Agricultural and Biological Chemistry

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The Volatile Constituents of Freesia Flower (Freesia

hybrida Hort.)

Kimihiro Harada & Satoru Mihara

To cite this article: Kimihiro Harada & Satoru Mihara (1984) The Volatile Constituents of Freesia
Flower (Freesia�hybrida Hort.), Agricultural and Biological Chemistry, 48:11, 2843-2845, DOI:
10.1080/00021369.1984.10866599

To link to this article: https://doi.org/10.1080/00021369.1984.10866599

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Agric. Bioi. Chern., 48 (II), 2843~2845, 1984 2843

Note
The Volatile Constituents of Freesia
Flower (Freesia hybrida Hort.)
Kimihiro HARADA and Satoru MIHARA
Ogawa & Co., Ltd.,
6-32-9 Akabanenishi, Kita-ku, Tokyo 115, Japan
Received March 22, 1984
Freesia (Freesia hybrida Hort.) is native to South Africa,
blooming with yellow flowers from winter until spring.
The flower gives a pleasant sweet odor. The volatile
constituents of its flowers have not been analyzed prior to
this study. The present investigation was conducted to
identify the volatile chemicals related to the pleasant sweet
odor using GC/MS techniques.
Freesia flowers (Rijnveld's Golden Yellow) were col-
lected in Wadomari Town, Oshima district, Kagoshima,
Japan, in March. Extraction of Freesia flowers (210 kg)
was accomplished with 637 kg of distilled n-hexane. The
extract was filtered and then concentrated to give 260 g of
extract. The extract was steam distilled under reduced
pressure (15 mmHg) in a nitrogen stream at 30°C. The
distillate was extracted three times with 900 ml of ethyl
ether. The ethyl ether extract of Freesia was dried over
anhydrous sodium sulfate and concentrated to give 20 g of
extract (essential oil, yield=O.OI% relative to the amount
of flowers used). The essential oil obtained above was
separated into basic, acidic, weak acidic and neutral
fractions. An analysis of each fraction was performed by
GC/MS using a fused silica capillary column (Carbowax
20M, 50 m x 0.25 mm i.d.; column temp. 80 ~ 200°C pro-
grammed for 2°C/min; carrier gas, helium; ionization
voltage: 70eV).
Table I shows the compounds identified in the essential
oil of Freesia flowers. Linalool and (X-terpineol, which
have a refreshingly floral odor with a citrusy note, were the
major components of Freesia oil. Benzothiazole and pyr-
azines were identified in the basic fraction. Benzothiazole,
which has been identified in coconut') and cocoa2 ) etc.,
was newly identified here in the essential oil. Tri-
methylpyrazine, 2-isopropyl-3-methoxypyrazine and 2-
isobuthyl-3-methoxypyrazine have been found in licorice
essential oil,3) tomato juice4 ) and essential oil of iris rhi-
zomes,5) respectively. Acetic acid, n-valeric acid, n-
hexanoic acid, n-heptanoic acid, n-octanoic acid, n-
nonanoic acid, n-decanoic acid, and fJ-geranic acid were
identified in the acidic fraction. Four phenolic compounds
such as guaiacol, 2,4-dimethylphenol, p-cresol and eugenol
were identified in the weak acidic fraction.
Freesia oil has a characteristic fresh green odor with an
earthy and sweet undertone. 3-Hexanol, 2-hexanol, cis-3-

TABLE I. VOLA TILE COMPOUNDS IDENTIFIED IN FREESIA ESSENTIAL OIL

Peak tRa Peak

Compound Evidence
No. (min) area b (%)

2 2- Methyl-l-pentene 5.92 0.12 MS

4' Acetone 6.02 MS,GC
4' Hexadiene MS
7 Ethyl acetate 6.18 MS,GC
9 Ethanol 6.41 MS, GC
10 3-Methylheptadiene 6.54 MS
16 Toluene 7.51 0.03 MS, GC
17 2,3-Dimethyl-2-butanol 7.93 MS
18 Methyl n-butyl ketone 7.95 MS,GC
23 2,2,6-Trimethyl-6-vinyltetrahydropyran 8.56 MS, GC
24 Myrcene 9.33 0.02 MS, GC
25 3-Hexanol 9.55 0.03 MS, GC
28 2-Hexanol 10.06 0.11 MS, GC
29 Limonene 10.31 0.79 MS, GC
31 1,8-Cineol 10.47 0.17 MS, GC
34 y- Terpinene 10.80 0.02 MS, GC
42 2-Methykyclopentanone 12.81 MS
44 cis-3-Hexenyl acetate 13.20 0.05 MS, GC
46 n-Hexanol 14.03 0.03 MS, GC
47 cis- 3-Hexenol 15.26 0.11 MS, GC
48' trans-2-Hexenol 16.07 0.13 MS, GC
48' n-Nonanal MS,GC
49 Trimethylpyrazine 16.29 MS,GC
2844 K. HARADA and S. MIHARA

