Cedrol

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 Edit this at Wikidata
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).

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 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.