710335C

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)])
• 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), chloroform
• Assay: >99% (TLC)
• form: solution
• packaging: pkg of 1 × 2.5 mL (710335C-25mg); pkg of 2 × 4 mL (710335C-200mg); pkg of 5 × 4 mL (710335C-500mg)
• manufacturer/tradename: Avanti Polar Lipids
• concentration: 10 mg/mL (710335C-25mg); 25 mg/mL (710335C-200mg); 25 mg/mL (710335C-500mg)
• lipid type: phospholipids; cardiolipins
• shipped in: dry ice
• storage temp.: −20°C

Description

General description

Cardiolipin has two phosphatidyl residues linked by glycerol. 18:1 Cardiolipin or tetraoleoyl cardiolipin (TOCL) is a monounsaturated phospholipid present in mitochondria. 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 possesses four acyl chains and a small headgroup.

Cardiolipin is an anionic phospholipid.

Application

18:1 Cardiolipin has been used as a lipid standard in radiolabeling assay.

18:1 Cardiolipin has been used for preparing solubilized lipids to assemble nanodiscs.

18:1 Cardiolipin has been used:

• in liposome preparation for reconstituting yeast AAA ATPase protein, Msp1
• in in vitro translation system for RNA transfection
• as a synthetic lipid component to mimic mitochondrial inner membrane

Biochem/physiol Actions

Cardiolipin (CL) plays a key role in coordinating energy metabolism in eukaryotes. Metabolic defect in the CL pathway is implicated in dilated cardiomyopathy. CL is essential for mitochondrial functions and apoptosis. Alternations in CL content and their acyl chain composition, contributes to mitochondrial dysfunction in various pathological conditions.

Cardiolipin is involved in the dynamic organization of membranes and in cell division. It modulates 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.

Cardiolipin participates in proton uptake pathway and also maintains the structure of enzymes involved. Cardiolipin maintains the mitochondrial function, membrane potential and structural support for the inner mitochondrial membrane and proteins in it. Concentration and composition changes of cardiolipin have been implicated in pathological conditions including ischemia, hypothyroidism, aging, heart failure and cardioskeletal myopathy.

Packaging

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

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

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

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H302 - H315 - H319 - H331 - H336 - H351 - H361d - H372 - H412
• Precautionary Statements: P201 - P273 - P301 + P312 + P330 - P302 + P352 - P304 + P340 + P311 - P308 + P313
• Hazard Classifications: Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3
• Target Organs: Central nervous system
• Storage Class Code: 6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
• WGK: WGK 3
• Flash Point(F): does not flash
• Flash Point(C): does not flash