Glycolaldehyde
| Glycolaldehyde | |
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2-hydroxyacetaldehyde |
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| Identifiers | |
| CAS number | 141-46-8  |
| PubChem | 756 |
| ChemSpider | 736 |
| KEGG | C00266 |
| ChEBI | CHEBI:17071 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C2H4O2 |
| Molar mass | 60.052 g/mol |
| Density | 1.065 g/mL |
| Boiling point |
131.3 °C, 404 K, 268 °F |
| Related compounds | |
| Related aldehydes | 3-Hydroxybutanal |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Glycolaldehyde (HOCH2-CH=O) is the smallest possible molecule that contains both an aldehyde group and a hydroxyl group. It is the only possible diose, a 2-carbon monosaccharide, although a diose is not strictly a saccharide. While not a true sugar, it is the simplest sugar-related molecule.[1]
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Formation [edit]
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This section needs additional citations for verification. (August 2012) |
Glycolaldehyde is an intermediate in the formose reaction. Glycolaldehyde forms from many precursors, including the amino acid glycine. It can form by action of ketolase on fructose 1,6-bisphosphate in an alternate glycolysis pathway. This compound is transferred by thiamine pyrophosphate during the pentose phosphate shunt.
In purine catabolism, xanthine is first converted to urate. This is converted to 5-hydroxyisourate, which decarboxylates to allantoin and allantoic acid. After hydrolyzing one urea, this leaves glycolureate. After hydrolyzing the second urea, glycolaldehyde is left. Two glycolaldehydes condense to form erythrose 4-phosphate, which goes to the pentose phosphate shunt again.
In space [edit]
Glycolaldehyde has been identified in gas and dust near the center of the Milky Way galaxy,[3] in a star-forming region 26000 light-years from Earth,[4] and around a protostellar binary star, IRAS 16293-2422, 400 light years from Earth.[5][6] Observation of in-falling glycolaldehyde spectra 60 AU from IRAS 16293-2422 suggests that complex organic molecules may form in stellar systems prior to the formation of planets, eventually arriving on young planets early in their formation.[7]
References [edit]
- ^ Carroll, P., Drouin, B., and Widicus Weaver, S., (2010). "The Submillimeter Spectrum of Glycolaldehyde". Astrophys. J. 723: 845–849.
- ^ "Sweet Result from ALMA". ESO Press Release. Retrieved 3 September 2012.
- ^ Hollis, J.M., Lovas, F.J., & Jewell, P.R. (2000). "Interstellar Glycolaldehyde: The First Sugar". The Astrophysical Journal 540 (2): 107–110. Bibcode:2000ApJ...540L.107H. doi:10.1086/312881.
- ^ Beltran, M. T.; Codella, C.; Viti, S.; Neri, R.; Cesaroni, R.; (11/2008). First detection of glycolaldehyde outside the Galactic Center. eprint arXiv:0811.3821.
- ^ Than, Ker (August 29, 2012). "Sugar Found In Space". National Geographic. Retrieved August 31, 2012.
- ^ Staff (August 29, 2012). "Sweet! Astronomers spot sugar molecule near star". AP News. Retrieved August 31, 2012.
- ^ Jørgensen, J. K.; Favre, C.; Bisschop, S.; Bourke, T.; Dishoeck, E.; Schmalzl, M. (2012). Detection of the simplest sugar, glycolaldehyde, in a solar-type protostar with ALMA. eprint.
External links [edit]
- "Cold Sugar in Space Provides Clue to the Molecular Origin of Life". National Radio Astronomy Observatory. September 20, 2004. Retrieved 2006-12-20.
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