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Name	6-Aminopenicillanic acid	EINECS	208-993-4
CAS No.	551-16-6	Density	1.52 g/cm³
PSA	108.93000	LogP	0.09880
Solubility	Soluble in water and hydrochoric acid.	Melting Point	198-200 °C (dec.)(lit.)
Formula	C₈H₁₂N₂O₃S	Boiling Point	460.2 °C at 760 mmHg
Molecular Weight	216.261	Flash Point	232.1 °C
Transport Information	N/A	Appearance	White to cream fine powder
Safety	22-36/37-45-37-24-36	Risk Codes	42/43
Molecular Structure		Hazard Symbols	Xn
Synonyms	4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-amino-3,3-dimethyl-7-oxo- (6CI,8CI);4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-amino-3,3-dimethyl-7-oxo-, [2S-(2a,5a,6b)]-;(+)-6-Aminopenicillanic acid;6-APA;6-APS;6b-Aminopenicillanic acid;NSC 50071;Phenacyl 6-aminopenicillinate;	Article Data	58

6-Aminopenicillanic acid Synthetic route

: 129096-81-7
(2S,5R,6R)-Benzyl 6-Azido-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate for 3h; Ambient temperature;	59%

: 61-33-6
penicillin G

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
With penicillin-amidase from penicillium chrysogenum-stems
With penicillin G acylase; water at 28 - 29℃; pH=Ca. 8; Enzymatic reaction;

: 40124-92-3
6R(β)-tritylaminopenicillanic acid

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
With hydrogenchloride; isopropyl alcohol
(i) aq. H3PO4, benzene, (ii) aq. HCl, iPrOH; Multistep reaction;

: 113-98-4
Penicillin G potassium

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Multistep reaction;
With sodium hydroxide In aq. phosphate buffer at 55℃; pH=7.8; Catalytic behavior; Kinetics; Reagent/catalyst; Temperature; pH-value; Enzymatic reaction;

: 55151-71-8
6β-(3-oxo-3H-isobenzofuran-1-ylideneamino)-penicillanic acid

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
With hydrazine In tetrahydrofuran

: 61-33-6
penicillin G

A: 103-82-2
phenylacetic acid

B: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
With sodium hydroxide at 28℃; Equilibrium constant; penicillin G amidase (E.C. 3.5.1.11) immobilized on polyacrylamide, pH 8; var. substrate concentrations;
With penicillin G acylase immobilized on aminopropyl functionalized mesocellular foam silica crooslinked using glutaraldehyde In aq. phosphate buffer at 50℃; pH=7; Kinetics; pH-value; Temperature; Concentration; Reagent/catalyst; Enzymatic reaction;

penicillins to 6β-amino-penicillanic acid: penicillins to 6β-amino-penicillanic acid

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
fermentative und enzymatische Spaltung;
chemische Spaltung;
fermentative und enzymatische Spaltung;
chemische Spaltung;

: 61-33-6
penicillin G

penicillin-amidase: penicillin-amidase

penicillium chrysogenum-stems: penicillium chrysogenum-stems

A: 103-82-2
phenylacetic acid

B: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Hydrolysis;

: 26939-76-4
(2S,5R,6R)-1-aza-3,3'-dimethyl-6-(4-carboxybutanamido)-7-oxo-4-thiabicyclo<3.2.0>heptane-2-carboxylic acid

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
With sodium hydroxide; glutaryl-7-aminocephalosporanic acid acylase In water at 25℃; pH=8.0; Enzyme kinetics; Enzymatic reaction;

: 6-N-[3-(2,2,5,5-tetramethyl-1-oxypyrrolin-3-yl)-propen-2-oyl]penicillanic acid

A: 551-16-6
6-Aminopenicillanic Acid

B: 86073-81-6
(E)-3-(1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)acrylic acid

Conditions

Conditions	Yield
With class A TEM-1 β-lactamase; HEPES buffer In water; dimethyl sulfoxide at 24℃; pH=7; Kinetics; Further Variations:; Reagents; Enzymatic reaction;

6-Aminopenicillanic acid Chemical Properties

Chemical Name: 6-Aminopenicillanic acid
IUPAC NAME: (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS No.: 551-16-6
EINECS: 208-993-4
Molecular Formula of Phenacyl 6-aminopenicillinate (CAS No.551-16-6): C₈H₁₂N₂O₃S
Molecular Weight: 216.26 g/mol
Structure:

Synonyms of Phenacyl 6-aminopenicillinate (CAS No.551-16-6): (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure ; 6-Aminopenicillanic acid ; 6-Apa ; 6-Aps ; AI3-52557 ; EINECS 208-993-4 ; NSC 50071 ; Penicin ; Penin ; Phenacyl 6-aminopenicillinate ; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)- ; 6-Aminopenicillamine acid
Polar Surface Area: 75.15 Å²
Index of Refraction: 1.656
Molar Refractivity: 52.22 cm³
Molar Volume: 142 cm³
Surface Tension: 74.4 dyne/cm
Density of Phenacyl 6-aminopenicillinate (CAS No.551-16-6): 1.52 g/cm³
Flash Point: 232.1 °C
Enthalpy of Vaporization: 78.99 kJ/mol
Boiling Point: 460.2 °C at 760 mmHg
Vapour Pressure: 9.54E-10 mmHg at 25°C

6-Aminopenicillanic acid Uses

Phenacyl 6-aminopenicillinate (CAS No.551-16-6) is used as a pharmaceutical intermediate and antibiotics for research and experimental

6-Aminopenicillanic acid Toxicity Data With Reference

mouse LD50 intraperitoneal > 1gm/kg (1000mg/kg) National Technical Information Service. Vol. AD691-490,

6-Aminopenicillanic acid Consensus Reports

Reported in EPA TSCA Inventory.

6-Aminopenicillanic acid Safety Profile

Hazard Codes: Harmful Xn
Risk Statements: 42/43
R42/43: May cause sensitization by inhalation and skin contact.
Safety Statements: 22-36/37-45-24
S22: Do not breathe dust.
S36/37: Wear suitable protective clothing and gloves.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S24: Avoid contact with skin.
WGK Germany: 2
RTECS: XH8225000
F: 10
HS Code: 29349990
Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes of NO_x and SO_x.

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