acetoacetyl-CoA

Base Information

• Chemical Name: acetoacetyl-CoA
• CAS No.: 1420-36-6
• Molecular Formula: C25H40 N7 O18 P3 S
• Molecular Weight: 851.616
• European Community (EC) Number: 215-815-9
• DSSTox Substance ID: DTXSID30931292
• Nikkaji Number: J670.888I
• Wikipedia: Acetoacetyl-CoA
• Wikidata: Q2639429
• Metabolomics Workbench ID: 4428
• Mol file: 1420-36-6.mol

Synonyms:acetoacetyl CoA;acetoacetyl coenzyme A

Chemical Property of acetoacetyl-CoA

Chemical Property:

• Density: 1.87g/cm³
• XLogP3: -5.8
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 23
• Rotatable Bond Count: 22
• Exact Mass: 851.13633962
• Heavy Atom Count: 54
• Complexity: 1490

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O
• Isomeric SMILES: CC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O

Technology Process of acetoacetyl-CoA

There total 12 articles about acetoacetyl-CoA which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

β-hydroxybutyryl CoA (2871-66-1,21804-29-5,22138-45-0) → acetoacetyl coenzyme A (1420-36-6)

Guidance literature:

With β-hydroxybutyryl CoA dehydrogenase from Clostridium acetobutylicum ATCC 824; In aq. buffer; at 50 ℃; Kinetics; Enzymatic reaction;

DOI:10.1016/j.molcatb.2013.10.014

Reference yield:

(2R)-2,4-dihydroxy-3,3-dimethyl-N-[2-([2-[(3-oxobutanoyl)sulfanyl]ethyl]carbamoyl)ethyl]butanamide + ATP (56-65-5,896506-78-8) → acetoacetyl coenzyme A (1420-36-6)

Guidance literature:

With CoaA, CoaD and CoaE enzymes were amplified from a colony of E_. coli BL₂₁(DE₃); In dimethyl sulfoxide; at 30 ℃; for 3h; pH=6.5 - 7.5; Enzymatic reaction;

DOI:10.1021/acs.orglett.5b02113

Reference yield:

3-{[(4R)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl]carbonylamino}propionic acid (167308-62-5) → acetoacetyl coenzyme A (1420-36-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h

2.1: toluene / 18 h / Reflux

2.2: 5 h

3.1: CoaA, CoaD and CoaE enzymes were amplified from a colony of E_. coli BL₂₁(DE₃) / dimethyl sulfoxide / 3 h / 30 °C / pH 6.5 - 7.5 / Enzymatic reaction

With CoaA, CoaD and CoaE enzymes were amplified from a colony of E_. coli BL₂₁(DE₃); benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1021/acs.orglett.5b02113

upstream raw materials:

S-phenyl 3-oxobutanethioate

coenzyme A

(S)-3-hydroxybutyryl-Coenzyme A

(R)-3-hydroxybutyryl-Coenzyme A

Downstream raw materials:

DL-3-hydroxy-3-methylglutaryl coenzyme A

acetoacetic acid anion

4-hydroxy-6-methyl-2-pyron

β-hydroxybutyryl CoA