Conditions | Yield |
---|---|
With recombinant Streptomyces lavendulae penicillinacylase In dimethyl sulfoxide at 30℃; for 10.8h; pH=7; Catalytic behavior; Kinetics; Concentration; pH-value; Solvent; Time; Enzymatic reaction; | 94.5% |
Penicillin-V-2'-bromethylester
penicilin V
Conditions | Yield |
---|---|
With lithium cobalt(I)-phthalocyanine; phenol In acetone for 4h; Ambient temperature; | 81% |
penicilin V
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; dihydrogen peroxide; iron(II) sulfate; ascorbic acid In water | 1.3% |
(R)-((2R)-4t-carboxy-5,5-dimethyl-thiazolidin-2r-yl)-(2-phenoxy-acetylamino)-acetic acid
penicilin V
Conditions | Yield |
---|---|
With 1,4-dioxane; sodium hydroxide; dicyclohexyl-carbodiimide |
6-aminopenicillanic acid trimethylsilyl ester
Phenoxyacetyl chloride
penicilin V
Conditions | Yield |
---|---|
(i) Et3N, CHCl3, dioxane, (ii) /BRN= 1082694/; Multistep reaction; |
6β-benzylideneamino-penicillanic acid; 1,1,3,3-tetramethyl-butylamine salt
Phenoxyacetyl chloride
penicilin V
Conditions | Yield |
---|---|
With sodium 2-ethylhexanoic acid In chloroform-d1 |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In acetone |
Conditions | Yield |
---|---|
Yield given; |
penicilin V
Conditions | Yield |
---|---|
With ammonium bicarbonate; iron(II) sulfate; catalase; ascorbic acid; diothiothreitol isopenicillin N synthetase from Cephalosporium acremonium CO728; | |
With isopenicillin N synthetase from Cephalosporium acremonium CO728; oxygen; ammonium bicarbonate; iron(II) sulfate; catalase; ascorbic acid; diothiothreitol In water at 27℃; Michaelis constant, maximum velocity; |
penicilin V
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; oxygen; iron(II) sulfate; ascorbic acid In water at 37℃; for 2h; |
Conditions | Yield |
---|---|
With phosphate buffer; Penicillium chrysogenum mycelium at 24℃; for 20h; Mechanism; <1-14C>- or <18O2>-labelled; |
penicillin V methoxymethyl ester
penicilin V
Conditions | Yield |
---|---|
With water-d2 In d(4)-methanol at 25℃; Rate constant; |
penicilin V
Conditions | Yield |
---|---|
With 2-phenoxyacetic acid |
penicilin V
Conditions | Yield |
---|---|
With N-(2-hydroxyethyl)-2-phenoxyacetamide | |
With bis-[2-(phenoxyacetyl-amino)-ethyl]-disulfide | |
With 2-phenoxyacetic acid | |
With 2-Phenoxyethanol |
penicilin V
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 0.1 M aq. NaOH / acetonitrile View Scheme |
penicilin V
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CF3COOH / benzene; various solvent(s) / 1 h / 20 °C 2: FeSO4, ascorbic acid, EDTA, O2 / H2O / 2 h / 37 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sodium acetate; aqueous ethanol 2: dioxane; N2H4+H2O / Behandeln des Reaktionsprodukts mit Essigsaeure und wss. HCl 3: triethylamine; CH2Cl2 4: HCl; CH2Cl2 5: dicyclohexylcarbodiimide; aqueous NaOH; dioxane View Scheme | |
Multi-step reaction with 6 steps 1: sodium acetate; aqueous ethanol 2: pyridine 3: dioxane; N2H4+H2O / Behandeln des Reaktionsprodukts mit Essigsaeure und wss. HCl 4: triethylamine; CH2Cl2 5: HCl; CH2Cl2 6: dicyclohexylcarbodiimide; aqueous NaOH; dioxane View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine; CH2Cl2 2: HCl; CH2Cl2 3: dicyclohexylcarbodiimide; aqueous NaOH; dioxane View Scheme |
(4S)-2t-((R)-amino-tert-butoxycarbonyl-methyl)-5,5-dimethyl-thiazolidine-4r-carboxylic acid
penicilin V
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine; CH2Cl2 2: HCl; CH2Cl2 3: dicyclohexylcarbodiimide; aqueous NaOH; dioxane View Scheme |
(4S)-2t-[(R)-tert-butoxycarbonyl-(2-phenoxy-acetylamino)-methyl]-5,5-dimethyl-thiazolidine-4r-carboxylic acid
penicilin V
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HCl; CH2Cl2 2: dicyclohexylcarbodiimide; aqueous NaOH; dioxane View Scheme |
(4S)-2t-((R)-tert-butoxycarbonyl-phthalimido-methyl)-5,5-dimethyl-thiazolidine-4r-carboxylic acid
penicilin V
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: dioxane; N2H4+H2O / Behandeln des Reaktionsprodukts mit Essigsaeure und wss. HCl 2: triethylamine; CH2Cl2 3: HCl; CH2Cl2 4: dicyclohexylcarbodiimide; aqueous NaOH; dioxane View Scheme |
