ChemicalBook > CAS DataBase List > L-Carnosine

L-Carnosine

Product Name
L-Carnosine
CAS No.
305-84-0
Chemical Name
L-Carnosine
Synonyms
CARNOSINE;N-B-ALANYL-L-HISTIDINE;Carnosin;Dragosine;β-Ala-His;H-β-Ala-His-OH;β-Alanyl-L-histidine;BETA-ALANYL-L-HISTIDINE;N-BETA-ALANYL-L-HISTIDINE;n-2-m
CBNumber
CB0433763
Molecular Formula
C9H14N4O3
Formula Weight
226.23
MOL File
305-84-0.mol
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L-Carnosine Property

Melting point:
253 °C (dec.) (lit.)
alpha 
20.9 º (c=1.5, H2O)
Boiling point:
367.84°C (rough estimate)
Density 
1.2673 (rough estimate)
vapor pressure 
0Pa at 25℃
refractive index 
21 ° (C=2, H2O)
storage temp. 
-20°C
solubility 
DMSO (Very Slightly), Water (Slightly)
form 
crystalline
pka
2.62(at 25℃)
color 
White
Odor
at 100.00?%. odorless
optical activity
+24.120
Water Solubility 
almost transparency
Merck 
14,1850
BRN 
87671
Stability:
Stable, but may be heat sensitive - store cold. Incompatible with strong oxidizing agents.
InChIKey
CQOVPNPJLQNMDC-ZETCQYMHSA-N
LogP
-3.8 at 22℃
CAS DataBase Reference
305-84-0(CAS DataBase Reference)
EPA Substance Registry System
L-Histidine, .beta.-alanyl- (305-84-0)
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Safety

Hazard Codes 
Xn
Risk Statements 
20/21/22-36/37/38
Safety Statements 
24/25-36-26
WGK Germany 
2
RTECS 
MS3080000
F 
3-10
TSCA 
Yes
HS Code 
29332900
Toxicity
LD50 oral in mouse: > 14930mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C9625
Product name
L-Carnosine
Purity
~99%, crystalline
Packaging
10mg
Price
$15.84
Updated
2024/03/01
Sigma-Aldrich
Product number
C9625
Product name
L-Carnosine
Purity
~99%, crystalline
Packaging
5g
Price
$134
Updated
2024/03/01
TCI Chemical
Product number
A0222
Product name
beta-Alanyl-L-histidine
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$19
Updated
2024/03/01
TCI Chemical
Product number
A0222
Product name
beta-Alanyl-L-histidine
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$55
Updated
2024/03/01
Alfa Aesar
Product number
H65668
Product name
beta-Alanyl-L-histidine, 95%
Packaging
5g
Price
$49.65
Updated
2024/03/01
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L-Carnosine Chemical Properties,Usage,Production

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.

Chemical Properties

white to off-white crystalline.

History

Carnosine, a dipeptide composed of beta-alanine and L-histidine, was first identified in beef extracts by Russian chemists Gulewitch and Amiradzibi in 1900.

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. Studies indicate an ability to boost the immunological functions. In cosmetics, it has anti-aging and skin-conditioning applications.

Definition

ChEBI: Carnosine is a dipeptide that is the N-(beta-alanyl) derivative of L-histidine. It has a role as an anticonvulsant, an antioxidant, an antineoplastic agent, a human metabolite, a Daphnia magna metabolite, a mouse metabolite, a neuroprotective agent and a geroprotector. It is a conjugate acid of a carnosinate. It is a tautomer of a carnosine zwitterion.

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%.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 392, 1983 DOI: 10.1021/jo00151a026

General 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

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.

Side effects

L-carnosine is generally considered safe when taken by mouth for short periods of time or when used by adults on the skin. However, there can be rare side effects, including rash, itchiness, dry mouth, changes in appetite, feelings of tiredness or vivid dreams. Rare but severe possible zinc carnosine side effects include decreased white blood cells, disorder of the digestive system and sideroblastic anemia. Less severe side effects may include stomach cramps, indigestion and nausea.

Safety Profile

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

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.]

