Name: 3,3-Dimethyl-D(-)-cysteine
SKU: 52-67-5

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Basic Information

Molecular Structure:
CAS No.:	52-67-5
Name:	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

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

Raw Materials

95-53-4

106-49-0

479-27-6

95-54-5

Downstream Products

61-33-6

640-68-6

87-08-1

72-18-4

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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.

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Specification