Dihydroedulan I

Formula: C₁₃H₂₂O
Molecular weight: 194.3132
IUPAC Standard InChI: InChI=1S/C13H22O/c1-10-6-7-11-12(2,3)8-5-9-13(11,4)14-10/h5,9-11H,6-8H2,1-4H3/t10-,11+,13+/m1/s1
IUPAC Standard InChIKey: IVTQSEFLDHBCDZ-MDZLAQPJSA-N
CAS Registry Number: 63335-66-0
Chemical structure:
This structure is also available as a 2d Mol file
Stereoisomers:
Other names: Edulan I dihydro; [2α,4aα,8a,α]-2H-1-Benzopyran,3,4,4a,5,6,8a-hexahydro-2,5,5,8a-tetramethyl; Dihydroedulan I (trans)
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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-5	1290.	Vundac, Pfeifhofer, et al., 2006	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 4. K/min; T_end: 300. C
Capillary	HP-5MS	1293.6	Zhao, Liang, et al., 2005	30. m/0.25 mm/0.25 μm, He, 2. K/min; T_start: 80. C; T_end: 290. C
Capillary	HP-5MS	1297.8	Zhao, Liang, et al., 2005	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 80. C; T_end: 290. C
Capillary	HP-5MS	1300.3	Zhao, Liang, et al., 2005	30. m/0.25 mm/0.25 μm, He, 6. K/min; T_start: 80. C; T_end: 290. C
Capillary	HP-5MS	1289.	Grujic-Jovanovic, Skaltsa, et al., 2004	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; T_end: 280. C
Capillary	HP-5	1289.	Skaltsa, Demetzos, et al., 2003	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; T_end: 280. C
Capillary	SPB-5	1286.	Pino, Marbot, et al., 2002	30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min
Capillary	HP-5	1289.	Lazari, Skaltsa, et al., 2000	30. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 4. K/min; T_end: 280. C

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1280.	Ferhat, Tigrine-Kordjani, et al., 2007	30. m/0.25 mm/0.25 μm, He, 60. C @ 8. min, 2. K/min, 250. C @ 15. min
Capillary	HP-5	1287.	Figuérédo, Cabassu, et al., 2006	30. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 5. K/min, 300. C @ 5. min
Capillary	HP-5	1294.	Kucuk, Gulec, et al., 2006	30. m/0.32 mm/0.25 μm, Helium, 60. C @ 2. min, 5. K/min, 260. C @ 13. min
Capillary	HP-5 MS	1280.	Tigrine-Kordiani, Meklati, et al., 2006	30. m/0.25 mm/0.25 μm, Helium, 60. C @ 8. min, 2. K/min, 250. C @ 15. min
Capillary	HP-5	1287.	Figuérédo, Cabassu, et al., 2005	30. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 5. K/min, 300. C @ 5. min
Capillary	HP-5	1291.0	Leffingwell and Alford, 2005	60. m/0.32 mm/0.25 μm, He, 30. C @ 2. min, 2. K/min, 260. C @ 28. min
Capillary	DB-5	1273.	Morteza-Semnani, Akbarzadeh, et al., 2005	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; T_end: 220. C
Capillary	HP-5	1293.	Yayli, Yasar, et al., 2005	30. m/0.32 mm/0.25 μm, He, 60. C @ 2. min, 5. K/min, 260. C @ 13. min
Capillary	HP-5	1292.	Campeol, Flamini, et al., 2001	30. m/0.25 mm/0.25 μm, N2, 60. C @ 10. min, 5. K/min; T_end: 220. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5	1289.	Kucuk, Gulec, et al., 2006	30. m/0.32 mm/0.25 μm, Helium; Program: not specified

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Carbowax	1506.	Ferhat, Tigrine-Kordjani, et al., 2007	60. m/0.2 mm/0.25 μm, He, 60. C @ 8. min, 2. K/min, 250. C @ 15. min
Capillary	Carbowax-PEG	1506.	Tigrine-Kordiani, Meklati, et al., 2006	60. m/0.20 mm/0.25 μm, Helium, 60. C @ 8. min, 2. K/min, 250. C @ 15. min

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1529.	Canuti, Conversano, et al., 2009	30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (4 min) 2.5 0C/min -> 80 0C 5 0C/min -> 110 0C 10 0C/min -> 220 0C (5 min)
Capillary	DB-Wax	1506.	Canuti, Conversano, et al., 2009	30. m/0.25 mm/0.25 μm, Helium; Program: not specified

References

Go To: Top, Gas Chromatography, Notes

Vundac, Pfeifhofer, et al., 2006
Vundac, V.B.; Pfeifhofer, H.W.; Brantner, A.H.; Males, Z.; Plazibat, M., Essential oils of seven Stachys taxa from Croatia, Biochem. Syst. Ecol., 2006, 34, 12, 875-881, https://doi.org/10.1016/j.bse.2006.04.010 . [all data]

Zhao, Liang, et al., 2005
Zhao, C.-X.; Liang, Y.-Z.; Fang, H.-Z.; Li, X.-N., Temperature-programmed retention indices for gas chromatography-mass spectroscopy analysis of plant essential oils, J. Chromatogr. A, 2005, 1096, 1-2, 76-85, https://doi.org/10.1016/j.chroma.2005.09.067 . [all data]

