L-cystine zwitterion
Basic information
- CAS
56-89-3- Standard SMILES
[NH3+][C@@H](CSSC[C@H]([NH3+])C(=O)[O-])C(=O)[O-]- InChIKey
LEVWYRKDKASIDU-IMJSIDKUSA-N- Molecular formula
- C6H12N2O4S2
- Average molar mass
- 240.3 g/mol
- Monoisotopic mass
- 240.02384922
Overview
L-cystine zwitterion is a cystine zwitterion. It is an enantiomer of a D-cystine zwitterion. It is a tautomer of a L-cystine.
Names & identifiers
- Preferred name
- L-cystine zwitterion
- IUPAC
- (2R)-2-azaniumyl-3-[[(2R)-2-azaniumyl-2-carboxylatoethyl]disulfanyl]propanoate
- English name
- L-Cystine
- Molecular formula
- C6H12N2O4S2
- Molecular weight
- 240.3
Names & synonyms
24645-67-8L-cystine zwitterionL-(-)-3,3'-Dithiobis(2-aminopropanoic acid)CHEBI:35491(2R,2'R)-3,3'-dithiobis(2-ammoniopropanoate)(2R,2'R)-3,3'-disulfanediylbis(2-ammoniopropanoate)(H-CYS-OH)2l-cystin3,3’-dithiobis(2-aminopropanoicacid)(2R,2'R)-3,3'-Disulfanediylbis(2-aminopropanoic acid)(2R,2'R)-3,3'-disulfanediylbis(2-aminopropanoic acid)(CYS)2
Show more names
-Cystine1-cystineCystine CRSCystine acid
Database identifiers
- CAS
56-89-3- PubChem CID
- 6992103
- ChEBI
CHEBI:35491
Properties
Computed structural properties
- XLogP
- -5
- Topological polar surface area
- 186 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 5
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 181
Experimental & physicochemical properties
LogP-5.08
Solubility0.19 mg/mL
Melting Point260.5 °C
Physical DescriptionSolid
Dissociation Constants1
Physicochemical properties
- Melting point
- 240 °C · >240 °C (dec.) (lit.)
- alpha
- -224 · -224 º(c=2 in 1M HCl)
- Boiling point
- 468.2 · 468.2±45.0 °C(Predicted)
- Density
- 1.68 · 1.68
- bulk density
- 300 kg/m3 · 300kg/m3
- FLAVIS Number
- 17.006 · 17.006 | L-Cystine
- refractive index
- -222.5 ° · -222.5 ° (C=1, 1mol/L HCl)
- storage temp.
- 2 · 2-8°C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- HA2690000
- ridadr
- 2811
- hs_code
- 29309014
- risk_code
- 36/37/38-22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- hazard_note
- Irritant
- safety_code
- 26-36-24/25
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P271-P280
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
Applications
DescriptionL-cystine (formula: (SCH2CH(NH2) CO2H)2), the L-form of cystine) is a covalently linked dimeric nonessential amino acid formed through the oxidation of cysteine. It is contained in many foods including eggs, meat, dairy products, and whole grains as well as in skin and hairs. L-cystine and L-methionine are the amino-acids required for wound healing and formation of epithelial tissue. It is able to stimulate the hematopoietic system and promote the formation of white and red blood cells. It can also be used as a component of parental and enteral nutrition. It can also be used for the treatment of dermatitis and protection of liver function. L-cystine is manufactured through the enzymatic conversion from DL-amino thiazoline carboxylic acid.
Related reactions
0 records
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Compound notes
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