Guaiol

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
CAS Number	489-86-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:5552 ;
ChEMBL	ChEMBL226915 ;
ChemSpider	198233 ;
ECHA InfoCard	100.007.003
PubChem CID	227829;
UNII	I7WP008A91 ;
CompTox Dashboard (EPA)	DTXSID40883399 ;
	InChI 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 Key: TWVJWDMOZJXUID-SDDRHHMPSA-N ; 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;
	SMILES OC([C@H]1C\C2=C(/[C@H](CC1)C)CC[C@@H]2C)(C)C;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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]

Reactions

Guaiol yields a deep purple color when treated with electrophilic bromine reagents.^[5] Upon heating with sulfur, guaiazulene can yield.

^ The Merriam-Webster Dictionary.
^ Wolfram Alpha Guaiol
^ 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.
^ 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.
^ 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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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
CAS Number	489-86-1^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:5552^Y
ChEMBL	ChEMBL226915^Y
ChemSpider	198233^Y
ECHA InfoCard	100.007.003
PubChem CID	227829
UNII	I7WP008A91^Y
CompTox Dashboard (EPA)	DTXSID40883399
InChI 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^Y Key: TWVJWDMOZJXUID-SDDRHHMPSA-N^Y 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
SMILES OC([C@H]1C\C2=C(/[C@H](CC1)C)CC[C@@H]2C)(C)C
Properties
Chemical formula	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). N verify (what is ^YN ?) Infobox references