Fatty Acid Metabolism

Acetyl coenzyme A is a central metabolite for both the biosynthesis and catabolism of fatty acids. Although the steps in the biosynthetic and catabolic schemes are closely related, there are specific differences. The individual steps are also independent by their spatial separation in biological cells, as biosynthesis occurs in the
cytosol while catabolism takes place in the mitochondria. The evennumbered ([C 2 ] n ) common fatty acids result from the sequential two-carbon elongation of acetyl CoA by a series of enzymatic reactions utilizing one or more molecules of acetyl CoA. The two-step elongation scheme of fatty acid biosynthesis is catalyzed by either discrete enzymes catalyzing specific steps or by a large multi-enzyme complex able to catalyze all steps in the pathway.

The first step of converting acetyl CoA into the more reactive acetylacyl carrier protein (Acetyl-ACP) is catalyzed by ACP transacylase. The acetyl group is then transferred from ACP to a cysteine residue of the synthase complex. In the third step, carboxylation of acetyl CoA is catalyzed by acetyl CoA carboxylase with bicarbonate and ATP to yield malonyl CoA and ADP. In this reaction, biotin acts as a carbon dioxide carrier which transfers carbon dioxide to acetyl CoA. The malonyl group is subsequently converted through a nucleophilic acyl substitution reaction into malonyl-ACP. Thus, both acetyl and malonyl groups are bound to an ACP arm of the synthase complex. The key fifth step consists of the Claisen condensation reaction between the bound acetyl and malonyl groups to give acetoacetyl-ACP. In the sixth step, an enantioselective reduction of the ketone carbonyl group catalyzed by ß-ketothioester reductase yields ß-hydroxybutyryl-ACP, with a new chiral center in the R -configuration. Enzymatic dehydration in step 7 yields trans -crotonyl-ACP, which is converted in step 8 by NADPH-dependent reduction of the carboncarbon double bond to butyryl-ACP.

Fatty acid catabolism in the mitochondria of cells provides energy by the ß-oxidation pathway and is composed of a repetitive sequence of four enzymatic reaction steps. The fatty acid chain is cleaved from the carboxy-terminus in a stepwise fashion. The first step of the ß-oxidation pathway starts with an acyl CoA-dehydrogenasecatalyzed desaturation at C2-C3 using an FAD cofactor to yield an a,ß-unsaturated acyl-CoA. An enoyl-CoA hydratase-catalyzed syn- addition of water to the a,ß-unsaturated acyl-CoA in the second step yields 3 S -hydroxyacyl-CoA. Next, 3 S -hydroxyacyl-CoA is oxidized to the corresponding ß-ketoacyl-CoA by NAD-dependent enantioselective 3-hydroxyacyl-CoA dehydrogenases. In the final step, the ß-ketoester is cleaved to two CoA esters in a ß-ketoacylthiolase-catalyzed retro-Claisen reaction. While the common fatty acids with an even number of carbon atoms produce two molecules of acetyl-CoA in the final passage, fatty acids with an odd number of carbon atoms lead to one molecule of acetyl-CoA and one molecule of propionyl-CoA.

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54920 (R)-3-Hydroxybutyric acid ≥98.0% (T)  
O6754 1-Oleoyl-2-acetyl-sn-glycerol ≥97% (TLC), oil Often used as an activator of calcium-dependent protein kinase C (PKC).
C6146 2-Butenoyl coenzyme A lithium salt ≥90% (HPLC)  
M2787 2-Oleoylglycerol ≥94% (TLC) 2-Monoolein (2-Oleoylglycerol) is used as a GPR119 agonist than regulates GLP-1 release. 2-Monoolein may be used to differentiate and study the kinetics of monoacylglycerol lipase(s).
