Effect of milling degrees on volatile profiles of raw and cooked black rice (Oryza sativa L. cv. Sintoheugmi)

Choi, Sehun; Seo, Han-Seok; Lee, Kwang Rag; Lee, Sunghee; Lee, Jihyun

doi:10.1007/s13765-017-0339-z

Applied Biological Chemistry

Table 2 Identified volatiles in raw and cooked black rice varying with milling degrees

From: Effect of milling degrees on volatile profiles of raw and cooked black rice (Oryza sativa L. cv. Sintoheugmi)

No.	Volatile compound	t ^a_R of unknown	Unknown RI^b	Literature RI	Extracted ion^c	Internal standard	Odor description^d	Odor threshold^e	After cooking
Aldehydes
12*	Hexanal	4.47	1080	1080	82	Octanal-d₁₆	Green tomato, green, grassy	4.5
29*	Octanal	8.78	1282	1284	84	Octanal-d₁₆	Citrus	0.7
32	(E)-2-heptenal	9.65	1316	1318	83	Octanal-d₁₆	Pungent, green, fatty	13	Absent
37*	Nonanal	11.34	1383	1390	98	Hexyl-d₁₃ alcohol	Aldehydic, waxy, citrus, tart, sweet	1
42*	(E)-2-octenal	12.23	1418	1416	83	Octanal-d₁₆	Cucumber, fatty, fresh, green, waxy	3
47	2-Furaldehyde	13.00	1449	1451	96	Octanal-d₁₆	Sweet, woody, almond, bread baked		New
49	Decanal	13.90	1484	1484	112	Octanal-d₁₆	Citrus	0.1
50*	Benzaldehyde	14.45	1505	1508	106	Octanal-d₁₆	Almond	350
51*	2-Nonenal	14.79	1519	1532	140	Octanal-d₁₆	Beany, cucumber	0.08
56	2,6,6-Trimethyl-1-cyclohexene-1-carbaldehyde	16.75	1598	1600	152	Octanal-d₁₆	Tropical, saffron, herbal, clean, rose		New
57	Phenylacetaldehyde	17.16	1617	1613	120	Octanal-d₁₆	Sweet, floral, nutty, fruity		New
58	2-Butyl-2-octenal	17.84	1646	1653	55	Octanal-d₁₆	Fruity, pineapple		New
72	Pentadecanal	25.46	2012	2040	96	Octanal-d₁₆	Fresh
96	4-Hydroxy-3-methoxybenzaldehyde (vanillin)	34.75		2566	151	Octanal-d₁₆	Vanilla, sweet, creamy	58	New
Ketone
1*	Acetone	1.97	815	814	58	Octanal-d₁₆	Acetone, ethereal, fruity	500,000
20*	2-Heptanone	6.39	1179	1180	58	Octanal-d₁₆	Cheesy	140
28*	2-Octanone	8.72	1280	1283	58	Octanal-d₁₆	Parmesan cheese like	50
31	2,5-Octanedione	9.60	1314	1319	99	Octanal-d₁₆			New
34	6-Methyl-5-hepten-2-one	9.99	1330	1339	108	Octanal-d₁₆
36	2-Nonanone	11.22	1378	1378	142	Octanal-d₁₆	Fruity, cheesy		New
39	3-Octen-2-one	11.68	1395	1408	126	Octanal-d₁₆	Creamy, earthy, oily, mushroom		New
48	2-Decanone	13.81	1480	1480	113	Octanal-d₁₆	Fermented, generic cheese notes
54	6-Methyl-3,5-heptadien-2-one	16.13	1574	1582	109	Octanal-d₁₆	Cinnamon, coconut, spicy		New
63	(5E)-6,10-dimethyl-5,9-undecadien-2-one	21.93	1832	1840	151	Octanal-d₁₆	Fresh, green, fruity, waxy	60	New
64	Geranyl acetone	21.97	1834	1843	136	Octanal-d₁₆	Floral, rose, fresh, slightly soapy	60	Absent
71	2-Pentadecanone	25.29	2002	1998	58	Octanal-d₁₆	Fresh, jasmine, celery		New
74	5-Pentyl-2(5H)-furanone	26.31	2059	2052	125	Octanal-d₁₆	Minty, fruity		New
77	6,10,14-Trimethyl-2-pentadecanone	27.29	2113	2110	250	Octanal-d₁₆	Oily, herbal, jasmine		New
78	Hexahydrofarnesyl acetone	27.33	2115	2110	43	Octanal-d₁₆	Fresh jasmine, celery		Absent
