trans-Linalool oxide (furanoid)

Formula: C₁₀H₁₈O₂
Molecular weight: 170.2487
IUPAC Standard InChI: InChI=1S/C10H18O2/c1-5-10(4)7-6-8(12-10)9(2,3)11/h5,8,11H,1,6-7H2,2-4H3/t8-,10+/m1/s1
IUPAC Standard InChIKey: BRHDDEIRQPDPMG-SCZZXKLOSA-N
CAS Registry Number: 34995-77-2
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Species with the same structure:
Stereoisomers:
Other names: 2-Furanmethanol, 5-ethenyltetrahydro-α,α,5-trimethyl-, trans-; trans-5-Ethenyltetrahydro-α,α,5-trimethyl-2-furanmethanol; 2-(5-Methyl-5-vinyltetrahydro-2-furanyl)-2-propanol, trans-; (E)-Furan linalool oxide; E-Furanoid linalool oxide; (E)-Linalool furanoxide; (E)-Linalool oxide A; E-Linalool oxide (furan); (E)-Linalool oxide, furanoid; Linalool oxide A (trans-THF); Linalool oxide II (trans, furanoid); Linalool oxide, trans-furanoid; Linalool oxide (trans-THF); t-Furan linalool oxide; trans-Furanic linalool oxid; trans-Furanic linalool oxide; trans-Furan linalool oxide; trans-Linalool furanoid oxide; trans-Linalool furanoxide; trans-Linalool oxide; trans-Linalool oxide (f); trans-Linalool oxide furan; trans-Linalool oxide (furanoid form); trans-Linalool oxide (furan type); trans-Linalool oxide (furanyl ring); trans-Linalool oxide (THF); 2-Furanmethanol, 5-ethenyltetrahydro-α,α,5-trimethyl-, (2R,5R)-rel-; Linalool A oxide; Linalool oxide 2; Linalool oxide A; Linalool oxide II; trans-2-Methyl-2-vinyl-5-(1-hydroxy-1-methylethyl)tetrahydrofuran; trans-2-Vinyl-2-methyl-5-(1-hydroxy-1-methylethyl)tetrahydrofuran; trans-f-Linalool oxide; trans-Furanoid linalool oxide; trans-Linalool 3,6-oxide; Linalool oxide, trans; trans-α,α,5-Trimethyl-5-vinyltetrahydrofurfuryl alcohol; 2-((2R,5R)-5-Methyl-5-vinyltetrahydrofuran-2-yl)propan-2-ol; (E)-Linalool oxide; trans-Linalol oxide (furanoid); trans-Linalol oxide; (E)-Linalol furanoxide; trans-Linalol oxide (f); trans-Linalol oxide fur.; t-Linalool oxide; (E)-Linalol oxide (furanoid); linalool oxide furanoside I; (E)-linalol oxide; trans-5-Trimethyl-2-furanmethanol; Trans linalol furanoxide; linalool oxide A (2-methyl-2-vinyl- 5-(2-hydroxy -2-propyl)-tetrahydrofuran; Linalool oxide 1; tetrahydro-α,α,5-trimethyl-5-vinylfuran-2-methanol
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Other data available:
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Normal alkane RI, polar column, custom temperature program

