L-Carnosine

Iupac Name：(2S)-2-(3-aminopropanoylamino)-3-(1H-imidazol-5-yl)propanoic acid

Molecular Weight：226.236

Modify Date.: 2023-03-27 07:56

Introduction: Carnosine is a dipeptide comprising beta-alanine and histidine. It is found in muscular and other tissues. It has strong oxidant property as it can scavenge both reactive oxygen species (ROS) and reactive nitrogen species (RNS). Carnosine acts as a cytosolic buffering agent and as a regulator of macrophage function.1 Attributing to its ability to form complexes with transition metals, it is used to regulate the content of transition metal ions in biological fluids and tissues.Carnosine can prevent aging and can be used to prevent or treat complications of diabetes such as nerve damage, eye disorders (cataracts), and kidney problems.2 Potential therapeutic actions of carnosine include antihypertensive effects, immunomodulation, would healing, and antitumor/chemopreventive effects. The chelate compound of zinc ion and carnosine has been used in Japan for gastritis, gastric ulcers, and dyspepsia symptoms.3 View more+

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1. Names and Identifiers

1.1 Name: L-Carnosine
1.2 Synonyms: (2S)-2-(3-Aminopropanamido)-3-(1H-imidazol-4-yl)propanoic acid (2S)-2-(3-aminopropanamido)-3-(1H-imidazol-5-yl)propanoic acid (2S)-2-(3-Aminopropanoylamino)-3-(1H-imidazol-5-yl)propanoic acid (2S)-2-(3-aminopropanoylamino)-3-(3H-imidazol-4-yl)propanoic acid (E)-N-(3-Amino-1-hydroxypropylidene)-L-histidine .beta.-Alanyl-L-histidine 2-(3-aminopropanoylamino)-3-(3H-imidazol-4-yl)propanoic acid 2: PN: WO2009033754 PAGE: 98 claimed protein B-ALANYL-L-HISTIDINE BETA-A-H beta-Alanyl-L-histidine Carnosin Carnosine, (D-His)-Isomer D002336 Dragosine EINECS 206-169-9 H-BETA-ALA-HIS-OH Histidine, β-(2-amino-1-oxopropyl)- H-Β-Ala-His-OH Ignotin Ignotine Karnozin karnozzn L-BETA-ALANINE HISTIDINE L-Carnosinc L-Carnosine Acetate L-Histidine, N-(3-amino-1-hydroxypropylidene)-, (E)- L-Histidine, N-.beta.-alanyl- L-Histidine, N-Β-alanyl- L-Histidine, β-alanyl- L-IGNOTINE MFCD00005207 N-(b-Alanyl)-L-histidine N-(β-Alanyl)-L-histidine N-2-M Nalpha-(beta-alanyl)-L-histidine N-B-ALANYL-L-HISTIDINE NSC 524045 N-Β-Alanyl-L-histidin N-Β-Alanyl-L-histidine Sevitin β Alanylhistidine β-(2-Aminopropanoyl)histidine β-Alanyl-L-histidine

1.3 CAS No.: 305-84-0

1.4 CID: 439224

1.5 EINECS(EC#): 206-169-9

1.6 Molecular Formula: C9H14N4O3 (isomer)

1.7 Inchi: InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1

1.8 InChkey: CQOVPNPJLQNMDC-ZETCQYMHSA-N

1.9 Canonical Smiles: C1=C(NC=N1)CC(C(=O)O)NC(=O)CCN

1.10 Isomers Smiles: C1=C(NC=N1)C[C@@H](C(=O)O)NC(=O)CCN

2. Properties

2.1 Density: 1.375

2.1 Melting point: 253℃

2.1 Boiling point: 656.2 oC at 760 mmHg

2.1 Refractive index: 21 ° (C=2, H2O)

2.1 Flash Point: 350.7 oC

2.1 Precise Quality: 226.10700

2.1 PSA: 121.10000

2.1 logP: -0.03840

2.1 Appearance: crystalline

2.2 Storage: Store at -20°C.

2.3 Chemical Properties: Crystalline

2.4 Color/Form: Powder

2.5 Physical: Solid

2.6 pKa: 2.62(at 25℃)

