4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl-

• Formula: C₆H₈O₄
• Molecular weight: 144.1253
• IUPAC Standard InChI: InChI=1S/C6H8O4/c1-3-5(8)6(9)4(7)2-10-3/h4,7-8H,2H2,1H3 Copy

  
• IUPAC Standard InChIKey: VOLMSPGWNYJHQQ-UHFFFAOYSA-N Copy
• CAS Registry Number: 28564-83-2
• 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.
• Other names: 3,5-Dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one; 2,3-dihydro-3,5-dihydroxy--6-methyl-4H-pyran-4-one; Pyranone; 2,3-Dihydro-3,5-dihydroxy-6-methyl-4-pyrone; 3-Hydroxy-2,3-dihydromaltol; 3,5-Dihydroxy-6-methyl-2H-pyran-4(3H)-one; 3,5-Dihydroxy-2,3-dihydro-6-methyl-4-pyran-4-one, dihydroxy maltol; 2,3-dihydro-3,5-dihydroxy-6-methyl-4(4H)-pyranone; 2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (pyranone); 2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyrene-4-one
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
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Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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

Kovats' RI, polar column, temperature ramp

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

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

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

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

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Normal alkane RI, non-polar column, temperature ramp

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

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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References

Go To: Top, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Yeo and Shibamoto, 1991
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Baltes, W.; Mevissen, L., Model reactions on roast aroma formation. VI. Volatile reaction products from the reaction of phenylalanine with glucose during cooking and roasting, Z. Lebensm. Unters. Forsch., 1988, 187, 3, 209-214, https://doi.org/10.1007/BF01043341 . [all data]

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Xu, Han, et al., 2009
Xu, L.-L.; Han, T.; Wu, J.-Z.; Zhang, Q.-Y.; Zhang, H.; Huang, B.-K.; Rahman, K., Comparative research of chemical constituents, antifungal and antitumor properties of ether extracts of Panax ginseng and its endophytic fungus, Phytomedicine: Int. J. Phytotherapy Phytopharmacology, 2009, 16, 6-7, 609-616, https://doi.org/10.1016/j.phymed.2009.03.014 . [all data]

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Buttery, Orts, et al., 1999
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Chen and Ho, 1999
Chen, J.; Ho, C.-T., Comparison of volatile generation in serine/threonine/glutamine-ribose/glucose/fructose model systems, J. Agric. Food Chem., 1999, 47, 2, 643-647, https://doi.org/10.1021/jf980771a . [all data]

Boylston and Viniyard, 1998
Boylston, T.D.; Viniyard, B.T., Isolation of volatile flavor compounds from peanut butter using purge-and-trap technique in Instrumental Methods in Food and Beverage Analysis, D. Wetzel and G. Charalambous, ed(s)., 1998, 225-243. [all data]

Chen and Ho, 1998
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Ong, Acree, et al., 1998
Ong, P.K.C.; Acree, T.E.; Lavin, E.H., Characterization of volatiles in rambutan fruit (Nephelium lappaceum L.), J. Agric. Food Chem., 1998, 46, 2, 611-615, https://doi.org/10.1021/jf970665t . [all data]

Tai and Ho, 1998
Tai, C.-Y.; Ho, C.-T., Influence of glutathione oxidation and pH on thermal formation of Maillard-type volatile compounds, J. Agric. Food Chem., 1998, 46, 6, 2260-2265, https://doi.org/10.1021/jf971111t . [all data]

Buttery, Ling, et al., 1997
Buttery, R.G.; Ling, L.C.; Stern, D.J., Studies on popcorn aroma and flavor volatiles, J. Agric. Food Chem., 1997, 45, 3, 837-843, https://doi.org/10.1021/jf9604807 . [all data]

D'Arcy, Rintoul, et al., 1997
D'Arcy, B.R.; Rintoul, G.B.; Rowland, C.Y.; Blackman, A.J., Composition of Australian honey extractives. 1. Norisoprenoids, monoterpenes, and other natural volatiles from blue gum (Eucalyptus leucoxylon) and yellow box (Eucalyptus melliodora) honeys, J. Agric. Food Chem., 1997, 45, 5, 1834-1843, https://doi.org/10.1021/jf960625+ . [all data]

