Chem. Pap.
Scheme 1 Synthetic route of
the five saturated branched fatty
acids
(
CH , m, 4H), 1.11–1.05 (CH , m, 4H), 0.86 (CH , t,
2
ppm): d = 183.5, 45.4, 34.3, 31.9, 29.5, 22.6, 20.6, 13.9,
13.8. MS (ESI): m/z (%) calcd for C H O : 159.1
2
3
1
J = 5.0 Hz, 6H). C NMR (125 MHz, DMSO, ppm):
3
9
18
2
?
[M ? H] , 181.1 [M ? Na] .
?
d = 173.6, 56.9, 31.8, 26.3, 23.0, 14.3. MS (ESI): m/z (%)
calcd for C H O : 217.3 [M ? H] , 239.1 [M ? Na] .
?
?
1
G . A clear, colorless, and odorless oil (95%). H NMR
1
1
20
4
2
1
c. A white solid (three steps, 68%). H NMR
3
(500 MHz, CDCl , ppm): d = 11.7 (COOH, s, 1H),
3
(
500 MHz, DMSO, ppm): d = 12.6 (COOH, s, 2H),
2.39–2.33 (CH, m, 1H), 1.66–1.64 (CH , m, 2H), 1.51–1.50
2
1
1
.73–1.67 (CH , m, 4H), 1.28–1.24 (CH , m, 6H),
2
(CH , m, 2H), 1.33 (CH , m, 8H), 0.90 (CH , t,
3
2
2
2
1
3
13
J = 5.0 Hz, 6H). C NMR (125 MHz, CDCl , ppm):
.16–1.10 (CH , m, 4H), 0.88–0.84 (CH , m, 6H).
2
C
3
3
NMR (125 MHz, DMSO, ppm): d = 173.6, 57.0, 34.4,
2.1, 31.5, 29.5, 24.0, 22.5, 17.5, 14.8, 14.3. MS (ESI): m/z
d = 183.4, 45.6, 31.9, 29.5, 22.6, 13. 9. MS (ESI): m/z (%)
calcd for C H O : 173.2 [M ? H] .
?
3
1
0 20 2
?
%) calcd for C H O : 231.0 [M ? H] , 253.1
1
G . A clear, colorless, and odorless oil (98%). H NMR
(
[
1
2
22
4
3
?
M ? Na] .
d. A white solid (three steps, 71%). H NMR
500 MHz, DMSO, ppm): d = 12.6 (COOH, s, 2H),
(500 MHz, CDCl , ppm): d = 11.85 (COOH, s, 1H),
3
1
3
2.40–2.34 (CH, m, 1H), 1.67–1.60 (CH , m, 2H), 1.50–1.42
2
(
(CH , m, 2H), 1.41–1.29 (CH , m, 10H), 0.94–0.88 (CH ,
2
2
3
1
3
1
1
.73–1.70 (CH , m, 4H), 1.30–1.24 (CH , m, 8H),
2
m, 6H). C NMR (125 MHz, CDCl , ppm): d = 183.5,
2
3
1
3
.11–1.05 (CH , m, 4H), 0.87–0.84 (CH , m, 6H).
3
C
45.4, 34.4, 32.2, 31.7, 29.2, 27.3, 22.6, 20.6, 14.0, 13.9. MS
?
(ESI): m/z (%) calcd for C H O : 187.2 [M ? H] , 209.2
2
NMR (125 MHz, DMSO, ppm): d = 173.7, 57.0, 32.1,
1.9, 31.5, 29.5, 26.3, 24.0, 23.0, 22.5, 14.3, 14.2. MS
1
1 22 2
?
[M ? Na] .
3
?
ESI): m/z (%) calcd for C H O : 245.2 [M ? H] , 267.1
1
G . A clear, colorless, and odorless oil (96%). H NMR
(
[
1
3
24
4
4
?
M ? Na] .
e. A white solid (three steps, 73%). H NMR
500 MHz, DMSO, ppm): d = 11.3 (COOH, s, 2H),
.97–1.93 (CH , m, 4H), 1.30 (CH , m, 16H), 1.11–1.08
(500 MHz, CDCl , ppm): d = 11.61 (COOH, s, 1H),
3
1
3
2.39–2.33 (CH, m, 1H), 1.68–1.61 (CH , m, 2H), 1.52–1.48
2
(
(CH , m, 2H), 1.33–1.30 (CH , m, 12H), 0.93–0.88 (CH ,
2
2
3
1
3
1
m, 6H). C NMR (125 MHz, CDCl , ppm): d = 183.3,
2
2
3
1
3
(
CH , m, 4H), 0.90 (CH , t, J = 5.0 Hz, 6H). C NMR
3
45.6, 32.2, 31.9, 31.7, 29.6, 29.2, 27.3, 22.6, 22.6, 14.0,
2
(
125 MHz, DMSO, ppm): d = 178.0, 58.0, 34.4, 31.4,
9.4, 24.5, 22.6, 14.0. MS (ESI): m/z (%) calcd for
13.9. MS (ESI): m/z (%) calcd for C H O : 201.0
1
2
24
2
?
[M ? H] .
2
?
C H O : 273.2 [M ? H] , 295.1 [M ? Na] .
?
1
G . A clear, colorless, and odorless oil (94%). H NMR
1
5
28
4
5
1
G . A clear, colorless, and odorless oil (96%).
1
H
(500 MHz, CDCl , ppm): d = 11.20 (COOH, s, 1H),
3
NMR (500 MHz, CDCl , ppm): d = 11.62 (COOH, s,
2.39–2.33 (CH, m, 1H), 1.65–1.64 (CH , m, 2H), 1.51
2
3
1
1
0
H), 2.41–2.35 (CH, m, 1H), 1.65–1.62 (CH , m, 2H),
2
(CH , m, 2H), 1.32–1.30 (CH , m, 16H), 0.91–0.89 (CH , t,
2
2
3
1
3
J = 5.0 Hz, 6H). C NMR (125 MHz, CDCl , ppm):
.51–1.47 (CH , m, 2H), 1.40–1.32 (CH , m, 6H),
2
2
3
1
.95–0.90 (CH , m, 6H). C NMR (125 MHz, CDCl3,
3
d = 183.4, 45.7, 32.2, 31.7, 29.2, 27.3, 22.6, 14.0. MS
3
123