D3385 3′-Dephosphocoenzyme A ≥90% (HPLC)  
H6132 DL-3-Hydroxy-3-methylglutaryl coenzyme A sodium salt hydrate ≥90% (HPLC) DL-3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) is a substrate used to study the specificity and kinetics of the enzyme 3-hydroxyl-3-methyl-glutaryl coenzyme A (HMG-CoA) reductase. HMG-CoA is the key intermediate in the biosynthsis of terpenes, cholesterol, and ketone bodies. Its metabolism is the target of statin drugs used to control cholesterol levels.
H0261 DL-β-Hydroxybutyryl coenzyme A lithium salt ≥90% 3-Hydroxybutyryl coenzyme A (HBCoA) is converted to bacterial polyhydroxyalkanoates (PHB) by polyhydroxybutyrate (PHB) synthases. 3-Hydroxybutyryl coenzyme A is a substrate used to measure the specificity and kinetics of β-hydroxyacyl CoA dehydrogenase.
A1625 Acetoacetyl coenzyme A sodium salt hydrate cofactor for acyl transfer  
A2181 Acetyl coenzyme A lithium salt ≥93% (HPLC) Acetyl-CoA is an essential cofactor and carrier of acyl groups in enzymatic acetyl transfer reactions. It is formed either by the oxidative decarboxylation of pyruvate in mitochondria, by the oxidation of long-chain fatty acids, or by the oxidative degradation of certain amino acids. Acetyl-CoA is the starting compound for the citric acid cycle (Kreb′s cycle). It is also a key precursor in lipid biosynthesis, and the source of all fatty acid carbons. Acetyl-CoA positively regulates the activity pyruvate carboxylase. It is a precursor of the neurotransmitter acetylcholine. Histone acetylases (HAT) use Acetyl-CoA as the donor for the acetyl group use in the post-translational acetylation reactions of histone and non-histone proteins.
Alterations in the gene encoding acetyl-CoA have been linked to Alzheimer′s disease and mild cognitive impairment. Defects in the gene cause myasthenic syndrome associated with episodic apnea.
A2056 Acetyl coenzyme A sodium salt ≥93% (HPLC), powder Acetyl-CoA is an essential cofactor and carrier of acyl groups in enzymatic acetyl transfer reactions. It is formed either by the oxidative decarboxylation of pyruvate in mitochondria, by the oxidation of long-chain fatty acids, or by the oxidative degradation of certain amino acids. Acetyl-CoA is the starting compound for the citric acid cycle (Kreb′s cycle). It is also a key precursor in lipid biosynthesis, and the source of all fatty acid carbons. Acetyl-CoA positively regulates the activity pyruvate carboxylase. It is a precursor of the neurotransmitter acetylcholine. Histone acetylases (HAT) use Acetyl-CoA as the donor for the acetyl group use in the post-translational acetylation reactions of histone and non-histone proteins.
ACOA-RO   Acetyl-Coenzyme A Acetyl-Coenzyme A (Ac-CoA) is the end product of glycolysis and takes part in the Ac-CoA pathway, which is a metabolic pathway for carbon compounds. Ac-CoA is important in cholesterol synthesis. It also takes part in fatty acid biosynthesis and catabolism of polyamines like spermine and spermidine. A low level of Ac-CoA leads to a loss in glial cell and neuronal function. Ketone bodies and triglycerides give rise to Ac-CoA on hydrolysis and this indirectly leads to increased histone acetylation.
10930 Arachidic acid synthetic, ≥99.0% (GC)  
10931 Arachidonic acid >95.0% (GC) Arachidonic acid (AA) is an unsaturated ω6 fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation. AA is subsequently metabolized to prostaglandins and thromboxanes by at least two cyclooxygenase (COX) isoforms, to leukotrienes and lipoxins by lipoxygenases, and to epoxyeicosatrienoic acids via cytochrome p450-catalyzed metabolism. AA and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis. AA has been demonstrated to bind to the a subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs). Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.
Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .
