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Key Documents

P6775

Sigma-Aldrich

Palmitoleoyl coenzyme A lithium salt

~90%

Synonym(s):

cis-9-Hexadecenoyl Coenzyme A

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About This Item

Empirical Formula (Hill Notation):
C37H64N7O17P3S
CAS Number:
18198-76-0
Molecular Weight:
1003.93
MDL number:
MFCD00079261
UNSPSC Code:
41106305
PubChem Substance ID:
24898796
NACRES:
NA.51

Assay

~90%

form

powder

storage temp.

−20°C

SMILES string

([Li].C(CCCCCCC\C=C/CCCCCC)(=O)SCCNC(CCNC([C@@H](C(COP(OP(OC[C@@H]1[C@H]([C@H]([C@@H](O1)N1C=NC=2C(N)=NC=NC12)O)OP(=O)(O)O)(=O)O)(=O)O)(C)C)O)=O)=O)

InChI

1S/C37H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h9-10,24-26,30-32,36,47-48H,4-8,11-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/b10-9+

InChI key

QBYOCCWNZAOZTL-MDZDMXLPSA-N

Application

Coenzyme A functions as an acyl group carrier, acetyl-CoA. Palmitoleoyl coenzyme A (Palmitoleoyl-CoA) may be used in comparative long chain fatty acyl-CoA studies such as the effects of long-chain acyl-coenzyme A esters on cardiac K(ATP) channels and lipotoxic footprinting.

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)

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Makoto Miyazaki et al.
Prostaglandins, leukotrienes, and essential fatty acids, 68(2), 113-121 (2003-01-23)
Stearoyl-CoA desaturase (SCD) (EC 1.14.99.5) is an endoplasmic reticulum-bound enzyme that catalyzes the delta9-cis desaturation of saturated fatty acyl-CoAs, the preferred substrates being palmitoyl- and stearoyl-CoA, which are converted to palmitoleoyl- and oleoyl-CoA, respectively. These monounsaturated fatty acids are used
Romain Harmancey et al.
Journal of lipid research, 51(6), 1380-1393 (2010-01-23)
The "lipotoxic footprint" of cardiac maladaptation in diet-induced obesity is poorly defined. We investigated how manipulation of dietary lipid and carbohydrate influenced potential lipotoxic species in the failing heart. In Wistar rats, contractile dysfunction develops at 48 weeks on a
Andrea J Lengi et al.
Lipids, 42(6), 499-508 (2007-05-01)
Stearoyl-CoA desaturase (SCD) is an enzyme responsible for the production of cis-9, trans-11 conjugated linoleic acid in ruminant fats, and for the synthesis of palmitoleoyl-CoA and oleoyl-CoA. To date, only one SCD isoform has been described in ruminant species, although
Dirk Schulze et al.
The Journal of physiology, 552(Pt 2), 357-367 (2003-10-17)
Phosphatidylinositol phosphates (PIPs, e.g. PIP2) and long-chain acyl-CoA esters (e.g. oleoyl-CoA) are potent activators of KATP channels that are thought to link KATP channel activity to the cellular metabolism of PIPs and fatty acids. Here we show that the two
G X Liu et al.
Circulation research, 88(9), 918-924 (2001-05-23)
ATP-sensitive K (K(ATP)) channels are inhibited by cytosolic ATP, a defining property that implicitly links these channels to cellular metabolism. Here we report a direct link between fatty acid metabolism and K(ATP) channels in cardiac muscle cells. Long-chain (LC) acyl-coenzyme
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