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Penicilloic acid

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Identification
Molecular formula
C16H18N2O5S
CAS number
87-08-1
IUPAC name
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
State
State

This compound is a solid at room temperature. It may exhibit partial solubility in water and is more significantly soluble in organic solvents.

Melting point (Celsius)
174.20
Melting point (Kelvin)
447.35
Boiling point (Celsius)
126.10
Boiling point (Kelvin)
399.25
General information
Molecular weight
350.39g/mol
Molar mass
350.3880g/mol
Density
1.3500g/cm3
Appearence

Penicilloic acid typically appears as a pale yellow to white crystalline solid. It is formed as a degradation product of penicillin and retains the beta-lactam structure, which influences its appearance.

Comment on solubility

Solubility of (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

This compound, with the chemical formula C16H18N2O5S, presents interesting characteristics regarding its solubility profile. Understanding solubility is crucial as it affects the compound's behavior in biological systems, pharmaceutical formulations, and synthetic processes.

Factors Influencing Solubility

The solubility of this compound can be influenced by several factors:

  • Polarity: Due to the presence of multiple functional groups including a carboxylic acid and amide, the compound is likely to exhibit polar characteristics, making it more soluble in polar solvents.
  • Hydrogen Bonding: The potential for hydrogen bonding, both intramolecular and intermolecular, can enhance solubility in aqueous environments, as highly polar solvents like water can solvate polar groups effectively.
  • pH Levels: The compound’s solubility might vary with changes in pH, especially due to the carboxylic acid group, which could ionize in basic conditions, leading to increased solubility.

Practical Implications

Practically, the solubility of this compound can lead to varying implications in both laboratory and clinical settings:

  • Drug Formulation: Its solubility characteristics must be considered while developing dosage forms to ensure appropriate bioavailability.
  • Analytical Applications: Water solubility can influence the choice of extraction methods or analytical techniques used for detection and quantification.

In summary, the solubility of (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is determined by a balance of its molecular structure, the physicochemical properties of the solvent employed, and environmental conditions. Understanding these factors will guide its practical applications effectively.

Interesting facts

Interesting Facts about (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

This compound is a fascinating example of a bicyclic structure with significant biological activity, primarily in the field of pharmaceuticals. Known for its potential therapeutic uses, it integrates several functional groups that enhance its reactivity and utility in drug design. Here are some key points of interest:

  • Bicyclic Nature: The bicyclic framework provides unique conformational properties that can influence biological activity and interactions with enzymes.
  • Sulfur Inclusion: The presence of a sulfur atom in its structure contributes to its stability and can modify the compound's interactions with biological targets.
  • Enantiomer Specificity: This compound possesses chiral centers, which means that different enantiomers may exhibit varied pharmacological effects, making stereochemistry crucial in its function.
  • Analogs and Derivatives: The compound can serve as a scaffold for derivatization, enabling chemists to create analogs that might show enhanced efficacy or selectivity towards specific biological targets.
  • Historical Relevance: Compounds with similar structures have been explored for their antimicrobial and antifungal properties, showcasing the ongoing relevance of bicyclic systems in medicinal chemistry.

As chemists continue to explore and synthesize compounds like this, the adaptability and potential of such molecular frameworks remain promising in developing new therapeutic agents.