A5837 Arachidonoyl coenzyme A lithium salt ≥85%  
A0580 Arachidonylethanolamide ≥97.0% (TLC), oil An arachidonic acid derivative that is an endogenous ligand for the CB cannabinoid receptor and for the VR1 vanilloid receptor. Inhibits calcium currents in neuroblastomas and neurons. Activates the MAP kinase signaling pathway. Inhibits proliferation and induces apoptosis of lymphocytes and human breast cancer cells.
216941 Behenic acid 99%  
B1508 Butyryl coenzyme A lithium salt hydrate ≥90% Butyryl CoA is a substrate for Butyryl CoA Dehydrogenase. Butyryl CoA is involved in both lipid and butanoate metabolism.
C4282 Coenzyme A hydrate ≥85% (UV, HPLC) Coenzyme A (CoA) is an essential metabolic cofactor synthesized from cysteine, pantothenate, and ATP. CoA plays important roles in many metabolic pathways, including the tricarboxylic acid cycle, and the synthesis and oxidation of fatty acids. One of the main functions of CoA is the carrying and transfer of acyl groups. Acylated deriviates, for example acetyl-CoA, are critical intermediates in many metabolic reactions. CoA levels can be altered during starvation, and in conditions such as cancer, diabetes, and alcoholism.
C3144 Coenzyme A sodium salt hydrate cofactor for acyl transfer Coenzyme A (CoA, CoASH, HSCoA) is a coenzyme that facilitates enzymatic acyl-group transfer reactions and supports the synthesis and oxidation of fatty acids. CoA is involved in the mechanisms of a wide variety of enzymes. In the presence of CoASH, organic carboxylic acids form acyl-CoA thioesters, which facilitates enzyme recognition. The acyl-CoA formed from xenobiotic carboxylic acids can add to the compound′s toxicity, which can lead to cellular metabolic dysfunction. It is involved in the oxidation of pyruvate in the Kreb′s cycle.
C3019 Coenzyme A trilithium salt ≥93%  
C2643 Coenzyme A, oxidized lithium salt ≥85%  
28007 Crotonoyl coenzyme A trilithium salt ~90% (HPLC)  
D5269 Decanoyl coenzyme A monohydrate ≥90%  
E4637 Elaidic acid ≥99.0% (GC)  
E3385 Erucic acid ≥99% (capillary GC)  
G9510 Glutaryl coenzyme A lithium salt ≥90%  
H2012 Hexanoyl coenzyme A trilithium salt hydrate ≥85% Coenzyme A functions as an acyl group carrier, acetyl-CoA. Hexanoyl CoA is involved in fatty acid oxidation, lipid biosynthesis, and ceramide formation. Ghrelin O-acyltransferase (GOAT) has a preference for n-hexanoyl-CoA over n-octanoyl-CoA as an acyl donor. Hexanoyl CoA is also used as a starter unit for polyketide biosynthesis.
I0383 Isobutyryl coenzyme A lithium salt ≥85% Coenzyme A functions as an acyl group carrier, acetyl-CoA. Isobutyryl coenzyme A (IB-CoA), a short-chain branched acyl-CoA, provides the starter unit for biosynthesis of myxalamid B. Isobutyryl coenzyme A is used as a substrate to study the specificity and kinetics of isobutyryl-coenzyme A (CoA) mutase (EC 5.4.99.13).
I9381 Isovaleryl coenzyme A lithium salt hydrate ≥90%  
L2659 Lauroyl coenzyme A lithium salt ≥90% (HPLC) Coenzyme A functions as an acyl group carrier, acetyl-CoA. Dodecanoyl-Coenzyme A (C12-CoA), a long-chain (C-12) saturated fatty acyl-CoA, is used as an intermediate in lipid metabolism and is involved in lipid biosynthesis and fatty acid transport.. Lauroyl CoA is a substrate for FAM34A proteins and a product of firefly luciferase.
