Pinocarveol

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]

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
ECHA InfoCard 100.025.187
UNII
  • 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 diamond
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).
Infobox references

Synthesis

Pinocarveol is formed 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

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


References
  1. Clarke, S (2008), "Families of compounds that occur in essential oils", Essential Chemistry for Aromatherapy, Elsevier, pp. 41–77, doi:10.1016/b978-0-443-10403-9.00003-0, ISBN 978-0-443-10403-9
  2. "LOTUS: Natural Products Online". lotus.naturalproducts.net. Retrieved 2022-02-22.
  3. Dob, T.; Dahmane, D.; Chelghoum, C. (2006-01-01). "Essential Oil Composition of Juniperus Oxycedrus. Growing in Algeria". Pharmaceutical Biology. 44 (1): 1–6. doi:10.1080/13880200500530922. ISSN 1388-0209. S2CID 84516218.
  4. Bansal, Anita; Boehme, Amelia K.; Eiter, Lauren C.; Schmidt, Jennifer M.; Setzer, William N.; Vincent, Michael A. (2006). "Chemical Composition and Bioactivity of the Leaf Oil of Calyptranthes pallens (Poir.) Griseb. from Abaco Island, Bahamas". Natural Product Communications. 1 (4): 1934578X0600100. doi:10.1177/1934578X0600100407. ISSN 1934-578X. S2CID 132063891.
  5. Coxon, James M.; Dansted, Erik; Hartshorn, Michael P. (1970). "trans-Pinocarveol from New Zealand turpentine". Journal of Chemical & Engineering Data. 15 (2): 336. doi:10.1021/je60045a013. ISSN 0021-9568.
  6. "Commission Implementing Regulation (EU) No 872/2012 of 1 October 2012 adopting the list of flavouring substances provided for by Regulation (EC) No 2232/96 of the European Parliament and of the Council, introducing it in Annex I to Regulation (EC) N 1334/2008 of the European Parliament and of the Council and repealing Commission Regulation (EC) No 1565/2000 and Commission Decision 1999/217/EC – Text with EEA relevance". 2 October 2012.


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