Pinocarveol

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
CAS Number	5947-36-4; (cis): 3917-59-7; (trans): 19889-99-7;
3D model (JSmol)	Interactive image; (cis): Interactive image; (trans): Interactive image;
ChemSpider	(cis): 79657; (trans): 79661;
ECHA InfoCard	100.025.187
PubChem CID	102667; (cis): 10931630; (trans): 88297;
UNII	0WG2C7KI43;
CompTox Dashboard (EPA)	DTXSID30863660 ;
	InChI 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;
	SMILES 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
Chemical formula	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)
Solubility in water	Insoluble in water
Solubility	Soluble in ethanol, soluble in oils
Hazards
NFPA 704 (fire 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

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

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

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

References

^ 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
^ "LOTUS: Natural Products Online". lotus.naturalproducts.net. Retrieved 2022-02-22.
^ 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.
^ 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.
^ 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.
^ "Pinocarveol". Evaluations of the Joint FAO/WHO Expert Committee on Food Additives.
^ "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.

[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] "Pinocarveol". Evaluations of the Joint FAO/WHO Expert Committee on Food Additives.

[7] "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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