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Home> Encyclopedia >Organic Intermediate>Pharmaceutical Intermediates>Vitamins, Amino Acids and Coenzymes
L-Cystine structure
L-Cystine structure

L-Cystine

Iupac Name:(2R)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]disulfanyl]propanoic acid
CAS No.: 56-89-3
Molecular Weight:240.30048
Modify Date.: 2022-11-05 12:50
Introduction: L-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. View more+
1. Names and Identifiers
1.1 Name
L-Cystine
1.2 Synonyms

(r-(r*,r*))-3,3’-dithiobis(2-aminopropanoicacid) 1-cystine 3,3’-dithiobis(2-amino-,(r-(r*,r*))-propanoicaci 3,3’-dithiobis(2-aminopropanoicacid) 3,3’-dithiobis-l-alanin 3,3'-Dithiobis(2-aminopropanoic acid) 3,3'-Dithiodialanine Alanine, 3,3'-dithiobis-

1.3 CAS No.
56-89-3
1.4 CID
67678
1.5 EINECS(EC#)
200-296-3
1.6 Molecular Formula
C6H12N2O4S2 (isomer)
1.7 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
1.8 InChkey
LEVWYRKDKASIDU-IMJSIDKUSA-N
1.9 Canonical Smiles
C(C(C(=O)O)N)SSCC(C(=O)O)N
1.10 Isomers Smiles
C([C@@H](C(=O)O)N)SSC[C@@H](C(=O)O)N
2. Properties
2.1 Density
1.571
2.1 Melting point
260-261℃
2.1 Boiling point
468.2 °C at 760 mmHg
2.1 Refractive index
-222.5 ° (C=1, 1mol/L HCl)
2.1 Flash Point
237 °C
2.1 Precise Quality
240.02400
2.1 PSA
177.24000
2.1 logP
0.59220
2.1 Solubility
1 M HCl: 100?mg/mL
2.2 Appearance
White crystalline powder
2.3 Storage
Ambient temperatures.
2.4 Chemical Properties
A white or almost white, crystalline powder, practically insoluble in water and in alcohol.
2.5 Color/Form
White
2.6 pKa
1.0, 2.1, 8.02, 8.71(at 25℃)
2.7 Water Solubility
0.112 g/L (25 °C) in water
2.8 Stability
Stable. Incompatible with strong oxidizing agents.
2.9 StorageTemp
Store at RT.
3. Use and Manufacturing
3.1 Purification Methods
Cystine disulfoxide impurity is removed by treating an aqueous suspension with H2S. The cystine is filtered off, washed with distilled water and dried at 100o under a vacuum over P2O5. Crystallise it by dissolving in 1.5M HCl, then adjusting to neutral pH with ammonia. Likely impurities are D-cystine, meso-cystine and tyrosine. Also purify it by dissolving it in 10% NH3 and adding gradually dilute AcOH until the point of precipitation and cooling slowly [Dughton & Harrison Acta Cryst 12 396, 402 1959.] Alternatively dissolve it in 6N NH4OH and evaporate it at room temperature for crystallisation to occur. [Chaney & Steinrauf Acta Cryst 30 711 1974, Beilstein 4 IV 3155.] L-Cystine Preparation Products And Raw materials Raw materials
3.2 Usage
L-Cystine is a non-essential amino acid for human development. L-Cystine is formed by the dimerization of two cysteines through the sulfur.
4. Safety and Handling
4.1 Hazard Codes
Xi
4.1 Risk Statements
R36/37/38
4.1 Safety Statements
S24/25
4.1 Packing Group
III
4.1 RIDADR
25kgs
4.1 Safety Profile
Low toxicity by ingestion. When heated to decomposition it emits toxic fumes of PO, and SOx
4.2 WGK Germany
3
4.2 RTECS
HA2690000
4.2 Safety

Hazard Codes:?Xi
Risk Statements: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.?
S24/25:Avoid contact with skin and eyes.
RIDADR: 2811
WGK Germany: 3
RTECS: HA2690000
Hazard Note: Irritant
PackingGroup: III
HS Code: 29309014

4.3 Specification

?Cystine , its cas register number is 56-89-3. It also can be called?(R-(R*,R*))-3,3'-Dithiobis(2-aminopropanoic acid) ; 1-Cystine ; 3,3'-Dithiobis(2-aminopropanoic acid) ; 3,3'-Dithiobis(2-aminopropanoic acid), (R-(R*,R*))- ; 3,3'-Dithiodialanine ; Alanine, 3,3'-dithiobis- ; Bis(beta-amino-beta-carboxyethyl)disulfide ; Cysteine disulfide ; beta,beta'-Diamino-beta,beta'-dicarboxydiethyl disulfide .It is a?white crystalline powder.

4.4 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 961mg/kg (961mg/kg) ? Yakugaku Zasshi. Journal of Pharmacy. Vol. 94, Pg. 1419, 1974.
rat LDLo oral 25gm/kg (25000mg/kg) ? Oyo Yakuri. Pharmacometrics. Vol. 15, Pg. 199, 1978.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

8. Other Information
8.0 Usage
L-Cystine is used as an antioxidant, protecting tissues against radiation and pollution. It finds application in protein synthesis. It is required for utilization of vitamin B6 and is useful in healing burns and wounds. It is also is required by certain malignant cell lines in the culture medium as well as for the growth of certain micro-organisms. It is useful in the stimulation of hematopoietic system and promotes the formation of white and red blood cells. It is an active ingredient in medications used to treat dermatitis.
8.1 Usage
L-cysteine acts as a major source of sulfur in cell culture. Cysteine has been used in pulse-chase experiments to study protein expression from an inducible promoter. L-Cysteine is used to supplement cell culture media.
9. Computational chemical data
  • Molecular Weight: 240.30048g/mol
  • Molecular Formula: C6H12N2O4S2
  • Compound Is Canonicalized: True
  • XLogP3-AA: -6.3
  • Exact Mass: 240.02384922
  • Monoisotopic Mass: 240.02384922
  • Complexity: 192
  • Rotatable Bond Count: 7
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 8
  • Topological Polar Surface Area: 177
  • Heavy Atom Count: 14
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADccBjOABgAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgQQCAAACCjFwASACABAAgAIAACQCAAAAAAAAAAAAIGAAAACAAAAAAAAQAAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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