2.7 Water Solubility: Very soluble

2.8 Stability: Stable, but may be heat sensitive - store cold. Incompatible with strong oxidizing agents.

2.9 StorageTemp: -20°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A dipeptide that is the N-(beta-alanyl) derivative of L-histidine.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 96 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 95 of 96 companies. For more detailed information, please visit ECHA C&L website

Of the 1 notification(s) provided by 1 of 96 companies with hazard statement code(s):

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362

3.3 Usage: antioxidant, antisenescense, antineoplastic

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: R20/21/22

4.1 Safety Statements: S24/25

4.1 RIDADR: NONH for all modes of transport

4.1 Safety Profile: Mildly toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

4.2 WGK Germany: 2

4.2 RTECS: MS3080000

4.2 Report: Reported in EPA TSCA Inventory.

4.3 Safety: Mildly toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NO_x.
The Hazard Codes of CARNOSINE(305-84-0): ? Xn
The Risk Statements information of Carnosine (305-84-0): 20/21/22-36/37/38
20/21/22:? Harmful by inhalation, in contact with skin and if swallowed?
36/37/38:? Irritating to eyes, respiratory system and skin?
The Safety Statements information of Carnosine (305-84-0): 24/25-36-26
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
36:? Wear suitable protective clothing?
24/25:? Avoid contact with skin and eyes?
WGK Germany: 2
RTECS: MS3080000
F: 3-10

4.4 Specification: Chemical Stability: Stable under normal temperatures and pressures.
Conditions to Avoid: Incompatible materials.
Incompatibilities with Other Materials Strong oxidizing agents.
Hazardous Decomposition Products Carbon monoxide, carbon dioxide, nitrogen oxides (NOx) and ammonia (NH3).
Hazardous Polymerization Will not occur.
?

4.5 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	9087mg/kg (9087mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	United States Patent Document. Vol. #4446149,
mouse	LD50	oral	> 14930mg/kg (14930mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	United States Patent Document. Vol. #4446149,

LD50/LC50: RTECS:
CAS# 305-84-0: Oral, mouse: LD50 = >14930 mg/kg;
Carcinogenicity: L-Carnosine - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.
Other: The toxicological properties have not been fully investigated. See actual entry in RTECS for complete information.
?

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Other Information

7.0 Merck: 14,1850

7.1 BRN: 87671

7.2 Description: Carnosine is a dipeptide comprising beta-alanine and histidine. It is found in muscular and other tissues. It has strong oxidant property as it can scavenge both reactive oxygen species (ROS) and reactive nitrogen species (RNS). Carnosine acts as a cytosolic buffering agent and as a regulator of macrophage function.¹ Attributing to its ability to form complexes with transition metals, it is used to regulate the content of transition metal ions in biological fluids and tissues.
Carnosine can prevent aging and can be used to prevent or treat complications of diabetes such as nerve damage, eye disorders (cataracts), and kidney problems.² Potential therapeutic actions of carnosine include antihypertensive effects, immunomodulation, would healing, and antitumor/chemopreventive effects. The chelate compound of zinc ion and carnosine has been used in Japan for gastritis, gastric ulcers, and dyspepsia symptoms.³

7.3 Reference

P. J. Quinn, A. A. Boldyrev, V. E. Formazuyk, Carnosine: Its properties, functions and potential therapeutic applications, Molecular Aspects of Medicine, 1992, vol. 13, pp. 379-444
https://www.webmd.com/vitamins/ai/ingredientmono-1038/carnosine
G. M. Halpern, Zinc-Carnosine: Nature’s Safe and Effective Remedy for Ulcers, 2005, ISBN-10 0757002749