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

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-Wax	Supelcowax 10	DB-Wax Etr	HP-Innowax	BP-20
Column length (m)	30.	50.	60.	30.	30.
Carrier gas	Helium	Helium	He	Helium	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.5	0.25	0.25
Program	not specified	45 0C (15 min) 3 0C/min -> 75 0C 5 0C/min -> 180 0C (10 min)	40C(3min) => 10C/min => 90C => 2C/min => 230C (37min)	30 0C (5 min) 5 0C/min -> 100 0C (5 min) 1 0C/min -> 130 0C 10 0C/min -> 195 0C (45 min)	50C(1min) => 2.5C/min => 100C => 2C/min => 180C => 15C/min => 220C
I	1463.	1477.	1476.	1424.	1439.
Reference	Zhao, Xu, et al., 2009	Soria, Martinez-Castro, et al., 2008	Loskos, Hernandez-Orte, et al., 2007	Narain, Galvao, et al., 2007	Pontes, Marques, et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-20	DB-Wax	Innowax FSC	HP-Innowax FSC	Carbowax 20M
Column length (m)	30.	30.	60.	60.
Carrier gas	He	Hydrogen	N2	N2
Substrate
Column diameter (mm)	0.25	0.32	0.25	0.25
Phase thickness (μm)	0.25	0.50	0.25	0.25
Program	50C(1min) => 2.5C/min => 100C => 2C/min => 180C => 15C/min => 220C	60 0C (3 min) 2 0C/min -> 220 0C 3 0C/min -> 245 0C (20 min)	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C => (10min) => 1C/min => 240C	not specified
I	1439.	1474.	1450.	1450.	1450.
Reference	Pontes, Marques, et al., 2007	Selli, 2007	Iscan, Kirimer, et al., 2006	Tabanca, Demirci, et al., 2006	Editorial paper, 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Carbowax 20M	Innowax FSC	HP-Innowax FSC	HP-Innowax FSC	HP-Innowax FSC
Column length (m)		60.	60.	60.	60.
Carrier gas		He	He	N2	He
Substrate
Column diameter (mm)		0.25	0.25	0.25	0.25
Phase thickness (μm)		0.25	0.25	0.25	0.25
Program	not specified	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
I	1451.	1450.	1450.	1450.	1450.
Reference	Editorial paper, 2005	Kosar, Özek, et al., 2005	Viljoen, Subramoney, et al., 2005	Demirci, Paper, et al., 2004	Kivcak, Akay, et al., 2004
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Carbowax 20M	Innowax FSC	HP-Innowax FSC	HP-Innowax	HP Innowax FSP
Column length (m)		60.	60.	30.	60.
Carrier gas		He	He	He	He
Substrate
Column diameter (mm)		0.25	0.25	0.32	0.25
Phase thickness (μm)		0.25	0.25	0.5	0.25
Program	not specified	60C(10min) => 4C/min => 220C (10min) => 1C/min => 240C	60C (10min) => 4C/min => 220C (10min) => 1C/min => 240C	50C(4min) => 10C/min => 230C(10min) => 10C/min => 250C	60C(10min) => 4C/min => 220C (10min) => 1C/min => 240C
I	1455.	1450.	1450.	1478.	1450.
Reference	Vinogradov, 2004	Baser, Demirci, et al., 2003	Demirci, Baser, et al., 2003	Piasenzotto, Gracco, et al., 2003	Tasdemir, Demirci, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP Innowax FSP	HP-Innowax	HP-Innowax	HP-Innowax	HP-Innowax FSC
Column length (m)	60.	60.	60.	60.	60.
Carrier gas	He		He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
Program	60C(10min) => 4C/min => 220C (10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60 0C (10 min) 4 K/min -> 220 0C (10 min) 1 K/min -> 240 0C	60 0C (10 min) 10 K/min -> 220 0C (10 min) 1K/min -> 240 0C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
I	1450.	1450.	1450.	1450.	1450.
Reference	Tasdemir, Demirci, et al., 2003	Viljoen, van Vuuren, et al., 2003	Baser, Demirci, et al., 2002	Baser, Demirci, et al., 2001	Kaya, Demirci, et al., 2001
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Innowax FSC	DB-Wax	HP-Innowax	HP-Innowax FSC	Innowax
Column length (m)	60.	30.	60.	60.	60.
Carrier gas	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.5	0.25	0.25	0.25
Program	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	30C => 70C/min => 60C (3min) => 3C/min => 245C (20min)	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C(20min)	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
I	1450.	1445.	1450.	1452.	1452.
Reference	Saglam, Gozler, et al., 2001	Schneider, Razungles, et al., 2001	Tabanca, Kirimer, et al., 2001	Kamariah, Lim, et al., 1999	Baser, Kürkcüoglu, et al., 1998
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Carbowax 20M	DB-Wax	DB-Wax	CP-Wax 52CB	CP-Wax 52 CB
Column length (m)		60.	60.	25.	30.
Carrier gas		N2	N2	H2	H2
Substrate
Column diameter (mm)				0.3	0.32
Phase thickness (μm)		0.25	0.25	1.2
Program	not specified	not specified	not specified	60C(3min) => 2C/min => 220C => 3C/min => 245C	60 0C 2 0C/min -> 220 0C 3 0C/min -> 245 0C
I	1458.	1447.	1438.	1449.	1449.
Reference	Vernin, Lageot, et al., 1998	Weyerstahl, Marschall, et al., 1998	Weyerstahl, Marschall, et al., 1998, 2	López-Tamames, Carro-Mariño, et al., 1997	Carro Marino, López Tamames, et al., 1995
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary
Active phase	Polyethylene Glycol
Column length (m)
Carrier gas
Substrate
Column diameter (mm)
Phase thickness (μm)
Program	not specified
I	1451.
Reference	MacLeod and Pieris, 1981
Comment	MSDC-RI

