Damascone hydroxy

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

Bicyclo[2.2.1]hepten 5-(2,2-Dieth-oxy-ethenyl)- E15/2, 1680 [ -CH(OR)2 + R-CHO] Bntan l,3-Dioxo-l-(2,6,6-trimethyl-1 -cyclohexenyl)-(9-Hydroxy- -damascon) El9b, 1261 (Hydroxy — carben - Keton) Cyclohexan... 

Several new natural products based on the ionone skeleton have been isolated. Damescenone (56), jS-damascone (57) and 3-keto-a-ionol (58) were isolated from tobacco, while 4-keto-/S-ionone (59) was isolated from black tea. Treatment of dehydro-/l-ionol [alcohol from (53)] with diborane gave 3-hydroxy- -ionol (60). Photochemical oxidation gave loliolide (67) and its C-3 epimer, and the allene (61). Manganese dioxide oxidation gave an isomer of grasshopper... 

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 ... 

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

Ci3-norisoprenoids analyzed hydroxy-3-,6-D-damascone, oxo-3-a-ionol, oxo-4-/)-ionol, hydroxy-3-/S-ionol and hydroxy-3-dihydro-... 

The other oxygenated Ci3-norisoprenoids identified in wine are 3-oxo-a-ionol (tobacco), 3-hydroxy-j6-damascone (tea and tobacco) and fi-damascone (tobacco and fruit). Their perception thresholds are much higher and their olfactory impact in wine negligible, in spite of relatively high concentrations in some cases. 

The synthetic chemistry of damascones and damascenones has been reviewed. New syntheses have been reported of /8-damascenone (141) from dimedone, of 3-hydroxy-/3-damascone (142) and 3-hydroxydihydro-/3-damas-cone (143),and of various damascones and their demethyl analogues. ... 

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). 

One of the most important discoveries recently made in the field of carotenoid aroma compounds relates to the class of damascones. Seven naturally occurring members (266) to (272) of this class are known today. The discovery of these new compounds started with the isolation of damascenone (268) from Bulgarian rose oil in 1970 120). Later, the same compound was detected in various tobacco brands 5, 110, 306), tea 491), raspberry oil 708), cooked apples 442), various grape and wine varieties 546, 549), beer 598), coffee oil 179), buchu leaf oil 283) and Roman camomile 638). 3-Hydroxy-(3-damascone (269) was shown to be an important aroma component of tobacco 108, 169, 285) in which it develops a green, rose-floral and sweet Burley-like note (556). (3-Damascone (267) was found in Burley tobacco 110) and rose oil 108), whereas a-damascone (266), accompanied by (3-compound (267) and damascenone (268), was exclusively observed in tea oil 491). Among the known cyclization products (270) to (272), the last two compounds were found in tobacco (779), while ketone (270) was detected in tea 491). 

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. 

Kancko and Harada have reported the presence of lactone (211) and of 4-hydroxy- -/ -damascone (212) in cigar leaf tobacco. ... 

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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