D-(-)-Penicillamine supplier

Name
3,3-Dimethyl-D(-)-cysteine
EINECS 200-148-8
CAS No. 52-67-5
Article Data44
CAS DataBase
Density 1.205 g/cm³
Solubility 11.1 g/100 mL (20 ºC)
Melting Point 210 °C (dec.)(lit.)
Formula C₅H₁₁NO₂S
Boiling Point 251.772 °C at 760 mmHg
Molecular Weight 149.214
Flash Point 106.068 °C
Transport Information
Appearance white powder
Safety 26-36-24/25-22
Risk Codes 36/37/38-40-20/21/22
Molecular Structure
Hazard Symbols Xi,T,Xn
Synonyms Valine,3-mercapto-, D- (8CI);(-)-Penicillamine;(2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid;(S)-3,3-Dimethylcysteine;(S)-Penicillamine;2-Amino-3-mercapto-3-methylbutanoic acid;Cuprenil;Cuprimine;Cupripen;D-3-Mercaptovaline;D-Mercaptovaline;D-Penamine;D-Penicillamine;DPA;Depamine;Depen;Kuprenil;Mercaptyl;Metalcaptase;NSC 81549;Pendramine;Penicillamin;Penicillamine;Perdolat;Reduced D-penicillamine;Reduced penicillamine;Sufirtan;Trolovol;b-Thiovaline;H-D-Pen-OH;
PSA 102.12000
LogP 0.80700

Synthetic route

: 113-98-4, 21794-94-5, 68244-03-1
benzylpenicillin potassium salt

: 106-49-0
p-toluidine

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 124827-15-2
(Z)-N-(p-methylphenyl)-3-(p-methylanilino)-2-(2-phenylacetamido)acrylamide

Conditions

Conditions	Yield
With acetic acid In water; toluene for 5h; Ambient temperature; Heating;	A 71% B 95%

...Expand

: 137-07-5
2-amino-benzenethiol

: 73184-06-2
(5R,3S)-benzyl-D-penilloic acid

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 2-(1-phenylacetylaminomethyl)-2,3-dihydrobenzothiazole

Conditions

Conditions	Yield
With acetic acid In water 1.) reflux, 2 h, 2.) room temperature, 1 h;	A 86% B 93%

...Expand

: 479-27-6
naphthalene-1,8-diamine

: 73184-06-2
(5R,3S)-benzyl-D-penilloic acid

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 2-(1-phenylacetylaminomethyl)-2,3-dihydro-1H-perimidine

Conditions

Conditions	Yield
With acetic acid In water for 2h; Heating;	A 93% B 87%

...Expand

: 73184-06-2
(5R,3S)-benzyl-D-penilloic acid

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 2-(1-phenylacetylaminomethyl)-2,3-dihydro-1H-perimidine

Conditions

Conditions	Yield
With acetic acid; naphthalene-1,8-diamine In water for 2h; Heating;	A 93% B 87%

: 121766-89-0
benzylpenicilloic acid α-phenylethylamide

A: 51-17-2
benzoimidazole

B: 52-67-5
3,3-dimethyl-D-cysteine

C: 102016-26-2
phenaceturic acid α-phenethylamide

Conditions

Conditions	Yield
With 1,2-diamino-benzene In water; acetic acid for 1.5h; Heating;	A 59% B 87% C 91%

...Expand

: 121766-89-0
benzylpenicilloic acid α-phenylethylamide

: 95-54-5
1,2-diamino-benzene

A: 51-17-2
benzoimidazole

B: 52-67-5
3,3-dimethyl-D-cysteine

C: 102016-26-2
phenaceturic acid α-phenethylamide

Conditions

Conditions	Yield
In water; acetic acid for 1.5h; Heating;	A 59% B 87% C 91%

...Expand

: 121766-89-0
benzylpenicilloic acid α-phenylethylamide

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 121766-91-4, 121842-57-7
N-phenethyl-α-phenylacetamido-2-benzothiazolidineacetamide

Conditions

Conditions	Yield
With 2-amino-benzenethiol In water; acetic acid for 2h; Heating;	A 83% B 89%

: 121766-89-0
benzylpenicilloic acid α-phenylethylamide

: 137-07-5
2-amino-benzenethiol

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 121766-91-4, 121842-57-7
N-phenethyl-α-phenylacetamido-2-benzothiazolidineacetamide

