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Merck
CN

710341C

Avanti

16:0-18:1 Cardiolipin

Avanti Research™ - A Croda Brand

Synonym(s):

1′,3′-bis[1-Palmitoyl-2-oleoyl-sn-glycero-3-phospho]-glycerol, sodium salt

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About This Item

Empirical Formula (Hill Notation):
C77H144Na2O17P2
CAS Number:
2260669-35-8
Molecular Weight:
1449.88
UNSPSC Code:
51191904
NACRES:
NA.25

Key Documents

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Product Name

16:0-18:1 Cardiolipin, Avanti Research™ - A Croda Brand

InChI

1S/C77H146O17P2.2Na/c1-5-9-13-17-21-25-29-33-35-39-43-47-51-55-59-63-76(81)93-72(67-87-74(79)61-57-53-49-45-41-37-31-27-23-19-15-11-7-3)69-91-95(83,84)89-65-71(78)66-90-96(85,86)92-70-73(68-88-75(80)62-58-54-50-46-42-38-32-28-24-20-16-12-8-4)94-77(82)64-6

InChI key

QTGHEOQPDHDHHT-IPKHONCISA-L

SMILES string

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

assay

>99% (TLC)

form

chloroform solution

packaging

pkg of 1 × 2.5 mL (710341C-25MG)

manufacturer/tradename

Avanti Research™ - A Croda Brand

concentration

10 mg/mL in chloroform (710341C-25MG)

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

Biochem/physiol Actions

Cardiolipin is a specific marker of mitochondria and is essential for multiple roles like energy transformation, apoptosis, and membrane integrity. 16:0-18:1 is a nascent cardiolipin acts as a precursor for the synthesis of tetralinoleoyl cardiolipin (TLCL).

General description

Cardiolipin is a 1,3-diphosphatidyl-sn-glycerol, a homodimeric phospholipid with four fatty acids. Cardiolipin is unique because of its atypical fatty acid composition. It is present in the mitochondrial membrane. CL species are complex in structure and several permutations exists due to variations in the chain length, degree of unsaturation, as well as combinations of four fatty acid substituents.

Packaging

5 mL Amber Glass Screw Cap Vial (710341C-25MG)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 Oral - STOT SE 3

target_organs

Central nervous system, Liver,Kidney

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

Regulatory Information

危险化学品
易制毒化学品（2类）
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Molecular symmetry in mitochondrial cardiolipins
Schlame M, et al.
Chemistry and Physics of Lipids, 138(1-2), 38-49 (2005)
Clare L Laut et al.
mBio, 11(2) (2020-04-03)
Bacillus anthracis is a spore-forming bacterium that causes devastating infections and has been used as a bioterror agent. This pathogen can survive hostile environments through the signaling activity of two-component systems, which couple environmental sensing with transcriptional activation to initiate
Characterization of cardiolipin as the sodiated ions by positive-ion electrospray ionization with multiple stage quadrupole ion-trap mass spectrometry
Hsu FF and Turk J
Journal of the American Society For Mass Spectrometry, 17(8), 1146-1157 (2006)
The phospholipase iPLA2gamma is a major mediator releasing oxidized aliphatic chains from cardiolipin, integrating mitochondrial bioenergetics and signaling
Liu GY, et al.
The Journal of Biological Chemistry, 292(25), 10672-10684 (2017)
Lavanya Visvabharathy et al.
PLoS pathogens, 16(4), e1008443-e1008443 (2020-04-29)
Staphylococcus aureus (SA) is the causative agent of both skin/soft tissue infections as well as invasive bloodstream infections. Though vaccines have been developed to target both humoral and T cell-mediated immune responses against SA, they have largely failed due to
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