References

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

Zhao, Xu, et al., 2009
Zhao, Y.; Xu, Y.; Li, J.; Fan, W.; Jiang, W., Profile of volatile compounds in 11 brandies by headspace solid-phase microextraction followed by gas chromatography-mass spectrometry, J. Food. Sci., 2009, 74, 2, c90-c99, https://doi.org/10.1111/j.1750-3841.2008.01029.x . [all data]

Soria, Martinez-Castro, et al., 2008
Soria, A.C.; Martinez-Castro, I.; Sanz, J., Some aspects of dynamic headspace analysis of volatile components in honey, Foog Res. International, 2008, 41, 8, 838-848, https://doi.org/10.1016/j.foodres.2008.07.010 . [all data]

Loskos, Hernandez-Orte, et al., 2007
Loskos, N.; Hernandez-Orte, P.; Cacho, J.; Ferreira, V., Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions, J. Agric. Food Chem., 2007, 55, 16, 6674-6684, https://doi.org/10.1021/jf0702343 . [all data]

Narain, Galvao, et al., 2007
Narain, N.; Galvao, M. deS.; Ferreira, D.DaS.; Navarro, D.M.A.F., Flavor biogeneration in Mangaba (Hancornia speciosa Gomes) fruit, BioEng. Campinas, 2007, 1, 1, 25-31. [all data]

Pontes, Marques, et al., 2007
Pontes, M.; Marques, J.C.; Camara, J.S., Screening of volatile composition from Portuguese multifloral honeys using headspace solid-phase microextraction-gas chromatography-quadrupole mass spectrometry, Talanta, 2007, 74, 1, 91-103, https://doi.org/10.1016/j.talanta.2007.05.037 . [all data]

Selli, 2007
Selli, S., Volatile constituents of orange obtained from moro oranges (Citrus Sinensis L. Osbeck), J. Food Quality, 2007, 30, 3, 330-341, https://doi.org/10.1111/j.1745-4557.2007.00124.x . [all data]

Iscan, Kirimer, et al., 2006
Iscan, G.; Kirimer, N.; Kurkcuoglu, M.; Arabaci, T.; Kupeli, E.; Baser, K.H.C., Biological Activity and Composition of the Essential Oils of Achillea schischkinii Sosn. and Achillea aleppica DC. subsp. aleppica, J. Agric. Food Chem., 2006, 54, 1, 170-173, https://doi.org/10.1021/jf051644z . [all data]

Tabanca, Demirci, et al., 2006
Tabanca, N.; Demirci, B.; Can Baser, K.H.; Aytac, Z.; Ekici, M.; Khan, S.I.; Jacob, M.R.; Wedge, D.E., Chemical Composition and Antifungal Activity of Salvia macrochlamys and Salvia recognita Essential Oils, J. Agric. Food Chem., 2006, 54, 18, 6593-6597, https://doi.org/10.1021/jf0608773 . [all data]

Editorial paper, 2005
Editorial paper, Solid Phase Microextraction (SPME) Application Guide, The Reporter Europe (Supelco), 2005, 16, 5, 12-12. [all data]