Conditions

Conditions	Yield
In water; acetic acid for 2h; Heating;	A 83% B 89%

...Expand

: 121766-90-3
benzylpenicilloic acid α-anilide

A: 51-17-2
benzoimidazole

B: 52-67-5
3,3-dimethyl-D-cysteine

C: 15440-35-4
N-phenyl-N2-(phenylacetyl)glycinamide

Conditions

Conditions	Yield
With 1,2-diamino-benzene In water; acetic acid for 1.5h; Heating;	A 58% B 86% C 81%

...Expand

: 137-07-5
2-amino-benzenethiol

: 66317-00-8
<2R-<2α(R*),4β>>-5,5-dimethyl-2-<2-oxo-1-<(phenylacetyl)amino>-2-<(phenylmethyl)amino>ethyl>-4-thiazolidinecarboxylic acid

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 121766-92-5, 121767-02-0
N-Benzyl-2-(2,3-dihydro-benzothiazol-2-yl)-2-phenylacetylamino-acetamide

Conditions

Conditions	Yield
In water; acetic acid for 2h; Heating;	A 81% B 86%

...Expand

: 66317-00-8
<2R-<2α(R*),4β>>-5,5-dimethyl-2-<2-oxo-1-<(phenylacetyl)amino>-2-<(phenylmethyl)amino>ethyl>-4-thiazolidinecarboxylic acid

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 121766-92-5, 121767-02-0
N-Benzyl-2-(2,3-dihydro-benzothiazol-2-yl)-2-phenylacetylamino-acetamide

Conditions

Conditions	Yield
With 2-amino-benzenethiol In water; acetic acid for 2h; Heating;	A 81% B 86%

: 66317-00-8
<2R-<2α(R*),4β>>-5,5-dimethyl-2-<2-oxo-1-<(phenylacetyl)amino>-2-<(phenylmethyl)amino>ethyl>-4-thiazolidinecarboxylic acid

A: 51-17-2
benzoimidazole

B: 52-67-5
3,3-dimethyl-D-cysteine

C: 15440-34-3
N-benzyl-2-(2-phenylacetamido)acetamide

Conditions

Conditions	Yield
With 1,2-diamino-benzene In water; acetic acid for 1.5h; Heating;	A 57% B 80% C 85%

...Expand

: 121766-89-0
benzylpenicilloic acid α-phenylethylamide

: 479-27-6
naphthalene-1,8-diamine

A: 204-02-4
1-H-perimidine

B: 52-67-5
3,3-dimethyl-D-cysteine

C: 102016-26-2
phenaceturic acid α-phenethylamide

Conditions

Conditions	Yield
In water; acetic acid for 2h; Heating;	A 85% B 69% C 74%

...Expand

: (S)-2-tert-butoxyamide-3-methyl-3-thioacetoxybutyric acid

: 52-67-5
3,3-dimethyl-D-cysteine

Conditions

Conditions	Yield
Stage #1: (S)-2-tert-butoxyamide-3-methyl-3-thioacetoxybutyric acid With hydrogenchloride In 1,4-dioxane; water at 0℃; Reflux; Stage #2: With pyridine In ethanol	81%

: 66317-01-9
<2R-<2α(R*),4β>>-2-<2-(ethylamino)-2-oxo-1-<(phenylacetyl)amino>ethyl>-5,5-dimethyl-4-thiazolidinecarboxylic acid

A: 51-17-2
benzoimidazole

B: 52-67-5
3,3-dimethyl-D-cysteine

C: 25443-71-4
N-phenylacetyl-glycine ethylamide

Conditions

Conditions	Yield
With 1,2-diamino-benzene In water; acetic acid for 1.5h; Heating;	A 55% B 71% C 79%

...Expand

: 66317-01-9
<2R-<2α(R*),4β>>-2-<2-(ethylamino)-2-oxo-1-<(phenylacetyl)amino>ethyl>-5,5-dimethyl-4-thiazolidinecarboxylic acid

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 121766-94-7, 121767-04-2
2-(2,3-Dihydro-benzothiazol-2-yl)-N-ethyl-2-phenylacetylamino-acetamide

