2-Pinanol

2-Pinanol
Names
	Other names 2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol
Identifiers
CAS Number	473-54-1; trans: 4948-29-2; cis: 4948-28-1;
3D model (JSmol)	Interactive image; trans: Interactive image; cis: Interactive image;
ChemSpider	9723; cis: 4933698;
ECHA InfoCard	100.006.789
EC Number	207-466-6;
PubChem CID	10128; trans: 1268143; cis: 6428289;
UNII	5DZK63N3UU;
CompTox Dashboard (EPA)	DTXSID5029180 ; trans: DTXSID8027583; cis: DTXSID3027582;
	InChI InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,11)8(9)6-7/h7-8,11H,4-6H2,1-3H3 Key: YYWZKGZIIKPPJZ-UHFFFAOYSA-N; trans: InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,11)8(9)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m0/s1 Key: YYWZKGZIIKPPJZ-QXFUBDJGSA-N; cis: InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,11)8(9)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10-/m0/s1 Key: YYWZKGZIIKPPJZ-XKSSXDPKSA-N;
	SMILES CC1(C2CCC(C1C2)(C)O)C; trans: CC1(C)[C@@H]2C[C@H]1[C@](C)(O)CC2; cis: CC1(C)[C@@H]2C[C@H]1[C@@](C)(O)CC2;
Properties
Chemical formula	C10H18O
Molar mass	154.253 g·mol−1
Appearance	colorless solid
Melting point	78–79 °C (cis); 58–59 °C (trans
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H311, H312, H315, H319
Precautionary statements	P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P316, P317, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Pinanol is a pair of isomeric organic compounds consisting of bicyclic terpenoid. They are obtained from the terpene pinene. Both cis and trans isomers exist. Both are chiral They are produced by hydrogenation of corresponding cis- and trans-2-pinane hydroperoxides, which in turn are produced by autoxidation of pinane with air.^[2] Heating 2-pinanol gives linalool.^[3]

References

^ "2-Pinanol". pubchem.ncbi.nlm.nih.gov.
^ Erman, Mark B.; Kane, Bernard J. (2008). "Chemistry Around Pinene and Pinane: A Facile Synthesis of Cyclobutanes and Oxatricyclo-Derivative of Pinane from cis- and trans-Pinanols". Chemistry & Biodiversity. 5 (6): 910–919. doi:10.1002/cbdv.200890104. PMID 18618388. S2CID 24782774.
^ Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 3527306730.