85	3-Ethyl-4-methyl-1 h-pyrrole-2,5-dione	29.93	2269	2260	139	Octanal-d₁₆			Absent
89	4,4,7a-Trimethyl-5,6,7,7a-tetrahydro-1-benzofuran-2(4H)-one	31.16	2271	2291	180	Octanal-d₁₆	Ripe, apricot, woody		Absent
99	7,9-Bis(2-methyl-2-propanyl)-1-oxaspiro[4.5]deca-6,9-diene-2,8-dione	37.45			149	Octanal-d₁₆	Green, woody		Absent
Alcohols
3*	Ethanol	2.71	927	926	46	Hexyl-d₁₃ alcohol	Strong alcoholic, ethereal, medical	100,000	Absent
18	1-Methoxy-2-propanol	5.57	1140	1135	45	Hexyl-d₁₃ alcohol			Absent
27*	1-Pentanol	8.06	1253	1246	55	Hexyl-d₁₃ alcohol	Fusel, oily, sweet, balsamic, fatty	4000	Absent
35*	1-Hexanol	10.52	1352	1358	56	Hexyl-d₁₃ alcohol	Green, fruity, apple-skin, oily	2500
46	1-Octen-3-ol	12.86	1444	1442	57	Hexyl-d₁₃ alcohol	Mushroom	1
53*	1-Octanol	15.47	1548	1555	84	Hexyl-d₁₃ alcohol	Waxy, green, citrus	110	Absent
59*	1-Nonanol	17.84	1647	1653	98	Hexyl-d₁₃ alcohol	Floral, rosy, fatty, citrus-like	50	Absent
88⁺	2,2′-[1,2-Ethanediylbis(oxy)]diethanol	31.03	2335		89	Hexyl-d₁₃ alcohol			Absent
Acids and esters
45*	Acetic acid	12.81	1441	1442	60	Hexyl-d₁₃ alcohol	Pungent, vinegar		Absent
52	Ethyl nonanoate	14.84	1522	1516	88	Hexyl-d₁₃ alcohol	Fatty, fruity brandy-like		Absent
60*	3-Methylbutanoic acid	18.05	1656	1684	60	Hexyl-d₁₃ alcohol	Cheesy, dairy, creamy		Absent
62	Hexanoic acid	21.89	1830	1850	73	Hexyl-d₁₃ alcohol	Cheesy, fatty	3000
68	2-Ethylhexanoic acid	24.06	1939	1933	88	Hexyl-d₁₃ alcohol			Absent
70*	Methyl myristate	25.12	1994	2008	143	Hexyl-d₁₃ alcohol	Fatty, waxy, petal		Absent
73*	Octanoic acid	26.19	2053	2050	101	Hexyl-d₁₃ alcohol	Oily, fatty, rancid	3000	Absent
75	Dibutyl (2Z)-2-butenedioate	26.75	2083		99	Hexyl-d₁₃ alcohol			New
79*	Nonanoic acid	28.17	2164	2169	129	Hexyl-d₁₃ alcohol	Cheese, dairy, fatty, waxy	3000
82*	Methyl palmitate	29.02	2206	2206	143	Hexyl-d₁₃ alcohol	Waxy, fat, candle
83*	Butyl myristate	29.22	2213	2215	229	Hexyl-d₁₃ alcohol	Oily, fatty		Absent
84	Ethyl palmitate	29.69	2227	2246	157	Hexyl-d₁₃ alcohol	Mild, waxy	2000	Absent
86	Decanoic acid	30.13	2241	2250	172	Hexyl-d₁₃ alcohol	Fatty, rancid	10,000
92*	Methyl (9Z)-9-octadecenoate	32.94	2449	2452	264	Hexyl-d₁₃ alcohol	Mild, fatty
93*	Benzoic acid	33.20	2465	2457	105	Hexyl-d₁₃ alcohol	Balsamic, urine		Absent
94	Methyl (9Z,12Z)-9,12-octadecadienoate	33.73	2497	2484	95	Hexyl-d₁₃ alcohol	Oily, fatty		Absent
101	Palmitic acid	40.12		2910	213	Hexyl-d₁₃ alcohol	Waxy, creamy fatty, soapy	10,000	Absent
Alkanes
4*	Decane	3.31	998	1000	142	Hexyl-d₁₃ alcohol			Absent
7	2-Methyldecane	4.08	1055	1053	141	Hexyl-d₁₃ alcohol			Absent
8	5-Ethyl-2,2,3-trimethylheptane	4.12	1058	1060	112	Hexyl-d₁₃ alcohol			Absent
9	3,7-Dimethylnonane	4.27	1067	1060	127	Hexyl-d₁₃ alcohol			Absent
10	3-Methyldecane	4.32	1070	1070	126	Hexyl-d₁₃ alcohol			Absent
11	3,7-Dimethyldecane	4.41	1076	1079	141	Hexyl-d₁₃ alcohol			Absent
13*	Undecane	4.57	1085	1100	71	Hexyl-d₁₃ alcohol
21*	Dodecane	6.47	1183	1200	170	Hexyl-d₁₃ alcohol