References

1. 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 DOI:10.1016/0098-2997(92)90006-L
2. https://www.webmd.com/vitamins/ai/ingredientmono-1038/carnosine
3. G. M. Halpern, Zinc-Carnosine: Nature’s Safe and Effective Remedy for Ulcers, 2005, ISBN-10 0757002749
4. l-Carnosine, a Substrate of Carnosinase-1, Influences Glucose Metabolism DOI:10.2337/db07-0177
5. L-carnosine (beta-alanyl-L-histidine) and carcinine (beta-alanylhistamine) act as natural antioxidants with hydroxyl-radical-scavenging and lipid-peroxidase activities. DOI:10.1042/BJ3040509
6. Boldyrev, A.A., Aldini, G., and Derave, W. Physiology and pathophysiology of carnosine. Physiol. Rev. 93(4), 1803-1845 (2013). DOI:10.1152/physrev.00039.2012
7. Ghodsi, R., and Kheirouri, S. Carnosine and advanced glycation end products: A systematic review. Amino Acids 50(9), 1177-1186 (2018). DOI:10.1007/s00726-018-2592-9
8. Tanaka, K.I., Sugizaki, T., Kanada, Y., et al. Preventive effects of carnosine on lipopolysaccharide-induced lung injury. Sci. Rep. 7:42813, (2017). DOI:10.1038/srep42813

L-Carnosine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from L-Carnosine manufacturers

Sichuan HongRi Pharma-Tech Co.,Ltd
Product
L-Carnosine 305-84-0
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1T+
Release date
2024-02-23
Sinoway Industrial co., ltd.
Product
L-Carnosine 305-84-0
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99% up by HPLC
Supply Ability
20 tons
Release date
2024-06-27
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
L-Carnosine 305-84-0
Price
US $100.00-80.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000kg/ week
Release date
2024-04-23

305-84-0, L-CarnosineRelated Search:

β-Alanine L-Alanyl-L-Glutamine EC 2.3.2.2 L-Malic acid L-Tyrosine L-Aspartic acid Methyl (S)-(-)-lactate L-Valine L-carnitine L-Lysine L-Glutamine H-LEU-LEU-OH L-Pyroglutamic acid L(+)-Arginine CARNOSINE, L-(P),CARNOSINE, L-(RG) n-acetyl carnosine,N-ACETYL-L-CARNOSINE,N-Aceyl-L-Carnosine L-ANSERINE NITRATE ZINC CARNOSINE,zinc l-carnosine complex,Zinc L-Carnosine,Zn Carnosine,carnosine, zinc- Carnosine

  • N-B-ALANYL-L-HISTIDINE
  • H-BETA-ALA-HIS-OH
  • L-IGNOTINE
  • L-BETA-ALANINE HISTIDINE
  • L-CARNOSINE
  • B-ALANYL-L-HISTIDINE
  • BETA-A-H
  • BETA-ALANYL-L-HISTIDINE
  • BETA-ALA-L-HIS
  • BETA-ALA-HIS
  • CARNOSINE
  • CARNOSINE, L-
  • N-BETA-ALANYL-L-HISTIDINE
  • β-Alanyl-L-histidine
  • Beta-Alanyl-L-Hystidine
  • L-CARNOSINE CRYSTALLINE
  • L-Carnosine(H-b-Ala-His-Oh)
  • N-β-Alanyl-L-histidine
  • (2S)-2-(3-aminopropanoylamino)-3-(3H-imidazol-4-yl)propanoic acid
  • L-HISTIDINE,N-BETA-ALANYL
  • Carnosin
  • H-SS-ALA-HIS-OH (L-CARNOSINE)
  • L-B-ALANINE HISTIDINE
  • L-CARNITINEOROTIC
  • H-SS-ALA-HIS-OH
  • H-b-Ala-His-OH
  • Karnozin
  • β-Ala-L-His-OH
  • L-Carnosine,98%
  • L-Carnosine L-Ignotine
  • H-Beta-Ala-His-OH(L-Carnosine)
  • 2,5-diamino-3-(1H-imidazol-5-yl)-4-oxohexanoic acid
  • beta-Alanyl-histidine
  • ignotine
  • karnozzn
  • n-2-m
  • Nalpha-(beta-alanyl)-L-histidine
  • n-beta-alanyl-l-histidin
  • L-Carnosine Vetec(TM) reagent grade, 98%
  • L-Histidine,beta-alanyl-
  • L-Carnosine (beta-Alanyl-L-histidine)
  • β-Ala-His-OH
  • L-Carnosine,N-beta-Alanyl-L-histidine
  • Polaprezinc Impurity 6
  • Dragosine
  • (2S)-2-(3-Aminopropanamido)-3-(4H-imidazol-4-yl)propanoicacid
  • Carnosin、L-Carnosine
  • L-Carnosine / Carnosine
  • L-Carnosine Reference Material
  • beta L
  • β-Alanyl-L-histidine&gt
  • L-Histidine, β-alanyl-
  • L-Carnosine USP/EP/BP
  • H-β-Ala-His-OH
  • carnosine/l-carnosine
  • β-Ala-His
  • β-Alanyl-L-histidine
  • (2S)-2-(3-aminopropanoylamino)-3-(1H-imidazol-5-yl)propanoic acid