D-Penicillamine disulfide

Base Information

• Chemical Name: D-Penicillamine disulfide
• CAS No.: 20902-45-8
• Deprecated CAS: 91308-89-3
• Molecular Formula: C10H20 N2 O4 S2
• Molecular Weight: 296.412
• Hs Code.: 2930904915
• European Community (EC) Number: 244-107-2
• UNII: Q98FPI4N5P
• DSSTox Substance ID: DTXSID201312638
• Nikkaji Number: J11.844C
• Wikidata: Q27130878
• Metabolomics Workbench ID: 61517
• Mol file: 20902-45-8.mol

Synonyms:D-Penicillamine disulfide;20902-45-8;3,3'-Dithiodi-D-valine;S,S'-Bi(D-penicillamine);(2S,2'S)-3,3'-disulfanediylbis(2-amino-3-methylbutanoic acid);3,3,3,',3'-tetramethyl-D-cystine;Q98FPI4N5P;(2S)-2-amino-3-[[(1S)-1-amino-1-carboxy-2-methylpropan-2-yl]disulfanyl]-3-methylbutanoic acid;CHEBI:61196;(2S,2'S)-3,3'-dithiobis(2-amino-3-methylbutanoic acid);(2S,2'S)-3,3'-dithiobis(2-amino-3-methylbutyric acid);D-Valine, 3,3'-dithiobis-;NSC-87505;(2S)-2-amino-3-{[(1S)-1-amino-1-carboxy-2-methylpropan-2-yl]disulfanyl}-3-methylbutanoic acid;NSC 87505;3,3'-Dithiobis(2-amino-3-methylbutyric acid);Epitope ID:140793;UNII-Q98FPI4N5P;Penicillamine disulfide D-form;SCHEMBL6501684;D-Penicillamine disulfide, 97%;DTXSID201312638;PENICILLAMINE DISULFIDE, D-;EINECS 244-107-2;CS-T-38833;PENICILLAMINE DISULFIDE [USP-RS];PENICILLAMINE DISULFIDE D-FORM [MI];Q27130878;Penicillamine disulfide, European Pharmacopoeia (EP) Reference Standard;Penicillamine disulfide, United States Pharmacopeia (USP) Reference Standard

Chemical Property of D-Penicillamine disulfide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 204 °C (dec.)(lit.)
• Boiling Point: 467°Cat760mmHg
• PKA: 1.76±0.12(Predicted)
• Flash Point: 236.2°C
• PSA: 177.24000
• Density: 1.353g/cm³
• LogP: 2.14940
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Base (Slightly), Water (Slightly)
• XLogP3: -5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 296.08644947
• Heavy Atom Count: 18
• Complexity: 302

Purity/Quality:

97% ^*data from raw suppliers

D-Penicillamine disulfide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C(C(=O)O)N)SSC(C)(C)C(C(=O)O)N
• Isomeric SMILES: CC(C)([C@H](C(=O)O)N)SSC(C)(C)[C@H](C(=O)O)N
• Uses: D-Penicillamine Disulfide is used in the treatment of neurodegenerative diseases such as Parkinson’s and Motor Neuron Disease. Inactivator of α1-antiproteinase, preventing deleterious effects of peroxynitrite.

Technology Process of D-Penicillamine disulfide

There total 10 articles about D-Penicillamine disulfide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

D-penicillamine disulfide dimethyl ester (115940-43-7) → D-Penicillamin-disulfid (20902-45-8)

Guidance literature:

With ethylenediaminetetraacetic dianhydride; In dichloromethane; for 24h; Cooling with ice;

DOI:10.1016/j.tetlet.2013.11.078

Reference yield: 88.0%

3,3-dimethyl-D-cysteine (52-67-5) → D-Penicillamin-disulfid (20902-45-8)

Guidance literature:

With oxygen; sodium carbonate; 1-butyl-3-methylimidazolium Tetrafluoroborate; at 20 ℃; for 0.5h;

DOI:10.1002/ejoc.201000126

Reference yield:

3,3-dimethyl-D-cysteine (52-67-5) + glutathione disulfide → D-Penicillamin-disulfid (20902-45-8) + GLUTATHIONE (70-18-8) + (S)-2-Amino-3-[(R)-2-((R)-4-amino-4-carboxy-butyrylamino)-2-(carboxymethyl-carbamoyl)-ethyldisulfanyl]-3-methyl-butyric acid (92000-26-5)

Guidance literature:

Equilibrium constant; Rate constant; pH 7.4;

DOI:10.1139/v84-287

upstream raw materials:

3,3-dimethyl-D-cysteine

ethyl ethanethiosulfinate

ammonia

iron(III) chloride

Downstream raw materials:

(S)-2-amino-3-hydroxy-3-methylbutanoic acid

D-Penicillaminsulfinsaeure

3,3'-dithiobis[N-[[4-(2-butynyloxy)phenyl]sulfonyl]-D-valine] dimethyl ester

Bis(D-1-(p-Tolylsulfonamido)-1-carboxy-2-methyl-2-propyl) Disulfide