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Aroma Constituents of Roasted Coconut
Aroma Constituents of Roasted Coconut
To cite this article: Sretsei Saittagaroon, Shunro Kawakishi & Mitsuo Namiki (1984) Aroma
Constituents of Roasted Coconut, Agricultural and Biological Chemistry, 48:9, 2301-2307, DOI:
10.1080/00021369.1984.10866491
The volatile components of roasted and unroasted dried coconut shreds, isolated by steam
distillation, were analyzed by GC and GC-MS. Seventeen compounds were identified from the
unroasted coconut, and nine of them were newly identified in coconut meat aroma. Saturated delta-
C8 , C 10 , and C 12 lactones were determined as the main components giving the characteristic mild,
sweet, and pleasant coconut flavor. The roasted coconut gave the strong characteristic sweet and
nutty aroma, and the GC-MS indicated the saturated delta-Iactones as main components, and six
pyrazines, two furans, and two pyrroles also found seemed to contribute greatly to the nut-like
aroma of roasted coconut. The defatted and roasted meal gave a strong nut-like and burnt odor,
but not the characteristic sweet aroma. A large increase in pyrazines and other Maillard reaction
products and an absence of lactones and fatty acid esters were observed in the volatiles of the
roasted-defatted coconut meal.
Coconuts (Cocos nucifera L.) are undoubt- addition, the role of lipids in coconut flavor
edly the most extensively grown and used was studied.
nuts in the world. The shredded and dried
kernel of the coconut yields desiccated coco-
MATERIALS AND METHODS
nut, which is widely used for improvements
of flavor and/or texture in bakery and con- Materials. Shredded dried coconut kernel was pur-
fectionary. Coconut meat also possesses a chased from a local market. The coconut meat was an
mild and pleasant characteristic aroma. imported product, packed in a vacuum, white, and no sign
of rancidity was detected. The product had a characteristic
AlIeni) has reported the presence of a series
flavor identical to that of a native sample purchased from
of saturated methyl ketones with odd num- a Bangkok market and used in a preliminary experiment.
bers of carbon atoms and a series of satu-
rated delta-Iactones with even numbers of Isolation of volatile components from roasted and un-
carbon atoms in the volatile constituents of roasted coconuts. The coconut was roasted by immersing a
1 liter round bottom flask containing 200 g of shredded
coconut oil, and further investigation has been
dried coconut meat into a 160°C oil bath for 35 min with
done by Pai et al. 2 ) Lin and Wilkens 3 ) have rotating (70 rpm). The meat turned yellow brown and
identified fifteen volatile compounds in fresh generated a strong characteristic sweet and nut-like
coconut meat. In addition to the lactones, a aroma. The roasted. and unroasted coconut meat (200 g)
number of alcohols and other minor con- were each blended with 1 liter of distilled water and steam-
stituents have been reported. 3 ) On the other distilled to obtain 2 liters of distillate. The oil layer was
separated from the distillate by extraction of 1 liter lots of
hand the origin of the strong flavor of roasted NaCI-saturated distillate, four times each with 250 ml
coconut with its unique quality, characterized redistilled ether. The ether fractions were combined, dried
as sweet and nutlike, has not been investigated over anhydrous N a2 S04 overnight, and concentrated to
so far. Here we report the results of our study -200 ml in a water bath, with a short distillation column. A
on the volatile compounds of roasted coconut. 50 ml portion of the concentrate was further concentrated
to a small volume, called the flavor concentrate, and the
We also isolated and identified the volatile
remaining 150 ml of the ether extract was fractionated into
compounds of -unroasted coconut, for com- basic, acidic, weak acidic, and neutral fractions as shown
parison and to gain more information. In in Fig. 1. The flavor concentrate and each fraction were
2302 S. SAITTAGAROON, S. KAWAKISHI and M. NAMIKI
Ether
(20 ml x 3) parameters were as follows: column temperature held at
Neutral Weak acidic Acidic Basic
60°C for 4 min then programmed to increase to 200°C at a
fraction fraction fraction fraction rate of 5°C/min; gas, helium (0.8 kg/cm 2 ); ionizing voltage,
28 eV; accelerating voltage, 3000 V; ion source tempera-
FIG. 1. Scheme for Fractionation of Volatile Com-
ture, 250°C. Areas of the chromatographic peaks were
pounds.