Kosar, Özek, et al., 2005
Kosar, M.; Özek, T.; Göger, F.; Kürkcüoglu, M.; Hüsnü Can Baser, K., Comparison of Microwave-Assisted Hydrodistillation and Hydrodistillation Methods for the Analysis of Volatile Secondary Metabolites, Pharm. Biol., 2005, 43, 6, 491-495, https://doi.org/10.1080/13880200500220136 . [all data]

Viljoen, Subramoney, et al., 2005
Viljoen, A.M.; Subramoney, S.; van Vuuren, S.F.; Baser, K.H.C.; Demirci, B., The composition, geographical variation and antimicrobial activity of Lippia javanica (Verbenaceae) leaf essential oils, J. Ethnopharmacol., 2005, 96, 1-2, 271-277, https://doi.org/10.1016/j.jep.2004.09.017 . [all data]

Demirci, Paper, et al., 2004
Demirci, F.; Paper, D.H.; Demirci, F.; Hüsnü Can Baser, K.; Franz, G., Essential oil of Betula pendula Roth. buds, eCAM, 2004, 1, 3, 301-303. [all data]

Kivcak, Akay, et al., 2004
Kivcak, B.; Akay, S.; Demirci, B.; Baser, K.H.C., Chemical composition of essential oils from leaves and twigs of Pistacia lentiscus, Pistacia lentiscus var. chia, and Pistacia terebinthus from Turkey, Pharm. Biol, 2004, 42, 4-5, 360-366, https://doi.org/10.1080/13880200490519677 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

Baser, Demirci, et al., 2003
Baser, K.H.C.; Demirci, B.; Dekebo, A.; Dagne, E., Essential oils of some Boswellia spp., myrrh and opopanax, Flavour Fragr. J., 2003, 18, 2, 153-156, https://doi.org/10.1002/ffj.1166 . [all data]

Demirci, Baser, et al., 2003
Demirci, B.; Baser, K.H.C.; Yildiz, B.; Bahcecioglu, Z., Composition of the essential oils of six endemic Salvia spp. from Turkey, Flavour Fragr. J., 2003, 18, 2, 116-121, https://doi.org/10.1002/ffj.1173 . [all data]

Piasenzotto, Gracco, et al., 2003
Piasenzotto, L.; Gracco, L.; Conte, L., Solid phase microextraction (SPME) applied to honey quality control, J. Sci. Food Agric., 2003, 83, 10, 1037-1044, https://doi.org/10.1002/jsfa.1502 . [all data]

Tasdemir, Demirci, et al., 2003
Tasdemir, D.; Demirci, B.; Demirci, F.; Dönmez, A.A.; Baser, K.H.C.; Rüedi, P., Analysis of the Volatile Components of Five Turkish Rhododendron Species by Headspace Solid-Phase Microextraction and GC-MS (HS-SPME-GC-MS), Z. Naturforsch., 2003, 58c, 797-803. [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]

Baser, Demirci, et al., 2002
Baser, K.H.C.; Demirci, B.; Kirimer, N.; Satil, F.; Tumen, G., The essential oils of Thymus migricus and T. fedtschenkoi var. handelii from Turkey, Flavour Fragr. J., 2002, 17, 1, 41-45, https://doi.org/10.1002/ffj.1036 . [all data]

Baser, Demirci, et al., 2001
Baser, K.H.C.; Demirci, B.; Tabanca, N.; Özek, T.; Gören, N., Composition of the essential oils of Tanacetum armenum (DC.) Schultz Bip., T. balsamita L., T. chiliophyllum (Fisch. Mey.) Schultz Bip. var. chiliophyllum and T. haradjani (Rech. fil.) Grierson and the enantiomeric distribution of camphor and carvone, Flavour Fragr. J., 2001, 16, 3, 195-200, https://doi.org/10.1002/ffj.977 . [all data]

Kaya, Demirci, et al., 2001
Kaya, A.; Demirci, B.; Baser, K.H.C., The composition of the essential oil of Stachys iberica subsp. stenostachya growing in Turkey, Chem. Nat. Compd. (Engl. Transl.), 2001, 37, 4, 326-328, https://doi.org/10.1023/A:1013762200024 . [all data]

