(6R,7R)-3-(Acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Basic Information

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CAS Number

957-68-6

Molecular Formula

C10H12N2O5S

Molecular Weight

272.28 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Amines

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Basic Physical Properties

Melting Point

>300 °C

Boiling Point

560.6 °C at 760 mmHg

Density

1.4667 (rough estimate)

Flash Point

292.9 °C

Refractive Index

1.5650 (estimate)

Specific Rotation

94 º (c=0.5, KH2PO4, PH 7)

SMILES

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CC(=O)OCC1=C(N2[C@H](SC1)[C@H](N)C2=O)C(=O)O

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

LogP

-0.8693999999999988

Topological Polar Surface Area

109.92999999999999 Å²

Hydrogen Bond Donor/Acceptor

3 / 7

Complexity

461

Safety Information

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GHS Hazard Pictograms

H317

H334

Hazard Statement

H317 May cause an allergic skin reaction
Sensitization, Skin

H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled
Sensitization, respiratory

Stability

Hygroscopic

Synonyms & References

English

7-Aminocephalosporanic acid
(6r,7s)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
3-acetoxymethylen-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,TRANS)-3-[(ACETYLOXY)METHYL]-7-AMINO-8-OXO-5-THIA-1-AZABICYCLO[4.2.0]-OCT-2-CARBOXYLID ACID
7-Amino
5-Thia-1-azabicyclo4.2.0oct-2-ene-2-carboxylic acid, 3-(acetyloxy)methyl-7-amino-8-oxo-, (6R,7R)-
7-AMINO CEPHALOSPORIC ACID
7-AMINOCEPHALOSPORANIC ACID (7-ACA)
7-ACA (7-AMINOCEPHALOSPORANIC ACID)
7-AMINOCEPHALOSPORIC ACID (7-ACA)
7-Amino-3-acetoxymethyl-3-cephem-4-carboxylic acid
7-Amino-3-acetoxymethyl-D3-cephem-4-carboxylic acid
7b-Amino-3-acetoxymethylcephemcarboxylic acid
(6R,7R)-7-Amino-3-[(acetyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(7R)-3-Acetyloxymethyl-7-aminocepham-3-ene-4-carboxylic acid
7-ACA
7-ACS
7-Aminocephalsporanic acid
7beta-aminocephalosporanic acid
7-Aminocephalosporinic acid
(7R)-7-aminocephalosporanic acid
(7R)-7-Aminocephalosporanate
Cephalosporanic acid, 7-amino
(6R,7R)-3-(acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
9XI67897RG
(6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
DSSTox_CID_25342
DSSTox_RID_80810
DSSTox_GSID_45342
3-ac

MDL Number

MFCD00005177

Customs Code

2934996000

FAQ

What is (6R,7R)-3-(Acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (CAS: 957-68-6)?

This compound is a complex bicyclic molecule with a molecular formula of C10H15N2O5S. It features a fused ring system containing nitrogen and sulfur atoms, along with functional groups such as amino, carboxylic acid, and acetoxymethyl. Its chemical structure is characterized by stereochemistry at the 6R,7R positions, contributing to its specific biological activity. It is commonly used as an intermediate in pharmaceutical research due to its reactivity and structural versatility.

What are the main uses of (6R,7R)-3-(Acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (CAS: 957-68-6)?

This compound is primarily used in pharmaceuticals as a key intermediate in the synthesis of drugs targeting neurological and cardiovascular disorders. It also finds applications in biochemical research for studying enzyme interactions and in industrial processes for creating specialized chemical derivatives. Its unique structure makes it valuable for developing compounds with tailored therapeutic properties.

Is (6R,7R)-3-(Acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (CAS: 957-68-6) safe?

Safety depends on handling conditions. It may exhibit irritant properties and requires adherence to safety standards such as those outlined in the Globally Harmonized System (GHS). Precautions include wearing protective gloves, goggles, and clothing to avoid skin and eye contact. Proper ventilation and storage are critical to minimize exposure risks, and it is advisable to consult safety data sheets (SDS) for detailed guidelines.

How should (6R,7R)-3-(Acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (CAS: 957-68-6) be stored?

Store in a cool, dry, and dark place at 2-8°C to maintain stability. Keep in a sealed, airtight container to prevent moisture absorption and contamination. Avoid exposure to light and air to preserve chemical integrity. Proper storage conditions are essential to ensure safety and prolong shelf life, as degradation may occur under improper handling.