7-Aminocephalosporanic acid
- Iupac Name：(6R,7R)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- CAS No.: 957-68-6
- Molecular Weight：272.275
- Modify Date.: 2022-11-29 06:06
- Introduction: Pharmaceutical intermediates. It is the starting material of many semi-synthetic cephalosporin. A variety of semi-synthetic cephalosporin industrial production is through fermentation to obtain cephalosporin C. Then obtain nucleus 7-ACA through chemical cleavage , and then the preparation is fininshed in chemically modified way .
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1. Names and Identifiers
- 1.1 Name
- 7-Aminocephalosporanic acid
- 1.2 Synonyms
(6R,7R)-3-(acetyloxymethyl)-7-ammonio-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (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 3-Acetoxymethyl-7-aminoceph-3-em-4-carboxylic acid 3-Acetoxymethyl-7β-aminoceph-3-em-4-carboxylic acid 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-amino-8-oxo-, (6R,7R)- 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 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) 7-ACA 7-ACA Impurity 7-ACS 7-Amino-3-acetoxymethyl-3-cephem-4-carboxylic acid 7-Amino-3-acetoxymethyl-Δ3-cephem-4-carboxylic acid 7β-Amino-3-acetoxymethylcephemcarboxylic acid 7β-Aminocephalosporanic acid Aminocephalosporanic Cefazolin EP Impurity H Cefazolin Sodium EP Impurity H (7-Aminocephalosporanic Acid) Ceftriaxone Impurity 18
- 1.3 CAS No.
- 957-68-6
- 1.4 CID
- 441328
- 1.5 EINECS(EC#)
- 213-485-0
- 1.6 Molecular Formula
- C10H12N2O5S (isomer)
- 1.7 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
- 1.8 InChkey
- HSHGZXNAXBPPDL-HZGVNTEJSA-N
- 1.9 Canonical Smiles
- CC(=O)OCC1=C(N2C(C(C2=O)N)SC1)C(=O)O
- 1.10 Isomers Smiles
- CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)N)SC1)C(=O)O
2. Properties
- 2.1 Density
- 1.6
- 2.1 Melting point
- 300℃
- 2.1 Boiling point
- 560.6 °C at 760 mmHg
- 2.1 Refractive index
- 1.66
- 2.1 Flash Point
- 292.9 °C
- 2.1 Precise Quality
- 272.04700
- 2.1 PSA
- 135.23000
- 2.1 logP
- -0.23120
- 2.1 Solubility
- 409.6mg/L(22.99 ºC)
- 2.2 Appearance
- Off-white to beige crystalline powder
- 2.3 Storage
- Keep Cold.
- 2.4 Chemical Properties
- Crystals.
- 2.5 Color/Form
- Off-white to beige
- 2.6 pKa
- 2.59±0.50(Predicted)
- 2.7 Water Solubility
- 409.6mg/L(22.99 oC)
- 2.8 Stability
- Hygroscopic
- 2.9 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: The alpha,beta-unsaturated monocarboxylic acid that is the active nucleus for the synthesis of cephalosporins and intermediates. 7-Aminocephalosporanic acid Preparation Products And Raw materials Preparation Products
- 3.2 Usage
- Pharmaceutical intermediates. It is the starting material of many semi-synthetic cephalosporin. A variety of semi-synthetic cephalosporin industrial production is through fermentation to obtain cephalosporin C. Then obtain nucleus 7-ACA through chemical cleavage , and then the preparation is fininshed in chemically modified way .
4. Safety and Handling
- 4.1 Hazard Codes
- Xn; Xi
- 4.1 Risk Statements
- R42/43
- 4.1 Safety Statements
- S24/25
- 4.1 Hazard Declaration
- H317-H334
- 4.1 RIDADR
- 25kgs
- 4.1 Caution Statement
- P261-P280-P342 + P311
- 4.1 WGK Germany
- 3
- 4.1 Safety
-
Hazard Codes:?
Xn,?
Xi
Risk Statements: 42/43-36/37/38-20/21/22?
