3-Hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexenecarbaldehyde
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Identifiers
CAS number
33399-08-5SMILES
CC1=C(O)C(=O)CC(C)(C)C1C=O
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Odor profile
Fragrance Sweet 45.98% Caramellic 45.82% Woody 43.57% Mint 41.5% Tobacco 36.38% Spicy 35.71% Herbal 33.84% Burnt 33.19% Camphoreous 30.31% Phenolic 29.56% Flavor Sweet 61.13% Caramel 50.2% Tobacco 44.49% Fruity 43.91% Maple 37.98% Phenolic 36.65% Woody 36.37% Sugar 33.59% Spice 31.96% Spicy 31.8% Odor impact est.
High -
Properties
pKa est.
7.37 (neutral)Vapor pressure est.
- hPa @ 20°C
- hPa @ 25°C
Evaporation rate
Ultra slowBoiling point est.
348°CFlash point
- 133.85 ˚C est.
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Applications
3-Hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexenecarbaldehyde (CAS 33399-08-5) is a versatile building block in fragrance chemistry and isoprenoid synthesis: its conjugated aldehyde–ketone and hydroxyl functionality enables efficient Knoevenagel/aldol condensations, chemoselective reductions, acetal formation, and oxime/hydrazone derivatization to access ionone/damascone-type aroma ingredients and profragrances; in industrial and academic routes it is commonly used as an intermediate to construct the ionone ring and elongate polyene chains en route to retinoids/carotenoids and other terpenoid derivatives; in medicinal chemistry it serves as a scaffold for structure–activity exploration, delivering enone and heterocyclic libraries via condensations/annulations; it is also employed as an analytical reference and as a model substrate to benchmark asymmetric catalysts (1,2 vs 1,4 selectivity) and to optimize reduction/oxidation and protecting-group strategies in process development.
gpt-5-nano
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Solubility @25˚C
Solvent Solubility (g/L) ethanol 262.22 methanol 483.53 isopropanol 150.76 water 17.38 ethyl acetate 123.42 n-propanol 177.98 acetone 184.36 n-butanol 109.97 acetonitrile 199.97 DMF 269.76 toluene 43.33 isobutanol 86.59 1,4-dioxane 383.09 methyl acetate 143.75 THF 652.87 2-butanone 127.89 n-pentanol 67.83 sec-butanol 94.96 n-hexane 3.52 ethylene glycol 111.45 NMP 205.72 cyclohexane 2.88 DMSO 335.43 n-butyl acetate 70.05 n-octanol 44.21 chloroform 188.99 n-propyl acetate 56.42 acetic acid 211.51 dichloromethane 184.7 cyclohexanone 158.67 propylene glycol 70.3 isopropyl acetate 65.24 DMAc 105.36 2-ethoxyethanol 160.78 isopentanol 69.94 n-heptane 3.69 ethyl formate 121.37 1,2-dichloroethane 142.18 n-hexanol 110.2 2-methoxyethanol 337.53 isobutyl acetate 33.69 tetrachloromethane 31.21 n-pentyl acetate 43.13 transcutol 177.52 n-heptanol 53.03 ethylbenzene 23.33 MIBK 73.94 2-propoxyethanol 222.34 tert-butanol 138.69 MTBE 63.27 2-butoxyethanol 96.13 propionic acid 119.95 o-xylene 27.86 formic acid 249.57 diethyl ether 97.04 m-xylene 40.37 p-xylene 27.27 chlorobenzene 64.02 dimethyl carbonate 56.01 n-octane 2.4 formamide 228.47 cyclopentanone 287.72 2-pentanone 111.89 anisole 62.35 cyclopentyl methyl ether 143.79 gamma-butyrolactone 377.32 1-methoxy-2-propanol 211.52 pyridine 146.34 3-pentanone 70.46 furfural 248.24 n-dodecane 2.05 diethylene glycol 219.5 diisopropyl ether 22.32 tert-amyl alcohol 82.53 acetylacetone 123.64 n-hexadecane 2.33 acetophenone 59.81 methyl propionate 106.77 isopentyl acetate 56.49 trichloroethylene 219.08 n-nonanol 37.6 cyclohexanol 70.84 benzyl alcohol 62.03 2-ethylhexanol 44.39 isooctanol 38.18 dipropyl ether 37.43 1,2-dichlorobenzene 58.13 ethyl lactate 43.85 propylene carbonate 136.07 n-methylformamide 263.5 2-pentanol 62.5 n-pentane 3.55 1-propoxy-2-propanol 114.56 1-methoxy-2-propyl acetate 85.18 2-(2-methoxypropoxy) propanol 63.66 mesitylene 22.33 ε-caprolactone 143.77 p-cymene 18.85 epichlorohydrin 360.1 1,1,1-trichloroethane 93.08 2-aminoethanol 149.54 morpholine-4-carbaldehyde 220.8 sulfolane 327.32 2,2,4-trimethylpentane 