Conditions

Conditions	Yield
With 2-amino-benzenethiol In water; acetic acid for 2h; Heating;	A 74% B 79%

: 66317-01-9
<2R-<2α(R*),4β>>-2-<2-(ethylamino)-2-oxo-1-<(phenylacetyl)amino>ethyl>-5,5-dimethyl-4-thiazolidinecarboxylic acid

: 137-07-5
2-amino-benzenethiol

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 121766-94-7, 121767-04-2
2-(2,3-Dihydro-benzothiazol-2-yl)-N-ethyl-2-phenylacetylamino-acetamide

Conditions

Conditions	Yield
In water; acetic acid for 2h; Heating;	A 74% B 79%

...Expand

: 62-53-3
aniline

: 73184-06-2
(5R,3S)-benzyl-D-penilloic acid

A: 52-67-5
3,3-dimethyl-D-cysteine

: (2R*,3R*,4S*)-3-phenylacetylamino-2-phenylacetylaminomethyl-4-phenylamino-1,2,3,4-tetrahydroquinoline

: (2R*,3S*,4R*)-3-phenylacetylamino-2-phenylacetylaminomethyl-4-phenylamino-1,2,3,4-tetrahydroquinoline

Conditions

Conditions	Yield
With acetic acid In water; toluene for 4h; Heating;	A 79% B 9% C 7%

...Expand

: 150-61-8
N,N'-diphenylethylenediamine

: (S)-5,5-Dimethyl-2-((R)-phenethylcarbamoyl-phenylacetylamino-methyl)-thiazolidine-4-carboxylic acid

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 55055-34-0
N-formyl-N,N'-diphenylethylenediamine

C: 102016-26-2
phenaceturic acid α-phenethylamide

Conditions

Conditions	Yield
In acetic acid Heating;	A 51% B 63% C 76%
In acetic acid for 5h; Mechanism; Heating; var. penicilloic acid α-amides;	A 51% B 63% C 76%

...Expand

: (S)-5,5-Dimethyl-2-((R)-phenethylcarbamoyl-phenylacetylamino-methyl)-thiazolidine-4-carboxylic acid

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 102016-26-2
phenaceturic acid α-phenethylamide

Conditions

Conditions	Yield
With N,N'-diphenylethylenediamine In acetic acid for 5h; Heating;	A 51% B 76%

: (S)-5,5-Dimethyl-2-((R)-phenylacetylamino-phenylcarbamoyl-methyl)-thiazolidine-4-carboxylic acid

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 15440-35-4
N-phenyl-N2-(phenylacetyl)glycinamide

Conditions

Conditions	Yield
With N,N'-diphenylethylenediamine In acetic acid Heating;	A 49% B 75%

acid α-phenethylamide: acid α-phenethylamide

: 106-47-8
4-chloro-aniline

: 52-67-5
3,3-dimethyl-D-cysteine

Conditions

Conditions	Yield
With acetic acid In methanol; water	73.2%

: (S)-2-((R)-Benzylcarbamoyl-phenylacetylamino-methyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 15440-34-3
N-benzyl-2-(2-phenylacetamido)acetamide

Conditions

Conditions	Yield
With N,N'-diphenylethylenediamine In acetic acid Heating;	A 47% B 72%

: 104-94-9
4-methoxy-aniline

: 121766-89-0
benzylpenicilloic acid α-phenylethylamide

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 3-[(E)-4-Methoxy-phenylimino]-N-phenethyl-2-phenylacetylamino-propionamide

Conditions

Conditions	Yield
In water; acetic acid; toluene Heating;	A 71% B n/a

...Expand

: 121766-90-3
benzylpenicilloic acid α-anilide

: 137-07-5
2-amino-benzenethiol

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 121766-93-6, 121767-03-1
2-(2,3-Dihydro-benzothiazol-2-yl)-N-phenyl-2-phenylacetylamino-acetamide

Conditions

Conditions	Yield
In water; acetic acid for 2h; Heating;	A 71% B 68%

...Expand

: 121766-90-3
benzylpenicilloic acid α-anilide

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 121766-93-6, 121767-03-1
2-(2,3-Dihydro-benzothiazol-2-yl)-N-phenyl-2-phenylacetylamino-acetamide