Yu and Ho, 1995
Yu, T.-H.; Ho, C.-T., Volatile compounds generated from thermal reaction of methionine and methionine sulfoxide with or without glucose, J. Agric. Food Chem., 1995, 43, 6, 1641-1646, https://doi.org/10.1021/jf00054a043 . [all data]

Nishibori and Bernhard, 1993
Nishibori, S.; Bernhard, R.A., Model system for cookies: Volatile components formed from the reaction of sugar and β-alanine, J. Agric. Food Chem., 1993, 41, 12, 2374-2377, https://doi.org/10.1021/jf00036a030 . [all data]

Alissandrakis, Kibaris, et al., 2005
Alissandrakis, E.; Kibaris, A.C.; Tarantilis, P.A.; Harizanis, P.C.; Polissiou, M., Flavour compounds of Greek cotton honey, J. Sci. Food Agric., 2005, 85, 9, 1444-1452, https://doi.org/10.1002/jsfa.2124 . [all data]

Teai, Claude-Lafontaine, et al., 2001
Teai, T.; Claude-Lafontaine, A.; Schippa, C.; Cozzolino, F., Volatile compounds in fresh pulp of pineapple (Ananas comosus [L.] Merr.) from French Polynesia, J. Essent. Oil Res., 2001, 13, 5, 314-318, https://doi.org/10.1080/10412905.2001.9712222 . [all data]

Wanakhachornkrai and Lertsiri, 9999
Wanakhachornkrai, P.; Lertsiri, S., Comparison of determination method for volatile compounds in Thai soy sauce, Analytical, Nutritional and Clinical Methods, 9999, 1-11. [all data]

Prososki, Etzel, et al., 2007
Prososki, R.A.; Etzel, M.R.; Rankin, S.A., Solvent type affects the number, distribution, and relative quantities of volatile compounds found in sweet whey powder, J. Dairy Sci., 2007, 90, 2, 523-531, https://doi.org/10.3168/jds.S0022-0302(07)71535-7 . [all data]

Osada and Shibamoto, 2006
Osada, Y.; Shibamoto, T., Antioxidative activity of volatile extracts from Maillard model systems, Food Chem., 2006, 98, 3, 522-528, https://doi.org/10.1016/j.foodchem.2005.05.084 . [all data]

Wanakhachornkrai and Lertsiri, 2003
Wanakhachornkrai, P.; Lertsiri, S., Analytical, nutritional, and clinical methods. Comparison of determination method for volatile compounds in Thai soy sauce, Food Chem., 2003, 83, 4, 619-629, https://doi.org/10.1016/S0308-8146(03)00256-5 . [all data]

Sekiwa, Kubota, et al., 1997
Sekiwa, Y.; Kubota, K.; Kobayashi, A., Characteristic flavor components in the brew of cooked clam (Meretrix lusoria) and the effect of storage on flavor formation, J. Agric. Food Chem., 1997, 45, 3, 826-830, https://doi.org/10.1021/jf960433e . [all data]

Eiserich, Macku, et al., 1992
Eiserich, J.P.; Macku, C.; Shibamoto, T., Volatile antioxidants formed from an L-cysteine/D-glucose Maillard model system, J. Agric. Food Chem., 1992, 40, 10, 1982-1988, https://doi.org/10.1021/jf00022a050 . [all data]

Vernin, Metzger, et al., 1992
Vernin, G.; Metzger, J.; Boniface, C.; Murello, M.-H.; Siouffi, A.; Larice, J.-L.; Parkanyi, C., Kinetics and thermal degradation of the fructose-methionine Amadori intermediates. GC-MS/SPECMA data bank identification of volatile aroma compounds, Carbohyd. Res., 1992, 230, 1, 15-29, https://doi.org/10.1016/S0008-6215(00)90510-X . [all data]

Pontes, Marques, et al., 2007
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Krings, Zelena, et al., 2006
Krings, U.; Zelena, K.; Wu, S.; Berger, R.G., Thin-layer high-vacuum distillation to isolate volatile flavour compounds of cocoa powder, Eur. Food Res. Technol., 2006, 223, 5, 675-681, https://doi.org/10.1007/s00217-006-0252-x . [all data]

Notes

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• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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