L6641 Lignoceric acid ≥99% (capillary GC)  
L1376 Linoleic acid ≥99% Linoleic acid increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes .
Linoleic acid is an n-6 polyunsaturated essential fatty acid (PUFA) used as a precursor of arachidonic acid (AA) and various prostaglandins. Linoleic acid may be used to improve the delivery and efficacy of anticancer drugs and in cancer protection.
L2376 Linolenic acid ≥99% An ω-3 fatty acid that serves as a precursor to eicosapentaenoic acid (EPA) but not docosahexaenoic acid. Conversion is greater in women than men, and conversely, β-oxidation metabolism is greater in men than women.
62170 Linolenic acid ~70% (GC) An ω-3 fatty acid that serves as a precursor to eicosapentaenoic acid (EPA) but not docosahexaenoic acid. Conversion is greater in women than men, and conversely, β-oxidation metabolism is greater in men than women.
L9754 Linoleoyl coenzyme A lithium salt ≥85% Coenzyme A functions as an acyl group carrier, acetyl-CoA. Linoleoyl coenzyme A is a substrate used to study the specificity and kinetics of mitochondrial linoleoyl-coenzyme monolysocardiolipin acyltransferase-1 (MLCL AT-1) and acyl-CoA: lysophosphatidylcholine acyltransferase (LPCAT).
M4263 Malonyl coenzyme A lithium salt ≥90% (HPLC) Coenzyme A functions as an acyl group carrier, acetyl-CoA. Malonyl Coenzyme A is a coenzyme A derivative that is utilized in fatty acid and polyketide synthesis and in the transport of α-ketoglutarate across the mitochondrial membrane. Malonyl CoA is formed by the Acetyl CoA Carboxylase-mediated carboxylation of acetyl CoA. Malonyl-CoA is exclusively used as the extender unit in the synthesis of bacterial aromatic polyketides.
63410 Malonyl coenzyme A tetralithium salt ≥90% (HPLC) Malonyl Coenzyme A is a Coenzyme A derivative that is utilized in fatty acid and polyketide synthesis and in the transport of α-ketoglutarate across the mitochondrial membrane. Malonyl CoA is formed by the Acetyl CoA Carboxylase-mediated carboxylation of acetyl CoA.
M1762 Methylmalonyl coenzyme A tetralithium salt hydrate ≥90% (HPLC)  
M4414   Myristoyl coenzyme A lithium salt ≥80.0%  
N1514 Nervonic acid ≥99% (capillary GC) Nervonic acid (C24:1), a component of membrane sphingolipids and phosphatidylethanolamines, may be a useful predictor of chronic kidney disease mortality and diabetes. Nervonic acid oils are being studied for pharmaceutical, nutraceutical and industrial applications. Nervonic acid is a major component of Lunaria oil.
O6877 Octanoyl coenzyme A lithium salt hydrate ≥95% (HPLC) Medium-chain fatty acid covalently linked to coenzyme A.
O1012   Oleoyl coenzyme A lithium salt ≥90% (HPLC)  
P6775 Palmitoleoyl coenzyme A lithium salt ~90%  
P9716 Palmitoyl coenzyme A lithium salt ≥90% Long chain fatty acid (C16) covalently linked to Coenzyme A. Covalent attachment of palmitate is a common occurrence on a wide variety of viral and cellular proteins and plays a role in promoting membrane binding. Palmitoylation may also be a general mechanism for prolonging or potentiating G-protein signaling.
S3381 Sodium stearate ≥99%  
S4751 Stearic acid Grade I, ≥98.5% (capillary GC)  
S0802 Stearoyl coenzyme A lithium salt ≥90% Stearoyl CoA is a saturated fatty acid metabolite involved in polyunsaturated fatty acid synthesis and the PPAR signaling pathway.
