P-Damascone

Of all these, probably P-phenethyl alcohol (2) comes closest to the odor of fresh rose petals however, mixing all these components does not reproduce the total fine character of the natural oil. It has been determined that a number of trace constituents representing less than 1% of the volatiles are critical to the development of the complete rose fragrance (10). These include cis- and trans-i.ose oxide (1), nerol oxide (12), rose furan (13), /)i7n7-menth-l-en-9-al (14), P-ionone (15), P-damascone (16), and P-damascenone (3). 

LInalool oxide-furan LInalool oxide-pyran 3-Hydroxy-p-damascone Fig. 18 Aromatic compounds occurring as glycosides... 

Figure 4.2. Principal norisoprenoid compounds in grape and wine. (29) TDN (1,1,6-trimethyl-l,2-dihydronaphthalene) (30) P-damascone (31) P-damascenone (32) vom-ifoliol (33) dihydrovomifoliol (34) 3-hydroxy-P-damascone (35) 3-oxo-a-ionol (36) 3-hydroxy-7,8-dihydro-P-ionol (37) oc-ionol (38) P-ionol (39) a-ionone (40) P-ionone (41) actinidols (42) vitispiranes (spiro [4.5]-2,10,10-trimethyl-6-methylene-l-oxa-7-decene) (43) Riesling acetal (2,2,6-tetramethyl-7,ll-dioxatricyclo[6.2.1.01,6] undec-4-ene).

Figure 4.8. The GC/MS-EI (70eV) SCAN mode chromatogram of compounds formed by acid hydrolysis of a Raboso grape skins extract. Peak 1. frans-furanlinalool oxide peak 2. cfs-furanlinalool oxide I.S.l, internal standard (1-octanol) peak 3. (Z)-ocimenol peak 4. ( )-ocimenol peak 5. a-terpineol I.S.2, internal standard (1-decanol) peak 6. 2-exo-hydroxy-l,8-cineol peak 7. benzyl alcohol peak 8. P-phenylethanol peak 9. actinidols A peak 10. actinidols B peak 11. endiol peak 12. eugenol peak 13. vinylguaiacol peak 14. p-menthenediol I peak 15. 3-hydroxy-P-damascone peak 16. vanillin peak 17. methyl vanillate peak 18. 3-oxo-a-ionol peak 19. 3-hydroxy-7,8-dihydro-P-ionol peak 20. homovanillic alcohol peak 21. vomifoliol.

Buten-1-one, 1-(3-hydroxy-2,6,6-trimethyI-1-cycIohexen-1 -yl)- 3-hydroxy-P-damascone 2601a 2338, 2917a, 4098a ... 

Buten-l-one, l-(2,6,6-trimethyl-cyclohex-l-enyl)- p-damascone 4-(2,6,6-trimethylcyclohex-2-enyl)-but-2-en-4- one + -1-... 

Demole, E. and D. Berthet Identification de la dama-scenone et de la P-damascone dans le tabac burley [Identification of damascenone and P-damascone in bur-ley tobacco] Helv. Chim. Acta 54 (1971) 681-682. 

Kaneko, H. and M. Harada 4-Hydroxy-P-damascone and 4-hydroxydihydro-P-damascone from cigar tobacco Agr. Biol. Chem. 36 (1972) 168-171. 

The ready availability of ionones as potential starting materials, was exploited by Btichi in an elegant synthesis of p-damascone (8.69) and... 

Norisoprenoids detected in negligible amounts or not found in the free fraction of studied wines, were relatively abundant in the bound fraction. The Qs-norisoprenoid pattern was composed by 3-hydroxy-P-damascone, 3-oxo-a-ionol, 3-hydroxy-7,8-dihydro-(3-ionol and, in smaller concentrations, a-ionone and 4-oxo-isophorone. By contrast, (3-damascenone -detected in the free fraction in wines- was not detected in bound form as this compwimd is formed principally from the precursors 3-hydroxy-P-damascone and 3-hydroxy-7,8-dehydro-P-ionol the highest concentration of both compounds found in fraction of aroma of Rojal wines could be related to that in the free fraction Rojal wines paosented lower concentration of P-damascenone. 

CYPIOICI Novosphingobium aromaticivorms 30FT, 30FU Hexane-2,5-diol, P-ionone lonone derivative (e.g., a- and p-ionone and P-damascone) hydroxylation [750]... 

FIGURE 20.156 Biotransformation of P-damascone (531) hy Aspergillus niger And Aspergillus terreus. 

P-Damascone (531) was also treated in Aspergillus niger to afford 5-hydroxy-P-damascone (532), 3-hydroxy-P-damascone (533), 5-oxo- (534), 3-oxo-P-damscone (535), and3-oxo-l, 9-dihy-droxy-l,2-dihydro-P-damascene (536) as the minor components. In case of Aspergillus terreus, 3-hydroxy-8,9-dihydro-P-damascone (537) was also obtained (Figure 15.156). 

IsOE, S., S. Katsumura, and T. Sakan The Synthesis of Damascenone and p-Damascone and the Possible Mechanism of Their Formation from Carotenoids. Helv. Chim. Acta 56, 1514 (1973). 

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