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AMB Express

Table 1 Chemical constituents of leaf and stem volatile oils of O. vulgare L. grown in Saudi Arabia and Jordan

From: Chemical diversity in leaf and stem essential oils of Origanum vulgare L. and their effects on microbicidal activities

No.

Compound*

LRILit

LRI aExp

LRI pExp

SOVS (%)b

SOVL (%)b

JOVS (%)b

JOVL (%)b

Identificationc

1

trans-2-Hexenal

846

852

1217

t

–

–

t

1,2

2

cis-3-Hexen-1-ol

850

854

1389

t

t

–

t

1,2,3

3

trans-2-Hexen-1-ol

854

857

1412

–

–

–

t

1,2

4

cis-2-hexen-1-ol

859

865

–

t

–

–

t

1,2

5

1-Hexanol

863

867

1358

–

–

–

t

1,2

6

2-Heptanol

894

897

–

t

t

–

–

1,2

7

Tricyclene

921

922

1010

–

t

–

t

1,2

8

α-Thujene

924

927

1023

0.2 ± 0.00

1.4 ± 0.06

t

1.0 ± 0.51

1,2,3

9

α-Pinene

932

934

1018

0.1

0.6

t

0.5

1,2,3

10

α-Fenchene

945

945

–

–

t

–

–

1,2

11

Camphene

946

949

1060

t

0.1

0.1

0.1

1,2,3

12

Benzaldehyde

952

961

1523

t

t

–

t

1,2

13

Sabinene

969

974

1118

0.1

0.6

–

0.1

1,2,3

14

β-Pinene

974

977

1104

t

0.3

–

0.1

1,2,3

15

1-Octen-3-ol

974

979

1455

0.2

0.4

0.8

1.2

1,2,3

16

3-Octanone

979

987

1255

t

t

0.1

0.1

1,2,3

17

6-Methyl-5-hepten-2-oned

981

–

1339

–

–

–

t

1,2

18

β-Myrcene

988

992

1163

0.4 ± 0.05

2.0 ± 0.07

0.1 ± 0.00

1.9 ± 0.14

1,2,3

19

3-Octanol

988

996

1399

0.3

0.4

1.3

2.0

1,2,3

20

α-Phellandrene

1002

1005

–

0.1

0.2

–

0.3

1,2

21

δ-3-Carene

1008

1011

1146

t

0.1

–

0.1

1,2

22

α-Terpinene

1014

1017

1177

0.4 ± 0.00

1.4 ± 0.00

0.1 ± 0.00

2.7 ± 0.07

1,2,3

23

m-Cymene

–

1023

–

–

t

–

–

1,2

24

p-Cymene

1020

1025

1269

1.4 ± 0.07

3.2 ± 0.00

1.6 ± 0.07

6.8 ± 0.00

1,2,3

25

Limonened

1024

–

1196

0.1

0.3

–

0.4

1,2

26

β-Phellandrene

1025

1030

1205

0.2

0.5

0.1

0.5

1,2

27

1,8-Cineole

1026

1033

1208

t

t

–

t

1,2

28

cis-β-Ocimene

1032

1039

1235

t

0.1

–

0.2

1,2

29

Benzeneacetaldehyde

1036

1045

1635

t

t

–

t

1,2

30

trans-β-Ocimene

1044

1049

1252

t

0.1

–

0.1

1,2

31

γ-Terpinene

1054

1060

1245

1.9 ± 0.06

6.2 ± 0.07

0.4 ± 0.00

17.0 ± 0.14

1,2,3

32

cis-Sabinene hydrate

1065

1068

1471

0.6

0.9

0.3

0.3

1,2

33

cis-Linalool oxided

1067

–

1048

–

–

–

t

1,2

34

trans-Linalool oxide

1084

1087

–

t

–

–

–

1,2

35

α-Terpinolene

1086

1090

1282

0.1

0.1

–

0.1

1,2,3

36

p-Cymenened

1089

–

1438

–

–

–

t

1,2

37

Linaloold

1095

–

1552

0.1

