Bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde, 6,6-dimethyl-

Formula: C₁₀H₁₄O
Molecular weight: 150.2176
IUPAC Standard InChI: InChI=1S/C10H14O/c1-10(2)8-4-3-7(6-11)9(10)5-8/h3,6,8-9H,4-5H2,1-2H3
IUPAC Standard InChIKey: KMRMUZKLFIEVAO-UHFFFAOYSA-N
CAS Registry Number: 564-94-3
Chemical structure:
This structure is also available as a 2d Mol file
Species with the same structure:
- (1R)-(-)-Myrtenal
Stereoisomers:
- Bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde, 6,6-dimethyl-, (1S)-
Other names: 2-Norpinene-2-carboxaldehyde, 6,6-dimethyl-; Myrtenal; Benihinal; 6,6-Dimethylbicyclo(3.1.1)hept-2-ene-2-carboxaldehyde; 2-Formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene; 6,6-Dimethyl-bicyclo[3,1,1]hept-2-ene-2-carboxaldehyde; 6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde; (-)-Myrtenal; (+)-myrtenal; 6,6-dimethyl-bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde (myrtenal); cis-Myrtenal; pin-2-ene-1-carbaldehyde
Information on this page:
Other data available:
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Normal alkane RI, polar column, temperature ramp

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

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Supelcowax-10	RTX-Wax	CP-Wax 52CB	TC-FFAP	TC-FFAP
Column length (m)	30.	60.	60.
Carrier gas	Helium	Helium	He	He	He
Substrate
Column diameter (mm)	0.20	0.22	0.25	0.25	0.25
Phase thickness (μm)	0.20	0.25	0.25	0.25	0.25
T_start (C)	70.	60.	40.	60.	60.
T_end (C)	220.	230.	220.	220.	220.
Heat rate (K/min)	3.	2.	3.	3.	3.
Initial hold (min)
Final hold (min)	15.	30.		30.	30.
I	1620.	1612.	1644.	1638.	1636.
Reference	Neves, Rosa, et al., 2010	Museli, Pau, et al., 2009	Chyau, Tsai, et al., 2007	Kurose, Okamura, et al., 2007	Kurose, Okamura, et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Supelcowax-10	Supelcowax-10	BP-20	Supelcowax 10	CP-Wax 52CB
Column length (m)	30.	30.	50.	30.	30.
Carrier gas	He	He		Helium	He
Substrate
Column diameter (mm)	0.2	0.25	0.22	0.20	0.32
Phase thickness (μm)	0.2	0.25	0.25	0.20	0.25
T_start (C)	70.	40.	60.	70.	60.
T_end (C)	220.	250.	220.	220.	220.
Heat rate (K/min)	3.	3.	2.	3.	3.3
Initial hold (min)		5.			7.
Final hold (min)	15.	10.	20.	15.	3.
I	1623.	1602.	1626.	1622.	1627.
Reference	Pinto, Salgueiro, et al., 2007	Vichi, Riu-Aumatell, et al., 2007	Boti, Yao, et al., 2006	Cavaleiro, Pinto, et al., 2006	Hymete, Rohloff, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	NB-20M	CP-Wax	DB-Wax	Supelcowax-10	Supelcowax-10
Column length (m)	30.	30.	60.	30.	60.
Carrier gas	He	He	Nitrogen		He
Substrate
Column diameter (mm)	0.2	0.32	0.32	0.25	0.2
Phase thickness (μm)	0.25	0.25	0.50	0.25	0.2
T_start (C)	50.	40.	35.	40.	60.
T_end (C)	250.	180.	235.	220.	200.
Heat rate (K/min)	2.	5.	2.	3.	4.
Initial hold (min)		2.	4.	5.
Final hold (min)			30.	10.	40.
I	1635.	1597.	1665.	1602.	1601.
Reference	Orav, Raal, et al., 2006	Ka, Choi, et al., 2005	Qian and Wang, 2005	Vichi, Riu-Aumatell, et al., 2005	Gauvin, Ravaomanarivo, et al., 2004
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Innowax FSC	Supelcowax-10	DB-Wax	Supelcowax-10	Innowax
Column length (m)	60.	50.	60.	50.	60.
Carrier gas	Helium	He	Helium	He	He
Substrate
