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 collection of bicyclic terpenoid derived from the terpene pinene, but containing a tertiary alcohol. Both cis and trans isomers exist. Both are chiral They are produced by deoxygenation of corresponding cis- and trans-2-pinane hydroperoxide, which in turn can be 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.

[1] "2-Pinanol". pubchem.ncbi.nlm.nih.gov.

[2] 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.

[3] Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 3527306730.

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