A phospholipid
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1,2-Didocosahexaenoyl-sn-glycero-3-Phosphocholine

Item No. 10733

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(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, inner salt, 4-oxide
CAS Number
99296-81-8
Synonyms
  • 1,2-Didocosahexaenoyl PC
  • 1,2-Didocosahexaenoyl-sn-glycero-3-PC
  • 1,2-Didocosahexaenoin-sn-glycero-3-Phosphatidylcholine
  • PC(22:6/22:6)
  • 22:6/22:6-PC
Molecular Formula
C52H80NO8P
Formula Weight
878.2
Purity
≥95%
Formulation (Request formulation change)
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Chloroform: Soluble
SMILES
O=P(OCC[N+](C)(C)C)([O-])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
InChi Code
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
InChi Key
XLKQWAMTMYIQMG-SVUPRYTISA-N
Side Chain Carbon Sum
44:12
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    1 mg

    $39

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    5 mg

    $166

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    10 mg

    $273

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    25 mg

    $341

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    Cayman Chemical
    Learn More About Leveraging Helper Lipids to Achieve Versatile LNPs
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    Product Description

    1,2-Didocosahexaenoyl-sn-glycero-3-phosphocholine is a phospholipid that contains docosahexaenoic acid (Item Nos. 90310 | 17950) at the sn-1 and sn-2 positions. It has been used in the formation of polyunsaturated endoplasmic reticulum-targeting liposomes (PERLs) that reduce cellular cholesterol levels in human peripheral blood mononuclear cells (PBMCs) and decrease the secretion of HIV-1 particles in PBMCs infected with HIV-1LAI.1 It has been used as a component of lipid monolayers and small unilamellar vesicles to study the effect of phospholipid composition on membrane fluidity.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pollock, S., Nichita, N.B., Böhmer, A., et al. Polyunsaturated liposomes are antiviral against hepatitis B and C viruses and HIV by decreasing cholesterol levels in infected cells. Proc. Natl. Acad. Sci. USA 107(40), 17176-17181 (2010).

    2. Zerouga, M., Jenski, L.J., and Stillwell, W. Comparison of phosphatidylcholines containing one or two docosahexaenoic acyl chains on properties of phospholipid monolayers and bilayers. Biochim Biophys Acta. 1236(2), 266-272 (1995).