Sample Name: Fret 09-0536(003) UV,Neutral pH Data. October 31, 2013Wavelength (nm)200250300350400

Absorbance (AU)-0.100.10.20.30.40.5 201Instrument: Hewlett-Packard 8453 Diode ArrayCell Pathlength: 1 cmCell: QuartzWavelength Range: 190-450 nmAbsorbance Range: -0.6 to +0.7Integration Time: 1 sReference Solvent (A): 10% (v/v) H2O/MethanolSample Conc.: 1.59 x 10-3M in solventASample pH: 7Wavelength Max.: 201 nmAbsorbance (max): 0.50384max: 316.6 Lmol-1cm-1Sample Name: Fret 09-0536 (003)UV, Acidic pH Data. October 31, 2013Wavelength (nm)175200225250275300325350375

Absorbance (AU)-0.100.10.20.30.4 202Instrument: Hewlett-Packard 8453 Diode ArrayCell Pathlength: 1 cmCell: QuartzWavelength Range: 190-450 nmAbsorbance Range: -0.6 to +0.7Integration Time: 1 sReference Solvent (B): 10% (v/v) 0.1 N HCl/MethanolSample Conc.: 1.29 x 10-3M in solventBSample pH: ~2-3Wavelength Max.: 202 nmAbsorbance (max): 0.40121max: 311.1 Lmol-1cm-1Sample Name: Fret 09-0536(003)UV, Basic pH Data. October 31, 2013Wavelength (nm)200250300350400