25	Tricyclo[5.2.1.0^2,6]decane	7.62	1234	1243	136	Hexyl-d₁₃ alcohol			New
30*	Tridecane	8.91	1286	1300	184	Hexyl-d₁₃ alcohol
38*	Tetradecane	11.42	1386	1400	198	Hexyl-d₁₃ alcohol
55*	Hexadecane	16.30	1581	1600	99	Hexyl-d₁₃ alcohol			Absent
76*	Heneicosane	26.81	2086	2100	85	Hexyl-d₁₃ alcohol	Waxy		Absent
100	1,4,7,10,13,16-Hexaoxacyclooctadecane	39.46			207	Hexyl-d₁₃ alcohol			Absent
Olefins
24	1-Dodecene	7.54	1231	1233	97	Hexyl-d₁₃ alcohol			Absent
40	3-Ethyl-2-methyl-1,3-hexadiene	11.87	1402	1404	124	Hexyl-d₁₃ alcohol			New
43	(Z)-4-Tetradecene	12.34	1423	1427	111	Hexyl-d₁₃ alcohol			Absent
44	1-Tetradecene	12.53	1430	1420	125	Hexyl-d₁₃ alcohol
66⁺	(4Z,8Z)-Tricyclo[10.2.1.02,11]pentadeca-4,8-diene	23.01	1885		79	Hexyl-d₁₃ alcohol			Absent
95⁺	Decanamide	34.65			59	Hexyl-d₁₃ alcohol			Absent
Additional compounds
2	Methyl acetate	2.02	823	825	74	Octanal-d₁₆	Ethereal, sweet		Absent
5*⁺	Acetonitrile	3.38	1005	1003	40	Hexyl-d₁₃ alcohol			Absent
6*⁺	Chloroform	3.59	1021	1021	83	Hexyl-d₁₃ alcohol	Floral, rose, green		Absent
14	Ethylbenzene	5.15	1118	1116	91	Hexyl-d₁₃ alcohol
15	2-Butylfuran	5.23	1123	1126	81	Hexyl-d₁₃ alcohol	Mild, fruity, wine, sweet, spicy
16	p-Xylene	5.30	1126	1130	91	Hexyl-d₁₃ alcohol	Medicinal	530
17	m-Xylene	5.42	1133	1140	106	Hexyl-d₁₃ alcohol
19	o-Xylene	6.33	1177	1176	91	Hexyl-d₁₃ alcohol	Peanut
22	Propylbenzene	6.81	1197	1203	120	Hexyl-d₁₃ alcohol	Solvent, sweet	6	New
23	2-Pentylfuran	7.36	1223	1226	138	Hexyl-d₁₃ alcohol	Floral, fruit	6
26	Styrene	8.00	1250	1254	104	Hexyl-d₁₃ alcohol	Sweet, balsam, floral, plastic	730
33	Isopropenylbenzene	9.75	1320	1321	118	Hexyl-d₁₃ alcohol			New
41	2-Heptylfuran	12.10	1412	1420	81	Octanal-d₁₆	Green, fatty, lactonic, oily, roasted, nutty		Absent
61	Calamenene	21.47	1809	1808	159	Hexyl-d₁₃ alcohol	Herb		Absent
65	Guaiacol	22.07	1839	1850	109	Hexyl-d₁₃ alcohol	Smoky, black rice-like	3
67⁺	4-Methyl-2,6-bis(2-methyl-2-propanyl)phenol	23.15	1892	1902	205	Hexyl-d₁₃ alcohol	Smoky, meaty, phenolic
69	Diethylene glycol	24.51	1963	1968	45	Hexyl-d₁₃ alcohol	Sweet		Absent
80	2-Sec-butylphenol	28.24	2168		150	Hexyl-d₁₃ alcohol			New
81	2-Methoxy-4-vinylphenol	28.55	2185	2180	135	Hexyl-d₁₃ alcohol	Amber, cedar, peanut	3	New
87⁺	2,4-Bis(2-methyl-2-propanyl)phenol	30.72	2258	2277	191	Hexyl-d₁₃ alcohol			Absent
90	4-Vinylphenol	32.02	2392	2382	120	Octanal-d₁₆	Chemical, phenolic, medicinal	10
91	1H-indole	32.87	2444	2441	117	2-Methylpyrazine-d6	Animal, fecal, naphthyl, with earthy	140
97⁺	Dibutyl phthalate	36.90		2680	149	Hexyl-d₁₃ alcohol	Faint odor		Absent

^at_R stands for retention time
^bRI stands for retention index. RI values were obtained from https://www.nist.gov or flavornet.org
^cExtracted ion from total ion scan used for quantitation
^dOdor-active compounds and ^eodor threshold (ppb) were described in previous studies [19, 20]
*Verified using authentic standards
⁺Putative contaminants

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