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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:
56-89-3
Molecular Weight:
240.30
NACRES:
NA.26
PubChem Substance ID:
329753347
eCl@ss:
32160406
UNSPSC Code:
12352209
EC Number:
200-296-3
MDL number:
MFCD00064228
Beilstein/REAXYS Number:
1728094

Product Name

L-Cystine, ≥99.7% (TLC)

InChI key

LEVWYRKDKASIDU-IMJSIDKUSA-N

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

SMILES string

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

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

Quality Level

200

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Related Categories

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

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCN7407
BCCM2201
BCCL1340
BCCJ0388
BCCJ0389

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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
Journal of the Chemical Society. Chemical Communications, 801-801 (1987)
T H Murphy et al.
Neuron, 2(6), 1547-1558 (1989-06-01)
Glutamate binds to both excitatory neurotransmitter binding sites and a Cl(-)-dependent, quisqualate- and cystine-inhibited transport site on brain neurons. The neuroblastoma-primary retina hybrid cells (N18-RE-105) are susceptible to glutamate-induced cytotoxicity. The Cl(-)-dependent transport site to which glutamate and quisqualate (but
K. Soai et al.
Journal of the Chemical Society. Chemical Communications, 413-413 (1984)
Anne C Conibear et al.
The Journal of biological chemistry, 288(15), 10830-10840 (2013-02-23)
θ-Defensins are ribosomally synthesized cyclic peptides found in the leukocytes of some primate species and have promising applications as antimicrobial agents and scaffolds for peptide drugs. The cyclic cystine ladder motif, comprising a cyclic peptide backbone and three parallel disulfide
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