A phospholipid
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Cardiolipin (bovine heart) (sodium salt)

Item No. 41880

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
bis((R)-2,3-bis(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)propyl) (2-hydroxypropane-1,3-diyl) bis(phosphate), disodium salt
CAS Number
383907-10-6
Synonyms
  • CL
  • Diphosphatidylglycerol
Molecular Formula
C81H140O17P2 • 2Na (for tetralinoleoyl)
Formula Weight
1493.9
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: Sparingly soluble: 1-10 mg/ml
SMILES
O=C(OC[C@H](COP([O-])(OCC(O)COP([O-])(OC[C@@H](COC(CCCCCCC/C=C\C/C=C\CCCCC)=O)OC(CCCCCCC/C=C\C/C=C\CCCCC)=O)=O)=O)OC(CCCCCCC/C=C\C/C=C\CCCCC)=O)CCCCCCC/C=C\C/C=C\CCCCC.[Na+].[Na+]
InChi Code
InChI=1S/C81H142O17P2.2Na/c1-5-9-13-17-21-25-29-33-37-41-45-49-53-57-61-65-78(83)91-71-76(97-80(85)67-63-59-55-51-47-43-39-35-31-27-23-19-15-11-7-3)73-95-99(87,88)93-69-75(82)70-94-100(89,90)96-74-77(98-81(86)68-64-60-56-52-48-44-40-36-32-28-24-20-16-12-8-4)72-92-79(84)66-62-58-54-50-46-42-38-34-30-26-22-18-14-10-6-2;;/h21-28,33-40,75-77,82H,5-20,29-32,41-74H2,1-4H3,(H,87,88)(H,89,90);;/q;2*+1/p-2/b25-21-,26-22-,27-23-,28-24-,37-33-,38-34-,39-35-,40-36-;;/t76-,77-;;/m1../s1
InChi Key
ZGSPNIOCEDOHGS-LBOJVHLDSA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $39

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    1 mg

    $74

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    5 mg

    $251

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    Product Description

    Cardiolipin is an anionic phospholipid found in bacteria and mitochondria.1,2,3 It is composed of a glycerol backbone linked to two phosphatidyl groups that each contain two fatty acyl chains. Cardiolipin makes up approximately 10% of the total phospholipid composition of bovine heart and approximately 20% of phospholipids in the mitochondrial membrane.4,5 It is involved in mitochondrial fusion, division, protein import, and apoptosis.2,3,6 Decreased cardiolipin levels, increased monolysocardiolipin levels, and alterations in cardiolipin fatty acyl chain composition are found in patients with Barth syndrome, a disease characterized by cardiomyopathy, skeletal myopathy, neutropenia, and growth retardation.3 This product contains cardiolipin molecular species with primarily C18:2 (~80%) and C18:1 (~14%) fatty acyl chain lengths.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kariyama, R. Increase of cardiolipin content in Staphylococcus aureus by the use of antibiotics affecting the cell wall. J. Antibiot. (Tokyo) 35(12), 1700-1704 (1982).

    2. Kameoka, S., Adachi, Y., Okamoto, K., et al. Phosphatidic acid and cardiolipin coordinate mitochondrial dynamics. Trends Cell Biol. 28(1), 67-76 (2018).

    3. Shen, Z., Ye, C., McCain, K., et al. The role of cardiolipin in cardiovascular health. Biomed Res. Int. 891707 (2015).

    4. Das, M.L., and Rouser, G. Lipid composition of beef heart ventricle. Lipids 2(1), 1-4 (1967).

    5. Fleischer, S., Rouser, G., Fleischer, B., et al. Lipid composition of mitochondria from bovine heart, liver, and kidney. J. Lipid Res. 8(3), 170-180 (1967).

    6. Iverson, S.L., and Orrenius, S. The cardiolipin-cytochrome c interaction and the mitochondrial regulation of apoptosis. Arch. Biochem. Biophys. 423(1), 37-46 (2004).