3- Hydroxy-p-damascone

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 ... 

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. 

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). 

Besides the Grasshopper ketone, another enin-diol (Formula 3.141) was identified in grape juices. When heated (pH 3), this enindiol yields 3-hydroxy- P-damascone as main and P-damascenone as minor product. 

Important fragrance components of rose oil include (4R)-cis-rose oxide, 4R)-trans-Tose oxide, ( )-nerol oxide, 3-(4-methyl-3-pentenyl)-2-buten-4-olide, 3-methyl-4-(3-methyl-2-butenyl)-2-buten-4-olide, cis- and tran5-2-(3-methyl-2-butenyl)-3-methyl tetra-hydrofuran, P-damascenone, 3-hydroxy-P-damascenone, and P-damascone. ... 

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