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Basic Information
CAS No.: 957-68-6
Name: 7-Aminocephalosporanic acid
Article Data: 19
Molecular Structure:
Molecular Structure of 957-68-6 (7-Aminocephalosporanic acid)
Formula: C10H12N2O5S
Molecular Weight: 272.282
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;
EINECS: 213-485-0
Density: 1.6 g/cm3
Melting Point: >300 °C(lit.)
Boiling Point: 560.6 °C at 760 mmHg
Flash Point: 292.9 °C
Solubility: 409.6mg/L(22.99 oC)
Appearance: off-white to beige crystalline powder
Hazard Symbols: IrritantXi, HarmfulXn
Risk Codes: 42/43-36/37/38-20/21/22
Safety: 22-36/37-24/25-36-26
PSA: 135.23000
LogP: -0.23120
Synthetic route
61-24-5

cephalosporin C

957-68-6

7-Aminocephalosporanic acid

Conditions
ConditionsYield
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;
27266-61-1, 54600-89-4

benzhydryl 7-aminocephalosporanate

957-68-6

7-Aminocephalosporanic acid

Conditions
ConditionsYield
With formic acid at 40 - 45℃; for 0.5h; Product distribution;84%
61-24-5

cephalosporin C

A

3184-35-8

2-oxohexanedioic acid

B

28242-83-3

7β-(5-carboxy-5-oxopentanamido)cephalosporanic acid

C

957-68-6

7-Aminocephalosporanic acid

Conditions
ConditionsYield
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%
64-19-7

acetic acid

2-(Amino-propylcarbamoyl-methyl)-5-methylene-5,6-dihydro-2H-[1,3]thiazine-4-carboxylic acid

A

107-10-8

propylamine

B

957-68-6

7-Aminocephalosporanic acid

Conditions
ConditionsYield
With potassium chloride In water at 30℃; Equilibrium constant;
27920-90-7

3-acetoxymethyl-7(R)-glutaroylaminoceph-3-em-4-carboxylic acid

957-68-6

7-Aminocephalosporanic acid

Conditions
ConditionsYield
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;
27920-90-7

3-acetoxymethyl-7(R)-glutaroylaminoceph-3-em-4-carboxylic acid

A

110-94-1

1,5-pentanedioic acid

B

957-68-6

7-Aminocephalosporanic acid

Conditions
ConditionsYield
With sodium hydroxide; glutaryl acylase (immobilized on polyethyleneimine) In phosphate buffer at 25℃; for 0.5h; pH=8.0; Enzymatic reaction;
28242-83-3

7β-(5-carboxy-5-oxopentanamido)cephalosporanic acid

A

3184-35-8

2-oxohexanedioic acid

B

957-68-6

7-Aminocephalosporanic acid

Conditions
ConditionsYield
With sodium hydroxide; glutaryl acylase (immobilized on polyethyleneimine) In phosphate buffer at 25℃; for 0.5h; pH=8.0; Enzymatic reaction;

7-[(2-carbomethoxy-1-methylethylene)amino]-3-hydroxymethyl-3-cephem-4-carboxylic acid potassium salt

957-68-6

7-Aminocephalosporanic acid

Conditions
ConditionsYield
With hydrogenchloride; 2-(Dimethylamino)pyridine; potassium hydroxide; acetic anhydride In water; ethyl acetate; acetone
51762-04-0

(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

957-68-6

7-Aminocephalosporanic acid

Conditions
ConditionsYield
With water at 25℃; pH=8; aq. phosphate buffer; Enzymatic reaction;
28242-83-3

7β-(5-carboxy-5-oxopentanamido)cephalosporanic acid

957-68-6

7-Aminocephalosporanic acid

Conditions
ConditionsYield
With water at 37℃; for 1h; pH=7.5; Kinetics; Reagent/catalyst; aq. phosphate buffer; Enzymatic reaction;
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Standards and Recommendations

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)

Analytical Methods

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.

Specification

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.