Guaiol

Guaiol or champacol is an organic compound, a sesquiterpenoid alcohol found in several plants, especially in the oil of guaiacum and cypress pine.[1] It is a crystalline solid that melts at 92 °C.[2] Guaiol is one of many terpenes found in Cannabis and it has been associated with anxiolytic activity.[3][4]

Guaiol
Names
IUPAC name
Guai-1(5)-en-11-ol
Systematic IUPAC name
2-[(3S,5R,8S)-3,8-Dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol
Other names
Champacol,
5-Azulenemethanol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.003
UNII
  • InChI=1S/C15H26O/c1-10-5-7-12(15(3,4)16)9-14-11(2)6-8-13(10)14/h10-12,16H,5-9H2,1-4H3/t10-,11-,12+/m0/s1 checkY
    Key: TWVJWDMOZJXUID-SDDRHHMPSA-N checkY
  • InChI=1/C15H26O/c1-10-5-7-12(15(3,4)16)9-14-11(2)6-8-13(10)14/h10-12,16H,5-9H2,1-4H3/t10-,11-,12+/m0/s1
    Key: TWVJWDMOZJXUID-SDDRHHMPBW
  • OC([C@H]1C\C2=C(/[C@H](CC1)C)CC[C@@H]2C)(C)C
Properties
C15H26O
Molar mass 222.372 g·mol−1
Density 0.961 g/mL
Melting point 92 °C (198 °F; 365 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Reactions

Guaiol yields a deep purple color when treated with electrophilic bromine reagents.[5]

See also

References
  1. The Merriam-Webster Dictionary.
  2. Wolfram Alpha Guaiol
  3. Hillig, Karl W (2004-10-01). "A chemotaxonomic analysis of terpenoid variation in Cannabis". Biochemical Systematics and Ecology. 32 (10): 875–891. doi:10.1016/j.bse.2004.04.004.
  4. Kamal, Brishna S.; Kamal, Fatima; Lantela, Daniel E. (2018). "Cannabis and the Anxiety of Fragmentation—A Systems Approach for Finding an Anxiolytic Cannabis Chemotype". Frontiers in Neuroscience. 12: 730. doi:10.3389/fnins.2018.00730. PMC 6204402. PMID 30405331.
  5. Waddell, TG; Arp, NW; Bodine, KD; Pagni, RM (2002). "The guaiol color reaction". Planta Medica. 68 (10): 949–50. doi:10.1055/s-2002-34931. PMID 12391567.


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