Conditions

Conditions	Yield
With 2-amino-benzenethiol In water; acetic acid for 2h; Heating;	A 71% B 68%

: (S)-2-((R)-Ethylcarbamoyl-phenylacetylamino-methyl)-5,5-dimethyl-thiazolidine-4-carboxylic acid

A: 52-67-5
3,3-dimethyl-D-cysteine

B: 25443-71-4
N-phenylacetyl-glycine ethylamide

Conditions

Conditions	Yield
With N,N'-diphenylethylenediamine In acetic acid Heating;	A 42% B 71%

: (S)-5,5-Dimethyl-2-[(R)-phenethylcarbamoyl-(2-phenoxy-acetylamino)-methyl]-thiazolidine-4-carboxylic acid

A: 52-67-5
3,3-dimethyl-D-cysteine

B: N-phenoxy-acetylglycine α-phenethylamide

Conditions

Conditions	Yield
With N,N'-diphenylethylenediamine In acetic acid Heating;	A 47% B 69%

: 106-49-0
p-toluidine

: 121766-89-0
benzylpenicilloic acid α-phenylethylamide

A: 52-67-5
3,3-dimethyl-D-cysteine

B: N-Phenethyl-2-phenylacetylamino-3-[(E)-p-tolylimino]-propionamide

Conditions

Conditions	Yield
In water; acetic acid; toluene Heating;	A 68% B n/a

...Expand

: 50-00-0
formaldehyd

: 52-67-5
3,3-dimethyl-D-cysteine

: (S)-1-aza-3-oxa-7-thiabicyclo[3.30]-6-dimethyloctan-4-one

Conditions

Conditions	Yield
With magnesium sulfate In dichloromethane for 168h; Ambient temperature;	100%

: 52-67-5
3,3-dimethyl-D-cysteine

: 24424-99-5
di-tert-butyl dicarbonate

: 6482-24-2
2-Bromoethyl methyl ether

: 856417-53-3
(2S)-2-((tert-butoxycarbonyl)amino)-3-((2-methoxyethyl)thio)-3-methylbutanoic acid

Conditions

Conditions	Yield
Stage #1: 3,3-dimethyl-D-cysteine; di-tert-butyl dicarbonate; 2-Bromoethyl methyl ether With sodium hydroxide; ethanol at 0 - 20℃; for 15h; Stage #2: di-tert-butyl dicarbonate With sodium hydroxide; water at 20℃; for 15h;	100%

...Expand

: 52-67-5
3,3-dimethyl-D-cysteine

: 74-88-4
methyl iodide

: 29913-84-6
S-methyl D-penicillamine

Conditions

Conditions	Yield
With sodium hydride In methanol at 20℃; Inert atmosphere;	99%
With sodium hydride In methanol at 20℃; Inert atmosphere;	99%

: 67-56-1
methanol

: 52-67-5
3,3-dimethyl-D-cysteine

: 34297-27-3
D-penicillamine methyl ester hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride at 20℃;	98%
With hydrogenchloride at 20℃;	98%
With thionyl chloride at 0 - 20℃; for 48.5h;	91%

: 52-67-5
3,3-dimethyl-D-cysteine

: 24424-99-5
di-tert-butyl dicarbonate

: 119222-62-7
Boc-D-Pen-OH

Conditions

Conditions	Yield
With sodium hydroxide In ethyl acetate; tert-butyl alcohol	98%
With sodium hydroxide In tert-butyl alcohol at 20℃;

: 72428-60-5
1,3-bis(diphenylphosphino)propane digold(I) dichloride

: 64-17-5
ethanol

: 52-67-5
3,3-dimethyl-D-cysteine

: 7732-18-5
water

: C37H46Au2N2O4P2S2*C2H6O*3H2O

Conditions

Conditions	Yield
With sodium hydroxide at 20℃; for 2h;	97%

...Expand

: 50-00-0
formaldehyd

: 52-67-5
3,3-dimethyl-D-cysteine

: 22916-26-3
(S)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

Conditions

Conditions	Yield
In ethanol; water at 20℃; for 18h;	96%
In water at 0 - 20℃; for 23h;	81%
With pyridine In ethanol; water at 110℃; for 0.0833333h; Microwave irradiation;	76%

