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Basic information
- CAS
56-89-3- Standard SMILES
N[C@@H](CSSC[C@H](N)C(=O)O)C(=O)O- InChIKey
LEVWYRKDKASIDU-IMJSIDKUSA-N- Molecular formula
- C6H12N2O4S2
- Average molar mass
- 240.3 g/mol
- Monoisotopic mass
- 240.02384886
Overview
L-cystine is the L-enantiomer of the sulfur-containing amino acid cystine. It has a role as an EC 1.2.1.11 (aspartate-semialdehyde dehydrogenase) inhibitor, a flour treatment agent, a mouse metabolite, a Saccharomyces cerevisiae metabolite and a human metabolite. It is a cystine, a non-proteinogenic L-alpha-amino acid and a L-cysteine derivative. It is a conjugate acid of a L-cystine anion. It is an enantiomer of a D-cystine. It is a tautomer of a L-cystine zwitterion.
Names & identifiers
- Preferred name
- (-)-Cystine
- IUPAC
- (2R)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]disulfanyl]propanoic acid
Names & synonyms
L-cystine56-89-3cystineL-Dicysteinebeta,beta'-DithiodialanineL-Cysteine disulfide1-CystineCystine, L-DicysteineCystine (L)-Cystine acidCysteine disulfide
Show more names
Cystin(-)-CystineAlanine, 3,3'-dithiodi-Alanine, 3,3'-dithiobis-beta,beta'-Dithioalanine, L-L-Alanine, 3,3'-dithiobis-DTXSID2046418L-alpha-Diamino-beta-dithiolactic acid
Database identifiers
- CAS
56-89-3、923-32-0- PubChem CID
- 67678
- DTXSID
DTXSID2046418- ChEMBL
CHEMBL590540- ChEBI
CHEBI:16283- UNII
- 48TCX9A1VT
- EC Number
- 200-296-3
- Nikkaji
- J9.172C
Properties
Computed structural propertiesFilling in
- XLogP
- -6.3
- Topological polar surface area
- 177 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 7
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 192
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics
Cosmetic ingredients (Cystine) -> CIR (Cosmetic Ingredient Review)
Antistatic; Hair conditioning
LogP-5.08
Food AdditivesDOUGH STRENGTHENER, FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT, NUTRIENT SUPPLEMENT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility0.19 mg/mL
Melting Point260.5 °C
Physical Description
Solid; [Merck Index] White powder; [Sigma-Aldrich MSDS]
Solid
Dissociation Constants1
Collision Cross Section
145 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
148.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
147.3 Ų [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
149.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
150.08 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
151.5 Ų [M+Na]+
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 97.8% (182 of 186) of all reports.
Not Classified
Aggregated GHS information provided per 186 reports by companies from 5 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: L-Cystine
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 13-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5911
L-cystine: Does not have an individual approval but may be used under an appropriate group standard
Cystine: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - L-Cystine: Environment tier I assessment
Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesNot Classified
Toxicology
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Chemistry & industry
Pharmacology
Pharmacodynamics
L-Cystine is a covalently linked dimeric nonessential amino acid formed by the oxidation of cysteine. Two molecules of cysteine are joined together by a disulfide bridge to form cystine. Cystine is a chemical substance which naturally occurs as a deposit in the urine, and can form a calculus (hard mineral formation) when deposited in the kidney. The compound produced when two cysteine molecules linked by a disulfide (S-S) bond. Cystine is required for proper vitamin B6 utilization and is also helpful in the healing of burns and wounds, breaking down mucus deposits in illnesses such as bronchitis as well as cystic fibrosis. Cysteine also assists in the supply of insulin to the pancreas, which is needed for the assimilation of sugars and starches. It increases the level of glutathione in the lungs, liver, kidneys and bone marrow, and this may have an anti-aging effect on the body by reducing age-spots etc.
Mechanism of ActionCertain conditions, e.g. an acetaminophen overdose, deplete hepatic glutathione and subject the tissues to oxidative stress resulting in loss of cellular integrity. L-Cystine serves as a major precursor for synthesis of glutathione.
Tissue LocationsAll Tissues
Cellular LocationsCytoplasm
Uses & manufacturing
Uses
CIR ingredient: Cystine
A non-essential amino acid (a dimerization of two cysteine molecules); [Merck Index] Used as a flavoring agent, dough strengthener, and nutritional supplement for foods; [FDA]
Use (kg; approx.) in Germany (2009): >500
Use ClassificationCosmetics -> Antistatic; Hair conditioning
General Manufacturing InformationL-Cystine: ACTIVE
Related reactions
11 records
Compound notes
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