Wine lactone

Formula: C₁₀H₁₄O₂
Molecular weight: 166.2170
IUPAC Standard InChI: InChI=1S/C10H14O2/c1-6-3-4-8-7(2)10(11)12-9(8)5-6/h5,7-9H,3-4H2,1-2H3/t7-,8-,9-/m1/s1
IUPAC Standard InChIKey: NQWBFQXRASPNLB-IWSPIJDZSA-N
CAS Registry Number: 182699-77-0
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.
Stereoisomers:
Other names: wine lactone (3a,4,5,7a-Tetrahydro-3,6-dimethyl-2(3H)-benzofuranone); Wine lactone, (3S, 3aS, 7aR); 3,4,5,7a-tetrahydro-3,6-dimethyl-2(3 H)-benzofuranone (wine lactone); 3a,4,5,7a-Tetrahydro-3,6-dimethyl-2(3H)-benzofuranon (wine lactone)
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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	ZB-5	1459.	Ruiz Perez-Cacho, Mahattanatawee, et al., 2007	30. m/0.32 mm/0.5 μm, He, 7. K/min, 265. C @ 5. min; T_start: 40. C
Capillary	DB-5	1459.	Ruiz Perez-Cacho, Mahattanatawee, et al., 2007	30. m/0.32 mm/0.5 μm, 7. K/min, 265. C @ 5. min; T_start: 40. C
Capillary	ZB-5	1470.	Bell, 2004	30. m/0.32 mm/0.50 μm, Helium, 7. K/min, 265. C @ 5. min; T_start: 40. C
Capillary	DB-5	1467.	Högnadóttir and Rouseff, 2003	30. m/0.32 mm/0.5 μm, 7. K/min, 265. C @ 5. min; T_start: 40. C
Capillary	DB-1	1409.	Lin and Rouseff, 2001	30. m/0.32 mm/0.25 μm, 7. K/min, 240. C @ 5. min; T_start: 40. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	SE-54	1452.	Jagella and Grosch, 1999	30. m/0.32 mm/0.25 μm, He; Program: 35C(2min) => 40C/min => 65C => 6C/min => 250C
Capillary	SE-54	1456.	Hinterholzer and Schieberie, 1998	30. m/0.32 mm/0.25 μm, He; Program: 35C(2min) => 40C/min => 50C(2min) => 6C/min => 180C => 10C/min => 230C(10min)

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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	2259.	Bell, 2004	30. m/0.32 mm/0.50 μm, Helium, 7. K/min, 240. C @ 5. min; T_start: 40. C
Capillary	DB-Wax	2263.	Högnadóttir and Rouseff, 2003	30. m/0.32 mm/0.5 μm, 7. K/min, 240. C @ 5. min; T_start: 40. C
Capillary	DB-Wax	2264.	Lin and Rouseff, 2001	30. m/0.32 mm/0.50 μm, He, 7. K/min, 240. C @ 5. min; T_start: 40. C

Van Den Dool and Kratz RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	2243.	Elston, Lin, et al., 2005	Program: not specified
Capillary	FFAP	2215.	Jagella and Grosch, 1999	30. m/0.32 mm/0.25 μm, He; Program: 40C(1min) => 40C/min => 60C => 6C/min => 230C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	BP-5	1467.	Lopez, Ferreira, et al., 1999	50. m/0.32 mm/1. μm, He, 40. C @ 5. min, 2. K/min; T_end: 190. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	SE-54	1456.	Buettner, Mestres, et al., 2003	30. m/0.32 mm/0.25 μm; Program: 35C (2min) => 40C/min => 50C (2min) => 6C/min => 180C => 10C/min => 230C (10min)
Capillary	DB-5	1455.	Guth, 1997	30. m/0.32 mm/0.25 μm; Program: 35C (1min) => 40C/min => 60C (1min) => 6C/min => 250C (10min)
Capillary	DB-5	1455.	Guth, 1996	Column length: 20. m; Column diameter: 0.25 mm; Program: not specified

Normal alkane RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax Etr	2245.	Ibarz, Ferreira, et al., 2006	60. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 230. C @ 100. min
Capillary	Carbowax 20M	2223.	Lopez, Ferreira, et al., 1999	60. m/0.32 mm/0.5 μm, He, 40. C @ 5. min, 2. K/min; T_end: 190. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	FFAP	2203.	Buettner, Mestres, et al., 2003	30. m/0.32 mm/0.25 μm; Program: 35C (2min) => 40C/min => 60C (2min) => 6C/min => 180C => 10C/min => 230C (10min
Capillary	DB-FFAP	2192.	Guth, 1997	30. m/0.32 mm/0.25 μm; Program: 35C (1min) => 40C/min => 60C (1min) => 6C/min => 250C (10min)
Capillary	FFAP	2192.	Guth, 1996	Column length: 20. m; Column diameter: 0.25 mm; Program: not specified

