| CAROTENOID INFO | |
|---|---|
| CAROTENOID NAME | Nostoxanthin |
| STRUCTURE |  |
| OTHER NAME | |
| SYSNAME/SYNONYMS | beta,beta-Carotene-2,3,2',3'-tetrol |
| MOLECULAR FORMULA | C40H56O4 |
| MOLECULAR WEIGHT | 600.8702 |
| IUPAC NAME | (1R,2R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R,5R)-4,5-dihydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,3,5-trimethylcyclohex-4-ene-1,2-diol |
| InChI | JVPASJUYZJKFHY-HWFHZMFDSA-N |
| CANONICAL SMILES | CC1=C(C(C(C(C1)O)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(CC(C(C2(C)C)O)O)C)C)C |
| ISOMERIC SMILES | CC1=C(C([C@H]([C@@H](C1)O)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2=C(C[C@H]([C@@H](C2(C)C)O)O)C)C)C)/C)/C |
| KEGG ID | C16284 |
| PUBCHEM ID | 47205592 |
| CHEBI ID | |
| UV SPECTRA | Lambda max (nm): methanol 275, 341, 425 (shoulder), 448, 475, %III/II=30.9 (Takaichi & Shimada,1992) ; acetone 431 (shoulder), 453, 480.5; CHCl3/methanol (2:1) (_) 456 (91.3), 484 (78.1) ; ethanol 429, 449, 477 (Watanabe et al, 2000) |
| NMR SPECTRA | 1H-NMR (CDCl3): 1.00 s (16-H3), 1.13 s (17-H3), 1.72 s (18-H3), 1.97 s (19, 20-H3), 2.14 dd (4-Hax), 2.48 dd (4-Heq), 3.33 d (J=10.1 Hz; 2-Hax), 3.84 m (3-Hax) (Takaichi et al, 1990); |
| MASS SPECTRA | FD-MS m/z: 600 (100%), 582 (M-18, 2%) (Takaichi et al, 1990). |
| HPLC CHROMATOGRAM | |
| OTHER SPECTRA | |
| REFERENCES |
1.Englert G, Noack K, Broger EA, Glinz E, Vecchi M, Zell R: Synthesis, Isolation, and Full Spectroscopic Characterization of Eleven (Z)-Isomers of (3R,3’R)-Zeaxanthin. Helv. Chim. Acta 1991, 74:969-982.
2.Enzell CR, Francis GW, Liaaen-Jensen S, Schultes RE, Lindberg AA, Jansen G, Lamm B, Samuelsson B: Mass Spectrometric Studies of Carotenoids. 2. A Survey of Fragmentation Reactions. Acta Chem. Scand. 1969, 23:727-750.(PMID: 5806308) 3. Maoka T, Arai A, Shimizu M, Matsuno T: The first isolation of enantiomeric and meso-zeaxanthin in nature. Comp. Biochem. Physiol. B. 1986, 83:121-4.(PMID: 3943294) 4. Moss GP: Carbon-13 NMR Spectra of Carotenoids. Pure Appl. Chem. 1976, 47:97-102 5. Kuwabara T, Hasegawa M, Kawano M, Takaichi S: Characterization of violaxanthin de-epoxidase purified in the presence of Tween 20: effects of dithiothreitol and pepstatin A. Plant Cell Physiol. 1999, 40:1119-26.(PMID: 10635115) 6. Sasa T, Takaichi S, Hatakeyama N, Watanabe MM: A Novel Carotenoid Ester, Loroxanthin Dodecenoate, from Pyramimonas parkeae (Prasinophyceae) and a Chlorarachniophycean Alga_: NATURAL PRODUCTS. Plant cell Physiol. 1992, 33:921-925. 7. Widmer E, Soukup M, Zell R, Broger E, Wagner HP, Imfeld M: Technical Procedures for the Syntheses of Carotenoids and Related Compounds from 6-Oxo-isophorone: Syntheses of (3R,3’R)-Zeaxanthin. Part I. Helv. Chim. Acta 1990, 73:861-867. 8. Watanabe K, Yasugi E, Oshima M : "How to search the glycolipid data in LIPIDBANK for Web: the newly developed lipid database" Japan Trend Glycosci. and Glycotechnol. 2000. 12, 175-184.(PMID:12058481) |
| CAROTENOID INFO | |
ProCarDB