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Merck

30200

L-Cystine

≥99.7% (TLC)

Synonym(s):

(R,R)-3,3′-Dithiobis(2-aminopropionic acid)

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About This Item

Linear Formula:
[-SCH2CH(NH2)CO2H]2
CAS Number:
Molecular Weight:
240.30
NACRES:
NA.26
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352209
EC Number:
200-296-3
MDL number:
Beilstein/REAXYS Number:
1728094
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Product Name

L-Cystine, ≥99.7% (TLC)

Quality Level

assay

≥99.7% (TLC)

form

powder or crystals

optical activity

[α]20/D −219±5°, c = 1% in 1 M HCl

ign. residue

≤0.1% (as SO4)

loss

≤0.1% loss on drying

color

white

mp

>240 °C (dec.) (lit.)

solubility

1 M HCl: 0.5 g/10 mL, clear, colorless

anion traces

chloride (Cl-): ≤500 mg/kg, sulfate (SO42-): ≤100 mg/kg

cation traces

Ca: ≤50 mg/kg, Cd: ≤5 mg/kg, Co: ≤5 mg/kg, Cr: ≤5 mg/kg, Cu: ≤6 mg/kg, Fe: ≤10 mg/kg, K: ≤50 mg/kg, Mg: ≤5 mg/kg, Mn: ≤5 mg/kg, Na: ≤150 mg/kg, Ni: ≤5 mg/kg, Pb: ≤5 mg/kg, Zn: ≤5 mg/kg

application(s)

peptide synthesis

SMILES string

N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=O

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

InChI key

LEVWYRKDKASIDU-IMJSIDKUSA-N

Application

L-Cystine has been used to prepare stock solution which in turn is utilized for determining the L-cysteine and L-cystine in pharmaceutical preparations as well as in urine samples by using spectrofluorimetric flow injection method.

Biochem/physiol Actions

Cystine is required for the synthesis of glutathione that protects the cells from oxidative stress. A specific x(c)-cysteine/glutamate antiporter mediates cellular uptake of cysteine in exchange for glutamate. Inhibition of cysteine uptake induces toxicity in neuronal cells.

Other Notes

Preparation of N,N′-dibenzoyl-L-cystine, an efficient auxiliary for enantioselective reductions of ketones


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Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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T Pérez-Ruiz et al.
The Analyst, 117(6), 1025-1028 (1992-06-01)
A flow injection configuration is proposed for the determination of L-cysteine and L-cystine individually and for mixtures of both analytes. The procedure is based on the rapid oxidation of L-cysteine by thallium(III) with concomitant formation of fluorescent thallium(I). The inclusion
K. Soai et al.
Journal of the Chemical Society. Chemical Communications, 413-413 (1984)
Journal of the Chemical Society. Chemical Communications, 801-801 (1987)