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78896

Sigma-Aldrich

1,2-Didocosahexaenoyl-sn-glycero-3-phosphocholine

≥99.0% (TLC)

Synonym(s):

PC, (7R,13Z,16Z,19Z,22Z,25Z,28Z)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[[(4Z,7Z,10Z,13Z,16Z,19Z)-1-oxo-4,7,10,13,16,19-docosahexaenyl]oxy]-3,5,9-trioxa-4-phosphahentriaconta-13,16,19,22,25,28-hexaen-1-aminium 4-oxide, inner salt, 1,2-Di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine, DHAPC, PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), PC(22:6/22:6)

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About This Item

Empirical Formula (Hill Notation):
C52H80NO8P
CAS Number:
99296-81-8
Molecular Weight:
878.17
MDL number:
MFCD00674317
UNSPSC Code:
12352211
PubChem Substance ID:
329768192

biological source

synthetic

Assay

≥99.0% (TLC)

form

paste

functional group

phospholipid

storage temp.

−20°C

SMILES string

[O-]P(OCC[N+](C)(C)C)(OC[C@]([H])(OC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O)COC(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)=O)=O

InChI

1S/C52H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-42-44-51(54)58-48-50(49-60-62(56,57)59-47-46-53(3,4)5)61-52(55)45-43-41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h8-11,14-17,20-23,26-29,32-35,38-41,50H,6-7,12-13,18-19,24-25,30-31,36-37,42-49H2,1-5H3/b10-8-,11-9-,16-14-,17-15-,22-20-,23-21-,28-26-,29-27-,34-32-,35-33-,40-38-,41-39-/t50-/m1/s1

InChI key

XLKQWAMTMYIQMG-SVUPRYTISA-N

General description

Phosphatidylcholine species with highly unsaturated acyl groups in both positions are relatively uncommon, but the didocosahexaenoyl (C22:6) species is unusually abundant in bonito muscle. The action of bonito cytosolic lysophosphatidylcholine transacylase on endogenous lysophosphatidylcholine produces this species as the most abundand product.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Augusta de Santis et al.
Soft matter, 16(46), 10425-10438 (2020-11-10)
Polyunsaturated omega-3 fatty acid docosahexaenoic acid (DHA) is found in very high concentrations in a few peculiar tissues, suggesting that it must have a specialized role. DHA was proposed to affect the function of the cell membrane and related proteins
Alessandro Emendato et al.
FEBS letters, 590(4), 582-591 (2016-01-30)
Many age-related neurodegenerative diseases, including Alzheimer Disease (AD), are elicited by an interplay of genetic, environmental, and dietary factors. Food rich in Omega-3 phospholipids seems to reduce the AD incidence. To investigate the molecular basis of this beneficial effect, we
Alessandra Manca et al.
Journal of pharmaceutical and biomedical analysis, 176, 112764-112764 (2019-08-12)
An accurate and specific gas chromatography-mass spectrometry (GC-MS) method was optimized to quantify specific polyunsaturated fatty acids (PUFAs) in plasma and in erythrocyte membranes for clinical purposes. The developed and fully-validated method showed optimal linearity in addition to adequate results
Ya Xie et al.
Food chemistry, 285, 194-203 (2019-02-25)
Microwave pretreatment of rapeseeds prior to cold-pressing is a simple and desirable method for producing high quality oils. In this study, a rapid and sensitive lipid profiling platform employing an accurate quantification strategy was established based on direct infusion electrospray
Marie Breton et al.
The Journal of membrane biology, 248(5), 827-835 (2015-08-05)
Giant unilamellar vesicles (GUV) are widely used cell membrane models. GUVs have a cell-like diameter and contain the same phospholipids that constitute cell membranes. The most frequently used protocol to obtain these vesicles is termed electroformation, since key steps of

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