Alkyl derivatives of cholic acid as organogelators: One-component and two-component gels

HM Willemen; T Vermonden; ATM Marcelis; EJR Sudholter

doi:10.1021/la025514l

Alkyl derivatives of cholic acid as organogelators: One-component and two-component gels

HM Willemen, T Vermonden, ATM Marcelis^*, EJR Sudholter

^*Corresponding author for this work

Pharmaceutics

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

Cholic acid was coupled to an alkyl tail via three different connecting groups, amide, urea, and ester group, and the gelation capabilities of these compounds in different solvents were compared. Both amide and urea derivatives form one-component gels. They give transparent and stable gels in aromatic solvents through a hydrogen bonded network of monomolecular fibers. Structural variations give information about the molecular requirements for gelation. A new kind of two-component gel was found for the ester derivatives with two carbohydrates, isomannide and isosorbide. Formation of wormlike, inverted micelles causes gelation of apolar solvents. The optimal stoichiometry of the co-gelators lies close to 1:1.

Original language	English
Pages (from-to)	7102-7106
Number of pages	5
Journal	Langmuir
Volume	18
Issue number	19
DOIs	https://doi.org/10.1021/la025514l
Publication status	Published - 17 Sept 2002
Event	2nd International Conference on Self-Assembled Fibrillar Networks - AUTRANS, France Duration: 24 Nov 2001 → 28 Nov 2001

Keywords

LOW-MOLECULAR-MASS
ORGANIC-SOLVENTS
RATIONAL DESIGN
GELATORS
GELATION
LIQUIDS
LIBRARY
ESTERS
SUGAR
UNITS

Access to Document

10.1021/la025514l

Cite this

@article{c616a04c99af4d249ef0fd4db52c3773,

title = "Alkyl derivatives of cholic acid as organogelators: One-component and two-component gels",

abstract = "Cholic acid was coupled to an alkyl tail via three different connecting groups, amide, urea, and ester group, and the gelation capabilities of these compounds in different solvents were compared. Both amide and urea derivatives form one-component gels. They give transparent and stable gels in aromatic solvents through a hydrogen bonded network of monomolecular fibers. Structural variations give information about the molecular requirements for gelation. A new kind of two-component gel was found for the ester derivatives with two carbohydrates, isomannide and isosorbide. Formation of wormlike, inverted micelles causes gelation of apolar solvents. The optimal stoichiometry of the co-gelators lies close to 1:1.",

keywords = "LOW-MOLECULAR-MASS, ORGANIC-SOLVENTS, RATIONAL DESIGN, GELATORS, GELATION, LIQUIDS, LIBRARY, ESTERS, SUGAR, UNITS",

author = "HM Willemen and T Vermonden and ATM Marcelis and EJR Sudholter",

year = "2002",

month = sep,

day = "17",

doi = "10.1021/la025514l",

language = "English",

volume = "18",

pages = "7102--7106",

journal = "Langmuir",

issn = "0743-7463",

publisher = "American Chemical Society : Division of Carbohydrate Chemistry",

number = "19",

note = "2nd International Conference on Self-Assembled Fibrillar Networks ; Conference date: 24-11-2001 Through 28-11-2001",

}

TY - JOUR

T1 - Alkyl derivatives of cholic acid as organogelators

T2 - 2nd International Conference on Self-Assembled Fibrillar Networks

AU - Willemen, HM

AU - Vermonden, T

AU - Marcelis, ATM

AU - Sudholter, EJR

PY - 2002/9/17

Y1 - 2002/9/17

N2 - Cholic acid was coupled to an alkyl tail via three different connecting groups, amide, urea, and ester group, and the gelation capabilities of these compounds in different solvents were compared. Both amide and urea derivatives form one-component gels. They give transparent and stable gels in aromatic solvents through a hydrogen bonded network of monomolecular fibers. Structural variations give information about the molecular requirements for gelation. A new kind of two-component gel was found for the ester derivatives with two carbohydrates, isomannide and isosorbide. Formation of wormlike, inverted micelles causes gelation of apolar solvents. The optimal stoichiometry of the co-gelators lies close to 1:1.

AB - Cholic acid was coupled to an alkyl tail via three different connecting groups, amide, urea, and ester group, and the gelation capabilities of these compounds in different solvents were compared. Both amide and urea derivatives form one-component gels. They give transparent and stable gels in aromatic solvents through a hydrogen bonded network of monomolecular fibers. Structural variations give information about the molecular requirements for gelation. A new kind of two-component gel was found for the ester derivatives with two carbohydrates, isomannide and isosorbide. Formation of wormlike, inverted micelles causes gelation of apolar solvents. The optimal stoichiometry of the co-gelators lies close to 1:1.

KW - LOW-MOLECULAR-MASS

KW - ORGANIC-SOLVENTS

KW - RATIONAL DESIGN

KW - GELATORS

KW - GELATION

KW - LIQUIDS

KW - LIBRARY

KW - ESTERS

KW - SUGAR

KW - UNITS

U2 - 10.1021/la025514l

DO - 10.1021/la025514l

M3 - Article

SN - 0743-7463

VL - 18

SP - 7102

EP - 7106

JO - Langmuir

JF - Langmuir

IS - 19

Y2 - 24 November 2001 through 28 November 2001

ER -

Alkyl derivatives of cholic acid as organogelators: One-component and two-component gels

Abstract

Keywords

Access to Document

Fingerprint

Cite this