(4S)-2c-((S)-tert-butoxycarbonyl-phthalimido-methyl)-5,5-dimethyl-thiazolidine-4r-carboxylic acid
penicilin V
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: pyridine 2: dioxane; N2H4+H2O / Behandeln des Reaktionsprodukts mit Essigsaeure und wss. HCl 3: triethylamine; CH2Cl2 4: HCl; CH2Cl2 5: dicyclohexylcarbodiimide; aqueous NaOH; dioxane View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: KHCO3 / acetone View Scheme | |
Multi-step reaction with 2 steps 1: CHCl3 2: (i) Et3N, CHCl3, dioxane, (ii) /BRN= 1082694/ View Scheme |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In water; acetone at 0 - 20℃; for 1.25h; | |
Stage #1: 6-Aminopenicillanic Acid; Phenoxyacetyl chloride With sodium hydrogencarbonate In water; acetone at 10 - 15℃; for 0.35h; Stage #2: With sulfuric acid pH=2; |
1,1-Diphenylmethanol
penicilin V
(2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate
Conditions | Yield |
---|---|
With pyridine; isocyanuric acid In dichloromethane at -7 - -5℃; for 0.666667h; | 91.8% |
penicilin V
6β-phenoxyacetamidopenicillanic acid 1β-sulfoxide
Conditions | Yield |
---|---|
With dihydrogen peroxide In dichloromethane at 25 - 30℃; for 6h; | 90% |
penicilin V
Conditions | Yield |
---|---|
With cesium hydroxide In tetrahydrofuran pH 5; | 88.3% |
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran pH 5; | 86% |
Conditions | Yield |
---|---|
With sodium carbonate In dimethyl sulfoxide for 20h; | 80% |
Conditions | Yield |
---|---|
In butan-1-ol | 80% |
penicilin V
Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran; water pH 5; | 78.3% |
Conditions | Yield |
---|---|
In ethanol for 7h; Inert atmosphere; Reflux; | 77% |
penicilin V
Conditions | Yield |
---|---|
With rubidium hydroxide In tetrahydrofuran pH 5; | 76.8% |
alanine trichloroethylester
penicilin V
(S)-2-{[(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carbonyl]-amino}-propionic acid 2,2,2-trichloro-ethyl ester
Conditions | Yield |
---|---|
With diisopropyl-carbodiimide In dichloromethane | 69% |
H-S-Leu-OTce
penicilin V
(S)-2-{[(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carbonyl]-amino}-4-methyl-pentanoic acid 2,2,2-trichloro-ethyl ester
Conditions | Yield |
---|---|
With diisopropyl-carbodiimide In dichloromethane | 67% |
L-Val-OCH2CCl3
penicilin V
(S)-2-{[(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carbonyl]-amino}-3-methyl-butyric acid 2,2,2-trichloro-ethyl ester
Conditions | Yield |
---|---|
With diisopropyl-carbodiimide In dichloromethane | 64% |
O-diphenylmethyl 2,2,2-trichloroacetimidate
penicilin V
(2S,5R,6R)-benzhydryl 6-(2-phenoxyacetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 18h; Inert atmosphere; | 63% |
2,2,2-trichloroethyl glycinate*HBr
penicilin V
{[(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carbonyl]-amino}-acetic acid 2,2,2-trichloro-ethyl ester
Conditions | Yield |
---|---|
With triethylamine; diisopropyl-carbodiimide In dichloromethane | 50% |
H2N-IleOTce
penicilin V
(2S,3S)-2-{[(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carbonyl]-amino}-3-methyl-pentanoic acid 2,2,2-trichloro-ethyl ester
Conditions | Yield |
---|---|
With diisopropyl-carbodiimide In dichloromethane | 37% |
H2N-OTroc-TyrOTce
penicilin V
(S)-2-{[(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carbonyl]-amino}-3-[4-(2,2,2-trichloro-ethoxycarbonyloxy)-phenyl]-propionic acid 2,2,2-trichloro-ethyl ester
Conditions | Yield |
---|---|
With diisopropyl-carbodiimide In dichloromethane | 36% |
(S)-2-Amino-pentanedioic acid bis-(2,2,2-trichloro-ethyl) ester; hydrobromide
penicilin V
(S)-2-{[(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carbonyl]-amino}-pentanedioic acid bis-(2,2,2-trichloro-ethyl) ester
Conditions | Yield |
---|---|
With triethylamine; diisopropyl-carbodiimide In dichloromethane | 26% |
H2N-TrpOTce
penicilin V
