710335P
Avanti
18:1 Cardiolipin
Avanti Polar Lipids
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)])
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About This Item
Empirical Formula (Hill Notation):
C81H148O17P2Na2
CAS Number:
Molecular Weight:
1501.96
UNSPSC Code:
51191904
NACRES:
NA.25
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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 Polar Lipids
lipid type
phospholipids
cardiolipins
shipped in
dry ice
storage temp.
−20°C
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)
also commonly purchased with this product
wgk_germany
WGK 3
flash_point_f
755.6 - 820.4 °F
flash_point_c
402 - 438 °C
Certificates of Analysis (COA)
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Evaluation of cytochrome c affinity to anionic phospholipids by means of surface plasmon resonance
Stepanov G, et al.
Febs Letters, 97?100-97?100 (2009)
The role of cardiolipin in cardiovascular health
Shen Z, et al.
BioMed Research International, 2015 (2015)
Lipidomics: Technologies and applications (2012)
Lipoperoxide radical production during oxidation of cardiolipin in the complex with cytochrome c
Vladimirov YA, et al.
Biochemistry (Moscow) Supplement Series A: Membrane and Cell Biology, 3(4), 467-477 (2009)
Structural and mechanical properties of cardiolipin lipid bilayers determined using neutron spin echo, small angle neutron and X-ray scattering, and molecular dynamics simulations
Pan J, et al.
Soft Matter, 11(1), 130-138 (2015)
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