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(+)-6-Aminopenicillanic acid - 98%, high purity , CAS No.551-16-6

1 Citations

≥98%

CAS#: 551-16-6
Formula: C₈H₁₂N₂O₃S
Molecular Weight: 216.26
Beilstein Registry Number: 15080
EC Number: 208-993-4
MDL number: MFCD00005176
PubChem CID: 11082

Item Number

A101337

Grouped product items
SKU	Size	Availability	Price
A101337-5g	5g	In stock	$15.90
A101337-25g	25g	In stock	$45.90
A101337-100g	100g	In stock	$164.90
A101337-500g	500g	Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!	$738.90

View related series

asymmetric synthesis Pharmaceutical ingredients

Basic Description

Synonyms	FLUCLOXACILLIN SODIUM MONOHYDRATE IMPURITY C [EP IMPURITY] \| PHENOXYMETHYLPENICILLIN IMPURITY C [EP IMPURITY] \| SR-01000640154-1 \| Flucloxacillin impurity C, European Pharmacopoeia (EP) Reference Standard \| NSC-50071 \| SULBACTAM SODIUM IMPURITY B [EP IMPU
Specifications & Purity	≥98%
Storage Temp	Store at 2-8°C
Shipped In	Wet ice

Associated Targets(Human)

SLC15A2 Tchem Solute carrier family 15 member 2 (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC22A6 Tclin Solute carrier family 22 member 6 (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC15A1 Tchem Solute carrier family 15 member 1 (0 Activities)

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HDAC6 Tclin Histone deacetylase 6 (0 Activities)

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SLC22A8 Tclin Solute carrier family 22 member 8 (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

SLC15A1 Tchem Oligopeptide transporter small intestine isoform (922 Activities)

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SLC22A8 Tclin Solute carrier family 22 member 8 (241 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Proteus mirabilis (3894 Activities)

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Streptococcus mutans (2687 Activities)

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Plasmodium falciparum (966862 Activities)

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Slc15a2 Oligopeptide transporter, kidney isoform (114 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Slc22a6 Solute carrier family 22 member 6 (141 Activities)

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mecA MecA (155 Activities)

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fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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SARS-CoV-2 (38078 Activities)

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Names and Identifiers

IUPAC Name	(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
INCHI	InChI=1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
InChi Key	NGHVIOIJCVXTGV-ALEPSDHESA-N
Canonical SMILES	CC1(C(N2C(S1)C(C2=O)N)C(=O)O)C
Isomeric SMILES	CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N)C(=O)O)C
WGK Germany	2
RTECS	XH8225000
PubChem CID	11082
Molecular Weight	216.26
Beilstein	15080
Reaxy-Rn	15080

Certificates

Certificate of Analysis(COA)

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6 results found

Lot Number	Certificate Type	Date	Item
F2425078	Certificate of Analysis	Apr 02, 2024	A101337
D2016050	Certificate of Analysis	Jan 30, 2024	A101337
B2321243	Certificate of Analysis	Feb 27, 2023	A101337
B2321242	Certificate of Analysis	Feb 27, 2023	A101337
B2321244	Certificate of Analysis	Feb 27, 2023	A101337
L2219109	Certificate of Analysis	Dec 22, 2022	A101337

Chemical and Physical Properties

Specific Rotation[α]	275° (C=1.2,0.1mol/L HCl)
Melt Point(°C)	198-200°C

Safety and Hazards(GHS)

Pictogram(s)	GHS08
Signal	Danger
Hazard Statements	H317:May cause an allergic skin reaction H334:May cause allergy or asthma symptoms or breathing difficulties if inhaled
Precautionary Statements	P261:Avoid breathing dust/fume/gas/mist/vapors/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P342+P311:IF experiencing respiratory symptoms: Call a POISON CENTER/doctor/... P302+P352:IF ON SKIN: wash with plenty of water. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P403:Store in a well-ventilated place. P270:Do not eat, drink or smoke when using this product. P272:Contaminated work clothing should not be allowed out of the workplace. P333+P313:IF SKIN irritation or rash occurs: Get medical advice/attention. P330:Rinse mouth. P285:In case of inadequate ventilation wear respiratory protection. P304+P341:IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. P301+P312:IF SWALLOWED: call a POISON CENTER/doctor/... IF you feel unwell.
WGK Germany	2
RTECS	XH8225000
Reaxy-Rn	15080
Merck Index	458