: bismuth (III) oxychloride

: 52-67-5
3,3-dimethyl-D-cysteine

: {D-(-)-penicillaminato-O,S,N}bismuth(III) chloride

Conditions

Conditions	Yield
In water stirring of BiOCl into a soln. of D-(-)-penicillamine in water at 40°C; stirring for 15 min at 40°C; filtration;; crystallization on storing at room temperature; washing with cold water; drying; elem. anal.;;	96%

: 52-67-5
3,3-dimethyl-D-cysteine

: 640-68-6
D-Val-OH

Conditions

Conditions	Yield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; triethyl phosphite In aq. phosphate buffer; acetonitrile at 20℃; for 0.5h; pH=6.5; Irradiation;	96%

: bis(triphenylphosphine)iminium gold(I) bis(acetylide)

: 52-67-5
3,3-dimethyl-D-cysteine

: bis(triphenylphosphoranylidene)ammonium bis(D-penicillaminato-S)aurate(I)

Conditions

Conditions	Yield
In dichloromethane byproducts: acetylacetone; N2-atmosphere; dropwise addn. of Au-complex soln. to 2 equiv. of ligand soln. (room temp.), stirring (1 h); filtration (Celite), concn., pptn. on Et2O addn., filtration, recrystn. (CH2Cl2/Et2O), drying (vac.); elem. anal.;	95%

: 52-67-5
3,3-dimethyl-D-cysteine

: 7732-18-5
water

: silver nitrate

: Ag[D-penicillamine]*H2O

Conditions

Conditions	Yield
With KOH In potassium hydroxide aq. KOH; AgNO3 soln. (pH 5) added to alkaline soln. of penicillamine; solid filtered, washed (EtOH), dried (P4O10); elem. anal.;	95%

...Expand

: 52-67-5
3,3-dimethyl-D-cysteine

: 7732-18-5
water

: potassium dicyanoaurate

: Au[D-penicillamine]*H2O

Conditions

Conditions	Yield
With KOH; HCl In water aurate soln. (pH 5) added to alkaline soln. of penicillamine, pH 9, thenHCl added dropwise, final pH 4; solid filtered, washed (EtOH), dried (P4O10); elem. anal.;	95%

...Expand

: 52-67-5
3,3-dimethyl-D-cysteine

: (tetrahydrothiophene)gold(I) chloride

: 7732-18-5
water

: 2071-20-7
bis-diphenylphosphinomethane

: [trigold(I)(bis(diphenylphosphino)methane)2(D-Hpenicillaminate)(D-penicillaminate)]*10H2O

Conditions

Conditions	Yield
Stage #1: 3,3-dimethyl-D-cysteine; tetrahydrothiophene gold(I)chloride; bis-diphenylphosphinomethane In ethanol; dichloromethane at 20℃; for 1h; Darkness; Stage #2: With sodium hydroxide In ethanol; dichloromethane Stage #3: water In methanol at 20℃; for 840h;	95%

...Expand

: 52-67-5
3,3-dimethyl-D-cysteine

: [(μ-bis(diphenylphosphino)ethane)Au2Cl2]

: 7732-18-5
water

: [Au2(1,2-bis(diphenylphosphino)ethane)(L-Hpenicillaminate)2]*9H2O

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 2h;	95%

...Expand

: 52-67-5
3,3-dimethyl-D-cysteine

: 623-27-8
terephthalaldehyde,

: 124652-16-0
C18H24N2O4S2

Conditions

Conditions	Yield
In methanol; water for 4h; Ambient temperature;	93%

: 52-67-5
3,3-dimethyl-D-cysteine

: 70-34-8
2,4-Dinitrofluorobenzene

: 1-Fluoro-2,4-dinitro-benzene; compound with (S)-2-amino-3-mercapto-3-methyl-butyric acid

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydrogencarbonate In water at 70℃; for 0.75h;	91.8%

: 52-67-5
3,3-dimethyl-D-cysteine

: 67-64-1
acetone

: 72744-87-7
(4S)-2,2,5,5-tetramethylthiazolidine-4-carboxylic acid

Conditions

Conditions	Yield
at 55℃; for 2h;	91.2%
for 2h; Condensation; Heating;	90%
In water	88%
In water for 15h; Ambient temperature;	70%

