A phospholipid
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Alternative(s)
150981,2-Dioleoyl-sn-glycero-3-PC
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1,2-Dioleoyl-sn-glycero-3-PC (solution)

Item No. 43870

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-hydroxy-N,N,N-trimethyl-10-oxo-7-[[(9Z)-1-oxo-9-octadecen-1-yl]oxy]-3,5,9-trioxa-4-phosphaheptacos-18Z-en-1-aminium, inner salt, 4-oxide
CAS Number
4235-95-4
Synonyms
  • sn-3-Dioleoyllecithin
  • 1,2-Dioleoyl-sn-glycero-3-Phosphocholine
  • DOPC
  • PDD 111
Molecular Formula
C44H84NO8P
Formula Weight
786.1
Purity
≥98%
Formulation (Request formulation change)
A 25 mM solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: Soluble: ≥10mg/ml
SMILES
CCCCCCCC/C=C\CCCCCCCC(O[C@@H](COP(OCC[N+](C)(C)C)([O-])=O)COC(CCCCCCC/C=C\CCCCCCCC)=O)=O
InChi Code
InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-/t42-/m1/s1
InChi Key
SNKAWJBJQDLSFF-NVKMUCNASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 ml

    $44

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    5 ml

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    10 ml

    $154

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

    1,2-Dioleoyl-sn-glycero-3-PC (DOPC) is a phospholipid that contains oleic acid (Item Nos. 90260 | 24659) at the sn-1 and sn-2 positions. It has commonly been used alone, or with other components, in the generation of micelles, liposomes, and other types of artificial membranes.1,2,3 It has also been used in combination with other lipids in the generation of lipid nanoparticles (LNPs) for the delivery of mRNA and microRNA in vivo.4,5 Intravenous administration of LNPs containing DOPC and encapsulating luciferase mRNA induce a 4-fold higher expression of luciferase in mouse liver compared to LNPs containing 1,2-dioleoyl-sn-glycero-3-PE (DOPE; Item No. 15091) or 1,2-distearoyl-sn-glycero-3-PC (DSPC; Item No. 15100).4 DOPC has also been used in the formation of artificial lipid droplets in combination with 1,2,3-trioleoyl glycerol (Item No. 26871) for the study of lipid peroxidation in lipid droplets.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Konyakhina, T.M., Goh, S.L., Amazon, J., et al. Control of a nanoscopic-to-macroscopic transition: Modulated phases in four-component DSPC/DOPC/POPC/Chol giant unilamellar vesicles. Biophys. J. 101(2), L8-L10 (2011).

    2. Rasch, M.R., Yu, Y., Bosoy, C., et al. Chloroform-enhanced incorporation of hydrophobic gold nanocrystals into dioleoylphosphatidylcholine (DOPC) vesicle membranes. Langmuir 28(36), 12971-12981 (2012).

    3. Aguilar, L.F., Pino, J.A., Soto-Arriaza, M.A., et al. Differential dynamic and structural behavior of lipid-cholesterol domains in model membranes. PLoS One 7(6), e40254 (2012).

    4. Qiu, M., Glass, Z., Chen, J., et al. Lipid nanoparticle-mediated codelivery of Cas9 mRNA and single-guide RNA achieves liver-specific in vivo genome editing of Angptl3. Proc. Natl. Acad. Sci. USA 118(10), e2020401118 (2021).

    5. Scheideler, M., Vidakovic, I., and Prassl, R. Lipid nanocarriers for microRNA delivery. Chem. Phys. Lipids 226, 104837 (2020).

    6. Lange, M., Wagner, P.V., and Fedorova, M. Lipid composition dictates the rate of lipid peroxidation in artificial lipid droplets. Free Radic. Res. 55(4), 469-480 (2021).