References

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Ruiz Perez-Cacho, Mahattanatawee, et al., 2007
Ruiz Perez-Cacho, P.; Mahattanatawee, K.; Smoot, J.M.; Rouseff, R., Identification of Sulfur Volatiles in Canned Orange Juices Lacking Orange Flavor, J. Agric. Food Chem., 2007, 55, 14, 5761-5767, https://doi.org/10.1021/jf0703856 . [all data]

Bell, 2004
Bell, W.A.-M., Examination of Aroma Volatiles Formed from Thermal Processing of Florida Reconstituted Grapefruit Juice. A Thesis presented to the graduate school of the university of Florida in partial fulfillment of the requirements for the degree of master of science, 2004. [all data]

Högnadóttir and Rouseff, 2003
Högnadóttir, Á.; Rouseff, R.L., Identification of aroma active compounds in organce essence oil using gas chromatography-olfactometry and gas chromatography-mass spectrometry, J. Chromatogr. A, 2003, 998, 1-2, 201-211, https://doi.org/10.1016/S0021-9673(03)00524-7 . [all data]

Lin and Rouseff, 2001
Lin, J.; Rouseff, R.L., Characterization of aroma-impact compounds in cold-pressed grapefruit oil using time-intensity GC-olfactometry and GC-MS, Flavour Fragr. J., 2001, 16, 6, 457-463, https://doi.org/10.1002/ffj.1041 . [all data]

Jagella and Grosch, 1999
Jagella, T.; Grosch, W., Flavour and off-flavour compounds of black and white pepper ( Piper nigrum L.) I. Evaluation of potent odorants of black pepper by dilution and concentration techniques, Eur. Food Res. Technol., 1999, 209, 1, 16-21, https://doi.org/10.1007/s002170050449 . [all data]

Hinterholzer and Schieberie, 1998
Hinterholzer, A.; Schieberie, P., Identification of the most odour-active volatiles in fresh, hand-extracted juice of valencia late oranges by odour dilution techniques, Flavour Fragr. J., 1998, 13, 1, 49-55, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<49::AID-FFJ691>3.0.CO;2-S . [all data]

Elston, Lin, et al., 2005
Elston, A.; Lin, J.; Rouseff, R., Determination of the role of valencene in orange oil as a direct contributor to aroma quality, Flavour Fragr. J., 2005, 20, 4, 381-386, https://doi.org/10.1002/ffj.1578 . [all data]

Lopez, Ferreira, et al., 1999
Lopez, R.; Ferreira, V.; Hernandez, P.; Cacho, J.F., Identification of impact odorants of young red wines made with Merlot, Cabernet Sauvignon and Grenache grape varieties: a comparative study, J. Sci. Food Agric., 1999, 79, 11, 1461-1467, https://doi.org/10.1002/(SICI)1097-0010(199908)79:11<1461::AID-JSFA388>3.0.CO;2-K . [all data]

Buettner, Mestres, et al., 2003
Buettner, A.; Mestres, M.; Fischer, A.; Guasch, J.; Schieberle, P., Evaluation of the most odour-active compounds in the peel oil of clementines ( citrus reticulata blanco cv. clementine), Eur. Food Res. Technol., 2003, 216, 11-14. [all data]

Guth, 1997
Guth, H., Identification of character impact odorants of different white wine varieties, J. Agric. Food Chem., 1997, 45, 8, 3022-3026, https://doi.org/10.1021/jf9608433 . [all data]

Guth, 1996
Guth, H., 131. Determination of the configuration of wine lactone, Helv. Chim. Acta, 1996, 79, 6, 1559-1571, https://doi.org/10.1002/hlca.19960790606 . [all data]

Ibarz, Ferreira, et al., 2006
Ibarz, M.J.; Ferreira, V.; Hernández-Orte, P.; Loscos, N.; Cacho, J., Optimization and evaluation of a procedure for the gas chromatographic-mass spectrometric analysis of the aromas generated by fast acid hydrolysis of flavor precursors extracted from grapes, J. Chromatogr. A, 2006, 1116, 1-2, 217-229, https://doi.org/10.1016/j.chroma.2006.03.020 . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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