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710337C

Avanti

14:1 Cardiolipin

Avanti Polar Lipids 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:
2260669-33-6
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 Polar Lipids 710337C

concentration

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

lipid type

phospholipids
cardiolipins

shipped in

dry ice

storage temp.

−20°C

Inchi Code

1S/C65H118O17P2.2Na/c1-5-9-13-17-21-25-29-33-37-41-45-49-62(67)75-55-60(81-64(69)51-47-43-39-35-31-27-23-19-15-11-7-3)57-79-83(71,72)77-53-59(66)54-78-84(73,74)80-58-61(82-65(70)52-48-44-40-36-32-28-24-20-16-12-8-4)56-76-63(68)50-46-42-38-34-30-26-22-18-14-10-6-2;;/h17-24,59-61,66H,5-16,25-58H2,1-4H3,(H,71,72)(H,73,74);;/q;2*+1/p-2/b21-17-,22-18-,23-19-,24-20-;;/t60-,61-;;/m1../s1

InChI key

KMIXSFXJUMNKKR-IVOFNDPZSA-L

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)

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

EU REACH Annex XVII (Restriction List)

CAS No.

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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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)
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)
Interactions of Monovalent and Divalent Cations with Cardiolipin Monolayers
Kensbock R, et al.
Langmuir, 35(10), 3624-3633 (2019)
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)
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)
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