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COMMON NAME | : | Adonixanthin/ 4-Ketozeaxanthin |
SYMBOL | : | |
FORMULA | : | C40H54O3 MOL.WT (average) : 582.855 |
BIOLOGICAL ACTIVITY |
PHYSICAL AND CHEMICAL PROPERTIES |
MELTING POINT | : | (3R,3'R)-Isomer: 180-181![]() ![]() ![]() |
BOILING POINT | : | |
REFRACTIVE INDEX | : | |
OPTICAL ROTATION | : | |
DENSITY | : | |
SOLUBILITY | : |
SPECTRAL DATA |
UV SPECTRA | : | lmax (nm) (e): CHCl3 304 (16695), 480 (105444) (Ref. 0077); hexane 297 (18116), 459 (118149) (Ref. 0077); benzene 472 (116980) (Ref. 0077); ethanol 299 (16252), 465 (108660) (Ref. 0077) |
IR SPECTRA | : | nmax/cm-1:3433s (OH), 1658s (conj. CO), 1557m, 1516m (conj. C=C), 1074m, 1038m (sek. OH), 964s (trans CH=CH) (Ref. 0077) |
NMR SPECTRA | : | 1H-NMR d(270 MHz, CDCl3): 1.075 (s, 1'-gem-Me), 1.213 (s, 1eq-Me), 1.322 (s, 1ax-Me), 1.48 (t, J 12, 2'ax-H), 1.738 (s, 5'-Me), 1.774 (m, 2'eq-H), 1.810 (t, J 13.5, 2ax-H), 1.948 (d, J 0.8, 5-Me), 1.974 (s, 9'-Me), ca. 1.983 (s, 13-, 13'-Me), 1.998 (s, 9-Me), 2.045 (dd, J 17.5, 10, 4'ax-H), 2.16 (dd, J 12.5, 5.5, 2eq-H), 2.39 (dd, J 17.5, 5, 4'eq-H), 3.704 (d, J 1.8, 3-OH), ca. 4.0 (br m, 3'ax-H), 4.33 (ddd, J 14, 6, 1.8, 3ax-H), ca. 6.13 (s, 7'-, 8'-H), 6.16 (d, J 11.5, 10'-H), 6.21 (d, J 16, 7-H), ca. 6.24-6.33 (m, 14-, 14'-, 10-H), 6.37 (d, J 15, 12'-H), 6.44 (d, J 16, 8-H), 6.45 (d, J 15, 12-H), ca. 6.65 (m, 11-, 11'-, 15-, 15'-H) (Ref. 0077) 13C-NMR d(100.6 MHz, CDCl3): 12.55 (9-Me), 12.76, 12.78, 12.85 (13-, 9'-13'-Me), 14.0 (5-Me), 21.62 (5'-Me), 26.14, 30.73 (1-gem-Me), 28.72 (1'ax-Me), 30.25 (1'eq-Me), 36.79 (C1), 37.11 (C1'), 42.54 (C4'), 45.38 (C2), 48.39 (C2'), 65.02 (C3'), 69.20 (C3), 123.11 (C7), 124.26 (C11), 125.26 (C11'), 125.75 (C7'), 126.23 (C5'), 126.72 (C5), 129.80, 130.94 (C15, C15'), 131.22 (C10'), 132.42 (C14'), 134.01 (C14), 134.29 (C9), 135.29 (C10), 135.94 (C9'), 136.07, 137.10 (C13, C13'), 137.42 (C12'), 137.71 (C6'), 138.42 (C8'), 139.86 (C12), 142.43 (C8), 162.27 (C6), 200.40 (C4) (Ref. 0077) |
MASS SPECTRA | : | m/z (ion, intensity relative to base peak in %): 566 (M, 31), 564 (9), 548 (5), 474 (4), 412 (6), 203 (62), 159 (50), 145 (45), 119 (74), 105 (81), 91 (100), 69 (68), 55 (68), 41 (67) (Ref. 0077) |
OTHER SPECTRA | : | CD data in EPA solution De: (3R,3'S)-isomer: 363 (-2.94), 307 (20.75), 290sh (11.38), 264 (-12.43) , 238 (10.43); (3R,3'R)-isomer: 369 (3.74), 307 (4.68), 293sh (2.66), 285sh (1.26) , 263 (-2.50), 246 (-0.63); (3S,3'R)-isomer: 366 (2.40), 307 (-18.95), 292sh (-11.64), 264 (11.12) , 238 (-9.85); (3S,3'S)-isomer: 371 (-3.83), 329 (-0.29), 307 (-4.87), 293sh (-2.95) , 283sh (-1.32), 264 (1.71), 243 (-0.21) (Ref. 0064/0077/0078) |
CHROMATOGRAM DATA |
SOURCE |
CHEMICAL SYNTHESIS |
METABOLISM |
GENETIC INFORMATION |
NOTE |
REFERENCES |
