L-DPPC | CAS#63-89-8

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

MedKoo CAT#: 530992

CAS#: 63-89-8

Description: L-DPPC, also known as 1,2-Dipalmitoyl-sn-glycero-3-PC and L-Dipalmitoyl Lecithin, is a zwitterionic phosphoglyceride that can be used for the preparation of liposomal monolayers. L-DPPC incorporated liposomes have potential in establishing active immunotherapy with antigens exhibiting poor immunogenicity, such as glycosphingolipid antigens.

Chemical Structure

L-DPPC

CAS# 63-89-8

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 530992
Name: L-DPPC
CAS#: 63-89-8
Chemical Formula: C40H80NO8P
Exact Mass: 733.56
Molecular Weight: 734.053
Elemental Analysis: C, 65.45; H, 10.99; N, 1.91; O, 17.44; P, 4.22

Price and Availability

Size	Price	Availability
200mg	USD 350	2 Weeks
1g	USD 750	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: L-DPPC; L-Dipalmitoyl Lecithin; 1,2-Dipalmitoyl-sn-glycero-3-PC;

IUPAC/Chemical Name: 1,2-dihexadecanoyl-sn-glycero-3-phosphorylcholine

InChi Key: KILNVBDSWZSGLL-KXQOOQHDSA-N

InChi Code: InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1

SMILES Code: CCCCCCCCCCCCCCCC(O[C@@H](COP([O-])(OCC[N+](C)(C)C)=O)COC(CCCCCCCCCCCCCCC)=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:

Product Data:

Product Data

Instruction:

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Biological target:	DPPC (129Y83) is a zwitterionic phosphoglyceride that can be used for the preparation of liposomal monolayers.
In vitro activity:	Furthermore, in a racemic DPPC monolayer with a moderate surface pressure, both chiral SHG and chiral SFG of CH3 groups are absent, whereas chiral SFG of CH2 groups is clearly present, indicating that L- and D-DPPC are diastereomers at the air/water interface and interfacial CH2 prefers a certain orientation regardless of the molecular handedness. Reference: J Chem Phys. 2022 Mar 7;156(9):094704. https://pubmed.ncbi.nlm.nih.gov/35259885/
In vivo activity:	On the other hand, the immune responses against GSL antigens in mice were detected after immunization with liposomes composed of dipalmitoylphosphatidylcholine (DPPC) (0.5 micromol), cholesterol (Chol) (0.5 micromol), Salmonella minnesota R595 lipopolysaccharides (LPS) (10 microg) and GSL (0.05 micromol) (DPPC-liposome). These results suggest that DPPC-liposome would serve effectively as a delivery vehicle for inducing immune responses against GSL antigen. Reference: J Vet Med Sci. 2005 Dec;67(12):1197-201. https://pubmed.ncbi.nlm.nih.gov/16397376/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Ethanol	27.5	37.46

Preparing Stock Solutions

The following data is based on the product molecular weight 734.05 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