Saglam, Gozler, et al., 2001
Saglam, H.; Gozler, T.; Kivcak, B.; Demirci, B.; Baser, K.H.C., Volatile compounds from Haplophyllum myrtifolium, Chem. Nat. Compd. (Engl. Transl.), 2001, 37, 5, 442-444, https://doi.org/10.1023/A:1014467225815 . [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]

Tabanca, Kirimer, et al., 2001
Tabanca, N.; Kirimer, N.; Demirci, B.; Demirci, F.; Can Baser, K.H., Composition and antimicrobial activity of the essential oils of Micromeria cristata subsp. phrygia and the enantiomeric distribution of borneol, J. Agric. Food Chem., 2001, 49, 9, 4300-4303, https://doi.org/10.1021/jf0105034 . [all data]

Kamariah, Lim, et al., 1999
Kamariah, A.S.; Lim, L.B.L.; Baser, K.H.C.; Ozek, T.; Demirci, B., Composition of the essential oil of Plumeria obtusa L., Flavour Fragr. J., 1999, 14, 4, 237-240, https://doi.org/10.1002/(SICI)1099-1026(199907/08)14:4<237::AID-FFJ817>3.0.CO;2-Y . [all data]

Baser, Kürkcüoglu, et al., 1998
Baser, K.H.C.; Kürkcüoglu, M.; Aytac, Z., Composition of the essential oil of Salvia euphratica Montbret ex Bentham var. euphratica from Turkey, Flavour Fragr. J., 1998, 13, 1, 63-64, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<63::AID-FFJ694>3.0.CO;2-Z . [all data]

Vernin, Lageot, et al., 1998
Vernin, G.; Lageot, C.; Parkanyi, C., GC-MS(EI, PCI, NCI, SIM, ITMS) Data Bank Analysis of Flavors and Fragrances. Kovats indices in Instrumental Methods on Food and Beverage Analysis, D. Wetzel, G. Charalambous, ed(s)., Elsevier Sci. B.V., Amsterdam, 1998, 245-301. [all data]

Weyerstahl, Marschall, et al., 1998
Weyerstahl, P.; Marschall, H.; Weirauch, M.; Thefeld, K.; Surburg, H., Constituents of commercial Labdanum oil, Flavour Fragr. J., 1998, 13, 5, 295-318, https://doi.org/10.1002/(SICI)1099-1026(1998090)13:5<295::AID-FFJ751>3.0.CO;2-I . [all data]

Weyerstahl, Marschall, et al., 1998, 2
Weyerstahl, P.; Marschall, H.; Thefeld, K.; Subba, G.C., Constituents of the essential oil from the rhizomes of Hedychium gardnerianum Roscoe, Flavour Fragr. J., 1998, 13, 6, 377-388, https://doi.org/10.1002/(SICI)1099-1026(199811/12)13:6<377::AID-FFJ755>3.0.CO;2-F . [all data]

López-Tamames, Carro-Mariño, et al., 1997
López-Tamames, E.; Carro-Mariño, N.; Gunata, Y.Z.; Sapis, C.; Baumes, R.; Bayonove, C., Potential aroma in several varieties of Spanish grapes, J. Agric. Food Chem., 1997, 45, 5, 1729-1735, https://doi.org/10.1021/jf960572w . [all data]

Carro Marino, López Tamames, et al., 1995
Carro Marino, N.; López Tamames, E.; García Jares, C.M., Contribution to the study of the aromatic potential of three muscat Vitis vinifera varieties: identification of new compounds, Food Sci. Technol. Int., 1995, 1, 2-3, 105-116, https://doi.org/10.1177/108201329500100206 . [all data]

MacLeod and Pieris, 1981
MacLeod, A.J.; Pieris, N.M., Volatile flavor components of beli fruit (Aegle marmelos) and a processed product, J. Agric. Food Chem., 1981, 29, 6, 1262-1264, https://doi.org/10.1021/jf00108a040 . [all data]

Notes

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

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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