0.2

0.6

t

1,2,3

38

trans-Sabinene hydrate

1098

1099

1556

2.6 ± 0.08

3.5 ± 0.07

–

0.5 ± 0.03

1,2,3

39

Nonanal

1100

1104

1394

–

–

–

t

1,2

40

p-Mentha-1(7), 8-diened

1003

–

1167

–

–

–

t

1,2

41

1-Octen-3-yl acetate

1110

1113

–

t

–

–

–

1,2

42

1,3,8-p-Menthatriene

1108

1113

–

–

t

–

–

1,2

43

cis-p-Menth-2-en-1-ol

1118

1123

–

0.1

0.1

0.1

t

1,2

44

α-Campholenal

1122

1128

1491

t

t

–

–

1,2

45

allo-Ocimene

1128

1130

1373

–

t

–

t

1,2

46

cis-p-Mentha-2,8-dien-1-ol

1133

1138

–

–

t

–

–

1,2

47

trans-Pinocarveol

1135

1142

–

0.1

t

t

–

1,2

48

trans-Verbenol

1140

1148

1685

t

t

0.1

–

1,2

49

Isoborneol

1155

1159

–

–

t

–

–

1,2

50

Borneol

1165

1168

1708

0.7

0.1

1.4

0.2

1,2

51

Umbellulone

1167

1175

1646

t

t

–

–

1,2

52

Terpinen-4-ol

1174

1180

1608

1.6 ± 0.06

0.9 ± 0.07

0.8 ± 0.00

0.5 ± 0.21

1,2,3

53

m-Cymen-8-ol

1176

1184

–

t

–

–

–

1,2

54

p-Cymen-8-ol

1179

1188

1854

t

t

0.2

t

1,2

55

α-Terpineol

1186

1193

1703

0.1

0.1

0.2

t

1,2

56

Myrtenal

1195

1196

–

0.2

0.1

–

–

1,2

57

cis-Dihydro carvone

1191

1199

1611

0.1

0.2

0.1

0.1

1,2

58

cis-Piperitold

1195

–

1753

t

t

–

–

1,2

59

trans-Dihydro carvone

1200

1203

1631

0.1

–

–

t

1,2

60

n-Decanal

1201

1207

1495

t

0.1

–

–

1,2

61

Verbenone

1204

1212

–

0.1

–

–

–

1,2

62

Linalool formated

1214

–

1577

–

t

–

–

1,2

63

trans-Carveol

1215

1215

1842

t

t

–

t

1,2

64

cis-Carveol

1226

1229

–

t

t

0.1

–

1,2

65

Methyl thymol

1232

1233

–

t

t

–

–

1,2

66

Isobornyl formate

1235

1235

1584

–

t

–

t

1,2

67

(E)-Ocimenone

1235

1238

–

–

t

–

–

1,2

68

Methyl carvacrol

1241

1246

–

0.1

t

–

–

1,2

69

Carvotanacetone

1244

1249

1683

t

t

–

–

1,2

70

Geraniol

1249

1253

–

–

–

0.1

–

1,2

71

Linalool acetate

1254

1256

–

0.1

–

0.1

–

1,2

72

Thymoquinone

1248

1259

–

–

0.1

 

t

1,2

73

cis-Chrysanthenyl acetate

1261

1262

–

t

–

0.1

–

1,2

74

(2E)-Decenal

–

1266

–

–

t

–

–

1,2

75

Perilla aldehyde

1269

1281

–

t

–

–

–

1,2

76

Bornyl acetate

1284

1287

1585

t

t

–

t

1,2

77

Thymol

1289

1294

2190

2.1 ± 0.00

0.8 ± 0.07

68.73 ± 4.50

59.1 ± 0.28

1,2,3,4

78

Carvacrol

1298

1311

2222

79.5 ± 0.77

72.8 ± 0.21

2.4 ± 0.14

2.0 ± 0.07

1,2,3,4

79

(2E,4E)-Decadienal

1315

1319

–

t

0.1

–

–

1,2

80

Myrtenyl acetate

1324

1328

–

t

–

–

–

1,2

81

trans-Carvyl acetate

1339

1333

 

