DOPC | CAS#4235-95-4

MedKoo Cat#: 555690 | Name: DOPC

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

DOPC, also known as 18:1 (Δ9-Cis) PC, is a phospholipid containing the unsaturated long-chain (18:1) oleic acid inserted at the sn-1 and sn-2 positions. It is commonly used alone, or with other components, in the generation of micelles, liposomes, and other types of artificial membranes.

Chemical Structure

DOPC

CAS#4235-95-4

Theoretical Analysis

MedKoo Cat#: 555690

Name: DOPC

CAS#: 4235-95-4

Chemical Formula: C44H84NO8P

Exact Mass: 785.5935

Molecular Weight: 786.13

Elemental Analysis: C, 67.23; H, 10.77; N, 1.78; O, 16.28; P, 3.94

Price and Availability

Size	Price	Availability
250mg	USD 150.00	Ready to ship
500mg	USD 250.00	Ready to ship
1g	USD 400.00	Ready to ship
2g	USD 650.00	Ready to ship
5g	USD 1,250.00	2 weeks

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Synonym

DOPC; 18:1 (Δ9-Cis) PC; PC(18:1(9Z)/18:1(9Z)); 1,2-dioleoyl-sn-glycero-3-phosphocholine; sn-3-Dioleoyllecithin

IUPAC/Chemical Name

(R)-2,3-Bis(oleoyloxy)propyl [2-(Trimethylammonio)ethyl] Phosphate

InChi Key

SNKAWJBJQDLSFF-NVKMUCNASA-N

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

SMILES Code

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

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot# C21M06C08

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	Chloroform	20.0	25.40
	Ethanol	25.0	31.80