7.4 Description: L-Carnosine is a dipeptide composed of β-alanine and L-histidine that has been found in rat olfactory bulb, skeletal muscle, brain, kidney, and spleen tissues, as well as human skeletal muscle, and has diverse biological activities. It is a metal chelator that forms complexes with copper, cobalt, nickel, cadmium, or zinc. Dietary administration of L-carnosine (60 mg/kg per day) reduces plasma levels of advanced glycation end products (AGEs) in diabetic rats. It reduces brain edema, blood-brain barrier disruption, microglial activation, and neuronal apoptosis in a rat model of intracerebral hemorrhage when administered at a dose of 1,000 mg/kg. L-Carnosine (250, 500, and 1,000 mg/kg, i.p.) reduces hepatic protein carbonylation and necrosis in a rat model of cirrhosis induced by bile duct ligation. It also reduces lung myeloperoxidase (MPO) activity, production of reactive oxygen species (ROS), and TNF-α and IL-6 levels, as well as alveolar hemorrhage, interstitial edema, and pulmonary leukocyte infiltration in a mouse model of LPS-induced lung injury.

7.5 Chemical Properties: Crystalline

7.6 Uses: antioxidant, antisenescense, antineoplastic

7.7 Uses: L-Carnosine is a naturally-occurring histidine-containing compound and the biological role of this dipeptide is to act as cytosolic buffering agents. Other roles ascribed to L-Carnosine include action s as neurotransmitters, modulation of enzymic activities and chelation of heavy metals.

7.8 Uses: carnosine is an anti-oxidant that works to prevent cellular damage because of free radical activity. Studies indicate an ability to boost the immunological functions. Carnosine is a naturally occurring amino acid. In cosmetics, it has anti-aging and skin-conditioning applications.

7.9 Definition: ChEBI: A dipeptide that is the N-(beta-alanyl) derivative of L-histidine.

7.10 benefits: L-Carnosine is a strong anti-glycosylation, free radical scavenging,anti-oxidant,anti-aging, anti-pollution.Brightenand repairthe skin. white powder.Its recommended dosage is 0.05~2%.

7.11 Synthesis Reference(s): The Journal of Organic Chemistry, 48, p. 392, 1983 DOI: 10.1021/jo00151a026

7.12 Biochem/physiol Actions: L-Carosine is a dipeptide found at millimolar concentration in brain, muscle and the lens of the eye. In model systems it is a potent antioxidant that scavenges oxygen free radicals and transition metal ions. It blocks protein-protein and protein-DNA cross-links induced by hypochlorite anions and toxic aldehydes such as acetaldehyde, formaldehyde, and malondialdehyde, the primary product of lipid peroxidation. It also inhibits nonenzymatic protein glycation induced by aldose and ketose reducing sugars and inhibits the formation of toxic advanced glycation end products (AGE). These activities make it of interest in studies of aging, atherosclerosis, Alzheimer′s disease, and the secondary effects of diabetes.

7.13 Safety Profile: Mildly toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.

7.14 Purification Methods: Likely impurities are histidine and β-alanine. Crystallise L-carnosine from water by adding EtOH in excess. Recrystallise it from aqueous EtOH by slow addition of EtOH to a strong aqueous solution of the dipeptide. Its solubility in H2O is 33.3% at 25o. [Vinick & Jung J Org Chem 48 392 1983, Turner J Am Chem Soc 75 2388 1953, Sifford & du Vigneaud J Biol Chem 108 753 1935, Beilstein 25 H 516, 25 I 717, 25 II 408.]

8. Computational chemical data

Molecular Weight: 226.236g/mol
Molecular Formula: C₉H₁₄N₄O₃
Compound Is Canonicalized: True
XLogP3-AA: -4
Exact Mass: 226.10659032
Monoisotopic Mass: 226.10659032
Complexity: 259
Rotatable Bond Count: 6
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 121
Heavy Atom Count: 16
Defined Atom Stereocenter Count: 1
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBzsAAAAAAAAAAAAAAAAAAAAWAAAAAAAAAAAAAAAAABgAAAHgAQCAAACCjBlgQtmBbJkgCoARX3fAAAgC2xEqABUYG4cAiCaBpA2SGUQAAMlgLQQCC8EQIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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