TABLE I. (continued)

Peak Peak
Compound Evidence
No. area" (%)

51 Acetic acid 17.62 MS, GC

52 2-Isopropyl-3-methoxypyrazine 17.72 MS, GC
53 Linalool oxide (furanoid) 17.96 0.11 MS,GC
54 Linalool oxide (furanoid) 19.24 0.13 MS,GC
56 3-Methylbicyclo(4,1 ,0)heptan-2-one 20.72 MS
59 2-Isobutyl-3-methoxypyrazine 22.05 MS,GC
60 Linalool 22.74 67.96 MS, GC
62 C ,s H 24 (sesquiterpene; M=204) 23.27 0.02 MS
64 n-Octanol 23.47 MS, GC
69 Terpinen-4-ol 25.86 0.11 MS, GC
70 fi-Caryophyllene 26.42 0.03 MS, GC
71 fi-Cyc1ocitral 26.90 0.04 MS, GC
72 Isovaleric acid 27.87 MS,GC
74 5-Methyl-5-vinyltetrahydrofuran -2-one 28.60 MS,GC
75 3-Methyl-3-decen-2-one 28.84 MS
80 a-Terpineol 30.61 19.09 MS, GC
83 n- Valerie acid 31.73 MS, GC
84 Geranial 32.12 0.02 MS,GC
85 Carvone 32.57 0.08 MS, GC
86 a-Selinene 32.73 0.71 MS,GC
IR, NMR
89 Linalool oxide (pyranoid) 33.90 0.06 MS,GC
90' Linalool oxide (pyranoid) 34.48 0.08 MS,GC
90 c 2,2,6-Trimethyl-I ,4-cyc1ohexandione MS
95 Nerol 36.04 MS,GC
96 y- Heptalactone 36.83 MS, GC
97 n-Hexanoic acid 37.64 MS,GC
100 Geraniol 38.52 0.02 MS, GC
102 a-Ionone 38.85 0.10 MS, GC
103 Guaiacol 39.24 MS,GC
105 Benzyl alcohol 39.38 MS,GC
106 Phenylethyl alcohol 41.28 0.07 MS,GC
108 Dimethyl benzyl carbinyl n-butyrate 42.01 1.11 MS, GC
113 fi-Ionone 43.38 0.28 MS, GC
114 n-Heptanoic acid 43.51 MS, GC
117 Benzothiazole 44.87 MS,GC
124 n-Octanoic acid 48.98 MS,GC
125 y- N onalactone 49.01 MS, GC
129 2,4-Dimethylphenol 49.78 MS,GC
130 p-Cresol 50.21 MS, GC
131 cis-p-Menthane-l,8-diol hydrate (Terpin hydrate) 50.70 0.03 MS, GC
139 trans-p-Menthane-l,8-diol 54.15 MS,GC
140 n-Nonanoic acid 54.26 MS, GC
141 Eugenol 54.45 MS,GC
144 3-(2-Pentenyl)-I ,2,4-cyc1opentatrione 56.04 MS
149 n-Decanoic acid 59.53 MS, GC
157 fi-Geranic acid 62.26 MS, GC
162 Dihydroactinidiolide 69.07 MS,GC

a The gas chromatographic column and oven conditions were as described for the GCjMS. Other operating
conditions were; nitrogen carrier gas flow rate, 0.67 ml/min; detector, FID; injector and detector temperature,
250°C.
" Hewlett-Packard Model 3385A reporting integrator was used to determine the peak area.
c More than two compounds in one peak.
d Peak area percent less than 0.01 %.
 The Volatile Consitituents of Freesia Flower
hexenyl acetate and cis-3-hexenol are important aromatic
constituents in the production of the green note. The
earthy and sweet odor may be due to the pyrazines and
lactones, respectively. However, further investigation of
the unknown compounds is necessary.
REFERENCES
I) F. M. Lin and W. F. Wilkens, J. Food Sci., 35, 538
2845
(1970).
2) I. Flament and B. Willhalm, Helv. ·Chim. Acta, 50,
2233 (1967).
3) C. Frattini, C. Bicchi, C. Barettini and G. M. Nano,
J. Agric. Food Chem., 25, 1238 (1977).
4) P. Schreier, F. Drawert and A. Junker, Z. Lebensm.
Unters.-Forsch., 165, 23 (1977).
5) J. Gamero and D. Joulain, Riv. Ital. EPPOS, 63, 141
(1981).