(6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 73065
• Molecular Formular: C10H12N2O5S
• Molecular Mass: 272.27768
• Monoisotopic Mass: 272.04669249
• SMILES: N12[C@H](SCC(=C1C(=O)O)COC(=O)C)[C@@H](C2=O)N
• Canonical SMILES: CC(=O)OCC1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)N
• InChI: InChI=1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)/t6-,9-/m1/s1
• InChIKey: HSHGZXNAXBPPDL-HZGVNTEJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: 7β-aminocephalosporanic acid
• Synonyms: (6R,7R)-3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; (7R)-7-Aminocephalosporanic Acid; 3-(Acetoxymethyl)-7-aminocephem-4-carboxylic Acid; 7-ACS; 7β-Aminocephalosporanic Acid; 7-Aminocephalosporinic acid; 7-ACA; 7-ACA; 7-Aminocephalosporanic acid; 7-Aminocephalosporanic acid; 7-氨基头孢烷酸

Database IDs

• CAS Number: 957-68-6
• EC Number: 213-485-0
• MDL Number: MFCD00005177
• Beilstein Number: 622637; 622637, 8919572
• PubChem SID: 24846046; 24851470; 162037985
• PubChem CID: 441328; 483168
• CHEBI ID: 2255
• CHEMBL: 1161449
• Chemspider ID: 390087
• KEGG ID: C07756
• MeSH Name: 7-Aminocephalosporanic+acid
• Wikipedia Title: 7-ACA

CALCULATED PROPERTIES

• Acid pKa: 3.4190428
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -3.8121455
• LogD (pH = 7.4): -4.088983
• Log P: -3.8148885
• Molar Refractivity: 62.7384 cm^3
• Polarizability: 24.72692 Å^3
• Polar Surface Area: 109.93 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: >260°C; >300 °C(lit.); 300°C
• Partition Coefficient: -1.87
• Optical Rotation: [α]19/D +90°, c = 0.5 in KH2PO4/trace NaOH
• pKa: 2.59
• pKb: 11.41

Safety Information

• Storage Condition: -20°C; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 42/43; R:22; R42/43
• Safety Statements: 22-36/37; S:36/37/39; S22 S36/37
• GHS Pictograms: GHS health hazard; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: 317, 334; H317-H334
• GHS Precautionary statements: 261, 280, 342+311; P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ~97%; ~98%; ≥95% (HPLC); 98%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C10H12N2O5S

DETAILS

MP Biomedicals - 02150347

Purity: Approx. 98%
Light yellow crystalline powder

Selleck Chemicals - S2530

Research Area

• Description: Infection

Biological Activity

• Description: 7-Aminocephalosporanic acid is used for synthesis of cephalosporin antibiotics and intermediates.
• In Vitro: 7-Aminocephalosporanic acid is the basic building block used in the synthesis of many important semisynthetic cephalosporin antibiotics. 7-Aminocephalosporanic acid commonly appears as a white or whitish powder, is an important intermediate for the manufacture of the semisynthetic cephalosporin. 7-Aminocephalosporanic acid is an amphoteric compound. ^[1]

References

• References: [1] Wang S, et al. Ind Eng Chem Res, 2005, 44 (10), 3783–3787

Sigma Aldrich - 191140

Packaging
5 g in glass bottle
Application
Potent inhibitor of bacterial (S. aureus) β-lactamase.1

Sigma Aldrich - 07300

Other Notes
Coupling to Sepharose® 4B for covalent affinity chromatography of penicillin-binding proteins1
Legal Information
Sepharose is a registered trademark of GE Healthcare

Toronto Research Chemicals - A603415

It is the starting material for semi-synthetic cephalosporins. Obtained by mild acid hydrolysis of cephalosporin C.

REFERENCES

• Wang S, et al. Ind Eng Chem Res, 2005, 44 (10), 3783–3787
• Matsuda, A., et al.: J. Bacteriol., 169, 5815 (1987)
• Aramori, I., et al.: J. Ferment. Bioeng., 72, 227 (1987)
• Park, S., et al.: J. Biosci. Bioeng., 94, 218 (1987)
• Takimoto, A., et al.: Appl. Microbiol. Biotechnol., 65, 263 (1987)