: 52-67-5
3,3-dimethyl-D-cysteine

: 519-05-1
opianic acid

: 97272-80-5
(3S,10R)-2,3,5,10-Tetrahydro-6,7-dimethoxy-2,2-dimethyl-5-oxo-<1,3>-thiazolo<2,3-a>isoindol-3-carbonsaeure

Conditions

Conditions	Yield
In water for 1h; Heating;	91%

: 52-67-5
3,3-dimethyl-D-cysteine

: 939-26-4
2-bromomethylnaphthyl bromide

: 1256761-30-4
C16H19NO2S

Conditions

Conditions	Yield
With N,N,N',N'-tetramethylguanidine In tetrahydrofuran at 50℃; for 1h; Inert atmosphere;	91%

: 52-67-5
3,3-dimethyl-D-cysteine

: 37128-99-7
N-methyl2-piperidone diethyl acetal

: 105099-13-6, 122861-60-3
(S)-3-Mercapto-3-methyl-2-[1-methyl-piperidin-(2E)-ylideneamino]-butyric acid

Conditions

Conditions	Yield
In ethanol at 20 - 25℃; for 5h;	90%

: 52-67-5
3,3-dimethyl-D-cysteine

: 1074-12-0
phenylglyoxal hydrate

: 2-benzoyl-5,5-dimethyl-thiazolidine-4-carboxylic acid

Conditions

Conditions	Yield
In phosphate buffer; water at 20℃; for 0.666667h; pH=7.4;	90%
In phosphate buffer at 37℃; pH=7.4; Product distribution; Kinetics;

: 123-75-1
pyrrolidine

: 52-67-5
3,3-dimethyl-D-cysteine

A: 4-carboxy-2,5,5-trimethylthiazolidine-2-acetopyrrolidide

B: 110-54-3
hexane

Conditions

Conditions	Yield
In benzene	A 90% B n/a

...Expand

: 84152-18-1
[(ClAu)]3(1,1,1-tris(diphenylphosphinomethyl)ethane)

: 52-67-5
3,3-dimethyl-D-cysteine

: 7732-18-5
water

: [Au3(1,1,1-tris(diphenylphosphinomethyl)ethane)(D-Hpenicillamine)3]*5H2O

Conditions

Conditions	Yield
In ethanol at 20℃; for 1h;	90%

...Expand

: 4-butynyloxybenzenesulfonyl chloride

: 52-67-5
3,3-dimethyl-D-cysteine

: 540-51-2
2-bromoethanol

: N-{[4-(2 butynyloxy)phenyl]-sulfonyl}-3-[(2-hydroxyethyl)sulfanyl]valine

Conditions

Conditions	Yield
With sodium hydroxide; sodium carbonate In methanol; water; N,N-dimethyl-formamide	89.6%

...Expand

D-(-)-Penicillamine Specification

The D,3-Mercaptovaline with CAS registry number of 52-67-5 is also called D-Valine, 3-mercapto-. The IUPAC name is (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid. Its EINECS registry number is 200-148-8. In addition, the molecular formula is C₅H₁₁NO₂S and the molecular weight is 149.21. It is a kind of white to off-white crystalline powder and belongs to the classes of Amino Acids; Biochemistry; non-Proteinorganic Amino Acids; Miscellaneous Compounds; Antibiotics. And it is stable and incompatible with strong oxidizing agents.

Physical properties about this chemical are: (1)ACD/LogP: 0.85; (2)# of Rule of 5 Violations: 0 ; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 3; (8)#H bond donors: 3; (9)#Freely Rotating Bonds: 4; (10)Polar Surface Area: 102.12 Å²; (11)Index of Refraction: 1.528; (12)Molar Refractivity: 38.134 cm³; (13)Molar Volume: 123.845 cm³; (14)Polarizability: 15.117 ×10^-24cm³; (15)Surface Tension: 48.155 dyne/cm; (16)Density: 1.205 g/cm³; (17)Flash Point: 106.068 °C; (18)Enthalpy of Vaporization: 53.854 kJ/mol; (19)Boiling Point: 251.772 °C at 760 mmHg; (20)Vapour Pressure: 0.006 mmHg at 25°C.

Preparation of D,3-Mercaptovaline: it can be prepared by penicillin through synthesis or degradation. It also can be prepared by penicillin G potassium by means of hydrolysis.

