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

Wavelength (nm) 200 250 300 350 400

Absorbance (AU)

-0.1

0

0.50.40.30.20.1

201

Instrument: Hewlett-Packard 8453 Diode Array Cell Pathlength: 1 cm Cell: Quartz Wavelength Range: 190-450 nm Absorbance Range: -0.6 to +0.7 Integration Time: 1 s Reference Solvent (A): 10% (v/v) H O/Methanol 2

Sample Conc.: 1.59 x 10-3 M in solvent A

Sample pH: 7 Wavelength Max.: 201 nm Absorbance (max): 0.50384 

max: 316.6 Lmol-1cm-1 
 Sample Name: Fret 09-0536 (003) UV, Acidic pH Data. October 31, 2013 

Wavelength (nm) 175 200 225 250 275 300 325 350 375

Absorbance (AU)

-0.1

0

0.40.30.20.1

202

Instrument: Hewlett-Packard 8453 Diode Array Cell Pathlength: 1 cm Cell: Quartz Wavelength Range: 190-450 nm Absorbance Range: -0.6 to +0.7 Integration Time: 1 s Reference Solvent (B): 10% (v/v) 0.1 N HCl/Methanol Sample Conc.: 1.29 x 10-3 M in solvent B

Sample pH: ~2-3 Wavelength Max.: 202 nm Absorbance (max): 0.40121 

max: 311.1 Lmol-1cm-1 
 Sample Name: Fret 09-0536(003) UV, Basic pH Data. October 31, 2013 

Wavelength (nm) 200 250 300 350 400

Absorbance (AU)

0

0.80.60.40.2

1

1.61.41.2

222

398

405

 Instrument: Hewlett-Packard 8453 Diode Array 

Cell Pathlength: 1 cm Cell: Quartz Wavelength Range: 190-450 nm Absorbance Range: -0.6 to +0.7 Integration Time: 1 s Reference Solvent (C): 10% (v/v) 0.1 N NaOH/Methanol 

Sample Conc.: 1.72x 10-2 M in solvent C

Sample pH: ~9-10 Wavelength Max.: 222 nm Absorbance (max): 1.704 

max: 99.0 Lmol-1cm-1 






Peak # R.T. Ie Area % IUPAC Name MW Structure Cas #

1 20.18 8.23 1.32 (3aS,7aR)‐1‐ethyloctahydro‐1H‐4,7‐methanoindene 164

2 38.01 11.27 62.10 3‐[(3aS,7aR)‐octahydro‐1H‐4,7‐methanoinden‐1‐yl]propanal 192

3 38.41 11.34 1.65

3‐[(3aR,7aS)‐3a,4,5,6,7,7a‐hexahydro‐1H‐4,7‐methanoinden‐

3‐yl]propanal 190

4 38.53 11.36 1.10

3‐[(3aR,7aS)‐3a,4,5,6,7,7a‐hexahydro‐1H‐4,7‐methanoinden‐

2‐yl]propanal 190

5 39.09 11.45 10.38

3‐[(2s,3aR,7aS)‐octahydro‐1H‐4,7‐methanoinden‐2‐

yl]propanal 192

6 39.34 11.50 3.05 3‐[(3aR,7aS)‐octahydro‐1H‐4,7‐methanoinden‐1‐yl]propanal 192

7 39.60 11.54 9.34

3‐[(2r,3aR,7aS)‐octahydro‐1H‐4,7‐methanoinden‐2‐

yl]propanal 192

8 39.79 11.58 1.94 3‐[(3aR,7aS)‐octahydro‐1H‐4,7‐methanoinden‐2‐yl]propanal 192

Fret 09‐0536 (003)

O

H

H

O

H

H

HH O

H

H O

H

H

O

H

H O

HH O

H

H

IFF International Flavors and Fragrances Inc. Confidential 11/6/2013 Page 1
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20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 180 190 200