R42/43:May cause sensitization by inhalation and skin contact.?
R36/37/38:Irritating to eyes, respiratory system and skin.?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-36/37-24/25-36-26?
S22:Do not breathe dust.?
S36/37:Wear suitable protective clothing and gloves.?
S24/25:Avoid contact with skin and eyes.?
S36:Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
- 4.2 Specification
-
?7-Aminocephalosporanic Acid (CAS NO.957-68-6) is also named as 7-ACA ; 7-ACS ; 7beta-Aminocephalosporanic acid ; 3-Acetoxymethylen-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid .?7-Aminocephalosporanic Acid (CAS NO.957-68-6) is off-white to beige crystalline powder.
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin sensitization, Category 1
Respiratory sensitization, Category 1
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Danger |
| Hazard statement(s) | H317 May cause an allergic skin reaction H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled |
| Precautionary statement(s) | |
| Prevention | P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P284 [In case of inadequate ventilation] wear respiratory protection. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P342+P311 If experiencing respiratory symptoms: Call a POISON CENTER/doctor/... |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
6. Synthesis Route
957-68-6Total: 9 Synthesis Route
8. Other Information
- 8.0 Merck
- 14,434
- 8.1 BRN
- 622638
- 8.2 Chemical Properties
- Crystals.
- 8.3 Uses
- Pharmaceutical intermediates. It is the starting material of many semi-synthetic cephalosporin. A variety of semi-synthetic cephalosporin industrial production is through fermentation to obtain cephalosporin C. Then obtain nucleus 7-ACA through chemical cleavage , and then the preparation is fininshed in chemically modified way .
- 8.4 production method
- Starting from the basic raw material of semi-synthetic cephalosporin-cephalosporin C, after esterification with trimethylchlorosilane , and then by phosphorus pentachloride chloride, and Butanol etherifying, and the production is obtained finally through hydrolysis. Yield from cephalosporin C sodium to 7-ACA is about 50%.
- 8.5 Chemical Properties
- Off-white to beige crystalline powder
- 8.6 Uses
- It is the starting material for semi-synthetic cephalosporins. Obtained by mild acid hydrolysis of cephalosporin C.
- 8.7 Uses
- Antibacterial;Bacterial transpeptidase inhibitor
- 8.8 Definition
- ChEBI: The alpha,beta-unsaturated monocarboxylic acid that is the active nucleus for the synthesis of cephalosporins and intermediates.
- 8.9 Mesh Entry Terms
- 7-ACA cpd
9. Computational chemical data
- Molecular Weight: 272.275g/mol
- Molecular Formula: C10H12N2O5S
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 272.04669266
- Monoisotopic Mass: 272.04669266
- Complexity: 461
- Rotatable Bond Count: 4
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 7
- Topological Polar Surface Area: 135
- Heavy Atom Count: 18
- Defined Atom Stereocenter Count: 2
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBzOABAAAAAAAAAAAAAAABYAAAAAAAgAAAAAAAQAAAAAAAAHgQQCAAADCjlwAaCCANABgiIAgXQWAAAAABAABAACIGIAEACRAggICAWEAAAFgCwMQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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11. Realated Product Infomation
-
15690-38-7
Hydroxymethyl-7-Aminocephalosporanic acid
-
71010-76-9
Decanoic acid, mixed esters with heptanoic acid, octanoic acid, pentaerythritol and valeric acid
-
68130-55-2
Hexanedioic acid, mixed esters with decanoic acid, heptanoic acid, octanoic acid and pentaerythritol
-
68130-51-8
Decanoic acid, mixed esters with heptanoic acid, isovaleric acid, octanoic acid and pentaerythritol
-
24939-03-5
Polyinosinic acid-polycytidylic acid
-
68441-66-7
Decanoic acid, mixed esters with dipentaerythritol, octanoic acid and valeric acid
-
68130-52-9
Decanoic acid, mixed esters with hexanoic acid, octanoic acid and trimethylolpropane
skype
1YR