Citations of This Product

1. Yixiang Cai, Hong Yu, Liheng Ren, Yingjuan Ou, Shilin Jiang, Youzheng Chai, Anwei Chen, Binghua Yan, Jiachao Zhang, Zhiyong Yan. (2023) Treatment of amoxicillin-containing wastewater by Trichoderma strains selected from activated sludge. SCIENCE OF THE TOTAL ENVIRONMENT, 867 (161565). [PMID:36642266]

References

1. G N Rolinson,A M Geddes. (2006-12-02) The 50th anniversary of the discovery of 6-aminopenicillanic acid (6-APA).. International journal of antimicrobial agents, 29 ((1)): (3-8). [PMID:17137753]
2. A T Karagulle Kendi,C Krenzel,F W Ott,J R Brace,S K Norberg,S A Kieffer. (2008-05-03) Poststreptococcal dystonia with bilateral striatal enlargement: MR imaging and spectroscopic findings.. AJNR. American journal of neuroradiology, 29 ((7)): (1276-1278). [PMID:18451091]
3. Yangyang Jiang,Hansong Xia,Chen Guo,Iram Mahmood,Huizhou Liu. (2008-05-06) Enzymatic hydrolysis of penicillin for 6-APA production in three-liquid-phase system.. Applied biochemistry and biotechnology, 144 ((2)): (145-159). [PMID:18456946]
4. Weihua Song,Weisang Chen,William J Cooper,John Greaves,George E Miller. (2008-07-22) Free-radical destruction of beta-lactam antibiotics in aqueous solution.. The journal of physical chemistry. A, 112 ((32)): (7411-7417). [PMID:18637660]
5. Rubina Arshad,Shafqat Farooq,Syed Shahid Ali. (2008-12-19) Comparative production of 6-aminopenicillanic acid by different E. coli strains and their acridine orange (AO) induced mutants.. Pakistan journal of biological sciences : PJBS, 10 ((21)): (3931-3935). [PMID:19090257]
6. Louis Anthony Tony Cox,Douglas A Popken,Jeremy J Mathers. (2009-06-06) Human health risk assessment of penicillin/aminopenicillin resistance in enterococci due to penicillin use in food animals.. Risk analysis : an official publication of the Society for Risk Analysis, 29 ((6)): (796-805). [PMID:19490520]
7. José Luis Martínez-Hernández,Marco Arnulfo Mata-Gómez,Cristóbal Noé Aguilar-González,Anna Ilyina. (2009-09-22) A process to produce penicillin G acylase by surface-adhesion fermentation using Mucor griseocyanus to obtain 6-aminopenicillanic acid by penicillin G hydrolysis.. Applied biochemistry and biotechnology, 160 ((7)): (2045-2053). [PMID:19768388]
8. Shu-Guang Fang,Tan Qiang,Rui-Jiang Liu,Xi-Ming Xu,Ye-Wang Zhang. (2009-12-22) Enhanced production of 6-aminopenicillanic acid in aqueous methyl isobutyl ketone system with immobilized penicillin G acylase.. Preparative biochemistry & biotechnology, 40 ((1)): (38-45). [PMID:20024793]
9. Ye-Wang Zhang,Rui-Jiang Liu,Xi-Ming Xu. (2010-06-23) One-pot, two-step enzymatic synthesis of amoxicillin by complexing with Zn2+.. Applied microbiology and biotechnology, 88 ((1)): (49-55). [PMID:20567815]
10. Nolwenn Coquart,Ingrid Kupfer-Bessaguet,Frédéric Staroz,Patrice Plantin. (2010-07-16) Acute generalized exanthematous pustulosis (AGEP) induced by terbinafine and two different antibiotics: four recurrences.. European journal of dermatology : EJD, 20 ((5)): (638-639). [PMID:20627850]
11. Junqi Zhao,Yujun Wang,Guangsheng Luo,Shenlin Zhu. (2010-10-23) Immobilization of penicillin G acylase on macro-mesoporous silica spheres.. Bioresource technology, 102 ((2)): (529-535). [PMID:20965720]
12. Zhiqiang Chen,Hongcheng Wang,Zhaobo Chen,Nanqi Ren,Aijie Wang,Yue Shi,Xiaoming Li. (2010-10-26) Performance and model of a full-scale up-flow anaerobic sludge blanket (UASB) to treat the pharmaceutical wastewater containing 6-APA and amoxicillin.. Journal of hazardous materials, 185 ((2-3)): (905-913). [PMID:20970923]
