carnosine determination in meat samples by pure micellar liquid chromatography.
PubMed: Safety evaluation of chicken breast extract containing carnosine and anserine.
PubMed: Hydrophilic chromatographic determination of carnosine, anserine, balenine, creatine, and creatinine.
PubMed: Anserine induced advantage effects on the antitumor activity of doxorubicin.
PubMed: Field-amplified on-line sample stacking for determination of carnosine-related peptides by capillary electrophoresis.
PubMed: Effect of lectins on the transport of food factors in caco-2 cell monolayers.
PubMed: Effects of the addition of amino acids and peptides on lipid oxidation in a powdery model system.
PubMed: Interaction of soluble peptides and proteins from skeletal muscle with volatile compounds in model systems as affected by curing agents.
PubMed: Effect of lectins on the transport of food ingredients in Caco-2 cell cultures.
PubMed: Effect of central administration of carnosine and its constituents on behaviors in chicks.
PubMed: Interactions of soluble peptides and proteins from skeletal muscle on the release of volatile compounds.
PubMed: Antioxidant peptides with Angiotensin converting enzyme inhibitory activities and applications for Angiotensin converting enzyme purification.
PubMed: Analysis of products of animal origin in feeds by determination of carnosine and related dipeptides by high-performance liquid chromatography.
PubMed: Concentrations and antioxidative activity of anserine and carnosine in poultry meat extracts treated with demineralization and papain.
PubMed: A re-evaluation of the antioxidant activity of purified carnosine.
PubMed: Influence of dietary β-alanine and histidine on the oxidative stability of pork.
PubMed: Antioxidants in food and chronic degenerative diseases.
PubMed: Endogenous skeletal muscle antioxidants.
PubMed: Human urinary excretion of L-histidine-related compounds after ingestion of several meats and fish muscle.
PubMed: Interorgan transport and catabolism of carnosine and anserine in rainbow trout.
PubMed: Anserine and free amino acid contents in the egg and fry stages of developing rainbow trout (Oncorhynchus mykiss).
PubMed: Highly site-specific oxygenation of 1-methylhistidine and its analogue with a copper (II)/ascorbate-dependent redox system.
PubMed: The influence of fibre-type composition and associated biochemical characteristics on the acid buffering capacities of several beef muscles.
PubMed: Use of histidine dipeptides and myoglobin to monitor adulteration of cooked beef with meat from other species.
PubMed: Ophidine (beta-alanyl-L-3-methylhistidine, "balenine') and other histidine dipeptides in pig muscles and tinned hams.
PubMed: Investigations on the origin of two radiation-induced compounds in irradiated meat.
PubMed: [Effect of anserine on formation and extinction of motor-alimentary conditioned reflexes].
PubMed: The detection of chicken meat in meat products by means of the anserine/carnosine ratio.
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