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MedKoo Cat#: 414869 | Name: DMPC
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Description:

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

DMPC is a phospholipid containing 14:0 fatty acids at the sn-1 and sn-2 positions. It is a synthetic phosopholipid that has been used for liposome production in order to study the properties of lipid bilayer. DMPC has been used in FDA approved drugs. It is to construct nanodiscs to reconstruct membrane proteins for protein structure determination with2-D NMR technologies. DMPC and DMPG has been used in several FDA approved liposomal formulation, including: the amphotericin B lipid complex formulation (Abelcet®), liposomal verteporphin (Visudyne®).

Chemical Structure

DMPC
DMPC
CAS#18194-24-6

Theoretical Analysis

MedKoo Cat#: 414869

Name: DMPC

CAS#: 18194-24-6

Chemical Formula: C36H72NO8P

Exact Mass: 677.4996

Molecular Weight: 677.94

Elemental Analysis: C, 63.78; H, 10.71; N, 2.07; O, 18.88; P, 4.57

Price and Availability

Size Price Availability Quantity
250mg USD 250.00 2 Weeks
1g USD 550.00 2 Weeks
2g USD 750.00 2 Weeks
5g USD 1,450.00 2 Weeks
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Related CAS #
No Data
Synonym
DMPC; 1,2-DMPC; colfoscerili miristas; colfosceril miristate
IUPAC/Chemical Name
1,2-Dimyristoyl-sn-glycero-3-phosphocholine
InChi Key
CITHEXJVPOWHKC-UUWRZZSWSA-N
InChi Code
InChI=1S/C36H72NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-35(38)42-32-34(33-44-46(40,41)43-31-30-37(3,4)5)45-36(39)29-27-25-23-21-19-17-15-13-11-9-7-2/h34H,6-33H2,1-5H3/t34-/m1/s1
SMILES Code
CCCCCCCCCCCCCC(O[C@@H](COP([O-])(OCC[N+](C)(C)C)=O)COC(CCCCCCCCCCCCC)=O)=O
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
>2 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
Franz Hagn, Mahmoud L. Nasr, and Gerhard Wagner: Assembly of phospholipid nanodiscs of controlled size for structural studies of membrane proteins by NMR. Nat Protoc. 2018 Jan; 13(1): 79–98. doi: 10.1038/nprot.2017.094
Product Data
Product Data
Instruction
View handling instruction
Biological target:
1,2-Dimyristoyl-sn-glycero-3-phosphocholine (DMPC) is a synthetic phospholipid used in liposomes.
In vitro activity:
In this study, the effect of polyols, erythritol, xylitol, mannitol, on a model membrane systems composed of DMPC was investigated using differential scanning calorimetry and Fourier transform infrared spectroscopy. The most important findings, obtained from thickness measurements, reveal that short-chain polyols may prevent the formation of bilayers by the DMPC molecules under high surface pressure. The changes in the organization of DMPC monolayers on the surface, as visualized by Brewster angle microscopy, showed that the domains observed for phospholipid film spread on pure water differ substantially from those containing polyols in the subphase. Reference: Biochim Biophys Acta Biomembr. 2018 Nov;1860(11):2166-2174. https://pubmed.ncbi.nlm.nih.gov/30409512/
In vivo activity:
HDL function was also dramatically improved in the mice receiving DMPC, and there was a significant reduction in aortic lesions (P=0.021) in the DMPC mice but not in those receiving lecithin. Adding 1.0 mg/mL of DMPC to the drinking water of 10-month-old apoE-null female mice for 5 weeks caused regression of aortic sinus lesions (P=0.003). DMPC (but not lecithin) raises HDL cholesterol and apoA-I, improves HDL function, and prevents lesions or causes their regression in apoE-null mice. Reference: Circulation. 2003 Oct 7;108(14):1735-9. https://pubmed.ncbi.nlm.nih.gov/14504179/
Solvent mg/mL mM
Solubility
Ethanol 25.0 36.88
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 677.94 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Budziak I, Arczewska M, Sachadyn-Król M, Matwijczuk A, Waśko A, Gagoś M, Terpiłowski K, Kamiński DM. Effect of polyols on the DMPC lipid monolayers and bilayers. Biochim Biophys Acta Biomembr. 2018 Nov;1860(11):2166-2174. doi: 10.1016/j.bbamem.2018.08.014. Epub 2018 Aug 29. PMID: 30409512. 2. Méléard P, Gerbeaud C, Pott T, Fernandez-Puente L, Bivas I, Mitov MD, Dufourcq J, Bothorel P. Bending elasticities of model membranes: influences of temperature and sterol content. Biophys J. 1997 Jun;72(6):2616-29. doi: 10.1016/S0006-3495(97)78905-7. PMID: 9168037; PMCID: PMC1184459. 3. Leung AWY, Chen KTJ, Ryan GM, Anantha M, Wretham N, Nosrati Z, Heroux D, Wang L, Chow N, Dai Z, Bally MB. DMPC/Chol liposomal copper CX5461 is therapeutically superior to a DSPC/Chol formulation. J Control Release. 2022 May;345:75-90. doi: 10.1016/j.jconrel.2022.03.004. Epub 2022 Mar 5. PMID: 35259461. 4. Navab M, Hama S, Hough G, Fogelman AM. Oral synthetic phospholipid (DMPC) raises high-density lipoprotein cholesterol levels, improves high-density lipoprotein function, and markedly reduces atherosclerosis in apolipoprotein E-null mice. Circulation. 2003 Oct 7;108(14):1735-9. doi: 10.1161/01.CIR.0000089375.60050.35. Epub 2003 Sep 22. PMID: 14504179.
