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52-67-5

Basic Information
CAS No.: 52-67-5
Name: 3,3-Dimethyl-D(-)-cysteine
Article Data: 44
Molecular Structure:
Molecular Structure of 52-67-5 (3,3-Dimethyl-D(-)-cysteine)
Formula: C5H11NO2S
Molecular Weight: 149.214
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;
EINECS: 200-148-8
Density: 1.205 g/cm3
Melting Point: 210 °C (dec.)(lit.)
Boiling Point: 251.772 °C at 760 mmHg
Flash Point: 106.068 °C
Solubility: 11.1 g/100 mL (20 ºC)
Appearance: white powder
Hazard Symbols: Xi,T,Xn
Risk Codes: 36/37/38-40-20/21/22
Safety: 26-36-24/25-22
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
ConditionsYield
With acetic acid In water; toluene for 5h; Ambient temperature; Heating;A 71%
B 95%
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
ConditionsYield
With acetic acid In water 1.) reflux, 2 h, 2.) room temperature, 1 h;A 86%
B 93%
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
ConditionsYield
With acetic acid In water for 2h; Heating;A 93%
B 87%
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
ConditionsYield
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
ConditionsYield
With 1,2-diamino-benzene In water; acetic acid for 1.5h; Heating;A 59%
B 87%
C 91%
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
ConditionsYield
In water; acetic acid for 1.5h; Heating;A 59%
B 87%
C 91%
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
ConditionsYield
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
ConditionsYield
In water; acetic acid for 2h; Heating;A 83%
B 89%
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
ConditionsYield
With 1,2-diamino-benzene In water; acetic acid for 1.5h; Heating;A 58%
B 86%
C 81%
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
ConditionsYield
In water; acetic acid for 2h; Heating;A 81%
B 86%
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  • D-Penicillamine CAS:52-67-5

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  • Casno:

    52-67-5

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  • Casno:

    52-67-5

    D-Valine, 3-mercapto-

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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.