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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

biological source

synthetic (Organic)

Quality Level

200

Assay

≥90%

form

powder

solubility

H2O: soluble~-50 g/L

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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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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