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A1625

Sigma-Aldrich

Acetoacetyl coenzyme A sodium salt hydrate

cofactor for acyl transfer

Sinonimo/i:

Acetoacetyl-CoANa3

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About This Item

Formula empirica (notazione di Hill):
C25H40N7O18P3S · xNa+ · yH2O
Numero CAS:
1420-36-6
Peso molecolare:
851.61 (anhydrous free acid basis)
Codice UNSPSC:
41106305
ID PubChem:
24890567
NACRES:
NA.51

Origine biologica

synthetic (Organic)

Livello qualitativo

200

Saggio

≥90%

Stato

powder

Solubilità

H2O: soluble~-50 g/L

Temperatura di conservazione

−20°C

Stringa SMILE

[Na+].[Na+].[Na+].CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n2cnc3c(N)ncnc23

InChI

1S/C25H40N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-12,14,18-20,24,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18-,19-,20+,24-/m1/s1
OJFDKHTZOUZBOS-CITAKDKDSA-N

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Applicazioni

Acetoacetyl coenzyme A (Acetoacetyl-CoA) may be used as a substrate for a number of enzymes including; acetoacetyl-CoA thiolase (EC 2.3.1) which produces acetyl-CoA in reverse condensation reaction and (3-Hydroxy-3-methylglutaryl coenzyme A (CoA) synthase (HMGCS)) which produces 3-hydroxy-3-methylglutaryl (HMG)-CoA in the mevalonate pathway leading to terpenoid biosynthesis. Acetoacetyl-CoA is also a precursor of poly-beta-hydroxybutyrate polymers in microorganisms.
Substrate for acetoacetyl-CoA thiolase EC 2.3.1.9; Role in the biosynthesis of nonactin.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
SLCH7757
058K5055
057K5055
019H5963
012K7054

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Tamay Seker et al.
Applied microbiology and biotechnology, 67(1), 119-124 (2004-09-28)
The mevalonate pathway plays an important role in providing the cell with a number of essential precursors for the synthesis of biomass constituents. With respect to their chemical structure, the metabolites of this pathway can be divided into two groups:
Petri Kursula et al.
Biochemistry, 41(52), 15543-15556 (2002-12-27)
Biosynthetic thiolase catalyzes the formation of acetoacetyl-CoA from two molecules of acetyl-CoA. This is a key step in the synthesis of many biological compounds, including steroid hormones and ketone bodies. The thiolase reaction involves two chemically distinct steps; during acyl
E B Taylor et al.
American journal of physiology. Endocrinology and metabolism, 288(6), E1055-E1061 (2005-01-13)
Activation of the AMP-activated protein kinase (AMPK) results in acute changes in cellular metabolism and transcriptional events that make the cell more robust when encountering an energy challenge. AMPK is thought to be inhibited by glycogen, the major storage form
Ryan Sillers et al.
Biotechnology and bioengineering, 102(1), 38-49 (2008-08-30)
Metabolic engineering (ME) of Clostridium acetobutylicum has led to increased solvent (butanol, acetone, and ethanol) production and solvent tolerance, thus demonstrating that further efforts have the potential to create strains of industrial importance. With recently developed ME tools, it is
Michael J Theisen et al.
Proceedings of the National Academy of Sciences of the United States of America, 101(47), 16442-16447 (2004-10-23)
The formation of carbon-carbon bonds via an acyl-enzyme intermediate plays a central role in fatty acid, polyketide, and isoprenoid biosynthesis. Uniquely among condensing enzymes, 3-hydroxy-3-methylglutaryl (HMG)-CoA synthase (HMGS) catalyzes the formation of a carbon-carbon bond by activating the methyl group
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