CAS 305-84-0 Carnosine (HCID 439224)

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Basic information

CAS: 305-84-0
Standard SMILES: NCCC(=O)N[C@@H](Cc1cnc[nH]1)C(=O)O
InChIKey: CQOVPNPJLQNMDC-ZETCQYMHSA-N
Molecular formula: C9H14N4O3
Average molar mass: 226.23 g/mol
Monoisotopic mass: 226.10659031

Overview

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

Names & identifiers

Preferred name: Carnosine
IUPAC: (2S)-2-(3-aminopropanoylamino)-3-(1H-imidazol-5-yl)propanoic acid
English name: L-Carnosine
Molecular formula: C9H14N4O3
Molecular weight: 226.23

Names & synonyms

L-CarnosineCarnosine305-84-0beta-Alanyl-L-histidineIgnotineKarnozinKarnozznL-Histidine, beta-alanyl-(2S)-2-(3-aminopropanamido)-3-(1H-imidazol-4-yl)propanoic acidNalpha-(beta-alanyl)-L-histidineL-HISTIDINE, N-beta-ALANYL-8HO6PVN24W

Show more names

CarnosinDragosineβ-Alanyl-L-histidineN-B-ALANYL-L-HISTIDINEβ-Ala-HisBETA-ALA-HISβ-Ala-His-OHH-β-Ala-His-OH

CHEBI:15727N-beta-alanyl-L-histidineNSC-524045(2S)-2-(3-aminopropanoylamino)-3-(1H-imidazol-5-yl)propanoic acidDTXSID80879594(2S)-2-(3-aminopropanamido)-3-(1H-imidazol-5-yl)propanoic acidL Carnosinebeta Alanylhistidine

Database identifiers

CAS: 305-84-0
PubChem CID: 439224
DTXSID: DTXSID80879594
ChEMBL: CHEMBL242948

Properties

Computed structural properties

XLogP: -4
Topological polar surface area: 121 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 5
Rotatable bonds: 6
Heavy atoms: 16
Formal charge: 0
Complexity: 259

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Amino Acids and Derivatives

DrugsPharmaceuticals -> Listed in ZINC15

Solubility384 mg/mL

Melting Point253 - 256 °C

Physical Description · 2 items

Solid; [Merck Index] White crystalline solid; [Sigma-Aldrich MSDS]

Solid

Collision Cross Section · 5 items

149.72 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

154.93 Å² [M-H]- [CCS Type: DT; Method: stepped-field]

145.38 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

152.1 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

154.5 Å² [M+Na]+

Physicochemical properties

Melting point: 253 °C · 253 °C (dec.) (lit.)
alpha

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 99% (104 of 105) of all reports.

Not Classified

Aggregated GHS information provided per 105 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationStatus: Active Update: 14-06-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/24638

Hazards Summary · 1 item

Causes somnolence, muscle contraction, and respiratory depression in oral and intraperitoneal lethal-dose studies of mice; [RTECS] Not considered hazardous by GHS classification; Reproductive toxicity observed in rats by intraperitoneal exposure; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesNot Classified

Safety data

F: 3-10
wgk: 2
tsca: TSCA listed
rtecs: MS3080000
hs_code: 29332900
Toxicity: LD50 oral in mouse: > 14930mg/kg
risk_code: 20/21/22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 24/25-36-26
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319

Chemistry & industry

Pharmacology

Tissue LocationsBrain

Cellular LocationsCytoplasm

Metabolite Pathwaysbeta-Alanine metabolism

Uses & manufacturing

UsesDipeptide present in skeletal muscle, brain, heart, and kidney; A water soluble antioxidant that functions as a free-radicle scavenger; [Merck Index]

Household ProductsInformation on 15 consumer products that contain Carnosine in the following categories is provided:

General Manufacturing InformationL-Histidine, .beta.-alanyl-: ACTIVE

Applications · 4 items

DescriptionL-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.

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