Formulation protocol:	1. Lin L, Li Y, Qin X, Yu C, Liu M, Zhang Z, Guo Y. In situ nonlinear optical spectroscopic study of the structural chirality in DPPC Langmuir monolayers at the air/water interface. J Chem Phys. 2022 Mar 7;156(9):094704. doi: 10.1063/5.0069860. PMID: 35259885. 2. Pentak D, Ploch-Jankowska A, Zięba A, Kozik V. The Advances and Challenges of Liposome-Assisted Drug Release in the Presence of Serum Albumin Molecules: The Influence of Surrounding pH. Materials (Basel). 2022 Feb 20;15(4):1586. doi: 10.3390/ma15041586. PMID: 35208126; PMCID: PMC8874444. 3. Daeichin V, van Rooij T, Skachkov I, Ergin B, Specht PA, Lima A, Ince C, Bosch JG, van der Steen AF, de Jong N, Kooiman K. Microbubble Composition and Preparation for High-Frequency Contrast-Enhanced Ultrasound Imaging: In Vitro and In Vivo Evaluation. IEEE Trans Ultrason Ferroelectr Freq Control. 2017 Mar;64(3):555-567. doi: 10.1109/TUFFC.2016.2640342. Epub 2016 Dec 15. PMID: 28113312. 4. Uemura A, Watarai S, Iwasaki T, Kodama H. Induction of immune responses against glycosphingolipid antigens: comparison of antibody responses in mice immunized with antigen associated with liposomes prepared from various phospholipids. J Vet Med Sci. 2005 Dec;67(12):1197-201. doi: 10.1292/jvms.67.1197. PMID: 16397376.
In vitro protocol:	1. Lin L, Li Y, Qin X, Yu C, Liu M, Zhang Z, Guo Y. In situ nonlinear optical spectroscopic study of the structural chirality in DPPC Langmuir monolayers at the air/water interface. J Chem Phys. 2022 Mar 7;156(9):094704. doi: 10.1063/5.0069860. PMID: 35259885. 2. Pentak D, Ploch-Jankowska A, Zięba A, Kozik V. The Advances and Challenges of Liposome-Assisted Drug Release in the Presence of Serum Albumin Molecules: The Influence of Surrounding pH. Materials (Basel). 2022 Feb 20;15(4):1586. doi: 10.3390/ma15041586. PMID: 35208126; PMCID: PMC8874444.
In vivo protocol:	1. Daeichin V, van Rooij T, Skachkov I, Ergin B, Specht PA, Lima A, Ince C, Bosch JG, van der Steen AF, de Jong N, Kooiman K. Microbubble Composition and Preparation for High-Frequency Contrast-Enhanced Ultrasound Imaging: In Vitro and In Vivo Evaluation. IEEE Trans Ultrason Ferroelectr Freq Control. 2017 Mar;64(3):555-567. doi: 10.1109/TUFFC.2016.2640342. Epub 2016 Dec 15. PMID: 28113312. 2. Uemura A, Watarai S, Iwasaki T, Kodama H. Induction of immune responses against glycosphingolipid antigens: comparison of antibody responses in mice immunized with antigen associated with liposomes prepared from various phospholipids. J Vet Med Sci. 2005 Dec;67(12):1197-201. doi: 10.1292/jvms.67.1197. PMID: 16397376.

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1: Lőrincz A, Mihály J, Németh C, Wacha A, Bóta A. Effects of ursolic acid on the structural and morphological behaviours of dipalmitoyl lecithin vesicles. Biochim Biophys Acta. 2015 May;1848(5):1092-8. doi: 10.1016/j.bbamem.2015.01.010. Epub 2015 Jan 22. PubMed PMID: 25620772.

2: Baser ME, Kennedy TP, Dodson R, Rao NV, Rawlings W Jr, Hoidal JR. Hydroxyl radical generating activity of hydrous but not calcined kaolin is prevented by surface modification with dipalmitoyl lecithin. J Toxicol Environ Health. 1990;29(1):99-108. PubMed PMID: 2299691.

3: Ma JY, Weber KC. Dipalmitoyl lecithin and lung surfactant adsorption at an air-liquid interface by respirable particles. Environ Res. 1986 Oct;41(1):120-9. PubMed PMID: 3757964.

4: Boroske E, Trahms L. A 1H and 13C NMR study of motional changes of dipalmitoyl lecithin associated with the pretransition. Biophys J. 1983 Jun;42(3):275-83. PubMed PMID: 6688189; PubMed Central PMCID: PMC1329236.

5: Lohninger A, Salzer H, Simbruner G, Husslein P, Martin G. Relationships among human amniotic fluid dipalmitoyl lecithin, postpartum respiratory compliance, and neonatal respiratory distress syndrome. Clin Chem. 1983 Apr;29(4):650-5. PubMed PMID: 6687565.

6: Fischbach F, Krieglsteiner P, Lohninger A, Hütter W, Erhardt W, Blümel G. [Pharmacological influences on fetal lung maturity, part V: Influencing the pulmonary DPL (dipalmitoyl lecithin) level with L-thyroxin (T4)]. Z Geburtshilfe Perinatol. 1982 Jun-Jul;186(3):150-6. German. PubMed PMID: 6896943.

