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7-Aminocephalosporanic acid - 2mM in DMSO, high purity , CAS No.957-68-6
Basic Description
Synonyms
7-Aminocephalosporanic acid | 957-68-6 | 7-ACA | 7-Aminocephalosporinic acid | 7-ACS | (7R)-7-aminocephalosporanic acid | 7beta-Aminocephalosporanic acid | Cephalosporanic acid, 7-amino | CHEBI:2255 | (6R,7R)-3-(acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-
Specifications & Purity
2mM in DMSO
Storage Temp
Store at -80°C
Shipped In
Ice chest + Ice pads
This product requires cold chain shipping. Ground and other economy services are not available.
Product Description
Product Application 7-Aminocephalosporanic acid (7-ACA) can be used as a starting material to synthesize:
Cefotaxime by acylation reaction with S-benzothiazol-2-yl(2-amino-4-thiazolyl)(methoxyimino)thioacetate (MAEM) in the presence of triethylamine.
Cefpodoxime proxetil, a third-generation antibiotic via cefotaxime intermediate.
Sodium 3′-substituted cephalosporanate sulfone derivatives as potential inhibitors of β-lactamase.
Taxonomic Classification
Kingdom
Organic compounds
Superclass
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Subclass
Amino acids, peptides, and analogues
Intermediate Tree Nodes
Amino acids and derivatives
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Cephems 1,3-thiazines Dicarboxylic acids and derivatives Tertiary carboxylic acid amides Amino acids Azetidines Carboxylic acid esters Thiohemiaminal derivatives Azacyclic compounds Dialkylthioethers Carboxylic acids Carbonyl compounds Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds
Molecular Framework
Aliphatic heteropolycyclic compounds
Substituents
Alpha-amino acid or derivatives - Cephem - Meta-thiazine - Dicarboxylic acid or derivatives - Beta-lactam - Tertiary carboxylic acid amide - Azetidine - Amino acid - Carboxamide group - Carboxylic acid ester - Lactam - Azacycle - Carboxylic acid - Organoheterocyclic compound - Dialkylthioether - Hemithioaminal - Thioether - Amine - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Carbonyl group - Organopnictogen compound - Primary aliphatic amine - Organonitrogen compound - Organooxygen compound - Primary amine - Organic oxide - Aliphatic heteropolycyclic compound
Description
This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
External Descriptors
alpha,beta-unsaturated monocarboxylic acid
Data sources
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Associated Targets(Human)
Associated Targets(non-human)
Mechanisms of Action
Mechanism of Action
Action Type
target ID
Target Name
Target Type
Target Organism
Binding Site Name
References
Names and Identifiers
IUPAC Name
(6R,7R)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
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
Smiles
CC(=O)OCC1=C(N2C(C(C2=O)N)SC1)C(=O)O
Isomeric SMILES
CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)N)SC1)C(=O)O
WGK Germany
3
Molecular Weight
272.28
Beilstein
622637
Reaxy-Rn
622637
Reaxys-RN_link_address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=622637&ln=
Certificates(CoA,COO,BSE/TSE and Analysis Chart)
Chemical and Physical Properties
Specific Rotation[α]
90° (C=0.5,buffer sol. pH7.0 KH2PO4)
Melt Point(°C)
>300°C
Molecular Weight
272.280 g/mol
XLogP3
-4.000
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
4
Exact Mass
272.047 Da
Monoisotopic Mass
272.047 Da
Topological Polar Surface Area
135.000 Ų
Heavy Atom Count
18
Formal Charge
0
Complexity
461.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
2
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Citations of This Product
1.
Weiwen Huang, Yichen Wang, Lumei Wang, Chaoqiang Pan, Guoqing Shen.
(2021)
Colorimetric detection of ciprofloxacin in aqueous solution based on an unmodified aptamer and the aggregation of gold nanoparticles.
Analytical Methods,
13
(1):
(90-98).
2.
Yi Haoyang, Yan Zhiyu, Wang Lumei, Zhou Xiaotong, Yan Rui, Zhang Dongwei, Shen Guoqing, Zhou Shanshan.
(2019)
Fluorometric determination for ofloxacin by using an aptamer and SYBR Green I.
MICROCHIMICA ACTA,
186
(10):
(1-9).
3.
Yanyan Zhao, Yongbo Wang, Xuhua Liang, Huanxian Shi, Cunjin Wang, Jun Fan, Xiaoyun Hu, Enzhou Liu.
(2019)
Enhanced photocatalytic activity of Ag-CsPbBr3/CN composite for broad spectrum photocatalytic degradation of cephalosporin antibiotics 7-ACA.
APPLIED CATALYSIS B-ENVIRONMENTAL,
247
(57).
4.
Xuan Ni, Bing Xia, Lumei Wang, Jing Ye, Gaoshang Du, Haiwei Feng, Xiaotong Zhou, Tong Zhang, Wenhao Wang.
(2017)
Fluorescent aptasensor for 17β-estradiol determination based on gold nanoparticles quenching the fluorescence of Rhodamine B.
ANALYTICAL BIOCHEMISTRY,
523
(17).
5.
Xiaotong Zhou,Lumei Wang,Guoqing Shen,Dongwei Zhang,Jialun Xie,Abdureyim Mamut,Weiwen Huang,Shanshan Zhou.
(2018-07-05)
Colorimetric determination of ofloxacin using unmodified aptamers and the aggregation of gold nanoparticles..
Mikrochimica acta,
185
((7)):
(355-355).
6.
Wei-Chuang Kong, Chen-Chen Li, Ai-Hong Zhang, Xin-Long Li, Qian-Rui Gong, Bing-Tan Jin, Xiao-Juan Jia, Xu-Ying Liu, Yan-Fei Kang.
(2024)
A colorimetric-aptamer-based assay for the determination of enrofloxacin through triggering the aggregation of gold nanoparticles.
Analytical Methods,
7.
Wen-Yuan Fan, Xin Zhang, Dong-Hua Xie, Kenneth Mei Yee Leung, Guo-Ping Sheng.
(2025)
Cerium-based nanohydrolase for fast catalytic hydrolysis of β-lactam antibiotics in wastewater effluents.
JOURNAL OF HAZARDOUS MATERIALS,
484
(136800).
8.
Zhenbin Chen, Haohan Cai, Feng Huang, Zongping Wang, Yiqun Chen, Zizheng Liu, Pengchao Xie.
(2024)
Degradation of β-lactam antibiotics by Fe(III)/HSO3− system and their quantitative structure-activity relationship.
ENVIRONMENTAL RESEARCH,
259
(119577).
9.
Shuqi Xing, Wei Xie, Guangli Hu, Chaocheng Luo, Hong Zhu, Laping He, Cuiqin Li, Xiao Wang, Xuefeng Zeng.
(2025)
The synthesis of cinnamyl acetate and deacetyl-7-aminocephalosporanic acid by a GDSL-type esterase and its substrate specificity analysis.
ENZYME AND MICROBIAL TECHNOLOGY,
182
(110532).
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