Preparation of reminiscent aroma mixture of Japanese soy sauce

Figures & data

Table 1. Volatile flavor compounds separated by LDPE membrane extraction method from soy sauce.

No.	RI^a	Compound^b	IS ratio^c	No.	RI^a	Compound^b	IS ratio^c
1	882	Ethyl acetate	5.36	73	1600	Hexadecane	0.05
2	903	2-Methylbutanal	0.75	74	1604	Benzeneacetaldehyde	0.02
3	935	Ethanol	34.76	75	1616	Unknown	tr
4	950	Ethyl propionate	0.05	76	1623	2-Furanmethanol	2.19
5	961	Ethyl 2-methylpropanoate	tr	77	1631	3-Methylbutanoic acid	1.42
6	1016	2-Butanol	tr	78	1641	Diethyl succinate	0.24
7	1054	Ethyl 3-methylbutanoate	0.04	79	1647	Butanediol (isomer of No. 60)	0.02
8	1077	2-Methylpropanol	3.60	80	1651	Unknown	0.20
9	1087	Unknown	tr	81	1660	Unknown	tr
10	1097	2,6,8-Trimethyldecane	0.02	82	1668	5-Ethyldihydro-2(3H)-furanone	0.02
11	1107	Unknown	0.02	83	1674	Unknown	tr
12	1130	1-Butanol	3.51	84	1682	3-(Methylthio)propanol (methionol)	1.34
13	1137	Unknown	0.02	85	1693	Unknown	0.08
14	1143	Unknown	tr	86	1699	Unknown	0.41
15	1166	Unknown	tr	87	1703	Unknown	tr
16	1170	Unknown	tr	88	1708	Unknown	tr
17	1191	3-Methylbutanol (isoamyl alcohol)	5.97	89	1714	2(5H)-Furanone	tr
18	1199	2-Buten-1-ol	0.04	90	1716	Unknown	tr
19	1211	Unknown	tr	91	1721	Unknown	tr
20	1217	Unknown	tr	92	1731	Unknown	tr
21	1228	3-Methyl-3-buten-1-ol	tr	93	1744	Unknown	tr
22	1232	1-Pentanol	tr	94	1748	Unknown	0.24
23	1233	Ethenyl benzene	0.03	95	1753	3-Methylpentanoic acid	0.02
24	1239	Dihydro-2-methyl-3(2H)-furanone	tr	96	1758	Unknown	tr
25	1243	2-Methylpyrazine	tr	97	1763	4-Methylpentanoic acid	0.09
26	1252	Unknown	tr	98	1767	Unknown	0.03
27	1259	3-Hydroxy-2-butanone	0.24	99	1775	Methyl laurate	0.57
28	1261	Unknown	tr	100	1783	Ethyl nicotinate	0.15
29	1266	Unknown	tr	101	1791	2-Hydroxy-3-methyl-2-cyclopenten-1-one	0.03
30	1271	1-Hydroxy-2-propanone	0.24	102	1803	Unknown	0.08
31	1289	Unknown	tr	103	1807	Unknown	0.02
32	1297	2,5-Dimethylpyrazine	0.02	104	1811	Unknown	0.58
33	1300	Tridecane	tr	105	1819	2-Methoxyphenol	0.25
34	1303	2,6-Dimethylpyrazine	0.03	106	1837	Phenylmethanol	0.04
35	1314	Ethyl 2-hydroxypropanoate	2.44	107	1857	3-Ethyl-2-hydroxy-2-cyclopenten-1-one	tr
36	1329	Unknown	0.04	108	1860	Unknown	0.38
37	1335	Unknown	0.02	109	1868	Unknown	0.05