calculated by the weighing method. Analysis of samples
in preliminary experiments used a Hitachi Model RMU-
analyzed by gas chromatography and gas chromatog- 6MG mass spectrometer equipped with a glass SCOT
raphy-mass spectrometry. Volatile compounds were column (0.28 mm i.d. x 50m) coated with Carbowax 20M.
identified by comparison of their mass spectra with refer-
ence spectra. 4 - 10 )
RESULTS AND DISCUSSION
Abundance a
Compounds MS data
(ppm)
Lactones
delta-Octalactone 33 99 (over scale), 71 (100), 42 (67), 70 (61),
43 (43), 55 (37), "', 142 M+ (1)
delta-Decalactone 82 99 (over scale), 71 (100), 70 (63), 43 (47),
114 (120), "',170 M+ (1)
delta-Dodecalactone 23 99 (100), 71 (59), 70 (37), 42 (29), 198 M+ (1)
Esters
Ethyl acetate b 3 43 (over scale), 45 (100), 61 (60), 44 (32),
70 (43), 73 (25), 88 M + (15)
Ethyl octanoateb 4 88 (100), 44 (61), 57 (41), 70 (33), 101 (28),
127 (23), 172 M+ (2)
Ethyl-5-hydroxy-octanoate b 5 99 (100), 88 (66), 55 (34), 70 (25), 43 (25), 145 (17)
Ethyl decanoate 15 88 (100), 101 (59), 70 (37), 73 (31),43 (26), 200M+ (9)
Ethyl-5-hydroxy-decanoate b 4 99 (100), 60 (64), 40 (55), 71 (49), 88 (43), 145 (17)
Ethyl dodecanoate b 30' 88 (over scale); 101 (l00), 57 (45),70 (41), 128 M+ (8)
Ethyl tetradecanoate b 3 57 (100), 88 (52), 71 (43), 83 (40), 165 (25), 256 M+ (3)
Ketones
2-U ndecanone 4 58 (100), 44 (40), 59 (32), 71 (29), 85 (11), 170 M + (3)
2-Tridecanone b 14 58 (100),59 (71), 43 (63), 71 (47),57 (41), 198 M+ (5)
Miscellaneous
2-Methylpyridineb,e 13 93 M + (over scale), 66 (100), 65 (57), 40 (35),
92 (34), 39 (26), 94 (26)
Benzothiazole 5 57 (l00), 71 (70), 135 M+ (57), 43 (47), 85 (43)
Furfuryl alcohol b 4 98 M+ (100), 41 (81), 81(50), 42 (48), 97 (42), 69 (40)
Butylhydroxytoluene (BHT) 2 57 (l00), 71 (52), 69 (41), 73 (34), 83 (33), 220 M+ (8)
Dibutylphthalate (DBP)d 14 149(100), 50 (29),/57 (28), 45 (24), 41 (17),278 M+ (1)
ported previously,3) and the nine that have not been known as the primary precursors -in the
been reported in unroasted coconut meat biosynthetic formation of lactones in most
flavor were ethyl acetate, ethyl-5-hydroxy- foods, the ethyl-5-hydroxy-esters identified
octanoate, ethyl-5-hydroxy-decanoate, 2- here might be the precursors of their cor-
methylpyridine, furfuryl alcohol, ethyl oc- responding lactones found in coconut meat.