AUTHOR | : | Buchecker,R., and Noack,K. (1995) Carotenoids Volume 1B: Spectroscopy Chapter 3: Circular Dichroism (Britton,G.,Liaaen-Jensen,S., and Pfander,H., eds), pp63-116, Birkhäuser Verlag,Basel,Boston,Berlin |
TITLE | : | |
JOURNAL | : | |
VOL | : | PAGE : - () |
AUTHOR | : | Yokoyama, A., Izumida, H., and Miki, W. |
TITLE | : | Production of Astaxanthin and 4-Ketozeaxanthin by the Marine Bacterium, Agrobacterium aurantiacum |
JOURNAL | : | Biosci. Biotechnol. Biochem. |
VOL | : | 58 PAGE : 1842 -1844 (1994) |
AUTHOR | : | Bernhard,K.,Englert,G.,Mayer,H.,Müller,R.K.,Rüttimann,A.,Vecchi,M.,Widmer,E., and Zell,R. |
TITLE | : | Synthese von optisch aktiven, natürlichen Carotenoiden und strukturell verwandten Naturprodukten IX. Synthese von (3R)-Hydroxyechinenon, (3R,3'R)- und (3R,3'S)-Adnixanthin, (3R)-Adonirubin, deren optischen Antipoden und verwandten Verbindungen |
JOURNAL | : | Helv. Chim. Acta |
VOL | : | 64 PAGE : 2469 -2484 (1981) |
AUTHOR | : | Noack,K. |
TITLE | : | Temperaturabhängiger Circulardichroismus von (3S,3'R)- und (3S,3'S)-Adnixanthin |
JOURNAL | : | Helv. Chim. Acta |
VOL | : | 64 PAGE : 1833 -136 (1981) |
AUTHOR | : | Yokoyama,A.,Adachi,K., and Shizuri,Y. |
TITLE | : | New Carotenoid Glucosides, Astaxanthin Glucoside and Adonixanthin Glucoside, Isolation from the Astaxanthin-Producing Marine Bacterium Agrobacterium aurantiacum |
JOURNAL | : | J. Nat. Prod. |
VOL | : | 58 PAGE : 1929 -1933 (1995) |
AUTHOR | : | Misawa, N., Satomi, Y., Kondo, K., Yokoyama, A., Kajiwara, S., Saito, T., Ohtani, T., and Miki, W. |
TITLE | : | Structure and functional analysis of a marine bacterial carotenoid biosynthesis gene cluster and astaxanthin biosynthetic pathway proposed at the gene level PubMed ID:7592436 |
JOURNAL | : | J Bacteriol. |
VOL | : | 177 PAGE : 6575-6584 (1995) |
AUTHOR | : | Yokoyama, A., and Miki, W. |
TITLE | : | Composition and Presumed Biosynthetic Pathway of Carotenoids in the Astaxanthin-Producing Bacterium Agrobacterium aurantiacum |
JOURNAL | : | FEMS Microbiol. Lett. |
VOL | : | 128 PAGE : 139 -144 (1995) |
AUTHOR | : | Egger,K. |
TITLE | : | Die Ketocarotinide In Adonis annua L. |
JOURNAL | : | Phytochemistry |
VOL | : | 4 PAGE : 609 -618 (1965) |
AUTHOR | : | Matsuno,T.,Kusumoto,T.,Watanabe,T., and Ishihara,Y. |
TITLE | : | Carotenoid pigments of spiny lobster |
JOURNAL | : | Bull. Jap. Soc. Sci. Fish. |
VOL | : | 39 PAGE : 43 -50 (1973) |
AUTHOR | : | Matsuno,T.,Matsutaka,H., and Nagata,S. |
TITLE | : | Metabolism of lutein and zeaxanthin to ketocarotenoids in goldfish, Carassius auratus |
JOURNAL | : | Bull. Jap. Soc. Sci. Fish. |
VOL | : | 47 PAGE : 605 -611 (1981) |
AUTHOR | : | Yokoyama, A., Miki, W., Izumida, H., Shizuri, Y. |
TITLE | : | New trihydroxy-keto-carotenoids isolated from an astaxanthin-producing marine bacterium |
JOURNAL | : | Biosci. Biotech. Biochem. |
VOL | : | 60 PAGE : 200 -203 (1996) |