28068-33-9

Basic information

• Product Name: 4-hydroxybutyl oleate
• Synonyms: 4-hydroxybutyl oleate;(Z)-9-Octadecenoic acid 4-hydroxybutyl ester
• CAS NO: 28068-33-9
• Molecular Formula: C₂₂H₄₂O₃
• Molecular Weight: 354.56708
• EINECS: 248-815-2
• Mol File: 28068-33-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 458.2°Cat760mmHg
• Flash Point: 170.2°C
• Appearance: /
• Density: 0.917g/cm³
• Vapor Pressure: 2.53E-10mmHg at 25°C
• Refractive Index: 1.467
• CAS DataBase Reference: 4-hydroxybutyl oleate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxybutyl oleate(28068-33-9)
• EPA Substance Registry System: 4-hydroxybutyl oleate(28068-33-9)

Safety Data

• Hazardous Substances Data: 28068-33-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H42O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-22(24)25-21-18-17-20-23/h9-10,23H,2-8,11-21H2,1H3/b10-9-

Upstream product

• 110-63-4 Butane-1,4-diol 
• 112-80-1 cis-Octadecenoic acid 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 145437-64-5 (Z)-9-octadecenoic acid 4-[(tetrahydro-2H-pyran-2-yl)oxy]butyl ester 

Downstream Products

• 183323-35-5 (Z)-Octadec-9-enoic acid 4-(bis-benzyloxy-phosphoryloxy)-butyl ester 

Relevant articles and documents

Structure/activity relationships in lysophosphatidic acid: The 2- hydroxyl moiety

Although lipid phosphoric acid mediators such as lysophosphatidic acid (LPA) are now recognized widely as intercellular signaling molecules, the medicinal chemistry of these mediators is poorly developed. With the goal of achieving a better understanding of the structure activity relationships in LPA, we have synthesized and tested a series of LPA analogs that lack the 2- hydroxyl moiety. Our series consisted of compounds with 2, 3, or 4 carbon diol or amino alcohol backbones and oleoyl or palmitoleoyl acyl groups. These molecules cannot be acylated further to form phosphatidic acids, nor do they have chiral centers. The rank order potency of these compounds in mobilization of calcium in MDA MB-231 cells suggested a maximum optimal chain length of 24-25 atoms. However, high potency for the inhibition of adenylyl cyclase in these cells was achieved only by one compound that also contained a dissociable proton five bond lengths from the phosphorus atom. That compound, N-oleoyl-2-hydroxyethyl-1-phosphate, was nearly equipotent to 1- oleoyl LPA in both assays. The striking mimicry of LPA by the ethanolamine- based compound and the presence of fatty acid amides in tissue prompts us to propose that phosphorylated N-acyl ethanolamides occur naturally.

TETRONIC AND THIOTETRONIC ACID DERIVATIVES AS PHOSPHOLIPASE A2 INHIBITORS

There are disclosed compounds of the formula: wherein X is ?CH2R; R is and further when Y=S, R may also be ?(CH2)eCH3; Y is ?O?or ?S?; R1 and R2 are each, independently, hydrogen or lower alkyl; R3 is indolyl, furyl, phenyl or phenyl optionally mono- or disubstituted independently by alkyl of 1-7 carbon atoms, ?C(CH3)3, ?C(CH3)2CH2C(CH3), ?C(CH3)2CH2CH3, haloloweralkyl, perfluoroalkyl, lower alkoxy, aryl alkoxy, halo or nitro; R4 and R5 are, independently, ?COCH2R7, ?CO2R7, ?CONHR7, geranyl or CH2R3; R6 is hydrogen or lower alkyl; R7 is geranyl and any moiety selected from R other than AR5 A and B are, independently, ?O?, ?S? or ?NR6 ?; and a is 0-8; b is 1-10 when Y=S, and 2-10 when Y=0; c is 1-3; d is 0-9; and e is 3-18; which by virtue of their ability to inhibit PLA2, are ofuse as antiinflammatory agents and there is also disclosed a method for the treatment of immunoinflammatory conditions, such as allergy, anaphylaxis, asthma and inflammation in mammals