710335P

18:1 Cardiolipin

Avanti Research^™ - A Croda Brand

• Synonym(s): tetraoleoyl cardiolipin; 1,1′,2,2′-tetra-(9Z-octadecenoyl) cardiolipin (sodium salt); CL(1′-[18:1(9Z)/18:1(9Z)],3′-[18:1(9Z)/18:1(9Z)])
• Empirical Formula (Hill Notation): C₈₁H₁₄₈O₁₇P₂Na₂
• CAS Number: 115404-77-8
• Molecular Weight: 1501.96
• UNSPSC Code: 51191904
• NACRES: NA.25

Properties

• description: 1′,3′-bis[1,2-dioleoyl-sn-glycero-3-phospho]-glycerol (sodium salt)
• assay: >99% (TLC)
• form: powder
• packaging: pkg of 2 × 100 mg (710335P-200mg); pkg of 5 × 100 mg (710335P-500mg); pkg of 1 × 25 mg (710335P-25mg)
• manufacturer/tradename: Avanti Research^™ - A Croda Brand
• lipid type: phospholipids; cardiolipins
• shipped in: dry ice
• storage temp.: −20°C

Description

General description

Cardiolipin has two phosphatidyl residues linked by glycerol. It is present in the bacterial membranes. 18:1 cardiolipin or tetraoleoyl cardiolipin (TOCL) is a monounsaturated mitochondrial phospholipid. The bilayer thickness of TOCL is higher than the heart cardiolipin. TOCL bilayers have a larger hydrocarbon chain thickness compared to dioleoyl phosphatidylcholine (DOPC) bilayer.

Cardiolipin is a unique phospholipid located in the inner mitochondrial membrane, which makes up to 20% of total lipids. Cardiolipin is a non-bilayer anionic phospholipid, which has four acyl chains and a small headgroup.

Cardiolipin is an anionic phospholipid.

Application

18:1 Cardiolipin has been used as a lipid substrate for luminol-enhanced chemiluminescence.

18:1 Cardiolipin has been used:

• to prepare pure (100%) cardiolipin vesicles
• to measure the intensity of cytochrome c peroxidase activity by luminescence assay
• to measure the fluorescence of cytochrome c Trp59 immobilized in biosensor chip
• to study the association of cytochrome c with anionic phospholipids

18:1 Cardiolipin has been used:

• in the preparation of liposomes for reconstitution of mechanosensitive channels from bacteria
• in the immobilization on lipophilic biosensor L1 chip surface
• as lipid substrate in peroxidase oxidation assay

Biochem/physiol Actions

18:1 Cardiolipin or tetraoleoyl cardiolipin (TOCL) regulates oxidative phosphorylation and respiration in mitochondria. Metabolic pathway defects in cardiolipin is associated with Barth syndrome patients. TOCL undergoes oxidation in the presence of cytochrome C.

Cardiolipin and cytochrome c interaction determines the function of proteins involved in oxidative phosphorylation and apoptosis. Cardiolipin involved in proton uptake pathway maintains the structure of enzymes participating. Cardiolipin controls the mitochondrial function and membrane potential. It offers structural support for the inner mitochondrial membrane and proteins in it. Altered cardiolipin concentration and composition have been implicated in pathological conditions including ischemia, hypothyroidism, aging, heart failure and cardioskeletal myopathy.

Cardiolipin is involved in the dynamic organization of membranes and in cell division. It regulates the proton uptake pathway. Cardiolipin plays a critical role in mitochondrial biogenesis, fusion and fission, respiration and protein import. It controls cell wall biogenesis, vacuole homeostasis, aging, cell cycle and apoptosis.

Packaging

5 mL Clear Glass Sealed Ampule (710335P-200mg)

5 mL Clear Glass Sealed Ampule (710335P-25mg)

5 mL Clear Glass Sealed Ampule (710335P-500mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: 755.6 - 820.4 °F
• flash_point_c: 402 - 438 °C