(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid

• ChemBase ID: 24
• Molecular Formular: C6H12N2O4S2
• Molecular Mass: 240.30048
• Monoisotopic Mass: 240.02384887
• SMILES: S(SC[C@H](N)C(=O)O)C[C@H](N)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)CSSC[C@@H](C(=O)O)N
• InChI: InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1
• InChIKey: LEVWYRKDKASIDU-IMJSIDKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid
• IUPAC Traditional name: L-cystine
• Synonyms: L-Cystine; Dicysteine; 3,3'-Dithiobis (2-aminopropanoic acid); Cystein disulfide; 3,3'-Dithiobis(2-aminopropanoic Acid); Bis(β-amino-β-carboxyethyl) Disulfide; Cystine Αcid; 3,3'-Dithiobis-L-Alanine; L-Cysteine Disulfide; L-Cystin; NSC 13203; Oxidized L-cysteine; [R-(R*,R*)]-3,3'-Dithiobis[2-aminopropanoic Acid]; l-Cystine; β,β'-Diamino-β,β'-dicarboxydiethyl Disulfide; β,β'-Dithiodialanine; (-)-Cystine; Cysteine disulfide; Cystine acid; L-alpha-Diamino-beta-dithiolactic acid; L-Dicysteine; L-Cystine; (R,R)-3,3′-Dithiobis(2-aminopropionicacid); H-(Cys)2-OH; (-)-3,3'-Dithiobis(2-aminopropionic acid); (R,R)-3,3′-二硫双(2-氨基丙酸); L-胱氨酸

Database IDs

• CAS Number: 56-89-3
• EC Number: 200-296-3
• MDL Number: MFCD00064228
• Beilstein Number: 1728094
• Merck Index: 142782
• PubChem SID: 24892581; 24892973; 46506670; 24858224; 160963487; 24893101
• PubChem CID: 67678
• E Number: E921

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.5564231
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -5.897319
• LogD (pH = 7.4): -5.9155164
• Log P: -5.897688
• Molar Refractivity: 54.8718 cm^3
• Polarizability: 22.177225 Å^3
• Polar Surface Area: 126.64 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.16
• LOG S: -1.16
• Solubility (Water): 1.68e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble0.2 M at 20 °C, clear, colorless; 1 M HCl: soluble100 mg/mL; Soluble
• Apperance: crystalline; powder
• Melting Point: >240 °C (dec.)(lit.); >240°C dec.; 260 - 261°C
• Density: 1.68
• Optical Rotation: [α]20/D -217.8°, c = 1 in 1 M HCl; [α]20/D -219±5°, c = 1% in 1 M HCl; -219 (c=1 in 1N HCl)
• Hydrophobicity(logP): -5.5

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: HA2690000
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (TLC); ≥98.5%; ≥99.0%; ≥99.5% (T); 97%; 98.5-101.0%; 99%
• Grade: certified reference material; EP; SAJ special grade; TraceCERT®
• Suitability: meets EP testing specifications; suitable for cell culture; suitable for manufacturing use
• Ignition Residue: ≤0.05% (as SO4)
• Impurities: ≤0.3% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test
• Cation Traces: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤10 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤500 mg/kg; sulfate (SO42-): ≤100 mg/kg
• Biological Source: from non-animal source
• Loss on Drying: ≤0.05% loss on drying, 20 °C (HV)
• Quality Level: GMP-COMPENDIA
• Product Line: BioUltra
• abs.: absorption0.2M/316 nm, 1 M HCl cut-off
• Linear Formula: [-SCH2CH(NH2)CO2H]2

DETAILS

MP Biomedicals - 05202117

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02194649

Cell Culture Reagent Purity: 99% White crystals

MP Biomedicals - 02101454

Purity: 99%
White crystals

DrugBank - DB00138

• Drug Groups: approved; nutraceutical
• Description: 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. [PubChem]
• Indication: It has been claimed that L-cysteine has anti-inflammatory properties, that it can protect against various toxins, and that it might be helpful in osteoarthritis and rheumatoid arthritis. More research will have to be done before L-cysteine can be indicated for any of these conditions. Research to date has mostly been in animal models.
• Pharmacology: 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.
• Toxicity: With typical doses of 1 to 1.5 grams daily, the most commonly reported side effects have been gastrointestinal, such as nausea. There are rare reports of cystine renal stone formation, Single injections of L-cysteine (0.6-1.5 g/kg) into 4-day-old pups resulted in massive damage to cortical neurons, permanent retinal dystrophy, atrophy of the brain and hyperactivity.
• Affected Organisms: Humans and other mammals
• External Links: PDRhealth

Sigma Aldrich - C8755

包装
100, 500 g in poly bottle

Sigma Aldrich - C7602

包装
10 mg in autosmp vl
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7602.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7602.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - C5735

Packaging
Manufactured and Packaged under cGMP

Sigma Aldrich - 30199

Other Notes
Certain malignant cell lines require cystine or cysteine in the culture medium1; Growth requirement of various microorganisms2

Sigma Aldrich - C122009

Packaging
2.5 g in glass bottle

Sigma Aldrich - 49603

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - C997860

L-Cystine is a non-essential amino acid for human development. L-Cystine is formed by the dimerization of two cysteines through the sulfur.

REFERENCES

• Fahey, R.C., et al.: J. Mol. Evol., 10, 155 (1977)
• Kao, P., et al.: J. Biol.Chem., 261, 8085 ( 1986), Nicke, A., et al.: J. Biol. Chem., 278, 3137 (1977)