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A1625

Sigma-Aldrich

Acetoacetyl coenzyme A sodium salt hydrate

cofactor for acyl transfer

Synonym(s):

Acetoacetyl-CoANa3

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About This Item

Empirical Formula (Hill Notation):
C25H40N7O18P3S · xNa+ · yH2O
CAS Number:
1420-36-6
Molecular Weight:
851.61 (anhydrous free acid basis)
UNSPSC Code:
41106305
PubChem Substance ID:
24890567
NACRES:
NA.51

Assay

≥90%

form

powder

storage temp.

−20°C

SMILES string

[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

InChI key

OJFDKHTZOUZBOS-CITAKDKDSA-N

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Application

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Alzheimer's disease (AD) is characterized by progressive synaptic dysfunction, neuronal death, and brain atrophy, with amyloid-β (Aβ) plaque deposits and hyperphosphorylated tau neurofibrillary tangle accumulation in the brain tissue, which all lead to loss of cognitive function. Pathogenic mutations in
Clementina Dellomonaco et al.
Nature, 476(7360), 355-359 (2011-08-13)
Advanced (long-chain) fuels and chemicals are generated from short-chain metabolic intermediates through pathways that require carbon-chain elongation. The condensation reactions mediating this carbon-carbon bond formation can be catalysed by enzymes from the thiolase superfamily, including β-ketoacyl-acyl-carrier protein (ACP) synthases, polyketide
Werner J Kovacs et al.
Progress in lipid research, 41(5), 369-391 (2002-07-18)
Peroxisomes contain enzymes catalyzing a number of indispensable metabolic functions mainly related to lipid metabolism. The importance of peroxisomes in man is stressed by the existence of genetic disorders in which the biogenesis of the organelle is defective, leading to
Toshiyuki Fukao et al.
Molecular genetics and metabolism, 100(1), 37-41 (2010-02-17)
Mitochondrial acetoacetyl-CoA thiolase (T2) deficiency is an inborn error of metabolism affecting isoleucine catabolism and ketone body utilization. This disorder is clinically characterized by intermittent ketoacidotic episodes with no clinical symptoms between episodes. In general, T2 gene mutations are heterogeneous.
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