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 786.13 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Golysheva EA, Dzuba SA. Lipid Chain Mobility and Packing in DOPC Bilayers at Cryogenic Temperatures. Chem Phys Lipids. 2019 Sep 13:104817. doi: 10.1016/j.chemphyslip.2019.104817. [Epub ahead of print] PubMed PMID: 31525380. 2: Owen MC, Karner A, Šachl R, Preiner J, Amaro M, Vácha R. Force Field Comparison of GM1 in a DOPC Bilayer Validated with AFM and FRET Experiments. J Phys Chem B. 2019 Aug 26. doi: 10.1021/acs.jpcb.9b05095. [Epub ahead of print] PubMed PMID: 31397569. 3: Škulj S, Vazdar M. Calculation of apparent pK(a) values of saturated fatty acids with different lengths in DOPC phospholipid bilayers. Phys Chem Chem Phys. 2019 May 15;21(19):10052-10060. doi: 10.1039/c9cp01204d. PubMed PMID: 31046041. 4: Stachura SS, Malajczuk CJ, Kuprusevicius E, Mancera RL. Influence of Bilayer Size and Number in Multi-Bilayer DOPC Simulations at Full and Low Hydration. Langmuir. 2019 Feb 12;35(6):2399-2411. doi: 10.1021/acs.langmuir.8b03212. Epub 2019 Jan 25. PubMed PMID: 30632763. 5: Kluzek M, Schmutz M, Marques CM, Thalmann F. Kinetic evolution of DOPC lipid bilayers exposed to α-cyclodextrins. Soft Matter. 2018 Jul 18;14(28):5800-5810. doi: 10.1039/c8sm01013g. PubMed PMID: 29947414. 6: Bacellar IOL, Baptista MS, Junqueira HC, Wainwright M, Thalmann F, Marques CM, Schroder AP. Permeability of DOPC bilayers under photoinduced oxidation: Sensitivity to photosensitizer. Biochim Biophys Acta Biomembr. 2018 Nov;1860(11):2366-2373. doi: 10.1016/j.bbamem.2018.06.001. Epub 2018 Jun 7. PubMed PMID: 29886032. 7: Rudolphi-Skórska E, Dyba B, Kreczmer B, Filek M. Impact of polyphenol-rich green tea extracts on the protection of DOPC monolayer against damage caused by ozone induced lipid oxidation. Acta Biochim Pol. 2018;65(2):193-197. doi: 10.18388/abp.2018_2612. Epub 2018 May 30. PubMed PMID: 29850658. 8: Elmer-Dixon MM, Bowler BE. Rapid quantification of vesicle concentration for DOPG/DOPC and Cardiolipin/DOPC mixed lipid systems of variable composition. Anal Biochem. 2018 Jul 15;553:12-14. doi: 10.1016/j.ab.2018.05.013. Epub 2018 May 25. PubMed PMID: 29775562. 9: Ileri Ercan N, Stroeve P, Tringe JW, Faller R. Molecular Dynamics Modeling of Methylene Blue-DOPC Lipid Bilayer Interactions. Langmuir. 2018 Apr 10;34(14):4314-4323. doi: 10.1021/acs.langmuir.8b00372. Epub 2018 Mar 28. PubMed PMID: 29553270. 10: Adhyapak PR, Panchal SV, Murthy AVR. Cholesterol induced asymmetry in DOPC bilayers probed by AFM force spectroscopy. Biochim Biophys Acta Biomembr. 2018 May;1860(5):953-959. doi: 10.1016/j.bbamem.2018.01.021. Epub 2018 Feb 1. PubMed PMID: 29408513. 11: Murthy AVR, Guyomarc'h F, Lopez C. Palmitoyl ceramide promotes milk sphingomyelin gel phase domains formation and affects the mechanical properties of the fluid phase in milk-SM/DOPC supported membranes. Biochim Biophys Acta Biomembr. 2018 Mar;1860(3):635-644. doi: 10.1016/j.bbamem.2017.12.005. Epub 2017 Dec 8. PubMed PMID: 29229528. 12: Jaschonek S, Cascella M, Gauss J, Diezemann G, Milano G. Intramolecular structural parameters are key modulators of the gel-liquid transition in coarse grained simulations of DPPC and DOPC lipid bilayers. Biochem Biophys Res Commun. 2018 Mar 29;498(2):327-333. doi: 10.1016/j.bbrc.2017.10.132. Epub 2017 Oct 31. PubMed PMID: 29101041. 13: Navon Y, Radavidson H, Putaux JL, Jean B, Heux L. pH-Sensitive Interactions between Cellulose Nanocrystals and DOPC Liposomes. Biomacromolecules. 2017 Sep 11;18(9):2918-2927. doi: 10.1021/acs.biomac.7b00872. Epub 2017 Aug 29. PubMed PMID: 28799758. 14: Elderdfi M, Zegarlińska J, Jones W, Sikorski AF. MPP1 interacts with DOPC/SM/Cholesterol in an artificial membrane system using Langmuir-Blodgett monolayer. Gen Physiol Biophys. 2017 Oct;36(4):443-454. doi: 10.4149/gpb_2017002. Epub 2017 Jun 27. PubMed PMID: 28653654. 15: Lyu Y, Xiang N, Zhu X, Narsimhan G. Potential of mean force for insertion of antimicrobial peptide melittin into a pore in mixed DOPC/DOPG lipid bilayer by molecular dynamics simulation. J Chem Phys. 2017 Apr 21;146(15):155101. doi: 10.1063/1.4979613. PubMed PMID: 28433027. 16: Ramadurai S, Werner M, Slater NKH, Martin A, Baulin VA, Keyes TE. Dynamic studies of the interaction of a pH responsive, amphiphilic polymer with a DOPC lipid membrane. Soft Matter. 2017 May 24;13(20):3690-3700. doi: 10.1039/c6sm02645a. PubMed PMID: 28327750. 17: Suga K, Tauchi A, Ishigami T, Okamoto Y, Umakoshi H. Preferential Adsorption of l-Histidine onto DOPC/Sphingomyelin/3β-[N-(N',N'-dimethylaminoethane)carbamoyl]cholesterol Liposomes in the Presence of Chiral Organic Acids. Langmuir. 2017 Apr 18;33(15):3831-3838. doi: 10.1021/acs.langmuir.6b03264. Epub 2017 Apr 4. PubMed PMID: 28272888. 18: Wagner MJ, Mitra R, McArthur MJ, Baze W, Barnhart K, Wu SY, Rodriguez-Aguayo C, Zhang X, Coleman RL, Lopez-Berestein G, Sood AK. Preclinical Mammalian Safety Studies of EPHARNA (DOPC Nanoliposomal EphA2-Targeted siRNA). Mol Cancer Ther. 2017 Jun;16(6):1114-1123. doi: 10.1158/1535-7163.MCT-16-0541. Epub 2017 Mar 6. PubMed PMID: 28265009; PubMed Central PMCID: PMC5457703. 19: Chen X, Liu S, Deme B, Cristiglio V, Marquardt D, Weller R, Rao P, Wang Y, Bradshaw J. Efficient internalization of TAT peptide in zwitterionic DOPC phospholipid membrane revealed by neutron diffraction. Biochim Biophys Acta Biomembr. 2017 May;1859(5):910-916. doi: 10.1016/j.bbamem.2017.01.036. Epub 2017 Jan 31. PubMed PMID: 28153495. 20: Lütgebaucks C, Macias-Romero C, Roke S. Characterization of the interface of binary mixed DOPC:DOPS liposomes in water: The impact of charge condensation. J Chem Phys. 2017 Jan 28;146(4):044701. doi: 10.1063/1.4974084. PubMed PMID: 28147550.