–

t

–

–

1,2

82

δ-Elemene

1335

1343

–

0.1

0.1

–

–

1,2

83

Thymol acetate

1349

1357

1870

t

t

–

t

1,2

84

Eugenol

1356

1361

2162

0.1

t

0.1

t

1,2

85

Carvacrol acetate

1370

1376

1876

0.2

0.1

–

t

1,2

86

α-Copaene

1374

1382

–

–

t

 

–

1,2

87

β-Bourbonene

1387

1391

–

–

t

t

–

1,2

88

β-Elemene

1389

1397

–

t

t

–

t

1,2

89

n-Tetradecane

1400

1400

–

t

t

–

–

1,2,3

90

Methyl eugenol

1403

1406

–

t

–

–

–

1,2

91

cis-α-Bergamotene

1411

1419

1570

t

t

t

–

1,2

92

β-Caryophyllene

1417

1427

1600

1.5 ± 0.00

1.2 ± 0.00

2.5 ± 0.14

0.9 ± 0.00

1,2,3

93

β-Copaene

1430

1436

–

t

t

–

–

1,2

94

trans-α-Bergamotene

1432

1440

1588

0.1

t

0.1

t

1,2

95

α-Guaiene

1437

1446

1592

t

t

–

–

1,2

96

Seychellene

1444

1453

–

–

t

–

–

1,2

97

α-Humulene

1452

1461

1672

0.1

0.1

0.1

t

1,2

98

cis-Muurola-4(14),5-diene

1465

1470

–

t

t

–

–

1,2

99

γ-Muurolene

1478

1483

1692

t

t

–

–

1,2

100

Germacrene-D

1484

1488

1712

0.2

0.2

0.1

t

1,2,3

101

n-Pentadecane

1500

1500

–

t

t

–

–

1,2,3

102

Bicyclogermacrene

1500

1504

1737

0.3

0.2

–

–

1,2,3

103

(E, E)-α-Farnesene

1505

1510

–

t

t

–

–

1,2

104

β-Bisabolene

1505

1513

1729

0.1

t

0.3

0.1

1,2

105

β-Ionol

1412

1517

1915

t

t

–

–

1,2

106

γ-Cadinene

1513

1521

1763

t

t

–

t

1,2

107

trans-Calamenene

1521

1529

1835

t

t

t

t

1,2

108

α-Cadinene

1537

1533

1777

t

–

–

–

1,2

109

cis-Nerolidol

1531

1547

2017

t

t

–

–

1,2

110

Thymohydro quinone

1553

1555

–

–

t

–

t

1,2

111

trans-Nerolidol

1561

1566

2046

t

–

 

0.1

1,2

112

Germacrene-d-4-ol

1574

1576

2057

t

t

–

–

1,2

113

Spathulenol

1577

1585

2132

0.1

t

–

–

1,2,3

114

Caryophyllene oxide

1582

1592

1991

0.1

t

0.3

0.1

1,2,3

115

Viridiflorol

1592

1600

–

t

t

–

–

1,2

116

Cedrol

1600

1610

–

–

–

–

t

1,2

117

Humulene epoxide II

1608

1614

–

t

–

–

–

1,2

118

1,10-di-epi-Cubenol

1618

1623

2065

t

t

–

–

1,2

119

α-Muurolol

1644

1646

–

–

t

–

t

1,2

120

τ-Cadinol

1638

1648

2179

0.1

–

–

–

1,2

121

β-Eudesmol

1649

1659

–

–

–

–

t

1,2

122

α-Cadinol

1652

1662

2237

t

t

0.t

–

1,2

123

β-Bisabolol

1674

1675

–

0.1

t

0.2

–

1,2

124

1-Tetradecanol

1671

1678

–

–

t

–

–

1,2

125

α-Bisabolol

1685

1689

–

–

–

t

–

1,2

126

n-Heptadecane

1700

1700

1700

t

t

–

–

1,2,3

127

Pentadecanal

–

1715

–

0.1

t

t

–

1,2

128

(E, E)-Farnesol

1742

1746

–

–

–

t

–

1,2

129

Tetradecanoic acid

–

1767

2693

–

–

0.1

 