Column diameter (mm)	0.25	0.2	0.25	0.2	0.25
Phase thickness (μm)		0.25		0.25
T_start (C)	60.	70.	70.	70.	60.
T_end (C)	220.	230.	210.	230.	220.
Heat rate (K/min)	4.	2.	2.	2.	4.
Initial hold (min)	10.				10.
Final hold (min)			60.		10.
I	1648.	1630.	1630.	1617.	1648.
Reference	Lourens, Reddy, et al., 2004	Orav, Stulova, et al., 2004	Mookdasanit, Tamura, et al., 2003	Orav, Kailas, et al., 2003	Suleimenov, Atazharova, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Carbowax 20M	Innowax	DB-Wax	DB-Wax	HP Innowax FSP
Column length (m)	50.	60.	60.	60.	60.
Carrier gas	He	He		He	He
Substrate
Column diameter (mm)	0.22	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	30.	40.	60.
T_end (C)	220.	220.	170.	200.	220.
Heat rate (K/min)	2.	4.	2.	2.
Initial hold (min)		10.	4.	2.	10.
Final hold (min)		10.	30.		10.
I	1646.	1648.	1626.	1621.	1648.
Reference	Vernin, Lageot, et al., 2001	Baser, Özek, et al., 2000	Buttery, Light, et al., 2000	Umano, Hagi, et al., 2000	Kaya, Baser, et al., 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Innowax	HP-Innowax	HP-Innowax	BP-20	DB-Wax
Column length (m)	60.	60.	60.	25.	30.
Carrier gas	He	He	He	H2	N2
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.33	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.5	0.25
T_start (C)	60.	60.	60.	80.	45.
T_end (C)	220.	220.	220.	220.	220.
Heat rate (K/min)				5.	3.
Initial hold (min)	10.	10.	10.
Final hold (min)
I	1648.	1648.	1648.	1647.	1642.
Reference	Kaya, Baser, et al., 1999, 2	Kaya, Baser, et al., 1999, 3	Kaya, Baser, et al., 1999, 3	Bignell, Dunlop, et al., 1998	Mölleken, Sinnwell, et al., 1998
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-20	BP-20	BP-20	BP-20	BP-20
Column length (m)	25.	25.	25.	25.	25.
Carrier gas	H2	H2	H2	H2
Substrate
Column diameter (mm)	0.33	0.33	0.33	0.33	0.33
Phase thickness (μm)	0.5	0.5	0.5	0.5	0.5
T_start (C)	80.	80.	80.	80.	80.
T_end (C)	220.	220.	220.	220.	220.
Heat rate (K/min)	5.	5.	5.	5.	5.
Initial hold (min)
Final hold (min)
I	1647.	1647.	1647.	1647.	1647.
Reference	Bignell, Dunlop, et al., 1997	Bignell, Dunlop, et al., 1997, 2	Bignell, Dunlop, et al., 1997, 3	Bignell, Dunlop, et al., 1997, 4	Bignell, Dunlop, et al., 1997, 5
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary
Active phase	BP-20	Carbowax 20M	DB-Wax
Column length (m)	25.	45.	60.
Carrier gas	H2	Hydrogen
Substrate
Column diameter (mm)	0.33	0.32	0.32
Phase thickness (μm)	0.5	1.0
T_start (C)	80.	60.	50.
T_end (C)	220.	200.	230.
Heat rate (K/min)	5.	2.	4.
Initial hold (min)		5.	0.1
Final hold (min)			10.
I	1647.	1603.	1622.
Reference	Bignell, Dunlop, et al., 1997, 6	Kollmannsberger, Nitz, et al., 1992	Binder, Flath, et al., 1989
Comment	MSDC-RI	MSDC-RI	MSDC-RI

References

Go To: Top, Normal alkane RI, polar column, temperature ramp, Notes

Neves, Rosa, et al., 2010
Neves, A.; Rosa, S.; Goncalves, J.; Rufino, A.; Judas, F.; Salgueiro, L.; Lopes, M.C.; Cavaleiro, C.; Mendes, A.F., Screening of five essential oils for identification of potential inhibitors of IL-1-unduced Nf-kB activation and NO production in human clondrocytes: characterization of the inhibitory activity of alpha-pinene, Plante Med., 2010, 76, 03, 303-308, https://doi.org/10.1055/s-0029-1186085 . [all data]

