Deacetylcephalothin
Basic information
- CAS
5935-65-9- Standard SMILES
O=C(Cc1cccs1)N[C@@H]1C(=O)N2C(C(=O)O)=C(CO)CS[C@H]12- InChIKey
HTBAVMIGXROYPQ-ZWNOBZJWSA-N- Molecular formula
- C14H14N2O5S2
- Average molar mass
- 354.4 g/mol
- Monoisotopic mass
- 354.0344139
Overview
RN given refers to (6R-trans)-isomer; structure
Names & identifiers
- Preferred name
- Deacetylcephalothin
- IUPAC
- (6R,7R)-3-(hydroxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- (6R-trans)-3-(hydroxymethyl)-8-oxo-7-(2-thienylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- Molecular formula
- C14H14N2O5S2
- Molecular weight
- 354.4
Names & synonyms
5935-65-9DesacetylcephalothindeacetylcephalothinL2J68R6FTPRefChem:132111227-690-8(6R,7R)-3-(hydroxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R-trans)-3-(hydroxymethyl)-8-oxo-7-(2-thienylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-3-(hydroxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCefalonium Impurity BCefalotin EP Impurity BDeacetylcephalothin (>90%)
Show more names
Deacetyl CefalotinCefalotin Impurity BDes-acetyl CephalothinCefalonium EP Impurity BCephalothin EP Impurity BCefalotin sodium impurity BCefalonium Impurity B (Cefalotin Impurity B)
(6R-trans)-3-(Hydroxymethyl)-8-oxo-7-(2-thienylacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidEINECS 227-690-8SCHEMBL9436419DTXSID70974769AKOS030255159(6R,7R)-3-(Hydroxymethyl)-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 3-(hydroxymethyl)-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-, (6R,7R)-DB-290060
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 160 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 5
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 580
Physicochemical properties
- Melting point
- 132 °C · >132°C (dec.)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- Dioxane (Very Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- color
- White to Pale Brown
Chemistry & industry
Applications
UsesDeacetylcephalothin (Cefalotin EP Impurity B) is an intermediate and the free acid analogue of Deacetylcephalothin Sodium Salt (D198210), which is an impurity in the synthesis of Cefalonium (C236800) and an analog of Cephalothin (C261150) a first-generation cephalosporin antibiotic used as a long-acting intramammary cerate for infusion of dairy cows.
Upstream & downstream products
Upstream raw materials
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Related reactions
4 records
Compound notes
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