Synonyms
penicillin g
Benzylpenicillin
61-33-6
Benzyl penicillin
Benzylpenicillinic acid
Free penicillin II
Pencillin G
Benzylpenicillin G
Bencilpenicilina
Dropcillin
Free penicillin G
Gelacillin
Liquacillin
Pharmacillin
Pradupen
Cilopen
Benzylpenicilline
Specilline G
Benzylpenicillinum
Cilloral
Cosmopen
PenicillinG
Pfizerpen
Free benzylpenicillin
Benzopenicillin
bensylpenicillin
(5R,6R)-Benzylpenicillin
6-(2-Phenylacetamido)penicillanic acid
Penicillin, (phenylmethyl)-
benzyl benicillin
Galofak
Compocillin G
Penicillin-G potassium
CHEBI:18208
HSDB 3166
Benzylpenicillinum [Latin]
Penicillinic acid, (phenylmethyl)-
Phenylacetamidopenicillanic acid
EINECS 200-506-3
UNII-Q42T66VG0C
NSC 193396
BRN 0044740
Q42T66VG0C
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(Phenylmethyl)penicillin
Benzyl-6-aminopenicillinic acid
Penicillinic acid, benzyl-
NSC-193396
DTXSID5046934
Ursopen
J01CE01
4-27-00-05861 (Beilstein Handbook Reference)
(Phenylmethyl)penicillinic acid
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)- (2S-(2alpha,5alpha,6beta))-
Benzylpenicillin (INN)
Benzylpenicillinum (Latin)
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-
BENZYLPENICILLIN [INN]
BENZYLPENICILLIN (MART.)
BENZYLPENICILLIN [MART.]
Cillora
Bencilpenicilina [Spanish]
Benzylpenicilline [French]
Benzylpenicillin [INN:BAN]
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- [2S-(2alpha,5alpha,6beta)]-
SMR000538912
PHENOXYMETHYLPENICILLIN IMPURITY A (EP IMPURITY)
PHENOXYMETHYLPENICILLIN IMPURITY A [EP IMPURITY]
NSC193396
Penicillin,(S)
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-
PENICILLIN-G
NSC131815
Spectrum_000933
CHEMBL29
Prestwick0_001078
Prestwick1_001078
Prestwick2_001078
Prestwick3_001078
Spectrum2_000518
Spectrum3_000542
Spectrum4_000471
Spectrum5_001108
Epitope ID:114070
PENICILLIN G [MI]
SCHEMBL3783
PENICILLIN G [HSDB]
BSPBio_001096
BSPBio_002183
KBioGR_000942
KBioSS_001413
PENICILLIN G [VANDF]
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)-, (2S-(2alpha,5alpha,6beta))-
MLS000766897
MLS001032123
MLS001173382
DivK1c_000316
SPBio_000475
SPBio_002998
BPBio1_001206
GTPL4796
DTXCID3026934
KBio1_000316
KBio2_001413
KBio2_003981
KBio2_006549
KBio3_001683
BENZYLPENICILLIN [WHO-DD]
NINDS_000316
GLXC-25718
HMS2875L09
HY-N7139
BDBM50022787
Phenylacetyl-6-aminopenicillanic acid
AKOS005203091
DB01053
IDI1_000316
NCGC00159348-02
NCGC00159348-03
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6- (2-phenylacetamido)-
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-
FP148625
SBI-0051476.P003
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-
Bicillin (*Benzathine Salt, Tetrahydrate*)
CS-0013727
NS00068016
C05551
D02336
(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]
EN300-19631164
Q258450
Benzylpenicillin 1000 microg/mL in Acetonitrile:Water
BRD-K55191674-236-03-7
BRD-K55191674-236-06-0
BRD-K55191674-236-07-8
BRD-K55191674-237-02-7
BRD-K55191674-237-12-6
BRD-K55191674-237-18-3
2,2-dimethyl-6beta-(phenylacetamido)penam-3alpha-carboxylic acid
PHENOXYMETHYLPENICILLIN POTASSIUM IMPURITY A [EP IMPURITY]
PHENOXYMETHYLPENICILLIN (BENZATHINE) TETRAHYDRATE IMPURITY A [EP IMPURITY]
(+)-3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid(penicillin G)
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid
(2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-[(PHENYLACETYL)AMINO]-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
(2S,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
200-506-3
3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid anion (Penicillin G)
3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid(penicillin G)
4,1-Thiaazabicyclo[3.2.0]heptane-2-carboxylic acid, 6-benzylcarbonylamino-3,3-dimethyl-7-oxo-
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]- (2S,5R,6R)-
4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-, (2S,5R,6R)-