Solubility of the sesquiterpene alcohol patchoulol in supercritical carbon dioxide

Journal of Chemical and Engineering Data

Volumn 52, Issue 1, 2007, Pages 235-238

  Hybertson, Brooks M ^a,b  

^a UNIVERSITY OF COLORADO SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIQUOTS; PATCHOULOL MEASUREMENTS; SESQUITERPENE ALCOHOL PATCHOULOL; SUPERCRITICAL CARBON DIOXIDE;

CARBON DIOXIDE; GAS CHROMATOGRAPHY; MASS SPECTROMETERS; PRESSURE MEASUREMENT; SOLUBILITY; SPECTROPHOTOMETRY; SUPERCRITICAL FLUIDS;

ALCOHOLS;

EID: 33847083968     PISSN: 00219568     EISSN: None     Source Type: Journal    
DOI: 10.1021/je060358w     Document Type: Article

References (29)

1. Magee, T. V.; Stork, G.; Fludzinski, P., A total synthesis of rac-patchouli alcohol. Tetrahedron Lett. 1995, 36, 7607-7610.
2. Buchi, G.; Erickson, R. E.; Terpenes, V. The structure of patchouly alcohol. J. Am. Chem. Soc. 1956, 78, 1262-1263.
3. Buchi, G.; MacLeod, W., Jr. Synthesis of patchouli alcohol. J. Am. Chem. Soc. 1962, 84, 3205-3206.
4. Kaliappan, K. P.; Subba Rao, G. S. R. Synthesis based in cyclohexadienes. Part 22. Formal syntheses of patchouli alcohol and norpatchoulenol. J. Chem. Soc., Perkin Trans. 1 1997, 9, 1385-1389.
5. Kraft, P.; Weymuth, C.; Nussbaumer, C. Total Synthesis and Olfactory Evaluation of (1R*,3S*,6S*,7S*,8S*)- 3-Hydroxy-6,8-dimethyltricyclo-[5.3.1.03-8]undecan-2-one: A New Synthetic Route to the Patchoulol Skeleton. Eur. J. Org. Chem. 2006, 2006 (6), 1403-1412.
6. Srikrishna, A.; Satyanarayana, G. An enantiospeciflc total synthesis of (-)-patchouli alcohol. Tetrahedron: Asymmetry 2005, 16, 3992-3997.
7. Bruneton, J. Pharmacognosy, Phytochemistry, Medicinal Plants, 2nd ed.; Lavoisier Publishing: Paris, 1999.
8. Aleu, J.; Hanson, J. R.; Galan, R. H.; Collado, I. G. Biotransformation of the fungistatic sesquiterpenoid patchoulol by botrytis cinerea. J. Nat. Prod. 1999, 62 (3), 437-440.
9. Aleu, J.; Hanson, J. R.; Hernandez Galan, R.; Collado, I. G. Biotransformation of the fungistatic sesquiterpenoids patchoulol, ginsenol, cedrol, and globulol by Botrytis cinerea. J. Mol. Catal. B: Enzymatic 2001, 11 (4-6), 329-334.
10. Trongtokit, Y.; Rongsriyam, Y.; Komalamisra, N.; Apiwathnasorn, C. Comparative repellency of 38 essential oils against mosquito bites. Phytother. Res. 2005, 19 (4), 303-309.
11. Wu, J.; Lu, X.; Tang, W.; Kong, H.; Zhou, S.; Xu, G. Application of comprehensive two-dimensional gas chromatography time-of-flight mass spectrometry in the analysis of volatile oil of traditional Chinese medicines. J. Chromatogr. A 2004, 1034 (1-2), 199-205.
12. Zhu, B. C. R.; Henderson, G.; Yu, Y.; Laine, R. A. Toxicity and Repellency of Patchouli Oil and Patchouli Alcohol against Formosan Subterranean Termites Coptotermes formosanus Shiraki (Isoptera: Rhinotermitidae). J. Agric. Food Chem. 2003, 51 (16), 4585-4588.
13. Bure, C. M; Sellier, N. M. Analysis of the essential oil of Indonesian patchouli (Pogostemon cablin Benth.) using GC/MS (EI/CI). J. Essent. Oil Res. 2004, 16 (1), 17-19.
14. Lucien, F. P.; Foster, N. R. Solubilities of solid mixtures in supercritical carbon dioxide: a review. J. Supercrit. Fluids 2000, 17 (2), 111-134.
15. Reverchon, E. Supercritical fluid extraction and fractionation of essential oils and related products. J. Supercrit. Fluids 1997, 10 (1), 1-37.
16. Reverchon, E.; Caputo, G. Fine particle generation techniques using supercritical fluids. Trends Chem. Eng. 2003, 8, 183-198.
17. Clifford, A. A.; Williams, J. R. Introduction to supercritical fluids and their applications. In Supercritical Fluid Methods and Protocols; Williams, J. R., Clifford, A. A., Eds.; Humana Press: Totowa, NJ, 2000; pp 1-16.
18. King, J. W. Critical fluid technology for the processing of lipid-related natural products. C. R. Chim. 2004, 7 (6-7), 647-659.
19. King, J. W.; Williams, L. L. Utilization of critical fluids in processing semiconductors and their related materials. Curr. Opin. Solid State Mater. Sci. 2003, 7 (4-5), 413-424.
20. Burgos-Solorzano, G. I.; Brennecke, J. F.; Stadtherr, M. A. Solubility measurements and modeling of molecules of biological and pharmaceutical interest with supercritical CO2. Fluid Phase Equilib. 2004, 220 (1), 55-67.
21. Lang, Q.; Wai, C. M. Supercritical fluid extraction in herbal and natural product studies - a practical review. Talanta 2001, 53 (4), 771-782.
22. McHugh, M.; Paulaitis, M. E. Solid solubilities of naphthalene and biphenyl in supercritical carbon dioxide. J. Chem. Eng. Data 1980, 25, 326-329.
23. Dobbs, J. M.; Wong, J. M.; Johnston, K. P. Nonpolar co-solvents for solubility enhancement in supercritical fluid carbon dioxide. J. Chem. Eng. Data 1986, 31 (3), 303-308.
24. Wells, P. A.; Chaplin, R. P.; Foster, N. R. Solubility of phenylacetic acid and vanillan in supercritical carbon dioxide. J. Supercrit. Fluids 1990, 3 (1), 8-14.
25. Ni, Y.; Zhang, G.; Kokot, S. Simultaneous spectrophotometric determination of maltol, ethyl maltol, vanillin and ethyl vanillin in foods by multivariate calibration and artificial neural networks. Food Chem. 2004, 89 (3), 465-473.
26. CRC handbook of chemistry and physics; CRC Press: Boca Raton, Fl, 1988.
27. Sane, A.; Taylor, S.; Sun, Y.-P.; Thies, M. C. A semicontinuous flow apparatus for measuring the solubility of opaque solids in supercritical solutions. J. Supercrit. Fluids 2004, 28 (2-3), 277-285.
28. Lemmon, E. W.; McLinden, M. O.; Friend, D. G. Thermophystcal properties of fluid systems. In NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Linstrom, P. J., Mallard, W. G., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, 2003.
29. Skerget, M.; Cretnik, L.; Knez, Z.; Skrinjar, M. Influence of the aromatic ring substituents on phase equilibria of vanillins in binary systems with CO2. Fluid Phase Equilib. 2005, 231 (1), 11-19.