Cedrol

Cedrol is a sesquiterpene alcohol found in the essential oil of conifers (cedar oil), especially in the genera Cupressus (cypress) and Juniperus (juniper). It has also been identified in Origanum onites, a plant related to oregano.[3] Its main uses are in the chemistry of aroma compounds.[4] It makes up about 19% of cedarwood oil Texas and 15.8% of cedarwood oil Virginia.[5]

Cedrol
Names
IUPAC name
8α-Cedran-8β-ol
Systematic IUPAC name
(3R,3aS,6R,7R,8aS)-3,6,8,8-Tetramethyloctahydro-1H-3a,7-methanoazulen-6-ol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.942
UNII
  • InChI=1S/C15H26O/c1-10-5-6-11-13(2,3)12-9-15(10,11)8-7-14(12,4)16/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14-,15+/m1/s1
    Key: SVURIXNDRWRAFU-OGMFBOKVSA-N
  • O[C@@]2(CC[C@]31[C@@H](CC[C@H]1C)C([C@H]2C3)(C)C)C
Properties
C15H26O
Molar mass 222.372 g·mol−1
Density 1.01 g/mL
Melting point 86 to 87 °C (187 to 189 °F; 359 to 360 K)[1]
Boiling point 273 °C (523 °F; 546 K)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cedrol has not been proven to be toxic in humans. It has been shown to have antioxidant and antiinflammatory along with other beneficial effects. In skin sensitization tests 2/20 people showed negative effects, and on the second test there was no sensitivity found. This compound and ones similar have been found to have antiseptic, anti-inflammatory, antispasmodic, tonic, astringent, diuretic, sedative, insecticidal, and antifungal activities in vitro.[6] These compounds are used globally in traditional medicine and cosmetics.[7] Results of a 2015 study suggest that cedrol strongly attracts pregnant female mosquitoes after they have fed, which can be used to create cedrol-baited traps.[8]

See also
  • Cedrene, another component of cedar oil

References
  1. Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123, 1961
  2. Sigma-Aldrich Co., (+)-Cedrol. Retrieved on 25 May 2011.
  3. Connolly, JD; Hill, RA, eds. (1991). Dictionary of Terpenoids. Vol. 1 Mono- and sesquiterpenoids. Chapman&Hall. SQ02555. ISBN 0-412-25770-X.
  4. Breitmeier, E (2006). Terpenes: flavors, fragrances, pharmaca, pheromones. Wiley-VCH. pp. 46–47. ISBN 3-527-31786-4.
  5. Susan Barclay-Nichols. "Point of Interest!". swiftcraftymonkey.blogspot.com.
  6. Jeong, H. U.; Kwon, S. S.; Kong, T. Y.; Kim, J. H.; Lee, H. S. (2014). "Inhibitory effects of cedrol, β-cedrene, and thujopsene on cytochrome P450 enzyme activities in human liver microsomes". Journal of Toxicology and Environmental Health. Part A. 77 (22–24): 1522–32. doi:10.1080/15287394.2014.955906. PMID 25343299.
  7. "Cedrol". TOXNET: Toxicology Data Network.
  8. Lindh, Jenny; Okal, Michael (March 2015). "Discovery of an oviposition attractant for gravid malaria vectors of the Anopheles gambiae species complex". Malaria Journal. 14 (119): 119. doi:10.1186/s12936-015-0636-0. PMC 4404675. PMID 25885703.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.