3.19 2-methyltetrahydrofuran 230.55 n-hexyl acetate 61.55 isooctane 3.55 2-(2-butoxyethoxy)ethanol 92.66 sec-butyl acetate 36.05 tert-butyl acetate 75.28 decalin 3.7 glycerin 125.93 diglyme 154.29 acrylic acid 116.2 isopropyl myristate 22.95 n-butyric acid 129.63 acetyl acetate 65.13 di(2-ethylhexyl) phthalate 28.2 ethyl propionate 53.85 nitromethane 335.8 1,2-diethoxyethane 58.75 benzonitrile 72.34 trioctyl phosphate 24.68 1-bromopropane 63.86 gamma-valerolactone 316.19 n-decanol 26.77 triethyl phosphate 26.93 4-methyl-2-pentanol 41.77 propionitrile 130.38 vinylene carbonate 126.4 1,1,2-trichlorotrifluoroethane 153.43 DMS 55.85 cumene 18.33 2-octanol 32.77 2-hexanone 58.64 octyl acetate 32.33 limonene 24.05 1,2-dimethoxyethane 195.93 ethyl orthosilicate 25.14 tributyl phosphate 24.71 diacetone alcohol 112.63 N,N-dimethylaniline 40.33 acrylonitrile 162.64 aniline 68.52 1,3-propanediol 185.86 bromobenzene 51.64 dibromomethane 115.09 1,1,2,2-tetrachloroethane 143.25 2-methyl-cyclohexyl acetate 43.08 tetrabutyl urea 32.6 diisobutyl methanol 25.87 2-phenylethanol 79.86 styrene 23.14 dioctyl adipate 31.25 dimethyl sulfate 98.64 ethyl butyrate 45.42 methyl lactate 69.13 butyl lactate 41.87 diethyl carbonate 31.1 propanediol butyl ether 72.82 triethyl orthoformate 31.05 p-tert-butyltoluene 19.79 methyl 4-tert-butylbenzoate 67.03 morpholine 359.32 tert-butylamine 58.96 n-dodecanol 19.08 dimethoxymethane 220.47 ethylene carbonate 103.07 cyrene 80.61 2-ethoxyethyl acetate 61.42 2-ethylhexyl acetate 40.7 1,2,4-trichlorobenzene 64.73 4-methylpyridine 116.76 dibutyl ether 24.38 2,6-dimethyl-4-heptanol 25.87 DEF 85.5 dimethyl isosorbide 118.95 tetrachloroethylene 102.25 eugenol 68.67 triacetin 48.3 span 80 55.36 1,4-butanediol 67.92 1,1-dichloroethane 122.27 2-methyl-1-pentanol 44.2 methyl formate 237.29 2-methyl-1-butanol 59.74 n-decane 3.54 butyronitrile 110.33 3,7-dimethyl-1-octanol 34.62 1-chlorooctane 20.27 1-chlorotetradecane 7.12 n-nonane 3.2 undecane 2.64 tert-butylcyclohexane 4.37 cyclooctane 1.59 cyclopentanol 121.57 tetrahydropyran 207.06 tert-amyl methyl ether 47.74 2,5,8-trioxanonane 99.94 1-hexene 16.57 2-isopropoxyethanol 93.45 2,2,2-trifluoroethanol 108.62 methyl butyrate 67.98 Scent© AI
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Recommendation
No restriction
| Maximum acceptable concentrations in the finished product (%) | |||
|---|---|---|---|
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Category 1
Products applied to the lips
|
No restriction |
Category 7A
Rinse-off products applied to the hair with some hand contact
|
No restriction |
|
Category 2
Products applied to the axillae
|
No restriction |
Category 7B
Leave-on products applied to the hair with some hand contact
|
No restriction |
|
Category 3
Products applied to the face/body using fingertips
|
No restriction |
Category 8
Products with significant anogenital exposure
|
No restriction |
|
Category 4
Products related to fine fragrance
|
No restriction |
Category 9
Products with body and hand exposure, primarily rinse off
|
No restriction |
|
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
|
No restriction |
Category 10A
Household care products with mostly hand contact
|
No restriction |
|
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
|
No restriction |
Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
|
No restriction |
|
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
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No restriction |
Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
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No restriction |
|
Category 5D
Baby Creams, baby Oils and baby talc
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No restriction |
Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
|
No restriction |
|
Category 6
Products with oral and lip exposure
|
No restriction |
Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
|
No restriction |
