MedKoo Cat#: 145071 | Name: C18-PAF

Description:

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

C18-PAF is a naturally occurring phospholipid. C18-PAF induces caspase-independent neuronal death in PAF receptor-deficient neurons. The sn-1 fatty acid is significant in modulating PAF-induced apoptosis and neuroprotection, whether mediated by PAF receptor signaling or not. C18-PAF constricts both upstream and venous segments of the pulmonary circulation.

Chemical Structure

C18-PAF
C18-PAF
CAS#74389-69-8

Theoretical Analysis

MedKoo Cat#: 145071

Name: C18-PAF

CAS#: 74389-69-8

Chemical Formula: C28H58NO7P

Exact Mass: 551.3951

Molecular Weight: 551.75

Elemental Analysis: C, 60.95; H, 10.60; N, 2.54; O, 20.30; P, 5.61

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
C18-PAF; C18PAF; C18 PAF; PAF (C18); Ro-14-8161; Ro148161; Ro 14 8161; Ro14-8161; Ro-148161; C18-PAF-acether;
IUPAC/Chemical Name
(R)-2-acetoxy-3-(octadecyloxy)propyl (2-(trimethylammonio)ethyl) phosphate
InChi Key
ZXCIEWBDUAPBJF-MUUNZHRXSA-N
InChi Code
1S/C28H58NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-23-33-25-28(36-27(2)30)26-35-37(31,32)34-24-22-29(3,4)5/h28H,6-26H2,1-5H3/t28-/m1/s1
SMILES Code
CCCCCCCCCCCCCCCCCCOC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(C)=O
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 551.75 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
1: Handa RK, Strandhoy JW, Buckalew VM Jr. Vasorelaxant effect of C16-PAF and C18-PAF on renal blood flow and systemic blood pressure in the anesthetized rat. Life Sci. 1991;49(10):747-52. doi: 10.1016/0024-3205(91)90107-m. PMID: 1875784. 2: Okumura N, Fukushima A, Igarashi A, Sumi T, Yamagishi T, Ueno H. Pharmacokinetic analysis of platelet-activating factor in the tears of guinea pigs with allergic conjunctivitis. J Ocul Pharmacol Ther. 2006 Oct;22(5):347-52. doi: 10.1089/jop.2006.22.347. PMID: 17076629. 3: Schwinger RH, Böhm M, La Rosée K, Erdmann E. Existence of PAF receptors in human platelets and human lung tissue but not in the human myocardium. Am Heart J. 1992 Aug;124(2):320-30. doi: 10.1016/0002-8703(92)90593-k. PMID: 1322030. 4: Kim Y, Stanley D. Eicosanoid Signaling in Insect Immunology: New Genes and Unresolved Issues. Genes (Basel). 2021 Feb 1;12(2):211. doi: 10.3390/genes12020211. PMID: 33535438; PMCID: PMC7912528. 5: Ryan SD, Harris CS, Carswell CL, Baenziger JE, Bennett SA. Heterogeneity in the sn-1 carbon chain of platelet-activating factor glycerophospholipids determines pro- or anti-apoptotic signaling in primary neurons. J Lipid Res. 2008 Oct;49(10):2250-8. doi: 10.1194/jlr.M800263-JLR200. Epub 2008 Jun 12. PMID: 18550892. 6: Toga H, Hibler S, Ibe BO, Raj JU. Vascular effects of platelet-activating factor in lambs: role of cyclo- and lipoxygenase. J Appl Physiol (1985). 1992 Dec;73(6):2559-66. doi: 10.1152/jappl.1992.73.6.2559. PMID: 1490969. 7: Stoddart NR, Roudebush WE, Fleming SD. Exogenous platelet-activating factor stimulates cell proliferation in mouse pre-implantation embryos prior to the fourth cell cycle and shows isoform-specific stimulatory effects. Zygote. 2001 Aug;9(3):261-8. doi: 10.1017/s0967199401001289. PMID: 11510473. 8: Adamson LM, Podsiadly B, Smart YC, Stanger JD, Roberts TK. Studies on murine embryo-derived platelet-activating factor (EPAF). Mol Reprod Dev. 1991 Nov;30(3):207-13. doi: 10.1002/mrd.1080300307. PMID: 1793598. 