exo-2-Hydroxycineole

Formula: C₁₀H₁₈O₂
Molecular weight: 170.2487
IUPAC Standard InChI: InChI=1S/C10H18O2/c1-9(2)7-4-5-10(3,12-9)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7?,8-,10?/m0/s1
IUPAC Standard InChIKey: YVCUGZBVCHODNB-ZCUBBSJVSA-N
CAS Registry Number: 92999-78-5
Chemical structure:
This structure is also available as a 2d Mol file
Stereoisomers:
Other names: 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octan-6-ol, (1α,4α,6β)-; 2α-Hydroxy-1,8-cineole; 2-exo-Hydroxy-1,8-cineole; 2-Hydroxycineole, exo-; trans-2-Hydroxy-1,8-cineole; exo-2-Hydroxycineol; exo-2-Hydroxy-1,8-cineole; 2α-Hydroxy-1,8-cineol; exo-2-Hydroxy-8-cineole; 1,8-cineole, 2α hydroxy
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Information on this page:
Other data available:
- Mass spectrum (electron ionization)
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Gas Chromatography

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Van Den Dool and Kratz RI, non-polar column, temperature ramp

Column type	Active phase	I	Reference	Comment
Capillary	HP-101	1212.	Politeo, Jukic, et al., 2007	25. m/0.20 mm/0.20 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 15. min
Capillary	HP-5MS	1228.	Lalel, Singh, et al., 2003	60. m/0.25 mm/0.25 μm, He, 40. C @ 1. min, 3. K/min, 310. C @ 20. min

Van Den Dool and Kratz RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1845.	Varming, Andersen, et al., 2006	30. m/0.25 mm/0.25 μm, He, 40. C @ 10. min, 6. K/min, 240. C @ 25. min
Capillary	DB-Wax	1870.	Shimoda, Wu, et al., 1996	60. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 50. C; T_end: 230. C
Capillary	DB-Wax	1834.	Suárez, Duque, et al., 1991	30. m/0.259 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; T_end: 240. C
Capillary	DB-Wax	1836.	Suárez, Duque, et al., 1991	30. m/0.259 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; T_end: 240. C
Capillary	DB-Wax	1834.	Suárez, Duque, et al., 1991	30. m/0.259 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; T_end: 240. C
Capillary	DB-Wax	1836.	Suárez, Duque, et al., 1991	30. m/0.259 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; T_end: 240. C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5 MS	1230.	Radulovic, Dordevic, et al., 2010	30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; T_start: 70. C
Capillary	HP-5MS	1218.	Setzer, Noletto, et al., 2006	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 3. K/min; T_end: 280. C
Capillary	HP-5MS	1219.	Setzer, Noletto, et al., 2005	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 3. K/min; T_end: 280. C
Capillary	HP-5MS	1228.	Southwell, Russell, et al., 2003	30. m/0.25 mm/0.25 μm, He, 50. C @ 1. min, 6. K/min; T_end: 240. C

Normal alkane RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	CBP-5	1196.	Cheriti, Saad, et al., 2007	30. m/0.25 mm/0.25 μm, He; Program: 60C(2min) => 3C/min => 240C => 10C/min => 300C

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1859.	Lan Phi N.T., Nishiyama C., et al., 2006	60. m/0.25 mm/0.25 μm, 70. C @ 2. min, 2. K/min, 230. C @ 20. min
Capillary	DB-Wax	1861.	Lee, Umano, et al., 2005	30. m/0.25 mm/0.25 μm, He, 3. K/min, 180. C @ 40. min; T_start: 50. C
Capillary	DB-Wax	1888.	Jiang, Kojima, et al., 2001	He, 60. C @ 4. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; T_end: 220. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	CP-Wax 52 CB	1857.	Genisheva and Oliveira, 2009	50. m/0.25 mm/0.20 μm, Helium; Program: 60 0C (5 min) 3 0C/min -> 250 0C (20 min) 1 0C/min -> 255 0C
Capillary	HP-Innowax	1875.	Viljoen, van Vuuren, et al., 2003	60. m/0.25 mm/0.25 μm; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
Capillary	DB-Wax	1840.	Schneider, Razungles, et al., 2001	30. m/0.25 mm/0.5 μm, He; Program: 30C => 70C/min => 60C (3min) => 3C/min => 245C (20min)

References

Go To: Top, Gas Chromatography, Notes

Politeo, Jukic, et al., 2007
Politeo, O.; Jukic, M.; Milos, M., Chemical Composition and Antioxidant Activity of Free Volatile Aglycones from Laurel (Laurus nobilis L.) Compared to Its Essential Oil, Croatica Chem. Acta, 2007, 80, 1, 121-126. [all data]

Lalel, Singh, et al., 2003
Lalel, H.J.D.; Singh, Z.; Chye Tan, S., Glycosidically-bound aroma volatile compounds in the skin and pulp of 'Kensington Pride' mango fruit at different stages of maturity, Postharvest Biol. Technol., 2003, 29, 2, 205-218, https://doi.org/10.1016/S0925-5214(02)00250-8 . [all data]

