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Supporting Information

Medium Chain Sugar Amphiphiles: An Alternative Vegetable Oil Structuring Agent

Swapnil R. Jadhava, Hyeondo Hwanga, Qingrong Huangb, George John a*

[a] Department of Chemistry, The City College of New York, and The Graduate School and University Center of The City University of New York, 160 Convent Ave, NY, NY-10031.USA. Tel: (+1) (212) 650-8353; Fax: (+1) (212) 650-6107. E-mail: john@sci.ccny.cuny.edu

[b] Department of Food Science, Rutgers, the State University of New Jersey, 65 Dudley Road, 12 New Brunswick, New Jersey 08901 USA Email: qhuang@aesop.rutgers.edu    

Table of contents

Experimental Section Experimental methods

Supplementary Figure S1 X-ray diffraction patterns.

Supplementary Figure S2 Effect of concentration on rheology and morphology of M8-CO gels

Supplementary Figure S3 Effect of concentration on rheology and morphology of S8-CO gels

Supplementary Figure S4 Effect of ageing on rheology and morphology of M8-CO gels

Supplementary Figure S5 Effect of ageing on rheology and morphology of S8-CO gels

Supplementary Figure S6 Effect of type of oils on rheology of M8 and S8 gels

Supplementary Figure S7 Mechanical and physical properties of M8 and S8 gels of various vegetable oils.

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Experimental Section

Enzyme catalytic method for synthesis of sugar alcohol dialkanoates: Novozyme 435 (0.35

g) was added to a mixture of mannitol (0.546 g, 3 mmol), vinyl esters (9 mmol; vinyl butyrate

and vinyl caprylate) and activated molecular sieves (10 g) in dry acetone (40 mL). The reaction

mixtures were shook at 200 rpm in an incubator shaker at 45 °C for 48 hr. After the completion

of reaction (monitored by TLC), reaction mixtures were filtered and solvent was removed in

rotary evaporator. The obtained crude products were purified by silica gel flash chromatography

using chloroform: methanol (9:1) as an eluent. All gelators were obtained as white solids. The

yields were above 70% for all the reaction.[1]

[1] F. M. Menger and K. L. Caran, J. Am. Chem. Soc., 2000, 122, 11679-11691.

Gel-sol melting temperature (Tg). Gel melting temperature was determined by typical tube

inversion method.[1,2] In a 2 mL scintillation vial gel was prepared as described above; the vial

was immersed in the oil-bath ‘upside down’ and slowly heated. The temperature at which the

viscous gel melted down was recorded as Tgel. [2] F. M. Menger and K. L. Caran, J. Am. Chem. Soc., 2000, 122, 11679-11691.

[3] P. K. Vemula and G. John, Chem. Commun., 2006, 2218-2220.

Optical Microscopy. A standard glass slide containing a small portion of gel was mounted on

Leica DM LB2 microscope stage and the phase changes were observed with 10x PH1 phase

contrast objective.

X-ray diffraction. A small portion of either oleogels or neat samples of M8/S8 was transferred

in a sample holder and immediately the reflectance was measured. The XRD measurement was

performed on PANalytical X’Pert PRO with MPD PW 3040/60 generator S/N DY 2974 and

monochromatic Cu-Co radiation (45 kV, 40 A). XRD measurement on the plain M8 powder was

also performed in same manner.

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Figure S1. Rheological and optical analyses of M8-CO gels at various concentrations of M8 (1, 3

and 5% wt/v). A) Oscillatory strain sweep measurements. B) Optical micrographs of gels taken at

10X magnification. The arrows indicate the yield strain points for M8-CO gels.

 

 

 

 

 

 

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Figure S2. Rheological and optical analyses of S8-CO gels at various concentrations of S8 (1, 3

and 5% wt/v). A) Oscillatory strain sweep measurements. B) Optical micrographs of gels taken at

10X magnification. The arrows indicate the yield strain points for S8-CO gels.

 

   

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Figure S3. Effect of ageing on the mechanical and structural properties of M8-CO gels (5 %

wt/v). A) Oscillatory frequency sweep measurements B) Optical microscope images of the CO

gel.

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Figure S4. Effect of ageing on the mechanical and structural properties of S8-CO gels (5 % wt/v).

A) Oscillatory frequency sweep measurements B) Optical microscope images of the CO gel.

 

   

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Figure S5. Frequency sweep measurements of different oil gels (5% wt/v). A) M8 and B) S8.

Oils listed in legend are arranged in increasing order of unsaturations in their triglycerides

profile.

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Oilsa M8 S8

Gʹ′ (Pa)b Gʹ′ʹ′ (Pa)c Tgel (°C) Gʹ′ (Pa) Gʹ′ʹ′ (Pa) Tgel (°C)

OO 4296 1289 108-111 2832 681 59-61

CO 4300 1176 109-111 2093 485 58-61

SO 4379 1219 109-112 1900 480 59-60

GO 3905 1293 109-111 2167 458 60-62

Figure S6. Structuring data obtained for M8 and S8 gels (5% wt/v) in different vegetable oils.

[a]Oils are arranged in increasing order of unsaturations in their triglycerides profile. [b]Average

value of elastic modulus in the linear viscoelastic region. [c]Average value of viscous modulus in

the linear viscoelastic region.