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710337C

Avanti

14:1 Cardiolipin

Avanti Research - A Croda Brand 710337C

Synonym(s):

1′,3′-bis[1,2-dimyristoleoyl-sn-glycero-3-phospho]-glycerol (sodium salt)

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About This Item

Empirical Formula (Hill Notation):
C65H116Na2O17P2
CAS Number:
Molecular Weight:
1277.53
UNSPSC Code:
12352211
NACRES:
NA.25

Assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 1 mL (710337C-5mg)
pkg of 1 × 2.5 mL (710337C-25mg)

manufacturer/tradename

Avanti Research - A Croda Brand 710337C

concentration

10 mg/mL (710337C-25mg)
5 mg/mL (710337C-5mg)

lipid type

phospholipids
cardiolipins

shipped in

dry ice

storage temp.

−20°C

SMILES string

O=P([O-])(OC[C@]([H])(OC(CCCCCCC/C=C\CCCC)=O)COC(CCCCCCC/C=C\CCCC)=O)OCC([H])(O)COP([O-])(OC[C@]([H])(OC(CCCCCCC/C=C\CCCC)=O)COC(CCCCCCC/C=C\CCCC)=O)=O.[Na+].[Na+]

General description

3β,7α-dihydroxy-5-cholestenoic acid is a sterol derived from cholestenoic acid.
Cardiolipin is an anionic phospholipid containing four acyl chains and small headgroup.
Cardiolipin is localized in the inner membrane of mitochondria. It contains 18 carbon atoms, 3-phosphatidyl groups connected via a glycerol bridge. It is an important component of ATP synthase enzyme.

Application

14:1 Cardiolipin may be used as reference standard in liquid chromatography with tandem mass spectrometry (LC-MS-MS). It may also be used in the quantification of mitochondrial phospholipids and yeast respiratory chain complex using mass spectrometry.

Biochem/physiol Actions

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.
TMCL (1,1′,2,2′-tetramyristoyl cardiolipin) bilayers are useful in generating multilamellar vesicles. Defects in the metabolic pathway of cardiolipin is associated with Barth syndrome patients. Liposomes of TMCL with 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) and cholesterol are potential drug-delivery systems. TMCL displays temperature dependant thermotropic phase transitions.

Packaging

5 mL Clear Glass Sealed Ampule (710337C-25mg)
5 mL Clear Glass Sealed Ampule (710337C-5mg)
ST503: 3 Vial/Ampule Tray with Outer Cardboard Box (3-1/8" x 29/32" x 2-15/16") (710337C-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

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, Liver,Kidney

WGK

WGK 3


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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DNAJC19, a mitochondrial cochaperone associated with cardiomyopathy, forms a complex with prohibitins to regulate cardiolipin remodeling
Richter-Dennerlein R, et al.
Cell Metabolism, 20(1), 158-171 (2014)
Simultaneous quantification of cardiolipin, bis (monoacylglycero) phosphate and their precursors by hydrophilic interaction LC- MS/MS including correction of isotopic overlap
Scherer M, et al.
Analytical Chemistry, 82(21), 8794-8799 (2010)
Arrangement of the respiratory chain complexes in Saccharomyces cerevisiae supercomplex III2IV2 revealed by single particle cryo-electron microscopy
Mileykovskaya E, et al.
The Journal of Biological Chemistry, 287(27), 23095-23103 (2012)
Calorimetric, X-ray diffraction, and spectroscopic studies of the thermotropic phase behavior and organization of tetramyristoyl cardiolipin membranes
Lewis RNAH, et al.
Biophysical Journal, 92(9), 3166-3177 (2007)
Cardiolipin binds selectively but transiently to conserved lysine residues in the rotor of metazoan ATP synthases
Duncan AL, et al.
Proceedings of the National Academy of Sciences of the USA, 113(31), 8687-8692 (2016)

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