Table 2.
A list of all the VOCs in the marking fluid of P. tigris altaica identified using GC-MS-O. Bolded entries are compounds that are characteristic of the total aroma of tiger MF. Compounds were identified using spectral matches with the top five ions, odor descriptor matching, chemical standard confirmation (except for 2-AP), retention time, and the NIST library spectral matching.
| No. | Compound Classification | RT (min) | CAS | Top 5 Ions and Relative Intensities (%) | R. Match Factor (%) | Aroma Descriptor by Panelist | Published Odor Descriptors | MOI (%) | PA | ODT (ppb) | SOAV |
|---|---|---|---|---|---|---|---|---|---|---|---|
| Nitrogen containing compounds | |||||||||||
| 1 | 2,5-Dimethyl-pyrazine a | 10.47 | 108-50-9 | 42(99),108(92),39(31),40(25),81(18) | 80 | Cocoa, Roasted Nuts, Roast Beef, Coffee b | 1.85 × 104 | 8.00 × 102–1.80 × 104c | 1.02 × 100–2.31 × 101 | ||
| 2 | 2-Acetyl-1-pyrroline ᶲ | 10.76 | 99583-29-6 | 43(99),41(54),42(24),83(13),39(11) | 84 | Basmati rice, Taco Shell, Nutty, Corn | Nutty, Popcorn, Toasted, Grain, Roasted, Basmati Rice, Malty b,d | 80 | 1.05 × 104 | 0.10 × 100e | 1.05 × 105 |
| 3 | Indole a | 26.9 | 120-72-9 | 117(99),90(43),89(20),63(9),118(9) | 96 | Animal, Floral, Moth Ball, Fecal, Naphthelene b,f | 4.79 × 103 | 1.40 × 102c | 3.42 × 101 | ||
| 4 | Urea a | 28.98 | 57-13-6 | 17(99),60(92),44(75),16(17),43(16) | 96 | Urinous, Ferret, Foul | Ammonia g | 30 | 8.35 × 103 | ||
| Ketones | |||||||||||
| 5 | Acetone a | 2.04 | 67-64-1 | 43(99),58(30),42(10),15(17),27(8) | 96 | Solvent, Ethereal, Apple, Pear b | 1.51 × 106 | 5.00 × 105c | 3.02 × 100 | ||
| 6 | 2-Butanone a | 2.56 | 78-93-3 | 43(99),73(32),29(18),57(10),27(8) | 99 | Acetone-like, Ethereal, Fruity, Camphor b | 6.98 × 105 | 5.00 × 104c | 1.40 × 101 | ||
| 7 | 3-Pentanone a | 3.62 | 96-22-0 | 43(99),57(54),44(35),86(32),41(27) | 90 | Body Odor, Plastic, Citrus, Bleach, Medicinal | Ethereal, Acetone b | 30 | 1.00 × 106 | 7.00 × 104c | 1.43 × 101 |
| 8 | 2,3-Butanedione a | 3.77 | 431-03-8 | 43(99),86(20),42(8),44(8),41(4) | 93 | Butter, Sweet, Cake Batter | Sweet, Buttery, Caramellic nuance b | 30 | 8.99 × 105 | ||
| 9 | 2-Methyl-3-pentanone a | 3.91 | 565-69-5 | 57(99),43(77),29(38),100(27),71(45) | 90 | Chemical | Mint b | 30 | 1.59 × 105 | 5.00 × 103h | 3.18 × 101 |
| 10 | 4-Heptanone a | 6.36 | 123-19-3 | 43(99),71(85),41(18),27(17),11(17) | 92 | Fruity, Cheese, Sweet, Cognac, Pineapple b | 5.54 × 105 | 0.82 × 101–4.10 × 101i | 1.35 × 104 | ||
| 11 | 2-Heptanone a | 7.62 | 110-43-0 | 43(99),58(40),27(35),71(12),29(12) | 95 | Soapy, Fruity, Spicy, Sweet, Herbal, Coconut, Woody b | 1.26 × 106 | 0.14 × 103–3.00 × 103 c | 4.20 × 102–9.02 × 103 | ||
