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870708P

Avanti

08:0 Coenzyme A

Avanti Polar Lipids 870708P, powder

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Synonym(s):
octanoyl Coenzyme A (ammonium salt)
Empirical Formula (Hill Notation):
C29H59N10O17P3S
CAS Number:
799812-82-1
Molecular Weight:
944.82
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 5 mg (870708P-5mg)

manufacturer/tradename

Avanti Polar Lipids 870708P

application(s)

lipidomics

lipid type

coenzymes

shipped in

dry ice

storage temp.

−20°C

SMILES string

O[C@@](C(NCCC(NCCSC(CCCCCCC)=O)=O)=O)(C(C)(COP([O-])(OP([O-])(OC[C@H]([C@H]1OP([O-])(O)=O)O[C@H]([C@@H]1O)N2C3=C(C(N)=NC=N3)N=C2)=O)=O)C)[H].[NH4+].[NH4+].[NH4+]

InChI

1S/C29H50N7O17P3S.3H3N/c1-4-5-6-7-8-9-20(38)57-13-12-31-19(37)10-11-32-27(41)24(40)29(2,3)15-50-56(47,48)53-55(45,46)49-14-18-23(52-54(42,43)44)22(39)28(51-18)36-17-35-21-25(30)33-16-34-26(21)36;;;/h16-18,22-24,28,39-40H,4-15H2,1-3H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44);3*1H3/t18-,22?,23+,24+,28-;;;/m1.../s1

InChI key

FTIQWXKUZWNHGD-DMTDIVBASA-N

General description

08:0 Coenzyme A, also referred as octanoyl Coenzyme A, is a medium-chain acyl CoA. It is a coenzyme A derivative of octanoic acid.

Application

08:0 Coenzyme A has been used as a substrate in microsomal ghrelin octanoyltransferase assay.

Biochem/physiol Actions

08:0 Coenzyme A acts as an intermediate in mitochondrial fatty acid β-oxidation. It hinders the activity of citrate synthase (CS) and glutamate dehydrogenase (GDH). Higher levels of octanoyl –CoA, due to reduced β-oxidation of octanoyl-CoA by medium-chain acyl CoA dehydrogenase (MCADH), is observed in patients with MCADH deficiency (MCD).

Packaging

5 mL Amber Glass Screw Cap Vial (870708P-5mg)

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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B A Amendt et al.
The Journal of clinical investigation, 76(3), 963-969 (1985-09-01)
Medium-chain acyl-coenzyme A (CoA) dehydrogenase (MCADH; EC 1.3.99.3) deficiency (MCD) is an inborn error of beta-oxidation. We measured 3H2O formed by the dehydrogenation of [2,3-3H]acyl-CoAs in a 3H-release assay. Short-chain acyl-CoA dehydrogenase (SCADH; EC 1.3.99.2), MCADH, and isovaleryl-CoA dehydrogenase (IVDH;
Robert Modre-Osprian et al.
BMC systems biology, 3, 2-2 (2009-01-08)
The oxidation of fatty acids in mitochondria plays an important role in energy metabolism and genetic disorders of this pathway may cause metabolic diseases. Enzyme deficiencies can block the metabolism at defined reactions in the mitochondrion and lead to accumulation
J C Lai et al.
Research communications in chemical pathology and pharmacology, 82(3), 331-338 (1993-12-01)
We investigated the hypothesis that one mechanism underlying fatty acid toxicity is the selective inhibition of rate-limiting and/or regulated tricarboxylic acid cycle and related enzymes by fatty acyl coenzyme A (CoA) derivatives by examining the effects of several fatty acyl
Martin S Taylor et al.
Bioorganic chemistry, 62, 64-73 (2015-08-08)
Ghrelin-O-Acyltransferase (GOAT) is an 11-transmembrane integral membrane protein that octanoylates the metabolism-regulating peptide hormone ghrelin at Ser3 and may represent an attractive target for the treatment of type II diabetes and the metabolic syndrome. Protein octanoylation is unique to ghrelin

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