9: Archer CB, Page CP, Paul W, Morley J, MacDonald DM. Inflammatory characteristics of platelet activating factor (PAF-acether) in human skin. Br J Dermatol. 1984 Jan;110(1):45-50. doi: 10.1111/j.1365-2133.1984.tb07310.x. PMID: 6581831. 10: Ring PC, Seldon PM, Barnes PJ, Giembycz MA. Pharmacological characterization of a receptor for platelet-activating factor on guinea pig peritoneal macrophages using [3H]apafant, a selective and competitive platelet-activating factor antagonist: evidence that the noncompetitive behavior of apafant in functional studies relates to slow kinetics of dissociation. Mol Pharmacol. 1993 Feb;43(2):302-12. PMID: 8381515. 11: Kahhak L, Roche A, Dubray C, Arnoux C, Benveniste J. Decrease of ciliary beat frequency by platelet activating factor: protective effect of ketotifen. Inflamm Res. 1996 May;45(5):234-8. doi: 10.1007/BF02259609. PMID: 8737746. 12: Gomez J, Bloom JW, Yamamura HI, Halonen M. Characterization of receptors for platelet-activating factor in guinea pig lung membranes. Am J Respir Cell Mol Biol. 1990 Sep;3(3):259-64. doi: 10.1165/ajrcmb/3.3.259. PMID: 2167700. 13: Tuffin DP, Davey P, Dyer RL, Lunt DO, Wade PJ. Specific binding of [3H]-1-O-octadecyl Paf-acether to washed human platelets. Adv Exp Med Biol. 1985;192:83-96. doi: 10.1007/978-1-4615-9442-0_7. PMID: 3834789. 14: Triggiani M, Chilton FH. Influence of immunologic activation and cellular fatty acid levels on the catabolism of platelet-activating factor within the murine mast cell (PT-18). Biochim Biophys Acta. 1989 Nov 6;1006(1):41-51. doi: 10.1016/0005-2760(89)90321-4. PMID: 2572273. 15: Godfroid JJ, Heymans F, Michel E, Redeuilh C, Steiner E, Benveniste J. Platelet activating factor (PAF-acether): total synthesis of 1-O-octadecyl 2-O-acetyl sn-glycero-3-phosphoryl choline. FEBS Lett. 1980 Jul 28;116(2):161-4. doi: 10.1016/0014-5793(80)80633-8. PMID: 7409144. 16: Kudolo GB, Yang YQ, Chen DB, Jones MA, Harper MJ. Differential metabolism of exogenous platelet-activating factor by glandular epithelial and stromal cells of rabbit endometrium. J Reprod Fertil. 1995 Nov;105(2):315-24. doi: 10.1530/jrf.0.1050315. PMID: 8568777. 17: Wissner A, Sum PE, Schaub RE, Kohler CA, Goldstein BM. Analogues of platelet activating factor (PAF). 1. Some modifications of the alkoxy chain. J Med Chem. 1984 Sep;27(9):1174-81. doi: 10.1021/jm00375a016. PMID: 6471071. 18: Balsa D, Merlos M, Giral M, Ferrando R, García-Rafanell J, Forn J. Characterization of [3H]apafant binding to PAF receptor on rabbit platelet membranes: a comparison of a microplate filtration system and a standard method. J Pharmacol Toxicol Methods. 1996 Sep;36(1):53-62. doi: 10.1016/1056-8719(96)00074-3. PMID: 8872920. 19: Hwang SB, Lam MH, Szalkowski DM, MacIntyre DE, Bach TJ, Luell S, Meuer R, Sahoo SP, Alberts AW, Chabala JC. MK 287: a potent, specific, and orally active receptor antagonist of platelet-activating factor. J Lipid Mediat. 1993 Jun;7(2):115-34. PMID: 8400114. 20: Callea L, Arese M, Orlandini A, Bargnani C, Priori A, Bussolino F. Platelet activating factor is elevated in cerebral spinal fluid and plasma of patients with relapsing-remitting multiple sclerosis. J Neuroimmunol. 1999 Feb 1;94(1-2):212-21. doi: 10.1016/s0165-5728(98)00246-x. PMID: 10376955.