| 12 | 2-Nonanone a | 11.63 | 821-55-6 | 58(99),57(28),43(27),41(26),55(16) | 81 | Earthy, Grassy, Skunky, Foul, Onion, Rancid, Green pepper | Earthy, Herbaceous, Weedy, Green, Dirty b | 80 | 3.78 × 104 | 0.05 × 102–2.00 × 102c | 1.89 × 102 |
| 13 | 2-Undecanone a | 15.22 | 112-12-9 | 58(99),43(58),59(32),71(29),41(18) | 93 | Waxy, Fruity, Creamy, Fatty, Orris Floral b | 2.90 × 104 | 7 × 100c | 4.15 × 103 | ||
| Amines | |||||||||||
| 14 | Trimethylamine a | 1.37 | 75-50-3 | 58(99),59(70),30(35),42(25),28(12) | 95 | Fish, Onion, Foul, Rancid, Skunky | Fishy, Oily, Rancid, Sweaty, Fruity b | 100 | 7.12 × 107 | 3.70 × 10−1–10.60 × 10−1c | 6.71 × 107–1.92 × 108 |
| Aldehydes | |||||||||||
| 15 | Hexanal a | 5.56 | 66-25-1 | 44(99),56(82),41(71),43(77),57(39) | 83 | Green b | 3.42 × 105 | 4.50 × 10−2–5.00 × 10−2c | 7.61 × 103–6.84 × 104 | ||
| 16 | 3-Methylbutanal a | 5.77 | 590-86-3 | 44(99),43 (86),41(49),57 (41),39(26) | 95 | Ethereal, Aldehydic, Chocolate, Peach, Fatty, Nutty b,d | 8.49 × 105 | 0.20 × 100–2.0 × 100c | 4.25 × 105–4.25 × 106 | ||
| 17 | Nonanal a | 11.82 | 124-19-6 | 57(99),41(92),43(91),56(80),44(76) | 88 | Fatty, Floral-Rose, Waxy b,c | 1.52 x 104 | 1.00 × 100c | 1.52 × 104 | ||
| 18 | Furfural a | 13.23 | 98-01-1 | 97(99),96(98),39(65),38(22),29(20) | 97 | Potato, Body odor, Earthy, Nutty | Sweet, Woody, Almond, Fragrant, Baked Bread b,f | 80 | 3.25 × 104 | 3.00 × 103–2.30 × 104c | 0.14 × 101–1.10 × 101 |
| 19 | Benzaldehyde a | 14.04 | 100-52-7 | 106(99),77(97),105(97),107(80),39(63) | Fruit loops, Fruity, Sweet | Almond-like, Fruity, Cherry, Sweet, Bitter, Sharp b | 100 | 1.75 x 105 | 3.50 × 102–3.50 × 103c | 5.00 × 101–5.00 × 102 | |
| Alcohols | |||||||||||
| 20 | Ethanol a | 3.02 | 64-17-5 | 31(99),45(55),29(32),27(24),46(21) | 97 | Strong, Alcoholic, Ethereal, Medical b | 1.58 × 106 | 1.00 × 105c | 1.58 × 101 | ||
| 21 | 1-Butanol a | 7.16 | 71-36-3 | 56(99),31(98),41(90),43(70),27(58) | 95 | Medicine, Fruit, Wine f | 4.43 × 105 | 5.00 × 102c | 8.86 × 102 | ||
| 22 | 3-Methyl-1-butanol a | 8.77 | 123-51-3 | 55(99),42(90),41(82),43(84),70(73) | 96 | Fusel, Alcoholic, Pungent, Etherial, Cognac, Fruity, Banana and Molasses b | 9.37 × 104 | 2.50 × 102-3.00 × 102c | 3.12 × 102–3.74 × 102 | ||
| 23 | 1-Hexanol a | 11.13 | 111-27-3 | 56(99),43(83),41(59),55(58),42(57) | 86 | Pungent, Etherial, Fusel Oil, Fruity and Alcoholic, Sweet with a Green Top Note b | 7.36 × 103 | 2.50 × 103 c | 2.94 × 100 | ||
| 24 | 1-Octanol a | 14.76 | 111-87-5 | 56(99),55(88),41(81),73(75),70(61) | 80 | Roasted, Earthy, Grassy, Green Pepper | Waxy, Green, Orange, Aldehydic, Rose, Mushroom b | 30 | 2.78 × 104 | 1.10 × 102 c | 2.53 × 102 |
| 25 | Benzyl Alcohol a | 19.68 | 100-51-6 | 79(99),77(57),108(90),107(70),51(22) | 92 | Floral, Rose, Phenolic, Balsamic b | 1.94 × 104 | 1.00 × 104c | 1.94 × 100 | ||
