Pinocarveol

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Pinocarveol
cis-Pinocarveol
trans-Pinocarveol
Names
IUPAC name
6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-ol
Other names
6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol
10-pinen-3-ol
Isopinocarveol
(1S,3R,5S)-2(10)-Pinen-3-ol
Identifiers
3D model (JSmol)
ChemSpider
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UNII
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  • InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-9,11H,1,4-5H2,2-3H3
    Key: LCYXQUJDODZYIJ-UHFFFAOYSA-N
  • (cis): InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-9,11H,1,4-5H2,2-3H3/t7-,8+,9-/m1/s1
    Key: LCYXQUJDODZYIJ-HRDYMLBCSA-N
  • (trans): InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-9,11H,1,4-5H2,2-3H3/t7-,8+,9-/m0/s1
    Key: LCYXQUJDODZYIJ-YIZRAAEISA-N
  • CC1(C2CC1C(=C)C(C2)O)C
  • (cis): CC1(C)[C@H]2C[C@@H]1C[C@@H](O)C2=C
  • (trans): CC1(C)[C@@H]2C[C@H]1C[C@H](O)C2=C
Properties
C10H16O
Molar mass 152.237 g·mol−1
Appearance Light yellow viscous liquid
Odor woody
Density 0.9730 g/cm3
Boiling point 217 °C (423 °F; 490 K)
Insoluble in water
Solubility Soluble in ethanol, soluble in oils
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
2
0
Flash point 90.1°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pinocarveol is an organic compound with the formula C10H16O. It is a bicyclic monoterpenoid, which is a combination of two isoprene units with one hydroxyl group as a substituent.[1] It exists as either trans- or cis-pinocarveol, referring to stereochemical orientation of the oxygen as compared to the methylene bridge. It is a naturally occurring molecule in numerous plant species including Eucalyptus globulus and Picea abies.[2] Pinocarveol is found in a variety of essential oils.[3][4]

Synthesis

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Pinocarveol can be synthesized by heating a mixture of turpentine, selenium dioxide, and hydrogen peroxide. The selenium dioxide acts as a catalyst while the hydrogen peroxide oxidizes the pinene found in turpentine. The other products in the turpentine are left unreacted.[5]

Use

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Pinocarveol is used as a food flavoring.[6] In the European Union it is designated Fl 02.100.[7]

References

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