In vitro protocol:
1. Budziak I, Arczewska M, Sachadyn-Król M, Matwijczuk A, Waśko A, Gagoś M, Terpiłowski K, Kamiński DM. Effect of polyols on the DMPC lipid monolayers and bilayers. Biochim Biophys Acta Biomembr. 2018 Nov;1860(11):2166-2174. doi: 10.1016/j.bbamem.2018.08.014. Epub 2018 Aug 29. PMID: 30409512. 2. Méléard P, Gerbeaud C, Pott T, Fernandez-Puente L, Bivas I, Mitov MD, Dufourcq J, Bothorel P. Bending elasticities of model membranes: influences of temperature and sterol content. Biophys J. 1997 Jun;72(6):2616-29. doi: 10.1016/S0006-3495(97)78905-7. PMID: 9168037; PMCID: PMC1184459.
In vivo protocol:
1. Leung AWY, Chen KTJ, Ryan GM, Anantha M, Wretham N, Nosrati Z, Heroux D, Wang L, Chow N, Dai Z, Bally MB. DMPC/Chol liposomal copper CX5461 is therapeutically superior to a DSPC/Chol formulation. J Control Release. 2022 May;345:75-90. doi: 10.1016/j.jconrel.2022.03.004. Epub 2022 Mar 5. PMID: 35259461. 2. Navab M, Hama S, Hough G, Fogelman AM. Oral synthetic phospholipid (DMPC) raises high-density lipoprotein cholesterol levels, improves high-density lipoprotein function, and markedly reduces atherosclerosis in apolipoprotein E-null mice. Circulation. 2003 Oct 7;108(14):1735-9. doi: 10.1161/01.CIR.0000089375.60050.35. Epub 2003 Sep 22. PMID: 14504179.
1: Surmeier G, Paulus M, Salmen P, Dogan S, Sternemann C, Nase J. Cholesterol modulates the pressure response of DMPC membranes. Biophys Chem. 2019 Sep;252:106210. doi: 10.1016/j.bpc.2019.106210. Epub 2019 Jun 20. PMID: 31265976. 2: Budziak I, Arczewska M, Sachadyn-Król M, Matwijczuk A, Waśko A, Gagoś M, Terpiłowski K, Kamiński DM. Effect of polyols on the DMPC lipid monolayers and bilayers. Biochim Biophys Acta Biomembr. 2018 Nov;1860(11):2166-2174. doi: 10.1016/j.bbamem.2018.08.014. Epub 2018 Aug 29. PMID: 30409512. 3: Nguyen MHL, DiPasquale M, Rickeard BW, Stanley CB, Kelley EG, Marquardt D. Methanol Accelerates DMPC Flip-Flop and Transfer: A SANS Study on Lipid Dynamics. Biophys J. 2019 Mar 5;116(5):755-759. doi: 10.1016/j.bpj.2019.01.021. Epub 2019 Jan 29. PMID: 30777306; PMCID: PMC6400822. 4: Sreij R, Prévost S, Dargel C, Dattani R, Hertle Y, Wrede O, Hellweg T. Interaction of the Saponin Aescin with Ibuprofen in DMPC Model Membranes. Mol Pharm. 2018 Oct 1;15(10):4446-4461. doi: 10.1021/acs.molpharmaceut.8b00421. Epub 2018 Aug 30. PMID: 30102549. 5: Fasanella A, Cosentino K, Beneduci A, Chidichimo G, Cazzanelli E, Barberi RC, Castriota M. Thermal structural evolutions of DMPC-water biomimetic systems investigated by Raman Spectroscopy. Biochim Biophys Acta Biomembr. 2018 Jun;1860(6):1253-1258. doi: 10.1016/j.bbamem.2018.02.021. Epub 2018 Feb 27. PMID: 29499189. 6: Sreij R, Dargel C, Hannappel Y, Jestin J, Prévost S, Dattani R, Wrede O, Hellweg T. Temperature dependent self-organization of DMPC membranes promoted by intermediate amounts of the saponin aescin. Biochim Biophys Acta Biomembr. 2019 May 1;1861(5):897-906. doi: 10.1016/j.bbamem.2019.01.015. Epub 2019 Feb 5. PMID: 30735626. 7: Lockhart C, Smith AK, Klimov DK. Methionine Oxidation Changes the Mechanism of Aβ Peptide Binding to the DMPC Bilayer. Sci Rep. 2019 Apr 11;9(1):5947. doi: 10.1038/s41598-019-42304-9. PMID: 30976055; PMCID: PMC6459879. 8: Madhumitha D, A B, Vaidyanathan VG, Reddy BGN, Sreeram KJ, Dhathathreyan A. Elastic compliance as a tool to understand Hofmeister ion specific effect in DMPC liposomes. Biophys Chem. 2019 Jun;249:106148. doi: 10.1016/j.bpc.2019.106148. Epub 2019 Apr 8. PMID: 30981138. 9: Escobar JFB, Restrepo MHP, Fernández DMM, Martínez AM, Giordani C, Castelli F, Sarpietro MG. Synthesis and interaction of sterol-uridine conjugate with DMPC liposomes studied by differential scanning calorimetry. Colloids Surf B Biointerfaces. 2018 Jun 1;166:203-209. doi: 10.1016/j.colsurfb.2018.03.023. Epub 2018 Mar 19. PMID: 29597153. 10: Lockhart C, Klimov DK. Cholesterol Changes the Mechanisms of Aβ Peptide Binding to the DMPC Bilayer. J Chem Inf Model. 2017 Oct 23;57(10):2554-2565. doi: 10.1021/acs.jcim.7b00431. Epub 2017 Oct 2. PMID: 28910085.

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