FComEx: L-Cystine (PC000071)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:59 UTC

Update date

2017-01-19 02:36:11 UTC

FoodComEx ID

PC000071

FoodDB Record

FDB012563

Chemical Information

Name

L-Cystine

Description

Flavouring ingredient; dietary supplement Cystine is an oxidized dimeric form of cysteine. It is formed by linking two cysteine residues via a disulfide bond (cys-S-S-cys) between the -SH groups. Cystine is found in high concentrations in the cells of the immune system, skeletal and connective tissues, skin, digestive enzymes, and in hair. Hair and skin are 10-14% cystine. Cystine is the preferred form of cysteine for the synthesis of glutathione in cells involved in the immune function including macrophages and astrocytes. Lymphocytes and neurons prefer cysteine for glutathione production. Optimizing glutathione levels in macrophages and astrocytes with cystine allows these cells to provide cysteine to lymphocytes and neurons directly upon demand. (http://en.wikipedia.org/wiki/Cystine); Cystine is the amino acid formed by the oxidation of cysteine molecules to give a disulfide bond. This organosulfur compound has the formula (SCH2CH(NH2)CO2H)2. It is a colorless solid, and melts at 247-249 °C. It was discovered in 1810 by William Hyde Wollaston but was not recognized as being derived of proteins until it was isolated from the horn of a cow in 1899. Through formation of disulfide bonds within and between protein molecules, cystine is a significant determinant of the tertiary structure of most proteins. Disulfide bonding, along with hydrogen bonding and hydrophobic interactions is partially responsible for the formation of the gluten matrix in bread. Human hair contains approximately 5% cystine by mass.; 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.

CAS Number

56-89-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(-)-Cystine	HMDB
(2R,2'R)-3,3'-disulfanediylbis(2-aminopropanoic acid)	biospider
(R-(R,R))-3,3'-Dithiobis	biospider
(R-(R,r))-3,3'-dithiobis(2-aminopropanoate)	Generator
(R-(R,R))-3,3'-Dithiobis(2-aminopropanoic acid)	biospider
(R,R)-3,3'-Dithiobis(2-aminopropanoate)	Generator
(R,R)-3,3'-dithiobis(2-aminopropanoic acid)	biospider
(R,R)-3,3'-Dithiobis(2-aminopropionicacid)	biospider
[R-(R,R)]-3,3'-Dithiobis	biospider
α-diamino-β-dithiolactic acid	biospider
β,β'-dithiobisalanine	biospider
β,β'-dithiodialanine	biospider
1-Cystine	biospider
2-amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoate	biospider
2-amino-3-(2-amino-2-Carboxy-ethyl)disulfanyl-propanoic acid	HMDB
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoate	biospider
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acid	biospider
3, 3'-Dithiobis(2-aminopropanoic acid)	biospider
3,3'-Dithiobis	biospider
3,3'-dithiobis-L-Alanine	biospider
3,3'-Dithiobis(2-aminopropanoic acid), (R-(R,R))-	biospider
3,3'-Dithiobis(2-aminopropionic acid)	biospider
3,3'-dithiobis[2-amino-[R-(R,R)]-Propanoate	biospider
3,3'-dithiobis[2-amino-[R-(R,R)]-Propanoic acid	biospider
3,3'-Dithiodialanine	HMDB
Alanine, 3, 3'-dithiobis-	biospider
B,b'-diamino-b,b'-dicarboxydiethyl disulfide	biospider
B,b'-dithiodialanine	biospider
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulfide	Generator
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulphide	Generator
b,Beta'-dithiodialanine	Generator
Beta,beta'-diamino-beta,beta'-dicarboxydiethyl disulfide	biospider
beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulphide	Generator
Beta,beta'-diamino-beta,beta'-dicarboxydiethyldisulfide	biospider
Beta,beta'-dithioalanine, l-	biospider
Beta,beta'-dithiobisalanine	biospider
Beta,beta'-dithiodialanine	biospider
Bis(β-amino-β-carboxyethyl) disulfide	biospider
Bis(β-amino-β-carboxyethyl)disulfide	biospider
Bis(b-amino-b-carboxyethyl) disulfide	biospider
Bis(b-amino-b-carboxyethyl) disulphide	Generator
Bis(b-amino-beta-carboxyethyl) disulfide	biospider
Bis(beta-amino-beta-carboxyethyl) disulfide	biospider
Bis(beta-amino-beta-carboxyethyl) disulphide	Generator
Bis(beta-amino-beta-carboxyethyl)disulfide	biospider
Bis(β-amino-β-carboxyethyl) disulfide	Generator
Bis(β-amino-β-carboxyethyl) disulphide	Generator
Cysteine disulfide	HMDB
Cystin	HMDB
Cystin (van)	biospider
Cystine	HMDB
Cystine (l)-	biospider
Cystine (usan/inn)	biospider
Cystine (van)	biospider
Cystine [usan]	biospider
Cystine acid	HMDB
Cystine d-form	biospider
Cystine, 9CI, USAN; L-form	db_source
Cystine, d-	biospider
Cystine, L- (8CI)	biospider
Cystine,d	biospider
D(+)-3,3'-Dithiobis(2-aminopropanoate	biospider
D(+)-3,3'-Dithiobis(2-aminopropanoic acid	biospider
Dicysteine	HMDB
e921	ChEBI
Gelucystine	biospider
Gelucystine (l form)	biospider
L-(-)-Cystine	HMDB
L-3,3'-dithiodialanine	biospider
L-a-Diamino-b-dithiolactate	Generator
L-a-Diamino-b-dithiolactic acid	Generator
L-Alanine, 3,3'-dithiobis-	biospider
L-alpha-Diamino-beta-dithiolactate	Generator
L-alpha-diamino-beta-dithiolactic acid	biospider
L-cysteine disulfide	biospider
L-cystin	biospider
L-Cystine (9CI)	biospider
L-dicysteine	biospider
L-α-diamino-β-dithiolactate	Generator
L-α-diamino-β-dithiolactic acid	Generator
Oxidized L-cysteine	ChEBI
Propanoic acid, 3,3'-dithiobis(2-amino-, (R-(R,R))-	biospider
β,beta'-diamino-β,beta'-dicarboxydiethyl disulfide	Generator
β,beta'-diamino-β,beta'-dicarboxydiethyl disulphide	Generator
β,beta'-dithiodialanine	Generator

Chemical Formula

C6H12N2O4S2

IUPAC name

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

InChI Identifier

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)

InChI Key

LEVWYRKDKASIDU-UHFFFAOYSA-N

Isomeric SMILES

NC(CSSCC(N)C(O)=O)C(O)=O

Average Molecular Weight

240.3

Monoisotopic Molecular Weight

240.023848262

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cysteine and derivatives

Alternative Parents

Substituents

Cysteine or derivatives
Alpha-amino acid
Dicarboxylic acid or derivatives
Organic disulfide
Dialkyldisulfide
Amino acid
Sulfenyl compound
Carboxylic acid
Hydrocarbon derivative
Organic nitrogen compound
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic disulfide (CHEBI:17376 )
sulfur-containing amino acid (CHEBI:17376 )
cysteine derivative (CHEBI:17376 )
Other amino acids (C01420 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-5.08	CHMELIK,J ET AL. (1991)
Experimental Water Solubility	0.19 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 258-261 dec. (sealed tube)	DFC

Foods of Origin