(S)-2-{[(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carbonyl]-amino}-3-(1H-indol-3-yl)-propionic acid 2,2,2-trichloro-ethyl ester
Conditions | Yield |
---|---|
With diisopropyl-carbodiimide In dichloromethane | 14% |
penicilin V
(R)-((2R)-4t-carboxy-5,5-dimethyl-thiazolidin-2r-yl)-(2-phenoxy-acetylamino)-acetic acid
Conditions | Yield |
---|---|
With water In 1,4-dioxane at 30℃; Rate constant; Bacillus cereus 569/H β-lactamase I, pH 7; also hydroxy ion instead of enzyme; | |
With sodium hydroxide |
diazomethane
penicilin V
(3S,5R,6R)-3-diazoacetyl-2,2-dimethyl-6-phenoxyacetamidopenam
Conditions | Yield |
---|---|
(i) Et3N, CH2Cl2, (ii) ClCO2Me, (iii) /BRN= 102415/; Multistep reaction; |
diazomethane
penicilin V
methyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Conditions | Yield |
---|---|
In diethyl ether |
methanol
penicilin V
methyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Conditions | Yield |
---|---|
With pyridine; dicyclohexyl-carbodiimide In dichloromethane |
Molecular Structure:
Molecular Formula: C16H18N2O5S
Molecular Weight: 350.3895
IUPAC Name: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Synonyms of Penicillin V (CAS NO.87-08-1): 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenoxyacetyl)amino)-, (2S,5R,6R)- ; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenoxyacetyl)amino)-, (2S-(2alpha,5alpha,6beta))- ; Penicillanic acid, 6-phenoxyacetamido- ; Phenoxymethylpenicillin
CAS NO: 87-08-1
Classification Code: Anti-Bacterial Agents ; Anti-Infective Agents ; Antibacterial ; Drug / Therapeutic Agent ; Human Data ; Mutation data
Melting point: 120-128°C
Index of Refraction: 1.65
Density: 1.45 g/cm3
Flash Point: 365.9 °C
Enthalpy of Vaporization: 105 kJ/mol
Boiling Point: 681.4 °C at 760 mmHg
Vapour Pressure: 1.69E-19 mmHg at 25 °C
Melting point: 120-128 °C
Storage tempreture: -20 °C
Solubility: Insoluble in water
Appearance: Crystalline solid
Penicillin V (CAS NO.87-08-1) has been used for antibacterial.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | intramuscular | 1096mg/kg (1096mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956. |
guinea pig | LD50 | intraperitoneal | 822mg/kg (822mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956. |
mouse | LD50 | intramuscular | > 1775mg/kg (1775mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956. |
mouse | LD50 | intraperitoneal | 1351mg/kg (1351mg/kg) | Antibiotics Annual. Vol. 3, Pg. 540, 1955/1956. | |
mouse | LD50 | oral | 6578mg/kg (6578mg/kg) | Antibiotiki. Vol. 3(4), Pg. 37, 1958. | |
mouse | LD50 | subcutaneous | > 4gm/kg (4000mg/kg) | Antibiotics Annual. Vol. 3, Pg. 540, 1955/1956. | |
rat | LD50 | intramuscular | > 1600mg/kg (1600mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956. |
rat | LD50 | intraperitoneal | > 2gm/kg (2000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956. |
rat | LD50 | intravenous | > 1775mg/kg (1775mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956. |
rat | LD50 | oral | > 2220mg/kg (2220mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956. |
women | TDLo | oral | 10mg/kg/2D (10mg/kg) | LIVER: LIVER FUNCTION TESTS IMPAIRED SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Lancet. Vol. 2, Pg. 1297, 1976. |
Poison by intraperitoneal, subcutaneous, and intravenous routes. Human systemic effects by ingestion: impaired liver function, dermatitis, fever. Mutation data reported. When heated to decomposition it emits very toxic fumes of SOx and NOx.
Hazard Codes of Penicillin V (CAS NO.87-08-1): Xn
Risk Statements: 42/43
R42/43: May cause sensitization by inhalation and skin contact.
Safety Statements: 22-36
S22: Do not breathe dust.
S36: Wear suitable protective clothing.
It is incompatible with acids, oxidizing agents (especially in the presence of trace metals), heavy metal ions such as copper, zinc and mercury; sympathomimetic amines, thiomersal, cetostearyl alcohol, hard paraffins, cocoa butter and many ionic an nonionic surface-active agents.
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View