| 26 | Phenylethyl alcohol a | 20.16 | 60-12-8 | 91(99),51(64),39(75),92(60),77(48) | 91 | Citrus, Sweet | Rose, Floral b | 30 | 9.04 × 104 | 7.50 × 102–1.10 × 103 c | 8.22 × 101 |
| Sulfur containing compounds | |||||||||||
| 27 | Dimethyl disulfide a | 5.39 | 75-18-3 | 94(99),79(58),45(50),46(25),47(20) | 97 | Sulfury, Onion, Sweet, Corn, Vegetable, Cabbage, Tomato, Green, Radish j | 4.71 × 105 | 2.00 × 100–1.20 × 100c | 3.93 × 104–2.94 × 106 | ||
| 28 | Dimethyl trisulfide a | 11.47 | 3658-80-8 | 126(99),79(56),45(33),47(23),111(18) | 92 | Onion, Skunky | Foul, Sulfur, Fish, Cabbage f | 60 | 1.08 × 104 | 0.50 × 10−2–1.00 × 10−2c | 1.08 × 106 |
| Acids | |||||||||||
| 29 | Valeric acid a | 17.6 | 109-52-4 | 60(99),73(37),41(15),29(14),27(12) | 98 | Rancid, Foul, Unknown | Rancid, Sickening, Putrid, Acidic, Sweaty, Sour, Cheese-like b | 30 | 8.90 × 103 | 3.00 × 103c | 2.97 × 100 |
| 30 | Octanoic acid a | 22.53 | 124-07-2 | 60(99),73(62),43(42),41(39),55(37) | 93 | Fatty, Waxy, Rancid Oily, Vegetable, Cheesy b | 1.55 × 104 | 3.00 × 102 c | 5.18 x 100 | ||
| Amides | |||||||||||
| 31 | Acetamide a | 17.94 | 60-35-5 | 59(99),44(89),43(60,42(29),18(27) | 98 | Mousy b | 1.87 × 105 | ||||
| Phenols | |||||||||||
| 32 | 4-Methylphenol a | 22.6 | 106-44-5 | 107(99),108(85),77(32),79(21),51(16) | 97 | Barnyard, Chemical, Animal, Earthy | Phenolic, Narcissus, Animal, Mimosa b | 80 | 2.97 × 103 | 5.50 × 101c | 5.40 × 101 |
| 33 | Phenol a | 21.54 | 108-95-2 | 93(99),66(39),65(28),39(25),40(15) | 97 | Phenolic, Plastic, Rubber b | 2.12 × 104 | 5.9 × 103c | 3.60 × 100 | ||
Abbreviations: CAR/PDMS—Carboxen polydimethylsiloxane; DVB/CAR/PDMS—divinylbenzene/Carboxen polydimethylsiloxane; PDMS—polydimethylsiloxane; polydimethylsiloxane/divinylbenzene; GC—gas chromatography; RT—retention time; CAS—Chemical Abstracts Service Numbers; RA-relative abundance; SOAV—surrogate odor activity value; MOC—Measured Odor characters; MOI—measured odor intensity; ODT—Odor detection threshold; bolded entries are compounds that are characteristic of the total aroma of tiger MF; 2-AP—2-acetyl-1-pyrroline—is placed in Table 2 because it was implicated as a characteristic odorant in Bengal tiger MF [4,5,32]; ᶲ Compounds verified with spectral matches with the top five ions, odor panelists’ detection, and published odor descriptors; a Compounds verified with retention time and ion confirmation of standards (except for 2-AP); b Good Scents Company [55]; c Leffingwell & Associates [56]; d Flavornet [57]; e Flavor Chemistry and Odor Thresholds [58]; f Encyclopedia Britannica [59]; g Urea (Ultra-Pure Grade) Safety Data Sheet [60]; h Measurement of Odor Threshold by Triangle Odor Bag Method [61]; i Fenaroli’s Handbook of Flavor Ingredients 5th Edition [62]; j Flinn Scientific, Inc. Safety Data Sheet (SDS) [63]; k Haz-Map [64].