7: Krieglsteiner P, Lohninger A, Fischbach F, Riedl W, Szudrowicz D, Erhardt W, Blümel G. [Pharmacologic influencing of fetal phospholipid synthesis. Part IV: influencing the DPL(dipalmitoyl-lecithin) content of fetal lung by betamethasone (author's transl)]. Z Geburtshilfe Perinatol. 1980 Oct;184(5):343-9. German. PubMed PMID: 6895135.

8: Mudd JB, McManus TT. Effect of steryl glycosides on the phase transition of dipalmitoyl lecithin. Plant Physiol. 1980 Jan;65(1):78-80. PubMed PMID: 16661148; PubMed Central PMCID: PMC440270.

9: Barrow RE, Hills BA. Surface tension induced by dipalmitoyl lecithin in vitro under physiological conditions. J Physiol. 1979 Dec;297(0):217-27. PubMed PMID: 583427; PubMed Central PMCID: PMC1458716.

10: Okada S, Nakagaki M. [Penetration of trifluoperazine into mixed monolayers of dipalmitoyl lecithin and cholesterol (author's transl)]. Yakugaku Zasshi. 1979 Oct;99(10):976-81. Japanese. PubMed PMID: 583495.

11: Lelkes PI, Kapitkovsky A, Eibl H, Miller IR. Headgroup-dependent modulation of phase transition in dipalmitoyl lecithin analogs: a fluorescence depolarization study. FEBS Lett. 1979 Jul 1;103(1):181-5. PubMed PMID: 582436.

12: Arias F, Pineda J, Johnson LW. Changes in human amniotic fluid lecithin/sphingomyelin ratio and dipalmitoyl lecithin associated with maternal betamethasone therapy. Am J Obstet Gynecol. 1979 Apr 15;133(8):894-8. PubMed PMID: 581927.

13: Nakagaki M, Okada S, Mochida K. [Penetration of phenothiazine derivatives into dipalmitoyl lecithin monolayer (author's transl)]. Yakugaku Zasshi. 1979 Apr;99(4):393-401. Japanese. PubMed PMID: 582606.

14: Bichler A, Wiesinger H, Mayr P. [Investigations of the effect and mechanism of action of the beta-sympathomimetic ritodrine on the synthesis and release of dipalmitoyl-lecithin in the fetal rabbit lung (author's transl)]. Arch Gynecol. 1979 Mar 28;227(1):29-38. German. PubMed PMID: 443864.

15: Colacicco G, Ray AK, Basu MK, Wittner M, Rosenbaum RM. Cultured lung cells: interplay effects of beta-mimetics, prostaglandins and corticosteroids in the biosynthesis of dipalmitoyl lecithin. Z Naturforsch C. 1979 Jan-Feb;34(1-2):101-5. PubMed PMID: 155940.

16: Colacicco G, Basu MK. Effect of serum albumin on dynamic force-area curve of dipalmitoyl lecithin. Respir Physiol. 1978 Mar;32(3):265-79. PubMed PMID: 580813.

17: Reinert JC, Lowry RR, Wickman HH. Synthesis of a monobrominated analog of dipalmitoyl lecithin. Lipids. 1978 Jan;13(1):85-7. doi: 10.1007/BF02533371. PubMed PMID: 27519999.

18: Haberkorn RA, Griffin RG, Meadows MD, Oldfield E. Deuterium nuclear magnetic resonance investigation of the dipalmitoyl lecithin-cholesterol-water system. J Am Chem Soc. 1977 Oct 26;99(22):7353-5. PubMed PMID: 578806.

19: Brosio E, Conti F, Di Nola A, Kovacs AL. A stereochemical model for phospholipids. I. Conformational energy refinement and molecular packing of L-alpha-dipalmitoyl-lecithin (DPL). J Theor Biol. 1977 Jul 21;67(2):319-34. PubMed PMID: 895167.

20: Mulay S, Khamsi F, Solomon S. Quantification of dipalmitoyl lecithin in lung wash and extracts. Anal Biochem. 1977 Feb;77(2):350-61. PubMed PMID: 576570.

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