Damascenone
Damascenones are a series of closely related chemical compounds that are part of a wide variety of essential oils. They belong to a family of chemicals called rose ketones that also contain damascones and jonones . Beta-Damascenone, despite its very low concentration, is an essential factor in the scent of roses and an important chemical fragrance in the perfume industry. It occurs naturally in apple juice, apricot, black currants, grapes, raspberries, strawberries, cognac, rum, whiskey, and scotch.
presentation
β-Damascenone can be prepared from prenylphenylsulfone . Of course, it is likely made by biosynthesis from carotenoids . γ-Damascenone can be produced from a γ-saffron acid ester with dimedonecarboxylate as the starting material by reacting the γ-ester with an aryl compound.
Representative
So far, four damascenones are known, which differ in the position of the double bonds.
| Damascenone | |||||||
| Surname | α-damascenone | β-damascenone | γ-damascenone | δ-damascenon | |||
| other names | ( EZ ) -1- (2,6,6-trimethyl-1-cyclohexa-2,4-dienyl) but-2-en-1-one ( E ) -1- (2,6,6-trimethyl-1-cyclohexa-2,4-dienyl) but-2-en-1-one |
( EZ ) -1- (2,6,6-trimethyl-1-cyclohexa-1,3-dienyl) but-2-en-1-one ( E ) -1- (2,6,6-trimethyl-1-cyclohexa-1,3-dienyl) but-2-en-1-one |
( EZ ) -1- (2-methylene-6,6-dimethylcyclohex-3-en-1-yl) but-2-en-1-one ( E ) -1- (2-methylene-6,6-dimethylcyclohex-3-en-1-yl) but-2-en-1-one |
( EZ ) -1- (2,6,6-trimethyl-1-cyclohexa-1,4-dienyl) but-2-en-1-one ( E ) -1- (2,6,6-trimethyl-1-cyclohexa-1,4-dienyl) but-2-en-1-one |
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| Structural formula of the trans form |
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| CAS number | 35044-63-4 876181-15-6 ( cis ) 41641-03-6 ( trans ) |
23696-85-7 59739-63-8 ( cis ) 23726-93-4 ( trans ) |
69522-93-6 41641-04-7 ( trans ) |
83218-16-0 53471-65-1 ( trans ) |
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| PubChem |
91668178 ( cis ) 68473438 ( trans ) |
5366074 | 54154127 | ||||
| Molecular formula | C 13 H 18 O | ||||||
| Molar mass | 190.28 g mol −1 | ||||||
| Physical state | liquid | ||||||
| Brief description | colorless liquid | ||||||
| Melting point | |||||||
| boiling point | 39 ° C (5 Pa) | 84-85 ° C (0.01 Pa) | 62 ° C (13 Pa) | ||||
| density | 0.9378 g cm −3 | ||||||
| Refractive index | 1.4989 | ||||||
| solubility | insoluble in water, soluble in ethanol |
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GHS labeling |
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| H and P phrases | see above | 317 | see above | ||||
| see above | no EUH phrases | see above | |||||
| see above | 280 | see above | |||||
Individual evidence
- ↑ Sachihiko Isoe, Shigeo Katsumura, Takeo Saka: The Synthesis of Damascenone and beta-Damascone and the possible mechanism of their formation from carotenoids. In: Helvetica Chimica Acta. 56, No. 5, 1973, pp. 1514-1516. doi : 10.1002 / hlca.19730560508 .
- ^ A b Leffingwell & Associates: Rose (Rosa damascena) .
- ↑ a b c Datasheet Damascenone from Sigma-Aldrich , accessed on April 6, 2012 ( PDF ).
- ↑ Sigeru Torii, Kenji Uneyama, Hisao Ichimura: Synthesis of beta-damascenone from prenyl phenyl sulfone. A (C5 + C5 + C3) procedure. In: J. Org. Chem. 44, No. 13, 1979, pp. 2292-2294, doi : 10.1021 / jo01327a059 .
- ↑ Patent JP56128727 : Preparation of gamma-Damascenone. Published October 8, 1981 , Applicant: Toyotama Koryo KK, Inventor: Shojiro Saito, Nobuhiko Ito.
- ↑ a b c d e Damascenone data sheet from Sigma-Aldrich , accessed on April 10, 2012 ( PDF ).
- ↑ a b Patent CH562186 : Procédé pour la preparation de cétones insaturées cycloaliphatiques. Published on May 30, 1975 , Applicant: Firmenich SA, Inventor: Dr. George Hermann Büchi, Hans Wüst.
- ↑ a b c Patent CH537352 : Procédé pour la preparation de cétones insaturées. Published on May 31, 1973 , Applicant: Firmenich SA, Inventor: Dr. Ervin Kovats, Dr. Günther Ohloff, Dr. Edouard Demole, Dr. Max Stoll.