Museli, Pau, et al., 2009
Museli, A.; Pau, M.; Desjobert, J.-M.; Foddai, M.; Usai, M.; Costa, J., Volatile constituents of Achllea ligustica All. by HS-SPME/GC/GC-MS. Comparison with essential oils obtained by hydrodistillation from Corsica and Sardinia, Chromatographia, 2009, 69, 5/6, 575-585, https://doi.org/10.1365/s10337-008-0939-1 . [all data]

Chyau, Tsai, et al., 2007
Chyau, C.-C.; Tsai, S.-Y.; Yang, J.-H.; Weng, C.-C.; Han, C.-M.; Shih, C.-C.; Mau, J.-L., The essential oil of Glossogyne tenuifolia, Food Chem., 2007, 100, 2, 808-812, https://doi.org/10.1016/j.foodchem.2005.10.044 . [all data]

Kurose, Okamura, et al., 2007
Kurose, K.; Okamura, D.; Yatagai, M., Composition of the essential oils from the leaves of nine Pinus species and the cones of three of Pinus species, Flavour Fragr. J., 2007, 22, 1, 10-20, https://doi.org/10.1002/ffj.1609 . [all data]

Pinto, Salgueiro, et al., 2007
Pinto, E.; Salgueiro, L.R.; Cavaleiro, C.; Palmeira, A.; Goncalves, M.J., In vitro susceptibility of some species of yeasts and filamentous fungi to essential oils of Salvia of?cinalis, Ind. Crops Prod., 2007, 26, 2, 135-141, https://doi.org/10.1016/j.indcrop.2007.02.004 . [all data]

Vichi, Riu-Aumatell, et al., 2007
Vichi, S.; Riu-Aumatell, M.; Mora-Pons, M.; Guadayol, J.M.; Buxaderas, S.; López-Tamames, E., Analytical, Nutritional and Clinical Methods. HS-SPME coupled to GC/MS for quality control of Juniperus communis L. berries used for gin aromatization, Food Chem., 2007, 105, 4, 1748-1754, https://doi.org/10.1016/j.foodchem.2007.03.026 . [all data]

Boti, Yao, et al., 2006
Boti, J.B.; Yao, P.A.; Koukoua, G.; N'Guessan, T.Y.; Casanova, J., Components and chemical variability of Isolona campanulata Engler Diels leaf oil, Flavour Fragr. J., 2006, 21, 1, 166-170, https://doi.org/10.1002/ffj.1555 . [all data]

Cavaleiro, Pinto, et al., 2006
Cavaleiro, C.; Pinto, E.; Gonsales, M.J.; Salguero, L., Antifungal activity of Juniperus essential oils agains dermatophyte, Asrgillus and Candida strains, J. Appl. Microbiol., 2006, 100, 6, 1333-1338, https://doi.org/10.1111/j.1365-2672.2006.02862.x . [all data]

Hymete, Rohloff, et al., 2006
Hymete, A.; Rohloff, J.; Iversen, T.-H., Essential oil from seeds and husks of Aframomum corrorima from Ethiopia, Flavour Fragr. J., 2006, 21, 4, 642-644, https://doi.org/10.1002/ffj.1634 . [all data]

Orav, Raal, et al., 2006
Orav, A.; Raal, A.; Arak, E.; Müürisepp, M.; Kailas, T., Composition of the essential oil of Artemisia absinthium L. of different geographical origin, Proc. Est. Acad. Sci. Chem., 2006, 55, 3, 155-165. [all data]

Ka, Choi, et al., 2005
Ka, M.-H.; Choi, E.H.; Chun, H.-S.; Lee, K.-G., Antioxidative Activity of Volatile Extracts Isolated from Angelica tenuissimae Roots, Peppermint Leaves, Pine Needles, and Sweet Flag Leaves, J. Agric. Food Chem., 2005, 53, 10, 4124-4129, https://doi.org/10.1021/jf047932x . [all data]

Qian and Wang, 2005
Qian, M.C.; Wang, Y., Seasonal Variations of Volatile Composition and Odor Activity Value of Marion (Rubus spp. hyb) and Thornless Evergreen (R.laciniatus L.) Blackberries, J. Food. Sci., 2005, 70, 1, c13-c20, https://doi.org/10.1111/j.1365-2621.2005.tb09013.x . [all data]

Vichi, Riu-Aumatell, et al., 2005
Vichi, S.; Riu-Aumatell, M.; Mora-Pons, M.; Buxaderas, S.; Lopez-Tamames, E., Characterization of Volatiles in Different Dry Gins, J. Agric. Food Chem., 2005, 53, 26, 10154-10160, https://doi.org/10.1021/jf058121b . [all data]