tanoate, elthyl dodecanoate, ethyl tetradeca- Esters are generally known to be. responsible
noate, and 2-tridacanone. The last four com- for the fruity and sweet aromas of various
pounds, however, have been identified in the fruits. Those identified here are expected to
volatiles of coconut oil.2) Consistent with the contribute to the sweet aroma of coconut as
reports of Allen l ) and Lin and Wilken,3) a well, though no such sensory evaluation on the
relatively large amount of saturated delta- ethyl-5-hydroxy-esters has been reported. Fur-
lactones was found. These lactones have been furyl alcohol has been found in the volatiles
determined to be primarily responsible for the from roasted filberts,9) other heated food-
sensory properties of coconut meat. 3) The exis- stuffs 7 ,10) and cooked meat,12) and has been
tence of lactones, their formation, and sensory reported as a very mild, warm-oily, "burnt"
properties in various food systems have been odor, though the chemically pure compound
widely studied. l l ) As hydroxy fatty acids have has been noted as odorless by many observ-
2304 S. SAITTAGAROON, S. KAWAKISHI and M. NAMIKI
ers. 13 ) 2-Methylpyridine, the only significant TABLE III. YIELDS* OF FLAVOR COMPONENTS OBTAINED
peak found in chromatography of the basic FROM ROASTED COCONUT MEAT
~
18
Table. III lists the approximate yield of the
~
/3
flavor concentrate and fractionated volatiles 22
Abundance
Compounds MS data
(ppm)
Lactones
delta-Octalactonee 56 99 (100), 71 (85), 42 (65), 70 (62), 55 (48), 114 (17),
109 (11),142 M+ (3)
delta-Decalactone e 58 99 (100), 71 (46), 70 (44), 43 (40), 42 (37), 55 (33),
114 (15), 170 M+ (1)
delta-Dodecalactonee 5 99 (100), 70 (30), 43 (30), 71 (28), 57 (26), 114 (15),
198 M+ (1)
Esters
Ethyl octanoate e 5 88 (100), 43 (42), 57 (37), 101 (28), 127 (22), 172 M + (2)
Ethyl~5-hydroxy-octanoatee 2 99 (100), 88 (66), 55 (34), 70 (25), 43 (25), 145 (17)
Ethyl decanoate e 9 88 (100), 101 (78),43 (41),57 (31),70 (31),200 M+ (9)
Ethyl-5-hydroxy-decanoate e 15 88 (100), 99 (75), 71 (50), 55 (46), 145 (37), 43 (37)
Ethyl dodecanoate e 6 88 (100), 101 (52),57 (46),43 (41),71 (30),228 M+ (8)
Ethyl tetradecanoate e 2 57 (100),88 (68), 43 (37), 165 (36), 101 (32),256 M+ (4)
Ketones
2-Undecanone e 58 (100), 43 (58), 59 (32), 71 (29), 91 (26), 108 (10),
170 M+ (6)
2-Tridecanone e 6 58 (100), 43 (52),59 (51),71 (40),85 (16), 198 M+ (7)
Pyrazines
Ethylpyrazine 3 94 M+ (100),57 (91), 45 (73),71 (73),67 (55)
2,5-Dimethylpyrazine 2 108 M+ (100), 42 (88), 39 (23), 40 (22), 81 (15)
2~Methyl-5-ethylpyrazine 2 121 (100), 122 M+ (76),43 (63),39 (30),56 (30),94 (17)
2,6-Diethylpyrazine 3 135 (100), 136 M+ (95),42 (53),56 (25), 108 (41),
121 (14)
2,6-Diethyl-3-methylpyrazine 43 (100), 149 (78), 150 M + (67), 135 (33), 56 (28),
122 (17)
Trimethylpyrazine 3 42 (100),43 (93), 122 M+ (89), 121 (47),81 (23), 39 (21)
Pyrroles
2-Acetylpyrrole 4 94 (over scale), 109 M+ (100),66 (61), 39 (31)
5-Methyl-2-formylpyrrole 1 109 M + (100), 108 (83), 57 (70), 43 (37), 53 (35)
Furans
Dimethylfuran c 6 96 M + (100), 95 (92), 43 (88), 39 (56), 57 (30)
5-Methylfurfural .3 110 M+ (100),57 (78), 109 (65), 43 (56), 71 (44),85 (27)
Furfuryl alcohol e 5 98 M+ (100),97 (56),81 (51), 39 (40), 42 (37),
53 (31), 69 (30), 70 (28)
M iscellaneous
Dichlorobenzene 2 146 (100), 148 M+ (70), 43 (40), 111 (35), 75 (26)
BHTe 8 57 (100), 205 (88), 71 (58), 43 (43), 85 (35),
220 M+ (30), 97 (31)
10 149 (100), 45 (27), 57 (27), 150 (25), 205 (14),
223 (14), 278 M+ (2)
C Tentatively identified.
