Synthesis of New Trans Double-Bond Sphingolipid Analogues:  Δ4,6and Δ6Ceramides

2002 ◽  
Vol 67 (8) ◽  
pp. 2600-2605 ◽  
Author(s):  
Jiong Chun ◽  
Guoqing Li ◽  
Hoe-Sup Byun ◽  
Robert Bittman
Keyword(s):  
Double Bond ◽  
Trans Double Bond

scholarly journals trans-Double Bond-Containing Liposomes as Potential Carriers for Drug Delivery

Molecules ◽  
2017 ◽  
Vol 22 (12) ◽  
pp. 2082 ◽  
Author(s):  
Giorgia Giacometti ◽  
Marina Marini ◽  
Kyriakos Papadopoulos ◽  
Carla Ferreri ◽  
Chryssostomos Chatgilialoglu
Keyword(s):  
Drug Delivery ◽  
Double Bond ◽  
Trans Double Bond

scholarly journals The 3-Hydroxy Group and 4,5-trans Double Bond of Sphingomyelin Are Essential for Modulation of Galactosylceramide Transmembrane Asymmetry

2005 ◽  
Vol 88 (4) ◽  
pp. 2670-2680 ◽  
Author(s):  
Barbara Malewicz ◽  
Jacob T. Valiyaveettil ◽  
Kochurani Jacob ◽  
Hoe-Sup Byun ◽  
Peter Mattjus ◽  
...  
Keyword(s):  
Double Bond ◽  
Hydroxy Group ◽  
Trans Double Bond

The Role of the Trans Double Bond in Skin Barrier Sphingolipids: Permeability and Infrared Spectroscopic Study of Model Ceramide and Dihydroceramide Membranes

Langmuir ◽  
2014 ◽  
Vol 30 (19) ◽  
pp. 5527-5535 ◽  
Author(s):  
Barbora Školová ◽  
Kateřina Jandovská ◽  
Petra Pullmannová ◽  
Ondřej Tesař ◽  
Jaroslav Roh ◽  
...  
Keyword(s):  
Double Bond ◽  
Spectroscopic Study ◽  
Skin Barrier ◽  
Trans Double Bond ◽  
Infrared Spectroscopic Study ◽  
Infrared Spectroscopic

scholarly journals Surface areas of 1-palmitoyl phosphatidylcholines and their interactions with cholesterol

1987 ◽  
Vol 245 (2) ◽  
pp. 455-462 ◽  
Author(s):  
R W Evans ◽  
M A Williams ◽  
J Tinoco
Keyword(s):  
Double Bond ◽  
Surface Pressure ◽  
Trans Double Bond ◽  
Double Bonds ◽  
Molecular Area ◽  
Monolayer Films ◽  
Surface Areas ◽  
Mixed Films ◽  
Carbon Acid ◽  
Carbon Series

1-Palmitoyl phosphatidylcholines (1-palmitoyl PCs), in which the 2-position was occupied respectively by C10:0, C12:0, C14:0, C14:1, n-7, C16:0, C16:1, n-7, C18:0, C18:1(t), n-9, C18:1, n-9, C18:2, n-6, C18:3, N-3, C18:3, n-6, C18:3(5t,9,12), C22:0, C22:1, n-9, C22:2, n-6, C22:3, n-3, C22:4, n-6, C22:5, n-6 or C22:6, n-3 fatty acids, were studied as monolayer films at the air/water interface. Results for molecular area indicated that the areas of the PC (phosphatidylcholine) did not continuously decrease as the length of one chain increased. For series of saturated, monoenoic and dienoic 1-palmitoyl PCs the smallest molecular area was occupied by the PC containing a 20-carbon acid at the 2-position. In the 18-carbon series, introduction of the first and third cis double bonds caused a large increase in molecular area, but in the 22-carbon series the first and second cis double bonds produced large increases in molecular area. Molecules containing three or more cis double bonds varied little in molecular area, regardless of chain length (18-22 carbon atoms). The influence of a trans double bond was intermediate between that of a saturated and a cis double bond. The 18- and 22-carbon series of PCs were studied in mixed monolayers with cholesterol and desmosterol. Condensation of molecular areas occurred in all sterol PC mixed films, and similar results were obtained with cholesterol and desmosterol. Condensation of PC containing a cis or trans double bond within 10 carbon atoms of the carboxy group initially increased with increasing surface pressure. Condensation of other PCs decreased as surface pressure increased. All cis- or trans-unsaturated PCs condensed maximally in mixtures of approximately equimolar ratios with sterols, but saturated PCs condensed to the greatest extent in mixtures that contained about 30 mol% sterol.

The Question of Conformational Restriction in the trans-Cyclononene Ring of Caryophyllene

1973 ◽  
Vol 51 (23) ◽  
pp. 3955-3962 ◽  
Author(s):  
E. W. Warnhoff ◽  
V. Srinivasan
Keyword(s):  
Double Bond ◽  
Room Temperature ◽  
Membered Ring ◽  
Trans Double Bond ◽  
Conformational Restriction

The possibility that the barrier to rotation of the trans double bond within the nine-membered ring of caryophyllene might be high enough to prevent the interconversion of conformers 2 and 3 near room temperature has been examined. Contrary to earlier reports, it has been found that two trans epoxides are formed on peracid epoxidation of caryophyllene and hence both conformers are present. Attempts to determine whether 2 and 3 are interconverting near room temperature were inconclusive.

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