[OH-].[Na+].[CH:3]([CH:15]1[CH2:20][C:19](=[O:21])[O:18][C:16]1=[O:17])=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].CCCCCCCCCC/C=C/C1C(=O)OC(=O)C1.C1COCC1>O.O1CCCC1>[CH3:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]/[CH:4]=[CH:3]/[CH:15]1[C:16](=[O:17])[O:18][C:19](=[O:21])[CH2:20]1Isolated soy protein (30 g) was dispersed in deionized water. The pH was adjusted to 8.5 with 1 N NaOH and the dispersion was heated to 50° C. Dodecenyl succinic anhydride (18 g) was dissolved in 100 ml of tetrahydrofuran. When the temperature of the soy dispersion reached 50° C., the DDSA/THF solution was added in 5 ml increments over 1 hour with concurrent adjustment of pH to 8.5 with 1 N NaOH. The solution was stirred for an additional hour to hydrolyze any unreacted anhydride. Protein was recovered by precipitation at pH 4.0 with 1 N HCl. The precipitate was washed and filtered three times with deionized water. The protein was dried at 60° C. and finely ground.
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