13. J-L Schmutz,A Barbaud,P Trechot. (2011-05-17) [Four recurrences of acute generalized exanthematous pustulosis (AGEP) with three different drugs in the same patient].. Annales de dermatologie et de venereologie, 138 ((5)): (456-456). [PMID:21570578]
14. V B Kurochkina,A V Sklyarenko,J E Satarova,S V Yarotsky. (2011-06-24) Ionization constants and solubility of compounds involved in enzymatic synthesis of aminopenicillins and aminocephalosporins.. Bioprocess and biosystems engineering, 34 ((9)): (1103-1117). [PMID:21698348]
15. Cătălina Daniela Stan,Alina Stefanache,Maria Drăgan,Antonia Poiată,D E Diaconu,Lenuţa Profire. (2011-11-04) [Research for the improvement of acylation conditions in antistaphylococcal penicillin synthesis].. Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi, 115 ((3)): (972-977). [PMID:22046818]
16. Faridoon,Waleed M Hussein,Nazar Ul Islam,Luke W Guddat,Gerhard Schenk,Ross P McGeary. (2012-03-01) Penicillin inhibitors of purple acid phosphatase.. Bioorganic & medicinal chemistry letters, 22 ((7)): (2555-2559). [PMID:22366658]
17. Joanna Skiba,Aleksandra Rajnisz,Kely Navakoski de Oliveira,Ingo Ott,Jolanta Solecka,Konrad Kowalski. (2012-10-18) Ferrocenyl bioconjugates of ampicillin and 6-aminopenicillinic acid--synthesis, electrochemistry and biological activity.. European journal of medicinal chemistry, 57 (234-239). [PMID:23072737]
18. Lucie Vobecká,Alexandr Romanov,Zdeněk Slouka,Pavel Hasal,Michal Přibyl. (2018-04-04) Optimization of aqueous two-phase systems for the production of 6-aminopenicillanic acid in integrated microfluidic reactors-separators.. New biotechnology, 47 (73-79). [PMID:29614323]
19. Terence S Crofts,Bin Wang,Aaron Spivak,Tara A Gianoulis,Kevin J Forsberg,Molly K Gibson,Lauren A Johnsky,Stacey M Broomall,C Nicole Rosenzweig,Evan W Skowronski,Henry S Gibbons,Morten O A Sommer,Gautam Dantas. (2018-05-02) Shared strategies for β-lactam catabolism in the soil microbiome.. Nature chemical biology, 14 ((6)): (556-564). [PMID:29713061]
20. Alexandr Romanov,Zdeněk Slouka,Michal Přibyl. (2020-10-14) Electric-field-enhanced selective separation of products of an enzymatic reaction in a membrane micro-contactor.. Biotechnology and bioengineering, 118 ((2)): (715-724). [PMID:33049066]
21. G N Rolinson. (1988-07-01) The Garrod lecture. The influence of 6-aminopenicillanic acid on antibiotic development.. The Journal of antimicrobial chemotherapy, 22 ((1)): (5-14). [PMID:2844714]
22. Pak-Ho Chan,Pui-Kin So,Dik-Lung Ma,Yanxiang Zhao,Tat-Shing Lai,Wai-Hong Chung,Kwok-Chu Chan,Ka-Fai Yiu,Hoi-Wan Chan,Fung-Ming Siu,Chun-Wai Tsang,Yun-Chung Leung,Kwok-Yin Wong. (2008-04-24) Fluorophore-labeled beta-lactamase as a biosensor for beta-lactam antibiotics: a study of the biosensing process.. Journal of the American Chemical Society, 130 ((20)): (6351-6361). [PMID:18429614]
23. Lisa M Bergeron,David L Shis,Lizabeth Gomez,Douglas S Clark. (2008-11-04) Small molecule inhibition of a Group II chaperonin: pinpointing a loop region within the equatorial domain as necessary for protein refolding.. Archives of biochemistry and biophysics, 481 ((1)): (45-51). [PMID:18976628]
