3D Mol Similar

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; Molecular Weight：216.255; Modify Date.: 2023-03-28 11:32; Introduction: (+)-6-Aminopenicillanic Acid is the core structure in penicillins, obtained from the fermentation brew of the Penicillium mold. (+)-6-Aminopenicillanic Acid is used as the main starting block for the preparation of numerous semisynthetic penicillins. View more+

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1. Names and Identifiers

: 1.1 Name; 6-Aminopenicillanic acid; 1.2 Synonyms; (+)-6-AMINOPENICILLANIC ACID (25,5R,6R)-6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (2S,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (5R,6R)-6-Amino-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptan-7-one acetate (1:1) [2S-(2a,5a,6b)]-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid 4-Thia-1-azabicyclo[3.2.0]heptan-7-one, 6-amino-3,3-dimethyl-, (5R,6R)-, acetate (1:1) 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)- 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,6R)- 6-AMINO PENICILLINIC ACID 6-AMINO-2,2-DIMETHYL-5-OXOPERHYDROAZETO[2,1-B][1,3]THIAZOLE-3-CARBOXYLIC ACID 6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID 6-Aminopenicillansure 6-APA 6-aps 6b-Aminopenicillanic Acid 7-AMINO-3,3-DIMETHYL-6-OXO-2-THIA-5-AZABICYCLO[3.2.0]HEPTANE-4-CARBOXYLIC ACID aminopenicillanicacid Amoxicillin Impurity 1 EINECS 208-993-4 MFCD00005176 penicin; View all

1.3 CAS No.: 551-16-6

1.4 CID: 11082

1.5 EINECS(EC#): 208-993-4

1.6 Molecular Formula: C8H12N2O3S (isomer)

1.7 Inchi: InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1

1.8 InChIkey: NGHVIOIJCVXTGV-ALEPSDHESA-N

1.9 Canonical Smiles: CC1(C(N2C(S1)C(C2=O)N)C(=O)O)C

1.10 Isomers Smiles: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N)C(=O)O)C

2. Properties

2.1 Density: 1.52

2.1 Melting point: 197-203℃

2.1 Boiling point: 460.2 oC at 760 mmHg

2.1 Refractive index: 1.656

2.1 Flash Point: 232.1°C

2.1 Precise Quality: 216.05700

2.1 PSA: 108.93000

2.1 logP: 0.09880

2.1 Solubility: 2.46g/l

2.2 Appearance: white to off white free flowing crystalline powder

2.3 Storage: Keep Cold.

2.4 Chemical Properties: WHITE TO CREAM FINE POWDER

2.5 Color/Form: Powder

2.6 PH: 3.4 (100g/l, H2O)

2.7 pKa: pKa 2.3 (Uncertain)

2.8 Water Solubility: Very soluble

2.9 Stability: Stable under normal temperatures and pressures.

2.10 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A penicillanic acid compound having a (6R)-amino substituent. The active nucleus common to all penicillins, it may be substituted at the 6-amino position to form the semisynthetic penicillins, resulting in a variety of antibacterial and phrmacologic characteristics.

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 49 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 40 of 49 companies. For more detailed information, please visit ECHA C&L website

Of the 5 notification(s) provided by 9 of 49 companies with hazard statement code(s):

H302 (11.11%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (22.22%): Causes skin irritation [Warning Skin corrosion/irritation]
H317 (77.78%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H319 (22.22%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H334 (88.89%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]
H335 (11.11%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P272, P280, P285, P301+P312, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501; View all

3.3 Purification Methods: This acid crystallises from water. [Kleppe & Stroninger J Biol Chem 254 4856 1979,Beilstein 27 III/IV 2858.] 6-Aminopenicillanic acid Preparation Products And Raw materials Raw materials

3.4 Usage: (+)-6-Aminopenicillanic Acid is the core structure in penicillins, obtained from the fermentation brew of the Penicillium mold. (+)-6-Aminopenicillanic Acid is used as the main starting block for the preparation of numerous semisynthetic penicillins.