d Probable solvent artifact.
e Identified in volatiles of unroasted coconut meat.
traction using a binary system formed by increase in the amount of methanol. The frac-
mixing equal volumes of hexane and 87% tion eluted with pure chloroform and possess-
ethanol. The ethanol phase, which possessed ing a sweet aroma was concentrated and sub-
an aroma, was extracted with ether, and then jected to a capillary column GC-MS analysis.
the concentrated extract was fractionated on a In addition to most of the compounds listed in
DEAE cellulose column, eluting with a chlo- Table IV, gamma-crotonolactone, gamma-
roform and methanol mixture with a stepwise butyrolactone, delta-hexalactone, delta-
2306 S. SAITTAGAROON, S. KAWAKISHI and M. NAMIKI
TABLE V. YIELDS* OF FLAVOR COMPONENTS OBTAINED zines and other Maillard reaction products
FROM ROASTED-DEFATTED COCONUT MEAL
by removal of lipids is similar to that observed
Fractions Weight (%)
by Mottram and Edwards 17 ) who studied
the role of triglycerides and phospholipids
Basic 29.64 in the development of the aroma of cook-
Acidic 15.86
ed beef and found that remo..val of both tri-
Weak acidic 2.89
Neutral 51.61 glycerides and phospholipids caused a sig-
nificant decrease in the quantities of aliphatic
* Yield was calculated as in Table I. aldehydes and alcohols, with a large increase
Total (flavor concentrate) =47. 12 mgj57.24 g of
in the amount of pyrazines. The large increase
roasted-defatted coconut meal = 823 ppm.
in pyrazines and other Maillard reaotion pro-
ducts observed here, which is approximatly 15
tetradecalactone, ethyl carproate, lauric acid, times that of the roasted one and far exceeds
cyclotene, and maltol were newly identified. the increased concentration of protein, was
These lactones have been described as having probably largely due to the absence of lipids or
sweet and buttery aromas and the last two their degradation products which are believed
compounds have sweet aromas. to inhibit the formation of Maillard reaction
products 17 ) and little of less the higher level
Volatile components of roasted-defatted co- of protein providing precursors for their,
conut meal formation.
To study the role of coconut lipids to the
roasted coconut flavor, shredded-dried co- Acknowledgment. We thank Drs. K. Hayashi, J.
conut was ground, defatted and roasted as Okumura, and T. Yanai of Kawasaki Research Labora-
tories of T. Hasegawa Co., Ltd., for performing the
described. The roasted defatted meal possessed
capillary column GC-MS analyses of samples of the
a strong nut-like and burnt odor but not the preliminary experiments and valuable discussions on the
sweet aroma. Table V lists the approximate interpretation of mass spectra.
yield of the flavor concentrate and each frac-
tion. The total amount of the flavor com- REFERENCES
pounds was 47.12mgj57.24g defatted meal
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F. W. Shephard, A. J. Shingler and M. A. Gianturco,
pleted. Table VI lists identified compounds in
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seventeen pyrazines which were present in Renner, F. W. Shephard and M. A. Gianturco, J.