24. Teresa Jackowska,Katarzyna Pawlik,Joanna Załeska-Ponganis,Magdalena Kłyszewska. (2009-05-08) [Etiology of urinary tract infections and antimicrobial susceptibility: a study conducted on a population of children hospitalized in the Department of Pediatrics at Warsaw Bielany Hospital; 2004-2006].. Medycyna wieku rozwojowego, 12 ((2 Pt 2)): (705-712). [PMID:19418948]
25. David A Harris,Michael E Powers,Floyd E Romesberg. (2009-05-12) Synthesis and biological evaluation of penem inhibitors of bacterial signal peptidase.. Bioorganic & medicinal chemistry letters, 19 ((14)): (3787-3790). [PMID:19427205]
26. Edson Romano Nucci,Antonio J G Cruz,Roberto C Giordano. (2009-09-04) Monitoring bioreactors using principal component analysis: production of penicillin G acylase as a case study.. Bioprocess and biosystems engineering, 33 ((5)): (557-564). [PMID:19727832]
27. J Swaminathan,M Ramalingam,V Sethuraman,N Sundaraganesan,S Sebastian,M Kurt. (2009-11-10) FT-IR, FT-Raman, ab initio and DFT structural and vibrational frequency analysis of 6-aminopenicillanic acid.. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 75 ((1)): (183-190). [PMID:19897407]
28. A K Dolui,S Das. (2011-05-28) Comparative study of 6-APA production by free and agar immobilized bacteria in nutrient broth culture.. Indian journal of experimental biology, 49 ((4)): (289-292). [PMID:21614893]
29. Chunqiu Tian,Huarong Tan,Liping Gao,Huqin Shen,Kezong Qi. (2012-03-08) [Determination of penicillin intermediate and three penicillins in milk by high performance capillary electrophoresis].. Se pu = Chinese journal of chromatography, 29 ((11)): (1128-1132). [PMID:22393704]
30. Francesco Crea,Daniela Cucinotta,Concetta De Stefano,Demetrio Milea,Silvio Sammartano,Giuseppina Vianelli. (2012-08-21) Modeling solubility, acid-base properties and activity coefficients of amoxicillin, ampicillin and (+)6-aminopenicillanic acid, in NaCl(aq) at different ionic strengths and temperatures.. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 47 ((4)): (661-677). [PMID:22903046]
31. Anand Pai,Yu Tanouchi,Lingchong You. (2012-11-13) Optimality and robustness in quorum sensing (QS)-mediated regulation of a costly public good enzyme.. Proceedings of the National Academy of Sciences of the United States of America, 109 ((48)): (19810-19815). [PMID:23144221]
32. Guolin Li,Cen Xie,Siyu Lu,Robert G Nichols,Yuan Tian,Licen Li,Daxeshkumar Patel,Yinyan Ma,Chad N Brocker,Tingting Yan,Kristopher W Krausz,Rong Xiang,Oksana Gavrilova,Andrew D Patterson,Frank J Gonzalez. (2017-09-19) Intermittent Fasting Promotes White Adipose Browning and Decreases Obesity by Shaping the Gut\xa0Microbiota.. Cell metabolism, 26 ((4)): (672-685). [PMID:28918936]
33. Yixiang Cai, Hong Yu, Liheng Ren, Yingjuan Ou, Shilin Jiang, Youzheng Chai, Anwei Chen, Binghua Yan, Jiachao Zhang, Zhiyong Yan. (2023) Treatment of amoxicillin-containing wastewater by Trichoderma strains selected from activated sludge. SCIENCE OF THE TOTAL ENVIRONMENT, 867 (161565). [PMID:36642266]

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(+)-6-Aminopenicillanic acid - 98%, high purity , CAS No.551-16-6

Basic Description

Associated Targets(Human)

Associated Targets(non-human)

Names and Identifiers

Certificates

Certificate of Analysis(COA)

Chemical and Physical Properties

Safety and Hazards(GHS)

Related Documents

Citations of This Product

References

Solution Calculators

Molarity Calculator

Dilution Calculator

Reconstitution Calculator