Gauvin, Ravaomanarivo, et al., 2004
Gauvin, A.; Ravaomanarivo, H.; Smadja, J., Comparative analysis by gas chromatography?mass spectrometry of the essential oils from bark and leaves of Cedrelopsis grevei Baill, an aromatic and medicinal plant from Madagascar, J. Chromatogr. A, 2004, 1029, 1-2, 279-282, https://doi.org/10.1016/j.chroma.2003.12.012 . [all data]

Lourens, Reddy, et al., 2004
Lourens, A.C.U.; Reddy, D.; Baser, K.H.C.; Viljoen, A.M.; Van Vuuren, S.F., In vitro Biological Activity and Essential Oil Composition of Four Indigenous South Africal Helichrysum Species, J. Ethnopharmacol., 2004, 95, 2-3, 253-258, https://doi.org/10.1016/j.jep.2004.07.027 . [all data]

Orav, Stulova, et al., 2004
Orav, A.; Stulova, I.; Kailas, T.; Müürisepp, M., Effect of storage on the essential oil composition of piper nigrum L. fruits of different ripening states, J. Agric. Food Chem., 2004, 52, 9, 2582-2586, https://doi.org/10.1021/jf030635s . [all data]

Mookdasanit, Tamura, et al., 2003
Mookdasanit, J.; Tamura, H.; Yoshizawa T.; Tokunaga T.; Nakanishi, K., Trace Volatile Compounds in Essential Oil of Citrus Sudachi by Means of Modified Solvent Extraction Method, Food Sci Technol. Res., 2003, 9, 1, 54-61, https://doi.org/10.3136/fstr.9.54 . [all data]

Orav, Kailas, et al., 2003
Orav, A.; Kailas, T.; Jegorova, A., Composition of the essential oil of dill, celery, and parsley from Estonia, Proc. Est. Acad. Sci. Chem., 2003, 52, 4, 147-154. [all data]

Suleimenov, Atazharova, et al., 2003
Suleimenov, E.M.; Atazharova, G.A.; Demirchi, B.; Baser, K.H.C.; Adekenov, S.M., Essential oil composition of Artemisia Lercheana and A. Sieversiana of Kazakhstan flora in Recent problems of development of new medicines of natural origin, Proceedings of symposium, St.Petersburg - Pushkin, 2003, 382-385. [all data]

Vernin, Lageot, et al., 2001
Vernin, G.; Lageot, C.; Gaydou, E.M.; Parkanyi, C., Analysis of the essential oil of Lippia graveolens HBK from El Salvador, Flavour Fragr. J., 2001, 16, 3, 219-226, https://doi.org/10.1002/ffj.984 . [all data]

Baser, Özek, et al., 2000
Baser, K.H.C.; Özek, T.; Demirci, B.; Kürkcüoglu, M.; Aytac, Z.; Duman, H., Composition of the essential oils of Zosima absinthifolia (Vent.) Link and Ferula elaeochytris Korovin from Turkey, Flavour Fragr. J., 2000, 15, 6, 371-372, https://doi.org/10.1002/1099-1026(200011/12)15:6<371::AID-FFJ919>3.0.CO;2-Z . [all data]

Buttery, Light, et al., 2000
Buttery, R.G.; Light, D.M.; Nam, Y.; Merrill, G.B.; Roitman, J.N., Volatile components of green walnut husks, J. Agric. Food Chem., 2000, 48, 7, 2858-2861, https://doi.org/10.1021/jf000288b . [all data]

Umano, Hagi, et al., 2000
Umano, K.; Hagi, Y.; Nakahara, K.; Shoji, A.; Shibamoto, T., Volatile chemicals identified in extracts from leaves of Japanese mugwort (Artemisia princeps Pamp.), J. Agric. Food Chem., 2000, 48, 8, 3463-3469, https://doi.org/10.1021/jf0001738 . [all data]

Kaya, Baser, et al., 1999
Kaya, A.; Baser, K.H.C.; Koca, F., Essential oils of Acinos troodi (Post) Leblebici subsp. vardaranus Leblebici and subsp. grandiflorus Hartvig Strid, Flavour Fragr. J., 1999, 14, 1, 50-54, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<50::AID-FFJ783>3.0.CO;2-7 . [all data]