Uses of D,3-Mercaptovaline: it can be used as antidoteit of some heavy metals such as copper and mercury. And it can be used in the treatment of Wilson's disease and rheumatoid arthritis. It does not apply to the hematopoiesis function obstacle patients, kidney function decline patients and who allergic to penicillin. In addition, it can react with formic acid to get N-formyl-penicillamine. This reaction will need reagent acetic anhydride. The reaction time is 3 hours at ambient temperature. The yield is about 78%.

D,3-Mercaptovaline can reacr with formic acid to get N-formyl-penicillamine

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin and harmful by inhalation, in contact with skin and if swallowed. The evidence of a carcinogenic effect is limited. During using it, do not breathe dust and wear suitable protective clothing. Moreover, avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(C)([C@H](C(=O)O)N)S
(2)InChI: InChI=1/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1
(3)InChIKey: VVNCNSJFMMFHPL-VKHMYHEABH

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	oral	40mg/kg/1W-I (40mg/kg)	BLOOD: LEUKOPENIA SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Archives of Internal Medicine. Vol. 145, Pg. 2271, 1985.
human	TDLo	oral	21mg/kg/D (21mg/kg)	KIDNEY, URETER, AND BLADDER: PROTEINURIS BLOOD: LEUKOPENIA BLOOD: THROMBOCYTOPENIA	JAMA, Journal of the American Medical Association. Vol. 240, Pg. 1870, 1978.
human	TDLo	oral	893mg/kg/30W- (893mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: DYSPNEA MUSCULOSKELETAL: OTHER CHANGES	Journal of Rheumatology. Vol. 11, Pg. 251, 1984.
man	TDLo	oral	400mg/kg/4W-I (400mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BLOOD: HEMORRHAGE	Journal of Rheumatology. Vol. 13, Pg. 963, 1986.
man	TDLo	oral	482mg/kg/19W- (482mg/kg)	BLOOD: THROMBOCYTOPENIA SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Archives of Internal Medicine. Vol. 143, Pg. 1487, 1983.
man	TDLo	unreported	3200mg/kg/84W (3200mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	British Medical Journal. Vol. 296, Pg. 1332, 1988.
mouse	LD50	intraperitoneal	298mg/kg (298mg/kg)		Yakugaku Zasshi. Journal of Pharmacy. Vol. 94, Pg. 1419, 1974.
mouse	LD50	intravenous	3840mg/kg (3840mg/kg)	LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 162, 1975.
mouse	LD50	oral	720mg/kg (720mg/kg)		Pharmaceutical Chemistry Journal Vol. 21, Pg. 842, 1987.
mouse	LD50	subcutaneous	3810mg/kg (3810mg/kg)		Drugs in Japan Vol. 6, Pg. 758, 1982.
rat	LD50	intraperitoneal	2080mg/kg (2080mg/kg)		Drugs in Japan Vol. 6, Pg. 758, 1982.
rat	LD50	intravenous	2gm/kg (2000mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1434, 1972.
rat	LD50	oral	6170mg/kg (6170mg/kg)		Drugs in Japan Vol. 6, Pg. 758, 1982.
rat	LD50	subcutaneous	4020mg/kg (4020mg/kg)		Drugs in Japan Vol. 6, Pg. 758, 1982.
women	LDLo	oral	150mg/kg/30D- (150mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Annals of Internal Medicine. Vol. 98, Pg. 327, 1983.
women	TDLo	oral	105mg/kg/6W-I (105mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	British Medical Journal. Vol. 294, Pg. 1101, 1987.
women	TDLo	oral	112mg/kg/1W-I (112mg/kg)	BLOOD: AGRANULOCYTOSIS SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Archives of Internal Medicine. Vol. 145, Pg. 2271, 1985.
women	TDLo	oral	900mg/kg/26W- (900mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Journal of Rheumatology. Vol. 12, Pg. 583, 1985.
women	TDLo	oral	650gm/kg/81W- (650000mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS MUSCULOSKELETAL: OTHER CHANGES	Arthritis and Rheumatism. Vol. 29, Pg. 560, 1986.

Product Name

3,3-Dimethyl-D(-)-cysteine

Synthetic route

D-(-)-Penicillamine Specification

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