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Name |
7-Aminocephalosporanic Acid |
EINECS | 213-485-0 |
CAS No. | 957-68-6 | Density | 1.6 g/cm3 |
PSA | 135.23000 | LogP | -0.23120 |
Solubility | 409.6mg/L(22.99 oC) | Melting Point |
>300 °C(lit.) |
Formula | C10H12N2O5S | Boiling Point | 560.6 °C at 760 mmHg |
Molecular Weight | 272.282 | Flash Point | 292.9 °C |
Transport Information | N/A | Appearance | off-white to beige crystalline powder |
Safety | 22-36/37-24/25-36-26 | Risk Codes | 42/43-36/37/38-20/21/22 |
Molecular Structure | Hazard Symbols | Xi, Xn | |
Synonyms |
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 3-[(acetyloxy)methyl]-7-amino-8-oxo-, (6R-trans)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-amino-3-(hydroxymethyl)-8-oxo-, acetate (ester) (8CI);(7R)-7-Aminocephalosporanic acid;3-(Acetoxymethyl)-7-aminocephem-4-carboxylicacid;3-Acetoxymethyl-7-aminoceph-3-em-4-carboxylic acid;3-Acetoxymethyl-7b-aminoceph-3-em-4-carboxylicacid;7-ACA;7-ACS;7-Amino-3-acetoxymethyl-3-cephem-4-carboxylic acid;7-Amino-3-acetoxymethyl-D3-cephem-4-carboxylic acid;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 3-[(acetyloxy)methyl]-7-amino-8-oxo-, (6R,7R)-;7b-Amino-3-acetoxymethylcephemcarboxylicacid;7b-Aminocephalosporanic acid; |
Article Data | 19 |
Conditions | Yield |
---|---|
With phosphate buffer; enzyme derivative DAO; enzyme derivative GA at 25℃; for 2h; pH 8; | 96% |
With glutaryl acylase; D-aminoacid oxidase In water for 2.5h; pH = 8, O2; | 96% |
With D-amino acid oxidase; glutaryl acylase; oxygen In phosphate buffer at 25℃; for 3h; pH=8; |
benzhydryl 7-aminocephalosporanate
7-Aminocephalosporanic acid
Conditions | Yield |
---|---|
With formic acid at 40 - 45℃; for 0.5h; Product distribution; | 84% |
cephalosporin C
A
2-oxohexanedioic acid
B
7β-(5-carboxy-5-oxopentanamido)cephalosporanic acid
C
7-Aminocephalosporanic acid
Conditions | Yield |
---|---|
With sodium hydroxide; D-amino acid oxidase; bovine catalase (on glyoxyl agarose); glutaryl acylase (immobilized on polyethyleneimine) In phosphate buffer at 25℃; for 3h; pH=8; Enzymatic reaction; | A n/a B 2.5% C 80% |
Conditions | Yield |
---|---|
With potassium chloride In water at 30℃; Equilibrium constant; |
3-acetoxymethyl-7(R)-glutaroylaminoceph-3-em-4-carboxylic acid
7-Aminocephalosporanic acid
Conditions | Yield |
---|---|
With sodium hydroxide; glutaryl-7-aminocephalosporanic acid acylase In water at 25℃; pH=8.0; Enzyme kinetics; Enzymatic reaction; | |
With water at 37℃; for 0.5h; pH=7.5; Kinetics; Reagent/catalyst; aq. phosphate buffer; Enzymatic reaction; | |
With recombinant VAC enzyme at 25℃; for 0.166667h; pH=8; Kinetics; Reagent/catalyst; aq. buffer; Enzymatic reaction; |
3-acetoxymethyl-7(R)-glutaroylaminoceph-3-em-4-carboxylic acid
A
1,5-pentanedioic acid
B
7-Aminocephalosporanic acid
Conditions | Yield |
---|---|
With sodium hydroxide; glutaryl acylase (immobilized on polyethyleneimine) In phosphate buffer at 25℃; for 0.5h; pH=8.0; Enzymatic reaction; |
7β-(5-carboxy-5-oxopentanamido)cephalosporanic acid
A
2-oxohexanedioic acid
B
7-Aminocephalosporanic acid
Conditions | Yield |
---|---|
With sodium hydroxide; glutaryl acylase (immobilized on polyethyleneimine) In phosphate buffer at 25℃; for 0.5h; pH=8.0; Enzymatic reaction; |
7-Aminocephalosporanic acid
Conditions | Yield |
---|---|
With hydrogenchloride; 2-(Dimethylamino)pyridine; potassium hydroxide; acetic anhydride In water; ethyl acetate; acetone |
(6R)-3-acetoxymethyl-7t-((R)-5-amino-5-carboxy-pentanoylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; monosodium salt
7-Aminocephalosporanic acid
Conditions | Yield |
---|---|
With water at 25℃; pH=8; aq. phosphate buffer; Enzymatic reaction; |
7β-(5-carboxy-5-oxopentanamido)cephalosporanic acid
7-Aminocephalosporanic acid
Conditions | Yield |
---|---|
With water at 37℃; for 1h; pH=7.5; Kinetics; Reagent/catalyst; aq. phosphate buffer; Enzymatic reaction; |
ASSAY (HPLC) of 7-Aminocephalosporanic Acid: 95.0 - 102.0 %
IDENTITY: corresponding (IR-spectrum, HPLC)
pH: 3.0 - 5.0
OPTICAL ROTATION: +88° min
SULFATED ASH: 0.3% max
HEAVY METALS: 50ppm max
MOISTURE: 1.5% max
TRANSMITTANCE: 88.0% min (420 nm)
The purity of the isolated 7-Aminocephalosporanic Acid is analysed by reverse phase C18 HPLC using a Shimadzu HPLC system (LC- 10AT, Shimadzu, Japan) equipped with a Merck C18 column (5μm, Merck, Ger- many). The mobile phase was 2﹪ Acetonitrile in 20 mM AMMONIUM ACETATE pH 5.7 at 1.2 ml/min flow rate. Sample size was 20μl. The absorbance of the eluent was monitored at 260 nm. 7-ACA from Sigma, USA, served as a standard.
The 7-Aminocephalosporanic Acid, with the CAS registry number 957-68-6, is also known as 7-ACA; (6R,7S)-3-(Acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.It belongs to the product categories of Biochemistry;Amines;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals. This chemical's molecular formula is C10H12N2O5S and molecular weight is 259.09. Its EINECS number is 213-485-0. What's more,Its systematic name is 3-Acetoxymethylen-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid.
Physical properties about 7-Aminocephalosporanic Acid are:(1)ACD/LogP: -1.87; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4.56; (4)ACD/LogD (pH 7.4): -5.55; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 7; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.661; (13)Molar Refractivity: 62.815 cm3; (14)Molar Volume: 170.008 cm3; (15)Surface Tension: 80.2900009155273 dyne/cm; (16)Density: 1.602 g/cm3; (17)Flash Point: 292.852 °C; (18)Enthalpy of Vaporization: 92.178 kJ/mol; (19)Boiling Point: 560.619 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C;
The 7-Aminocephalosporanic Acid may cause sensitization by inhalation and skin contact.It is harmful by inhalation, in contact with skin and if swallowed,irritating to eyes, respiratory system and skin.When you use it,do not breathe dust,
avoid contact with skin and eyes,wear suitable protective clothing and gloves.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES:O=C2N1/C(=C(\CS[C@@H]1[C@@H]2N)COC(=O)C)C(=O)O;
(2)Std. 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;
(3)Std. InChIKey:HSHGZXNAXBPPDL-HZGVNTEJSA-N.