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: R42/43

4.1 Safety Statements: S24;S37;S45

4.1 RIDADR: 25kgs

4.1 Safety Profile: Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes of NOx and SOx.

4.2 WGK Germany: 2

4.2 RTECS: XH8225000

4.2 Report: Reported in EPA TSCA Inventory.

4.3 Safety: Hazard Codes: 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.

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

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

Mass

7. Synthesis Route

551-16-6Total: 20 Synthesis Route

61-33-6 89 Suppliers

551-16-6 180 Suppliers

Literatures:
Nippon Nogei Kagaku Kaishi, , vol. 29, p. 404 Chem.Abstr., , p. 8160 J. agirc. chem. Soc. JapanChem.Abstr., , vol. 23, p. 411 J. agirc. chem. Soc. JapanChem.Abstr., , p. 1197
Yield: null

87-08-1 13 Suppliers

551-16-6 180 Suppliers

122-59-8 173 Suppliers

Literatures:
US2005/20685 A1, ; Page 2-3 ;
Yield: null

61-33-6 89 Suppliers

551-16-6 180 Suppliers

Literatures:
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, , vol. 32, # 1 p. 40 - 43
Yield: null

View all

8. Precursor and Product

precursor:

20425-27-8

51056-25-8

15139-36-3

113-98-4

21027-18-9

69-53-4

129096-81-7

47449-42-3

128971-90-4

128971-92-6

55151-71-8

87-08-1

128971-96-0

128971-91-5

40124-92-3

128971-94-8

128971-93-7

26939-76-4

61-33-6

View all

product :

3485-08-3

147-55-7

89786-04-9

26787-78-0

26631-90-3

14796-35-1

61-72-3

26552-51-2

205320-24-7

24158-88-1

551-27-9

554-68-7

2315-05-1

5187-94-0

76646-91-8

760-67-8

875-74-1

69-53-4

642-78-4

68373-14-8

1752-26-7

132-98-9

147-52-4

343-55-5

66-79-5

View all

9. Other Information

9.0 Merck: 14,458

9.1 BRN: 15080

9.2 Chemical Properties: WHITE TO CREAM FINE POWDER

9.3 Uses: (+)-6-Aminopenicillanic Acid is the core structure in penicillins, obtained from the fermentation brew of the Penicillium mold. (+)-6-Aminopenicillanic Acid is used as the main starting block for the preparation of numerous semisynthetic penicillins.

9.4 Definition: ChEBI: A penicillanic acid compound having a (6R)-amino substituent. The active nucleus common to all penicillins, it may be substituted at the 6-amino position to form the semisynthetic penicillins, resulting in a variety of antibacterial and ph rmacologic characteristics.

9.5 General Description: Chemical structure: ?-lactam

9.6 Usage: 6-Aminopenicillanic acid is the basic unit in penicillin?s, which is obtained from the fermentation brew of the Penicillium mold. It acts as a starting material for the preparation of many semisynthetic penicillins. Further, it serves as apharmaceutical intermediate. In addition to this, it is used in antibiotics research and experimental application.

10. Computational chemical data

Molecular Weight: 216.255g/mol
Molecular Formula: C₈H₁₂N₂O₃S
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 216.05686342
Monoisotopic Mass: 216.05686342
Complexity: 318
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 109
Heavy Atom Count: 14
Defined Atom Stereocenter Count: 3
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBzMABAAAAAAAAAAAAAAABYAWAAAAAAAAAABYAAAAAAAAAAHgQQCAAADCjFwASCCANAAggIAAGQGAAAAABAABAAAIGIAAACQBggACAUQAAEFgCwAAAAAAAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

What is 6-Aminopenicillanic Acid (6-APA)? May 16 2023
6-Aminopenicillanic acid (6-APA) is a white or slightly yellow crystalline powder with a melting point of 208-209℃ (decomposition). It is slightly soluble in water and insoluble in butyl acetate, eth..

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