Varming, Andersen, et al., 2006
Varming, C.; Andersen, M.L.; Poll, L., Volatile Monoterpenes in Black Currant (Ribes nigrum L.) Juice: Effects of Heating and Enzymatic Treatment by β-Glucosidase, J. Agric. Food Chem., 2006, 54, 6, 2298-2302, https://doi.org/10.1021/jf051938k . [all data]

Shimoda, Wu, et al., 1996
Shimoda, M.; Wu, Y.; Osajima, Y., Aroma compounds from aqueous solution of Haze (Rhus succedanea) honey determined by adsorptive column chromatography, J. Agric. Food Chem., 1996, 44, 12, 3913-3918, https://doi.org/10.1021/jf9601168 . [all data]

Suárez, Duque, et al., 1991
Suárez, M.; Duque, C.; Wintoch, H.; Schreier, P., Glycosidically bound aroma compounds from the pulp and the peelings of lulo fruit (Solanum vestissimum D.), J. Agric. Food Chem., 1991, 39, 9, 1643-1645, https://doi.org/10.1021/jf00009a022 . [all data]

Radulovic, Dordevic, et al., 2010
Radulovic, N.; Dordevic, N.; Markovic, M.; Palic, R., Volatile constituents of Glechoma Hirsuta Waldst. Kit. and G. Hederacea L. (Lamiaceae), Bull. Chem. Soc. Ethiop., 2010, 24, 1, 67-76, https://doi.org/10.4314/bcse.v24i1.52962 . [all data]

Setzer, Noletto, et al., 2006
Setzer, W.N.; Noletto, J.A.; Lawton, R.O., Chemical composition of the floral essential oil of Randia matudae from Monteverde, Costa Rica, Flavour Fragr. J., 2006, 21, 2, 244-246, https://doi.org/10.1002/ffj.1567 . [all data]

Setzer, Noletto, et al., 2005
Setzer, W.N.; Noletto, J.A.; Lawton, R.O.; Haber, W.A., Leaf essential oil composition of five Zanthoxylum species from Monteverde, Costa Rica, Molecular Diversity, 2005, 9, 1-3, 3-13, https://doi.org/10.1007/s11030-005-1298-6 . [all data]

Southwell, Russell, et al., 2003
Southwell, I.A.; Russell, M.F.; Maddox, C.D.A.; Wheeler, G.S., Differential metabolism of 1,8-cineole in insects, J. Chem. Ecol., 2003, 29, 1, 83-94, https://doi.org/10.1023/A:1021976513603 . [all data]

Cheriti, Saad, et al., 2007
Cheriti, A.; Saad, A.; Belboukhari, N.; Ghezali, S., The essential oil composition of Bubonium graveolens (Forssk.) Maire from the algerian Sahara, Flavour Fragr. J., 2007, 22, 4, 286-288, https://doi.org/10.1002/ffj.1794 . [all data]

Lan Phi N.T., Nishiyama C., et al., 2006
Lan Phi N.T.; Nishiyama C.; Choi H.-S.; Sawamura M., Evaluation of aroma characteristic compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil, Biosci. Biotechnol. Biochem., 2006, 70, 8, 1832-1838, https://doi.org/10.1271/bbb.50705 . [all data]

Lee, Umano, et al., 2005
Lee, S.-J.; Umano, K.; Shibamoto, T.; Lee, K.-G., Identification of volatile components in basil (Ocimum basilicum L.) and thyme leaves (Thymus vulgaris L.) and their antioxidant properties, Food Chem., 2005, 91, 1, 131-137, https://doi.org/10.1016/j.foodchem.2004.05.056 . [all data]

Jiang, Kojima, et al., 2001
Jiang, L.; Kojima, H.; Yamada, K.; Kobayashi, A.; Kubota, K., Isolation of some glycosides as aroma precursors in young leaves of Japanese pepper (Xanthoxylum piperitum DC.), J. Agric. Food Chem., 2001, 49, 12, 5888-5894, https://doi.org/10.1021/jf0104937 . [all data]

Genisheva and Oliveira, 2009
Genisheva, Z.; Oliveira, J.M., Monoterpenic characterization of white cultivars from Vinhos Verdes appelation of origin (North Portugal), J. Inst. Brewing, 2009, 115, 4, 308-317, https://doi.org/10.1002/j.2050-0416.2009.tb00386.x . [all data]

Viljoen, van Vuuren, et al., 2003
Viljoen, A.; van Vuuren, S.; Ernst, E.; Klepser, M.; Demirci, B.; Baser, H.; van Wyk, B.-E., Osmitopsis asteriscoides (Asteraceae)-the antimicrobial activity and essential oil composition of a Cape-Dutch remedy, J. Ethnopharmacol., 2003, 88, 2-3, 137-143, https://doi.org/10.1016/S0378-8741(03)00191-0 . [all data]

Schneider, Razungles, et al., 2001
Schneider, R.; Razungles, A.; Augier, C.; Baumes, R., Monoterpenic and norisoprenoidic glycoconjugates of Vitis vinifera L. cv. Melon B. as precursors of odorants in Muscadet wines, J. Chromatogr. A, 2001, 936, 1-2, 145-157, https://doi.org/10.1016/S0021-9673(01)01150-5 . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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