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A1625

Sigma-Aldrich

Acetoacetyl coenzyme A sodium salt hydrate

cofactor for acyl transfer

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Synonym(s):
Acetoacetyl-CoANa3
Empirical Formula (Hill Notation):
C25H40N7O18P3S · xNa+ · yH2O
CAS Number:
Molecular Weight:
851.61 (anhydrous free acid basis)
PubChem Substance ID:
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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1 of 4

This Item
295892A8509688983
vibrant-m

295892

Benzyl acetoacetate

vibrant-m

A8509

Lithium acetoacetate

vibrant-m

688983

Ethyl acetoacetate

assay

≥90%

assay

97%

assay

≥90% (HPLC)

assay

≥99.0% (GC)

storage temp.

−20°C

storage temp.

-

storage temp.

−20°C

storage temp.

-

form

powder

form

-

form

powder

form

liquid

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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James J Truglio et al.
The Journal of biological chemistry, 278(43), 42352-42360 (2003-08-12)
Bacterial enzymes of the menaquinone (Vitamin K2) pathway are potential drug targets because they lack human homologs. MenB, 1,4-dihydroxy-2-naphthoyl-CoA synthase, the fourth enzyme in the biosynthetic pathway leading from chorismate to menaquinone, catalyzes the conversion of O-succinylbenzoyl-CoA (OSB-CoA) to 1,4-dihydroxy-2-naphthoyl-CoA
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
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
Ken'ichiro Matsumoto et al.
Bioscience, biotechnology, and biochemistry, 75(2), 364-366 (2011-02-11)
A biosynthetic pathway for poly(3-hydroxybutyrate) [P(3HB)] was developed in Escherichia coli and Corynebacterium glutamicum by an acetoacetyl-coenzyme A (CoA) synthase (AACS) recently isolated from terpenoid-producing Streptomyces sp. strain CL190. Expression of AACS led to significant productions of P(3HB) in E.

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