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Pinocarveol

January 01, 1970

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
  • 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
  • 102667
  • (cis): 10931630
  • (trans): 88297
UNII
  • 0WG2C7KI43
  • DTXSID30863660
  • 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)
Health 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).

Synthesis edit

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 edit

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

References edit

  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.

January 01, 1970
pinocarveol, organic, compound, with, formula, c10h16o, bicyclic, monoterpenoid, which, combination, isoprene, units, with, hydroxyl, group, substituent, exists, either, trans, pinocarveol, referring, stereochemical, orientation, oxygen, compared, methylene, b. 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 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 3H3Key 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 s1Key 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 s1Key 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 C 10H 16O 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 020 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 referencesSynthesis editPinocarveol 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 editPinocarveol is used as a food flavoring 6 In the European Union it is designated Fl 02 100 7 References edit 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 amp 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 Retrieved from https en wikipedia org w index php title Pinocarveol amp oldid 1216883102, wikipedia, wiki, book, books, library,

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