135391-28-5

Basic information

• Product Name: (R,Z)-1-(2-(hydroxymethyl)pyrrolidin-1-yl)octadecan-9-en-1-one
• CAS NO: 135391-28-5
• Molecular Weight: 365.6
• Mol File: 135391-28-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (R,Z)-1-(2-(hydroxymethyl)pyrrolidin-1-yl)octadecan-9-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R,Z)-1-(2-(hydroxymethyl)pyrrolidin-1-yl)octadecan-9-en-1-one(135391-28-5)
• EPA Substance Registry System: (R,Z)-1-(2-(hydroxymethyl)pyrrolidin-1-yl)octadecan-9-en-1-one(135391-28-5)

Safety Data

• Hazardous Substances Data: 135391-28-5(Hazardous Substances Data)

Upstream product

• 112-80-1 cis-Octadecenoic acid 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 68832-13-3 D-prolinol 
• 59485-81-3 cis-1-chloro-9-octadecene 
• 498-63-5 2-hydroxymethylpyrrolidine 

Relevant articles and documents

Pyrrolidine-based 3-deoxysphingosylphosphorylcholine analogs as possible candidates against neglected tropical diseases (NTDs): identification of hit compounds towards development of potential treatment of Leishmania donovani

A rational-based process was adopted for repurposing pyrrolidine-based 3-deoxysphingosylphosphorylcholine analogs bearing variable acyl chains, different stereochemical configuration and/or positional relationships. Structural features were highly influential on activity. Amongst, enantiomer 1e having 1,2-vicinal relationship for the -CH2O- and the N-acyl moieties, a saturated palmitoyl chain and an opposite stereochemical configuration to natural sphingolipids was the most potent hit compound against promastigotes showing IC50 value of 28.32 μM. The corresponding enantiomer 1a was 2-fold less potent showing a eudismic ratio of 0.54 in promastigotes. Compounds 1a and 1e inhibited the growth of amastigotes more potently relative to promastigotes. Amongst, enantiomer 1a as the more selective and safer. In silico docking study using a homology model of Leishmania donovani inositol phosphoceramide synthase (IPCS) provided plausible reasoning for the molecular factors underlying the found activity. Collectively, this study suggests compounds 1a and 1e as potential hit compounds for further development of new antileishmanial agents.

The anandamide membrane transporter. Structurea€"activity relationships of anandamide and oleoylethanolamine analogs with phenyl rings in the polar head group region

A new series of arachidonic and oleic acids derivatives, most of which with aromatic moieties in the head group region, has been synthesized and evaluated as inhibitors of anandamide uptake. A new series of anandamide and N-oleoylethanolamine analogs, most of which with aromatic moieties in the head group region, has been synthesized and evaluated as inhibitors of anandamide uptake. Some of them efficaciously inhibit the uptake process with Ki values in the low micromolar range (2.4-21.2 μM). Strict structural requisites are needed to observe a significant inhibition and in no case inhibition of fatty acid amidohydrolase overlaps with inhibition of anandamide uptake.

Pantothenic acid derivatives

Compounds represented by general formula (I) below wherein R1 and R2, which are the same or different, each represent a hydrogen atom or a protective group for a hydroxyl group;, R3 represents a saturated or unsaturated, linear, branched or cyclic, monovalent C5～C25-aliphatic hydrocarbon group which may be substituted with an aro-matic group, or a group of formula where R4 represents a saturated or unsaturated, linear, branched or cyclic, monovalent C5～C25--aliphatic hydrocarbon group which may be sub-stituted with an aromatic group, and, R5 represents a hydrogen atom, or a saturated or unsaturated, linear, branched or cyclic, monovalent hydrocarbon group which may be substituted with an aromatic group; Q represents (a) a group of formula -X1-A-Y1-,where A represents a saturated or unsaturated, linear, branched or cyclic divalent C2～C16--aliphatic hydrocarbon group which may be sub-stituted with an aromatic group, a divalent aromatic hydrocarbon group or a divalent aro-matic heterocyclic group;, one of X1 and Y1 represents and the other represents -O-, -S- or in which R6 and R7 each represent a hydrogen atom or a lower alkyl group; (b) a group of formula -X2-(CH2)l-Y2-,where one of X2 and Y2 represents a group of formula and the other represents -O-, -S- or represents a 4～7--membered, divalent nitrogen-containing aromatic heterocyclic group, and R6 has the same meaning as defined above, and l is 0, 1 or 2; or (c) a group of formula where m is 2 or 3;, n is an integer of from 1 to 4. The compounds have excellent inhibitory activ-ity against acyl Co A-cholesterol-acyltransferase.