Supplementary information Figure S1 1H-NMR spectrum of SPheOCH

1

ppm (f1)

0.0 1.0

2.0 3.0

4.0 5.0

6.0 7.0

8.0

3.00

2.11 31.81

5.31 0.83 0.79 3.16 1.88 2.00

Figure S1

1H-NMR spectrum of SPheOCH3 and peak attribution.

b

c b

a

a c

d e

e f d

g f

h + CHCl3

g h i

i

OCH₃ O

CH₂ NH

C O

CH₃ CH₂ 14

CH₂

2 Figure S2

ORTEP views of STyrOCH3 (A) and SPheOCH3 (C). Ellipsoids drawn at 30%

probability level. Hydrogen atoms are represented by spheres of arbitrary size.

Monoclinic crystal lattice for STyrOCH3 (B) and SPheOCH3 (D). a, b and c are the lattice parameters.

a

c b

o

B

D

b o a

c

A

C

3 Figure S3

Thermograms of STyrOCH3 (0.1 mmol.g^-1) gel in safflower oil. The temperature gradient was set at 10 (a) or 5°C/min (b) during the cooling and heating cycles.

Cooling Cooling Heating

4 Figure S4

Thermal evolution of FTIR spectra of SPheOCH3 (A), STrpOCH3 (B) and LTyrOCH3

(C) formulations in safflower oil at 0.2 mmol.g^-1. Arrows indicate the evolution of characteristic bands when the system was heated from 20 to 70°C.

B A

C

5 Figure S5

In vitro release of RHT (3% w/w) from 300-µL SAlaOCH3 gels at 0.1 (‹) and 0.05 mmol.g^-1 (‘) with an NMP/organogelator molar ratio of 5. Mean ± SEM (n=3).

SAlaOCH3 was synthesized according to reference 7.