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41

55

67

80

91

105 120 133

148

161

174

192

O

HH

Peak #2 *

 26 0.17 53 11.51 74 0.10 97 2.07 118 2.62 139 0.14 163 1.10 27 3.02 54 4.80 75 0.23 98 0.12 119 17.98 140 0.09 164 2.88 28 0.81 55 14.27 76 0.28 99 0.16 120 25.31 141 0.06 165 0.40 29 5.60 56 1.28 77 28.99 100 0.09 121 4.18 142 0.10 166 0.07 30 0.17 57 3.27 78 12.22 101 0.08 122 0.34 143 0.06 169 0.36 31 0.33 58 0.99 79 80.95 102 0.24 123 7.71 144 0.11 170 0.07 32 0.08 59 0.25 80 100.00 103 2.00 124 0.78 145 2.36 171 0.07 37 0.04 60 0.13 81 69.21 104 1.92 125 9.39 146 7.79 172 0.06 38 0.31 61 0.06 82 8.09 105 23.65 126 0.72 147 3.21 173 0.26 39 11.93 62 0.12 83 3.62 106 16.68 127 0.61 148 66.72 174 3.77 40 2.64 63 1.27 84 0.80 107 23.49 128 0.20 149 12.24 175 0.61 41 26.63 64 0.37 85 0.19 108 6.25 129 0.15 150 2.02 176 0.07 42 2.03 65 12.93 86 0.04 109 2.47 130 0.05 151 1.39 177 0.12 43 2.27 66 30.49 89 0.36 110 0.44 131 3.45 152 0.24 179 0.06 44 0.45 67 69.12 90 0.31 111 0.16 132 1.77 153 0.12 190 0.04 45 0.11 68 9.78 91 43.62 112 0.28 133 24.19 154 0.06 191 0.21 47 0.16 69 5.21 92 17.72 113 0.09 134 4.06 157 0.04 192 21.17 49 0.03 70 0.81 93 35.80 114 0.04 135 5.38 159 1.37 193 3.26 50 0.53 71 0.74 94 10.42 115 0.95 136 1.11 160 0.74 194 0.37 51 3.51 72 0.13 95 18.76 116 0.32 137 0.56 161 10.17 195 0.08 52 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%
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41

55

67

79

91

105

125

133

148

159

174

192

HH O

Peak #5 *

 25 0.03 49 0.03 71 0.86 94 13.60 116 0.53 138 0.92 163 1.47 26 0.24 50 1.28 73 0.05 95 12.03 117 6.04 139 0.08 164 1.01 27 7.81 51 5.83 75 0.14 96 2.43 118 2.54 142 0.03 165 0.12 28 0.29 52 3.90 76 0.17 97 1.05 119 13.61 143 0.03 166 0.03 29 13.84 53 21.85 77 44.21 99 0.10 120 11.19 144 0.05 172 0.05 30 0.34 54 9.14 78 16.71 100 0.08 121 2.32 145 4.34 173 0.30 31 0.59 55 28.69 79 100.00 101 0.03 122 0.19 146 4.65 174 7.12 32 1.12 56 1.66 80 72.10 102 0.41 123 1.39 147 3.22 175 0.93 33 0.03 57 6.37 81 35.83 103 2.49 124 3.40 148 75.85 176 0.10 36 0.03 58 1.66 82 4.63 104 2.49 125 15.57 149 11.85 177 0.42 37 0.15 59 0.35 83 5.75 105 40.74 126 0.89 150 1.49 178 0.14 38 0.45 60 0.05 84 0.96 106 31.75 127 0.33 151 4.22 182 0.03 39 26.11 62 0.16 85 0.25 107 26.25 128 0.45 152 0.52 190 0.22 40 5.65 63 1.82 86 0.15 108 4.81 129 0.00 153 0.03 191 0.16 41 58.28 64 0.95 87 0.14 109 3.04 131 6.31 155 0.02 192 12.02 42 3.92 65 20.24 88 0.18 110 0.55 132 2.96 156 0.03 193 1.83 43 5.55 66 35.54 89 0.53 111 0.10 133 44.53 157 0.05 194 0.12 44 1.37 67 90.21 90 0.16 112 0.31 134 6.97 159 1.87 45 0.64 68 13.70 91 67.05 113 0.22 135 6.16 160 0.62 46 0.03 69 6.77 92 23.62 114 0.03 136 0.95 161 1.07 47 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