1,2

130

14-Hydroxy-α-muurolene

1779

1780

–

t

–

–

–

1,2

131

Eudesm-7(11)-en-4-ol, acetate

1839

1846

–

t

–

t

–

1,2

132

Pentadecanoic acid

–

1871

–

t

t

t

–

1,2

133

cis-Spiroether

1879

1889

–

t

–

–

–

1,2

134

trans-Spiroether

1890

1896

–

t

t

–

–

1,2

135

2-Heptadecanone

–

1908

–

t

t

–

–

1,2

136

Methyl hexadecanoate

1921

1926

2208

t

–

–

–

1,2

137

Palmitic acid

1959

1959

 

t

–

0.3

–

1,2

138

n-Hexadecyl acetate

2003

2005

2301

0.1

t

0.2

–

1,2

139

(E, E)-Geranyl linalool

2026

2033

2541

0.7

t

0.9

–

1,2

140

Manool

2056

2068

2668

t

–

0.1

–

1,2

141

3,3,4,5,5,8-hexamethyl-2,6-dihydro-s-indacene-1,7-dione

–

2083

2437

0.3 ± 0.00

0.1 ± 0.00

1.5 ± 0.00

–

1,2

142

Phytol

1942

2105

2622

–

–

0.1

–

1,2

143

2-tert-Butyl-4-(dimethylbenzyl)phenol

–

2125

2612

0.1 ± 0.05

t

2.1 ± 0.00

–

1,2

144

Linoleic acid

2132

2141

–

0.2

t

1.2

–

1,2

145

Methyl octadecanoate

2124

2149

–

–

–

0.1

–

1,2

146

Octadecanoic acid

–

2179

–

–

–

0.1

–

1,2

147

cis-13-Octadecen-1-yl acetate

–

2193

–

t

–

0.1

–

1,2

148

n-Docosane

2200

2200

2200

0.1

t

0.2

–

1,2,3

149

n-Tricosane

2300

2300

2300

t

–

0.9

–

1,2,3

150

trans-Totarol

2314

2320

–

t

–

–

–

1,2

151

3α-Acetoxy manool

2359

2378

–

t

–

0.2

–

1,2

152

n-Pentacosane

2500

2500

2500

t

–

0.1

–

1,2,3

153

n-Hexacosane

2600

2600

2600

–

–

t

–

1,2,3

Total identified

98.4

99.0

91.8

99.2

 
  1. * Components are listed in their order of elution from HP-5 MS column; b=Mean percentage calculated from flame ionization detector (FID) data and compounds higher than 1.0% are highlighted in italicface and their ± SD (n = 2) are mentioned; LRILit, linear retention index from the literature (Adams 2007); LRI aExp , determined linear retention index against mixture of n-alkanes (C8-C31) on HP-5 MS column; LRI pExp , determined linear retention index against mixture of n-alkanes (C8-C31) on DB-wax column; SOVS, stem volatile oils of Saudi O. vulgare L.; SOVL, leaves volatile oil of Saudi O. vulgare L.; JOVS stem volatile oils of Jordanian O. vulgare L.; JOVL leaves volatile oil of Jordanian O. vulgare L.; cIdentification by; 1, linear retention index (LRI) identical to literatures (cf. exp. part); 2, comparison of mass spectra (MS) with the library entries of mass spectra databases (cf. exp. part); 3, co-injection/comparison with the LRI and mass spectra of standards; 4, 1H and 13C NMR spectra; t, trace (<0.05%); dIdentified from DB-Wax column
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