S1129 Succinyl coenzyme A sodium salt ≥85% Succinyl CoA is an intermediate in the citric acid cycle. It is formed by α-ketoglutarate dehydrogenase by the decarboxylation of α-ketoglutarate. Succinyl CoA is also formed from propionyl CoA during the β-oxidation of odd-chain fatty acids. Succinyl CoA serves as a precursor in heme synthesis. It is also required for the oxidation of ketone bodies.
D1797 all-cis-7,10,13,16,19-Docosapentaenoic acid synthetic, ≥97%  
M3013 β-Methylcrotonyl coenzyme A lithium salt ≥90%  
E7752 cis-11,14-Eicosadienoic acid ethyl ester ≥98% (capillary GC), liquid  
E7877 cis-11,14-Eicosadienoic acid methyl ester ≥98% (capillary GC), liquid  
E3127 cis-11,14-Eicosadienoic acid ≥98%, liquid  
E3635 cis-11-Eicosenoic acid ≥99% (capillary GC)  
D4034 cis-13,16-Docosadienoic acid methyl ester ≥98%  
E3512 cis-13-Eicosenoic acid methyl ester ~99% (capillary GC), liquid  
E3387 cis-13-Eicosenoic acid ~99% (capillary GC)  
E6001 cis-11,14,17-Eicosatrienoic acid methyl ester ≥98%, liquid  
D8768 cis-4,7,10,13,16,19-Docosahexaenoic acid sodium salt ≥95%, waxy solid  
D2534 cis-4,7,10,13,16,19-Docosahexaenoic acid ≥98% Docosahexaenoic acid, DHA, is an omega-3 polyunsaturated fatty acid with 22 carbons and six double bonds, the first double bond occuring at position three from the methyl terminus (22:6 n-3). DHA is a component of lipid membranes and the myelin sheath. DHA also serves as a precursor for signaling molecules such as prostaglandins and eicosanoids.
E6627   cis-5,8,11,14,17-Eicosapentaenoic acid sodium salt ≥99% (capillary GC) 5-Lipoxygenase inhibitor; reduces thromboxane A2 production.
E2011 cis-5,8,11,14,17-Eicosapentaenoic acid ≥99% 5-Lipoxygenase inhibitor; reduces thromboxane A2 production.
E6013 cis-5,8,11-Eicosatrienoic acid methyl ester ~10 mg/mL in methanol, ≥90%  
E5888 cis-5,8,11-Eicosatrienoic acid ~10 mg/mL in ethanol, ≥90%  
E3511 cis-8,11,14-Eicosatrienoic acid methyl ester ≥99%  
E4504 cis-8,11,14-Eicosatrienoic acid ≥99%  
L2378 γ-Linolenic acid ≥99%, liquid Gamma-linolenate (C18:6,9,12) differs from α-linolenate (C18:9,12,15) in the positions of the double bonds.
γ-Linolenic acid , a polyunsaturated fatty acid, exerts anti-inflammatory effect by decreasing both interleukin (IL) 6 and IL-8 production in the human enterocyte-like cell line Caco-2 and humandendritic cells in vitro .
H1385 n-Heptadecanoyl coenzyme A lithium salt ≥90% Coenzyme A functions as an acyl group carrier, acetyl-CoA. Heptadecanoyl Coenzyme A (C17-CoA), a long-chain (C-17) saturated fatty acyl-CoA, is used as an intermediate in lipid metabolism. It is a substrate of acyl-CoA dehydrogenase (EC 1.3.99.3) within the mitochondria and of carnitine O-palmitoyltransferase (EC 2.3.1.21) within the cytoplasm. Heptadecanoyl Coenzyme A is an inhibitor of general acyl-coenzyme A dehydrogenase (EC 1.3.99.3).
P5397 n-Propionyl coenzyme A lithium salt ≥85% Propionyl coenzyme A (CoA) is the coenzyme A derivative of propionic acid. Propionyl CoA is formed during the β-oxidation of odd-chain fatty acids. Propionyl CoA is also formed during the metabolism of isoleucine and valine.