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Aroma Constituents of Roasted Coconut 2307
Abundance
Compounds MS data
(ppm)
Pyrazines
Methylpyrazine 9 . 94 M + (100), 43 (100), 39 (39), 53 (29)
2,3-Dimethylpyrazine 8 67 (100), 108 M+ (97), 42 (44), 40 (30)
2,5-Dimethylpyrazine 4 42 (100), 43 (87), 108 M+ (74), 39 (44), 81 (13)
2,6-Dimethylpyrazine 28 42 (100), 108 M+ (71), 39 (43), 40 (29), 43 (23),
107 (16),81 (14)
2- Methyl-3-ethylpyrazine 28 121 (100), 122 M+ (80), 39 (38), 67 (34), 94 (23), 80 (19)
2-Methyl-5- or -6-ethylpyrazine 3 121 (100), 122 M+ (59), 39 (47), 43 (38), 56 (17), 94 (17)
Trimethylpyrazine 7 42 (100), 122 M+ (52),43 (50), 39 (31),81 (18)
2,6-Diethylpyrazine 32 135 (100), 136 M+ (78), 42 (65), 43 (63), 39 (52),
56 (30), 108 (22), 107 (17)
2-Ethyl-3,5-dimethylpyrazine 3 43 (100), 135 (31), 136 M+ (20),45 (17), 39 (15), 42 (14)
2,5-Dimethyl-3-ethylpyrazine 6 43 (100), 135 (83), .136 M+ (64), 42 (42), 39 (34),
56 (20), 107 (14), 108 (14), 121 (13)
2,3-Diethyl-5-methylpyrazine tr 150 M+ (100), 149 (67), 135 (60),56 (50)
2,5-Dimethyl-3-isopentyl 39 122 (100), 39 (63), 41 (44), 42 (34), 163 (8),
pyrazine 178 M+ (tr)
6,7-Dihydro-5H-cyclopenta 4 119 (100),120 M+ (77), 39 (66),108 (64),41 (44),
pyrazine 65 (38), 121 (28), 122 (28)
2-Methyl-6,7-dihydro-5H- 3 134 M+ (100), 133 (95),39 (95),66 (66)
cyclopentapyrazine
5-Methyl-6,7-dihydro-5H- 4 119 (100), 122 (33), 39 (31), 121 (30), 134 M+ (29),
cyclopentapyrazine 43 (26), 78 (23), 108 (21)
~(or 3),5-Dimethyl-6,7-dihydro- 6 133 (100), 148 M+ (29),39 (28), 147 (28)
5H -cyclopentapyrazine
3-Methyl-2(2/-furyl)pyrazine c tr 41 (100), 39 (95), 44 (95), 160 M+ (86), 52 (67),
92 (62), 149 (57)
fyrroles
2-AcetylpyrroIe 39 94 (100), 109 M+ (64), 66 (56), 39 (35)
5-Methyl-2-formylpyrrole 2 109 M+ (100), 80 (90), 53 (87), 108 (77), 57 (63)
Furans
Furfural 16 39 (100), 96 M+ (76), 95 (64), 43 (51), 44 (50)
5-Methylfurfural tr 110 M+ (100), 109 (80), 53 (87), 108 (77), 57 (63)
Acetylfuran 7 43 (100), 95 (93), 39 (50), 110 M+ (41), 44 (38)
Furfurylalcohol 39 98 M+ (100), 41 (96), 53 (86), 81 (73), 39 (73)
Furfurylmethylketonec 58 82 (100), 54 (38), 124 M+ (21), 109 (8)
Ketones
6-Methyl-6-hepten-2-one 47 43 (100), 55 (87), 69 (68), 41 (55), 111 (45), 126 M+ (24)
5-Methyl-3-hexen-2-one 24 43 (100), 41 (74),69 (52),112 M+ (46),97 (37)
Miscellaneous
2-Methylpyridine 6 93 M+ (100), 66 (46), 65 (23), 39 (23), 92 (12), 94 (8)
Benzaldehyde 13 43 (100), 95 (85), 39 (63), 67 (57), 77 (49), 106 M+ (44)
Benzothiazole 16 135 M + (100), 39 (46), 44 (46),' 41 (36), 43 (36),
55 (36), 108 (32)
BHT 15 57 (100), 205 (88), 71 (58), 43 (43), 85 (35),
220 M+ (30), 97 (31)
c Tentatively identified.
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