Kaya, Baser, et al., 1999, 2
Kaya, A.; Baser, K.H.C.; Demirci, B.; Koca, F., The essential oil of Acinos alpinus (L.) Moench growing in Turkey, Flavour Fragr. J., 1999, 14, 1, 55-59, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<55::AID-FFJ784>3.0.CO;2-Q . [all data]

Kaya, Baser, et al., 1999, 3
Kaya, A.; Baser, K.H.C.; Tümen, G.; Koca, F., The essential oil of Acinos suaveolens (Sm.) G. Don fil. Acinos arvensis (Lam.) Dandy and Acinos rotundifolius Pers. growing wild in Turkey, Flavour Fragr. J., 1999, 14, 1, 60-64, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<60::AID-FFJ785>3.0.CO;2-0 . [all data]

Bignell, Dunlop, et al., 1998
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series 1). Part XIX, Flavour Fragr. J., 1998, 13, 2, 131-139, https://doi.org/10.1002/(SICI)1099-1026(199803/04)13:2<131::AID-FFJ710>3.0.CO;2-X . [all data]

Mölleken, Sinnwell, et al., 1998
Mölleken, U.; Sinnwell, V.; Kubeczka, K.-H., Essential oil composition of Smyrnium olusatrum, Phytochemistry, 1998, 49, 6, 1709-1714, https://doi.org/10.1016/S0031-9422(98)00195-2 . [all data]

Bignell, Dunlop, et al., 1997
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J.; Fookes, C.J.R., Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series I). Part XIV: Subgenus Monocalyptus, Flavour Fragr. J., 1997, 12, 3, 177-183, https://doi.org/10.1002/(SICI)1099-1026(199705)12:3<177::AID-FFJ626>3.0.CO;2-9 . [all data]

Bignell, Dunlop, et al., 1997, 2
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series I). Part XV: Subgenus symphyomyrtus, section bisectaria, series levispermae, Flavour Fragr. J., 1997, 12, 3, 185-193, https://doi.org/10.1002/(SICI)1099-1026(199705)12:3<185::AID-FFJ627>3.0.CO;2-B . [all data]

Bignell, Dunlop, et al., 1997, 3
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series I). Part XVI: Subgenus symphyomyrtus, section bisectaria, series cneorifoliae, series porantherae and series falcatae, Flavour Fragr. J., 1997, 12, 261-267. [all data]

Bignell, Dunlop, et al., 1997, 4
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series I). Part XVII: Subgenus symphyomyrtus (i) section bisectaria, series calycogonae and (ii) section dumaria, series dumosae, series rigentes and series ovulares, Flavour Fragr. J., 1997, 12, 269-275. [all data]

Bignell, Dunlop, et al., 1997, 5
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some Queensland and Norther Australian species of the genus Eucalyptus (Series II) Part II. Subgenera (a) Blakella, (b) Corymbia, (c) Unnamed, (d) Idiogenes, (e) Monocalyptus and (f) Symphyomyrtus, Flavour Fragr. J., 1997, 12, 4, 277-284, https://doi.org/10.1002/(SICI)1099-1026(199707)12:4<277::AID-FFJ642>3.0.CO;2-B . [all data]

Bignell, Dunlop, et al., 1997, 6
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some south-western and southern Australian speices of the genus Eucalyptus (Series I). Part XVIII. A. Subgenus monocalyptus. B. Subgenus Symphyomyrtus: (i) section Guilfoyleanae; (ii) section bisectaria, series accedentes, series occidentales, series levispermae, series loxophlebae, series macrocarpae, series orbifoliae, series calycogonae; (iii) section dumaria, series incrassatae and series ovulares, Flavour Fragr. J., 1997, 12, 423-432. [all data]

Kollmannsberger, Nitz, et al., 1992
Kollmannsberger, H.; Nitz, S.; Drawert, F., UBer die Aromastoffzusammensetzung von Hochdruckextrakten. I. Pfeffer (Piper nigrum, Var. muntok), Z. Lebensm. Unters Forsch., 1992, 194, 6, 545-551, https://doi.org/10.1007/BF01185481 . [all data]

Binder, Flath, et al., 1989
Binder, R.G.; Flath, R.A.; Mon, T.R., Volatile components of bittermelon, J. Agric. Food Chem., 1989, 37, 2, 418-420, https://doi.org/10.1021/jf00086a032 . [all data]

Notes

Go To: Top, Normal alkane RI, polar column, temperature ramp, References

Symbols used in this document:

T_end Final temperature

T_start Initial temperature
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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