38	1343	1-Hydroxy-2-butanone	0.10	110	1873	2-Phenylethanol	2.69
39	1350	3-Ethoxy-1-propanol	0.07	111	1902	Unknown	tr
40	1359	2-Ethoxy-butane	0.25	112	1923	Unknown	0.20
41	1368	Nonanal	tr	113	1926	3-Hydroxy-2-methyl-4H-pyran-4-one	0.20
42	1374	Ethyl 2-hydroxy-4-methylpentanoate	tr	114	1930	1-(1H-Pyrrol-2-yl)ethanone	1.08
43	1381	4-Hydroxy-3-hexanone	tr	115	1941	3,4-Dihydro-2H-pyran-2-carboxaldehyde	0.04
44	1385	Unknown	tr	116	1947	Unknown	tr
45	1400	Tetradecane	0.35	117	1961	Phenol	tr
46	1410	Acetic acid	9.38	118	1965	Unknown	tr
47	1421	1-Octen-3-ol	0.03	119	1982	1H-Pyrrole-2-carboxaldehyde	0.03
48	1428	2-Furancarboxaldehyde	0.02	120	1992	4-Hydroxy-2,5-dimethyl-3(2H)-furanone	0.63
49	1431	Methyl 2-oxohexanoate	0.35	121	2003	Unknown	0.03
50	1433	3-(Methylthio)propanal (methional)	0.004^d	122	2016	Unknown	0.02
51	1438	2,3-Dimethyl-5-ethylpyrazine	tr	123	2054	4-Hydroxy-2(or5)-ethyl-5(or2)-methyl-3(2H)-furanone (HEMF)	5.91
52	1440	Unknown	tr	124	2082	Unknown	0.03
53	1452	Tetramethylpyrazine	tr	125	2087	Unknown	tr
54	1455	3,5,5-trimethyl-2-hexene	tr	126	2098	Unknown	0.03
55	1465	Methanoic acid	tr	127	2150	2-Methoxy-4-vinylphenol	0.13
56	1472	Decanal	tr	128	2216	2,6-Dimethoxyphenol	0.25
57	1487	Ethyl 3-hydroxybutanoate	tr	129	2221	3,5-Dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one	0.15
58	1500	Pentadecane	0.11	130	2232	Unknown	0.10
59	1506	Propanoic acid	0.12	131	2240	Unknown	0.03
60	1514	Butanediol	1.27	132	2248	Unknown	0.11
61	1531	2-Methylpropanoic acid	0.34	133	2260	Glycerol	0.56
62	1535	Ethyl 3-(methylthio)propanoate	tr	134	2313	Unknown	0.09
63	1539	Unknown	0.09	135	2317	4-Ethoxy-4-oxobutanoic acid	0.27
64	1545	Butanediol (isomer of No. 60)	2.13	136	2344	Unknown	0.18
65	1551	Vinyl hexanoate	0.97	137	2363	Benzoic acid	0.41
66	1556	Dihydro-3-methyl-2(3H)-furanone	0.13	138	2394	Unknown	0.27
67	1561	Unknown	tr	139	2414	Dodecanoic acid	0.25
68	1564	Unknown	0.04	140	2424	Unknown	0.10
69	1576	Dihydro-5-methyl-2(3H)-furanone	0.39	141	2471	Phenylacetic acid	0.43
70	1582	Unknown	0.76	142	2542	Ethyl 4-hydroxy-3-methoxy benzoate	0.26
71	1590	Butanoic acid	0.05	143	2605	Tetradecanoic acid	0.30
72	1592	Dihydro-2(3H)-furanone	0.05	144	2613	Unknown	0.13

