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CAS No.: | 52-67-5 |
---|---|
Name: | 3,3-Dimethyl-D(-)-cysteine |
Article Data: | 44 |
Molecular Structure: | |
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 |
benzylpenicillin potassium salt
p-toluidine
A
3,3-dimethyl-D-cysteine
B
(Z)-N-(p-methylphenyl)-3-(p-methylanilino)-2-(2-phenylacetamido)acrylamide
Conditions | Yield |
---|---|
With acetic acid In water; toluene for 5h; Ambient temperature; Heating; | A 71% B 95% |
2-amino-benzenethiol
(5R,3S)-benzyl-D-penilloic acid
A
3,3-dimethyl-D-cysteine
Conditions | Yield |
---|---|
With acetic acid In water 1.) reflux, 2 h, 2.) room temperature, 1 h; | A 86% B 93% |
naphthalene-1,8-diamine
(5R,3S)-benzyl-D-penilloic acid
A
3,3-dimethyl-D-cysteine
Conditions | Yield |
---|---|
With acetic acid In water for 2h; Heating; | A 93% B 87% |
(5R,3S)-benzyl-D-penilloic acid
A
3,3-dimethyl-D-cysteine
Conditions | Yield |
---|---|
With acetic acid; naphthalene-1,8-diamine In water for 2h; Heating; | A 93% B 87% |
benzylpenicilloic acid α-phenylethylamide
A
benzoimidazole
B
3,3-dimethyl-D-cysteine
C
phenaceturic acid α-phenethylamide
Conditions | Yield |
---|---|
With 1,2-diamino-benzene In water; acetic acid for 1.5h; Heating; | A 59% B 87% C 91% |
benzylpenicilloic acid α-phenylethylamide
1,2-diamino-benzene
A
benzoimidazole
B
3,3-dimethyl-D-cysteine
C
phenaceturic acid α-phenethylamide
Conditions | Yield |
---|---|
In water; acetic acid for 1.5h; Heating; | A 59% B 87% C 91% |
benzylpenicilloic acid α-phenylethylamide
A
3,3-dimethyl-D-cysteine
B
N-phenethyl-α-phenylacetamido-2-benzothiazolidineacetamide
Conditions | Yield |
---|---|
With 2-amino-benzenethiol In water; acetic acid for 2h; Heating; | A 83% B 89% |
benzylpenicilloic acid α-phenylethylamide
2-amino-benzenethiol
A
3,3-dimethyl-D-cysteine
B
N-phenethyl-α-phenylacetamido-2-benzothiazolidineacetamide
Conditions | Yield |
---|---|
In water; acetic acid for 2h; Heating; | A 83% B 89% |
benzylpenicilloic acid α-anilide
A
benzoimidazole
B
3,3-dimethyl-D-cysteine
C
N-phenyl-N2-(phenylacetyl)glycinamide
Conditions | Yield |
---|---|
With 1,2-diamino-benzene In water; acetic acid for 1.5h; Heating; | A 58% B 86% C 81% |
2-amino-benzenethiol
<2R-<2α(R*),4β>>-5,5-dimethyl-2-<2-oxo-1-<(phenylacetyl)amino>-2-<(phenylmethyl)amino>ethyl>-4-thiazolidinecarboxylic acid
A
3,3-dimethyl-D-cysteine
B
N-Benzyl-2-(2,3-dihydro-benzothiazol-2-yl)-2-phenylacetylamino-acetamide
Conditions | Yield |
---|---|
In water; acetic acid for 2h; Heating; | A 81% B 86% |
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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%.
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. |