Grujic-Jovanovic, Skaltsa, et al., 2004
Grujic-Jovanovic, S.; Skaltsa, H.D.; Marin, P.; Sokovic, M., Composition and antibacterial activity of the essential oil of six Stachys species from Serbia, Flavour Fragr. J., 2004, 19, 2, 139-144, https://doi.org/10.1002/ffj.1275 . [all data]

Skaltsa, Demetzos, et al., 2003
Skaltsa, H.D.; Demetzos, C.; Lazari, D.; Sokovic, M., Essential oil analysis and antimicrobial activity of eight Stachys species from Greece, Phytochemistry, 2003, 64, 3, 743-752, https://doi.org/10.1016/S0031-9422(03)00386-8 . [all data]

Pino, Marbot, et al., 2002
Pino, J.; Marbot, R.; Rosado, A., Volatile constituents of star apple (Chrysophyllum cainito L.) from Cuba, Flavour Fragr. J., 2002, 17, 5, 401-403, https://doi.org/10.1002/ffj.1116 . [all data]

Lazari, Skaltsa, et al., 2000
Lazari, D.M.; Skaltsa, H.D.; Constantinidis, T., Volatile constituents of Centaurea pelia DC., C. thessala Hausskn. subsp. drakiensis (Freyn Sint.) Georg. and C. zuccariniana DC. from Greece, Flavour Fragr. J., 2000, 15, 1, 7-11, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<7::AID-FFJ860>3.0.CO;2-3 . [all data]

Ferhat, Tigrine-Kordjani, et al., 2007
Ferhat, M.A.; Tigrine-Kordjani, N.; Chemat, S.; Meklati, B.Y.; Chemat, F., Rapid Extraction of Volatile Compounds Using a New Simultaneous Microwave Distillation: Solvent Extraction Device, Chromatographia, 2007, 65, 3-4, 217-222, https://doi.org/10.1365/s10337-006-0130-5 . [all data]

Figuérédo, Cabassu, et al., 2006
Figuérédo, G.; Cabassu, P.; Chalchat, J.-C.; Pasquier, B., Studies of Mediterranean oregano populations. VIII. Chemical composition of essential oils of oreganos of various origins, Flavour Fragr. J., 2006, 21, 1, 134-139, https://doi.org/10.1002/ffj.1543 . [all data]

Kucuk, Gulec, et al., 2006
Kucuk, M.; Gulec, C.; Yasar, A.; Ucuncu, O.; Yayh, N.; Coskuncelebi, K.; Terzioglu, S.; Yayh, N., Chemical composition and antimicrobial activities of the essential oils of Teucrium chamaedrys subsp. chamaedrys, T. orientale var. puberulens, and T. chamaedrys subsp. lydium, Pharm. Biol., 2006, 44, 8, 592-599, https://doi.org/10.1080/13880200600896868 . [all data]

Tigrine-Kordiani, Meklati, et al., 2006
Tigrine-Kordiani, N.; Meklati, B.Y.; Chemat, F., Abalysis by gas chromatography - mass spectrometry of the essential oil of Zygophyllum album L., an aromatic and medicinal plant growing in Algeria, Int. J. Aromatherapy, 2006, 16, 3-4, 187-191, https://doi.org/10.1016/j.ijat.2006.09.008 . [all data]

Figuérédo, Cabassu, et al., 2005
Figuérédo, G.; Cabassu, P.; Chalchat, J.-C.; Pasquier, B., Studies of Mediterranean oregano populations- V. Chemical composition of essential oils of oregano: Origanum syriacum L. var. bevanii (Holmes) Ietswaart, O. syriacum L. var. sinaicum (Boiss.) Ietswaart, and O. syriacum L. var. syriacum from Lebanon and Israel, Flavour Fragr. J., 2005, 20, 164-168. [all data]

Leffingwell and Alford, 2005
Leffingwell, J.C.; Alford, E.D., Volatile constituents of Perique tobacco, Electron. J. Environ. Agric. Food Chem., 2005, 4, 2, 899-915. [all data]

Morteza-Semnani, Akbarzadeh, et al., 2005
Morteza-Semnani, K.; Akbarzadeh, M.; Rostami, B., The essential oil composition of Teucrium chamaedrys L. from Iran, Flavour Fragr. J., 2005, 20, 5, 544-546, https://doi.org/10.1002/ffj.1479 . [all data]

Yayli, Yasar, et al., 2005
Yayli, N.; Yasar, A.; Gülec, C.; Usta, A.; Kolayli, S.; Coskuncelebi, K.; Karaoglu, S., Composition and antimicrobial activity of essential oils from Centaurea sessilis and Centaurea armena, Phytochemistry, 2005, 66, 14, 1741-1745, https://doi.org/10.1016/j.phytochem.2005.04.006 . [all data]

Campeol, Flamini, et al., 2001
Campeol, E.; Flamini, G.; Chericoni, S.; Catalano, S.; Cremonini, R., Volatile compounds from three cultivars of Olea europaea from Italy, J. Agric. Food Chem., 2001, 49, 11, 5409-5411, https://doi.org/10.1021/jf010455n . [all data]

Canuti, Conversano, et al., 2009
Canuti, V.; Conversano, M.; Li Calzi, M.; Heymann, H.; Matthews, M.A.; Ebeler, S.E., Headspace solid-phase microextraction - gas chromatography - mass spectrometry for profiling free volatile compounds in Cabernet Sauvignon grapes and vines, J. Chromatogr. A., 2009, 1216, 15, 3012-3022, https://doi.org/10.1016/j.chroma.2009.01.104 . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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