^a Retention index.

^b These compounds were identified by comparing the mass spectra and the retention indices.

^c The peak area ratio of the respective compounds to IS (10 mg/L).

^d It was determined by single ion monitoring mode (m/z=104).

Table 2. Odor-active compounds in soy sauce aroma concentrate by GC-MS-O.

RI^a	Compound^b	Odor attributes^c
903	2-Methylbutanal	Nutty, pungent
935	Ethanol	Alcoholic
950	Ethyl propionate	Pineapple-like
961	Ethyl 2-methylpropanoate	Fruity
1016	2-Butanol	Pungent
1054	Ethyl 3-methylbutanoate	Apple-like
1077	2-Methylpropanol	Malty
1130	1-Butanol	Fusel-like
1166	Unknown	Fruity
1191	3-Methylbutanol (isoamyl alcohol)	Fruity
1252	Unknown	Bitter
1259	3-Hydroxy-2-butanone	Peanut-like
1271	1-Hydroxy-2-propanone	Peanut-like
1297	2,5-Dimethylpyrazine	Malty
1303	2,6-Dimethylpyrazine	Malty
1314	Ethyl 2-hydroxypropanoate	Nutty
1343	1-Hydroxy-2-butanone	Metallic
1410	Acetic acid	Sour, vinegar-like
1433	3-(Methylthio)propanal (methional)	Cooked potato-like
1506	Propanoic acid	Sour
1531	2-Methylpropanoic acid	Rancid, cheesy
1590	Butanoic acid	Butter-like, sour
1682	3-(Methylthio)propanol (methionol)	Cooked potato-like
1708	Unknown	Onion-like
1811	Unknown	Caramel-like
1819	2-Methoxyphenol	Smoky
2054	HEMF	Sweet, caramel-like

^a Retention index.

^b These compounds were identified by comparing the mass spectra, the retention indices, and the odor qualities with those of the respective reference compounds.

^c Odor attribute perceived at the sniffing port.

Table 3. Odor-active compounds of the third fraction of 60% ether by AEDA.

No	Compound	Odor attributes	FD factor^a
1	2-Methylpropanol	Malty	16
2	1-Butanol	Fusel-like	2
3	Isoamyl alcohol	Fruity	32
4	3-Hydroxy-2-butanone	Peanut-like	16
5	Hexanol	Fruity, green	2
6	Acetic acid	Sour, vinegar-like	32
7	Methional	Cooked potato-like	32
8	HEMF	Sweet, caramel-like	32

^a FD factor defines the maximum dilution degree for detection.

Table 4. Determination of odor impact compounds in commercial soy sauce A, B, C, D, and E.

Compound	Concentration (mg/L)
	A	B	C	D	E
Acetic acid	1200 ± 10	1400 ± 10	1100 ± 2	1000 ± 8	1000 ± 20
HEMF	36 ± 0.7	33 ± 1.0	24 ± 0.3	32 ± 0.8	29 ± 1.0
Isoamyl alcohol	10 ± 0.2	11 ± 0.3	13 ± 0.1	11 ± 0.1	10 ± 0.3
Methional	0.17 ± 0.01	0.32 ± 0.01	0.24 ± 0.004	0.24 ± 0.01	0.38 ± 0.01

Table 5. Aroma profile of mixtures of odor impact compounds.

	Acetic acid	HEMF	Isoamyl alcohol	Methional	Aroma profiles
Combination ratio	2500	300	100	1
1	+	+	−	−	Sweet, sour
2	+	−	+	−	Sour, green
3	+	−	−	+	Sour, cooked potato-like
4	−	+	+	−	Caramel-like
5	−	+	−	+	Sweet, cooked potato-like
6	−	−	+	+	Cooked potato-like, green
7	+	+	+	−	Vinegar-like, sweet
8	+	+	−	+	Cooked potato-like
9	+	−	+	+	Light sour
10	−	+	+	+	Heavy sweet
11	+	+	+	+	Soy sauce-like

Table 6. Sensory scores of soy sauce A and prepared mixture.

Odor attribute	Sensory score
	Soy sauce A	Prepared mixture
Caramel-like^a	4.0 ± 0.5	4.3 ± 0.7
Cooked potato-like^a	3.9 ± 0.5	4.1 ± 0.7
Fruity^a	3.1 ± 0.4	3.9 ± 0.4
Vinegar-like^a	4.3 ± 0.7	4.5 ± 0.6
Reminiscent of salty^a	4.6 ± 0.8	4.3 ± 0.7
Reminiscent of umami^a	4.3 ± 0.6	4.0 ± 0.8

^a There was no significant difference between soy sauce A and prepared mixture (p < 0.05).