Absorbance (AU)00.20.40.60.811.21.41.6 222 398 405Instrument: Hewlett-Packard 8453 Diode ArrayCell Pathlength: 1 cmCell: QuartzWavelength Range: 190-450 nmAbsorbance Range: -0.6 to +0.7Integration Time: 1 sReference Solvent (C): 10% (v/v) 0.1 N NaOH/MethanolSample Conc.: 1.72x 10-2M in solventCSample pH: ~9-10Wavelength Max.: 222 nmAbsorbance (max): 1.704max:99.0 Lmol-1cm-1Peak#R.T.IeArea%IUPACNameMWStructureCas#1 20.18 8.23 1.32(3aS,7aR)‐1‐ethyloctahydro‐1H‐4,7‐methanoindene1642 38.01 11.27 62.103‐[(3aS,7aR)‐octahydro‐1H‐4,7‐methanoinden‐1‐yl]propanal1923 38.41 11.34 1.653‐[(3aR,7aS)‐3a,4,5,6,7,7a‐hexahydro‐1H‐4,7‐methanoinden‐3‐yl]propanal1904 38.53 11.36 1.103‐[(3aR,7aS)‐3a,4,5,6,7,7a‐hexahydro‐1H‐4,7‐methanoinden‐2‐yl]propanal1905 39.09 11.45 10.383‐[(2s,3aR,7aS)‐octahydro‐1H‐4,7‐methanoinden‐2‐yl]propanal1926 39.34 11.50 3.053‐[(3aR,7aS)‐octahydro‐1H‐4,7‐methanoinden‐1‐yl]propanal1927 39.60 11.54 9.343‐[(2r,3aR,7aS)‐octahydro‐1H‐4,7‐methanoinden‐2‐yl]propanal1928 39.79 11.58 1.943‐[(3aR,7aS)‐octahydro‐1H‐4,7‐methanoinden‐2‐yl]propanal192Fret09‐0536(003)OHHOHHHHOHHOHHOHHOHHOHHIFFInternationalFlavorsandFragrancesInc.Confidential11/6/2013Page1MassLib6.11.2013 14:46MassLib V9.4 0IFF private and confidential informationIFF-Union Beach2030405060708090100110120130140150160170180190200B2387(40.35)(866.N) 325 10% 8002506401 * 0025064 tof2-2912 syn 107-40 ov1100%294155678091105120133148161174192OHHPeak #2*26 0.17 53 11.51 74 0.10 97 2.07 118 2.62 139 0.14 163 1.1027 3.02 54 4.80 75 0.23 98 0.12 119 17.98 140 0.09 164 2.8828 0.81 55 14.27 76 0.28 99 0.16 120 25.31 141 0.06 165 0.4029 5.60 56 1.28 77 28.99 100 0.09 121 4.18 142 0.10 166 0.0730 0.17 57 3.27 78 12.22 101 0.08 122 0.34 143 0.06 169 0.3631 0.33 58 0.99 79 80.95 102 0.24 123 7.71 144 0.11 170 0.0732 0.08 59 0.25 80 100.00 103 2.00 124 0.78 145 2.36 171 0.0737 0.04 60 0.13 81 69.21 104 1.92 125 9.39 146 7.79 172 0.0638 0.31 61 0.06 82 8.09 105 23.65 126 0.72 147 3.21 173 0.2639 11.93 62 0.12 83 3.62 106 16.68 127 0.61 148 66.72 174 3.7740 2.64 63 1.27 84 0.80 107 23.49 128 0.20 149 12.24 175 0.6141 26.63 64 0.37 85 0.19 108 6.25 129 0.15 150 2.02 176 0.0742 2.03 65 12.93 86 0.04 109 2.47 130 0.05 151 1.39 177 0.1243 2.27 66 30.49 89 0.36 110 0.44 131 3.45 152 0.24 179 0.0644 0.45 67 69.12 90 0.31 111 0.16 132 1.77 153 0.12 190 0.0445 0.11 68 9.78 91 43.62 112 0.28 133 24.19 154 0.06 191 0.2147 0.16 69 5.21 92 17.72 113 0.09 134 4.06 157 0.04 192 21.1749 0.03 70 0.81 93 35.80 114 0.04 135 5.38 159 1.37 193 3.2650 0.53 71 0.74 94 10.42 115 0.95 136 1.11 160 0.74 194 0.3751 3.51 72 0.13 95 18.76 116 0.32 137 0.56 161 10.17 195 0.0852 2.19 73 0.10 96 3.46 117 4.10 138 0.16 162 1.56B2387(40.35)(866.N)325 10% 8002506401 * 0025064 tof2-2912 syn 107-40 ov1 lim: 0.03%MassLib6.11.2013 14:44MassLib V9.4 0IFF private and confidential informationIFF-Union Beach2030405060708090100110120130140150160170180190200B2469(41.73)(886.N) 74 8% 8002506401 * 0025064 tof2-2912 syn 107-40 ov1100%294155677991105125133148159174192HHOPeak #5*25 0.03 49 0.03 71 0.86 94 13.60 116 0.53 138 0.92 163 1.4726 0.24 50 1.28 73 0.05 95 12.03 117 6.04 139 0.08 164 1.0127 7.81 51 5.83 75 0.14 96 2.43 118 2.54 142 0.03 165 0.1228 0.29 52 3.90 76 0.17 97 1.05 119 13.61 143 0.03 166 0.0329 13.84 53 21.85 77 44.21 99 0.10 120 11.19 144 0.05 172 0.0530 0.34 54 9.14 78 16.71 100 0.08 121 2.32 145 4.34 173 0.3031 0.59 55 28.69 79 100.00 101 0.03 122 0.19 146 4.65 174 7.1232 1.12 56 1.66 80 72.10 102 0.41 123 1.39 147 3.22 175 0.9333 0.03 57 6.37 81 35.83 103 2.49 124 3.40 148 75.85 176 0.1036 0.03 58 1.66 82 4.63 104 2.49 125 15.57 149 11.85 177 0.4237 0.15 59 0.35 83 5.75 105 40.74 126 0.89 150 1.49 178 0.1438 0.45 60 0.05 84 0.96 106 31.75 127 0.33 151 4.22 182 0.0339 26.11 62 0.16 85 0.25 107 26.25 128 0.45 152 0.52 190 0.2240 5.65 63 1.82 86 0.15 108 4.81 129 0.00 153 0.03 191 0.1641 58.28 64 0.95 87 0.14 109 3.04 131 6.31 155 0.02 192 12.0242 3.92 65 20.24 88 0.18 110 0.55 132 2.96 156 0.03 193 1.8343 5.55 66 35.54 89 0.53 111 0.10 133 44.53 157 0.05 194 0.1244 1.37 67 90.21 90 0.16 112 0.31 134 6.97 159 1.8745 0.64 68 13.70 91 67.05 113 0.22 135 6.16 160 0.6246 0.03 69 6.77 92 23.62 114 0.03 136 0.95 161 1.0747 0.03 70 1.72 93 52.40 115 1.79 137 0.53 162 0.33B2469(41.73)(886.N)74 8% 8002506401 * 0025064 tof2-2912 syn 107-40 ov1

# INTERNATIONAL FLAVORS & FRAGRANCES (IFF R&D) 1515 HIGHWAY 36, UNION BEACH, NJ 07735 (732) 264-4500

CREATORS AND MANUFACTURERS OF FLAVORS, FRAGRANCES AND AROMA CHEMICALS CABLE: INTERIFF NEW YORK



# OPTICAL ACTIVITY DETERMINATION

Sample name: FRET 09-0536

IPC number: N/A

LOT number: RDIA5595

Instrument: Bellingham & Stanley LTD model ADP220 Polarimeter

Cell path length 1 DM (decameter)

Date: November 1, 2013

Optical Rotation: 0o

Comments: none

Prepared by: Gary Mertz

International Flavors & Fragrances

1515 Highway 36

Union Beach, NJ 07735