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Safety Information

710339C

Sigma-Aldrich

16:1 Cardiolipin

Avanti Research™ - A Croda Brand

Synonym(s):

1′,3′-bis[1,2-dipalmitoleoyl-sn-glycero-3-phospho]-glycerol

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About This Item

Empirical Formula (Hill Notation):
C73H132Na2O17P2
Molecular Weight:
1389.75
UNSPSC Code:
12352211
NACRES:
NA.25

description

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

Assay

>99% (TLC)

form

chloroform solution

packaging

pkg of 1 × 2.5 mL (710339C-25mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

concentration

10 mg/mL (710339C-25mg)

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

General description

Cardiolipin (CL) is an anionic mitochondrial membrane associated phospholipid. Structurally, cardiolipin comprises three glycerol moieties and four acyl chains and is localized in the inner membrane of mitochondria. CL, also called as tetra-acylated diphosphatidylglycerols, are present in microbes, plants and mammals. 16:1 Cardiolipin contains four palmitic acid as acyl chain.

Biochem/physiol Actions

Cardiolipin (CL) stabilizes respiratory complexes and is crucial for mitochondrial function. It also mediates energy production and activates apoptosis. CL deficiency and abnormal composition is implicated in pathological conditions. Reduced levels of CL causes diabetes and age-related heart failure. Anomalies associated with CL composition is observed in Barth Syndrome (BTHS). The 16:1 CL is an antagonist of toll-like receptor-4 (TLR4). Apart from inhibiting lipopolysaccharide signaling, it also mediates tumor necrosis factor α secretion by activating the nuclear factor κ -light-chain-enhancer of activated B cells.

Packaging

5 mL Clear Glass Sealed Ampule (710339C-25mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

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, Liver,Kidney

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 Information

危险化学品
易制毒化学品（2类）

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Saturation of acyl chains converts cardiolipin from an antagonist to an activator of Toll-like receptor-4
Pizzuto M, et al.
Cellular and Molecular Life Sciences, 76(18), 3667-3678 (2019)
Yonghong Zhou et al.
Journal of lipid research, 57(7), 1308-1321 (2016-05-15)
Cardiolipin (CL), an anionic phospholipid of the inner mitochondrial membrane, provides essential functions for stabilizing respiratory complexes and is involved in mitochondrial morphogenesis and programmed cell death in animals. The role of CL and its metabolism in plants are less
Anastacia M Garcia et al.
American journal of physiology. Heart and circulatory physiology, 318(4), H787-H800 (2020-02-15)
Despite advances in both medical and surgical therapies, individuals with single ventricle heart disease (SV) remain at high risk for the development of heart failure (HF). However, the molecular mechanisms underlying remodeling and eventual HF in patients with SV are
Nikita Ikon et al.
Biochemical and biophysical research communications, 464(2), 580-585 (2015-07-15)
The concentration and composition of cardiolipin (CL) in mitochondria are altered in age-related heart disease, Barth Syndrome, and other rare genetic disorders, resulting in mitochondrial dysfunction. To explore whether exogenous CL can be delivered to cells, CL was combined with

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