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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/10/23 23:47:35」(JST)
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Glycolaldehyde |
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Identifiers |
CAS number |
141-46-8 Y |
PubChem |
756 |
ChemSpider |
736 Y |
KEGG |
C00266 Y |
ChEBI |
CHEBI:17071 Y |
Jmol-3D images |
Image 1 |
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InChI=1S/C2H4O2/c3-1-2-4/h1,4H,2H2 Y
Key: WGCNASOHLSPBMP-UHFFFAOYSA-N Y
InChI=1/C2H4O2/c3-1-2-4/h1,4H,2H2
Key: WGCNASOHLSPBMP-UHFFFAOYAH
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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
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Related compounds |
Related aldehydes |
3-Hydroxybutanal
Lactaldehyde
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Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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]
Contents
- 1 Formation
- 2 In space
- 3 References
- 4 External links
Formation[edit]
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This section needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (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.
Glycolaldehyde is the second most abundant chemical formed when preparing pyrolysis oil (up to 10% by weight).[2]
In space[edit]
Sugar molecules in the gas surrounding a young Sun-like star.
[3]
Glycolaldehyde has been identified in gas and dust near the center of the Milky Way galaxy,[4] in a star-forming region 26000 light-years from Earth,[5] and around a protostellar binary star, IRAS 16293-2422, 400 light years from Earth.[6][7] 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.[8]
References[edit]
- ^ Carroll, P., Drouin, B., and Widicus Weaver, S., (2010). "The Submillimeter Spectrum of Glycolaldehyde". Astrophys. J. 723: 845–849. Bibcode:2010ApJ...723..845C. doi:10.1088/0004-637X/723/1/845.
- ^ Moha, Dinesh; Charles U. Pittman, Jr. & Philip H. Steele (10th). "Pyrolysis of Wood/Biomass for Bio-oil: A Critical Review". Energy & Fuels 206 (3): 848–889. doi:10.1021/ef0502397. Retrieved 5 September 2013.
- ^ "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.
Types of carbohydrates
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General |
- Aldose
- Furanose
- Ketose
- Pyranose
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Geometry |
- Anomer
- Cyclohexane conformation
- Mutarotation
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Monosaccharides |
Dioses |
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Trioses |
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Tetroses |
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Pentoses |
- Aldopentose
- Arabinose
- Lyxose
- Ribose
- Xylose
- Deoxy sugar
- Ketopentose
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Hexoses |
- Aldohexose
- Allose
- Altrose
- Galactose
- Glucose
- Gulose
- Idose
- Mannose
- Talose
- Deoxy sugar
- Ketohexose
- Fructose
- Psicose
- Sorbose
- Tagatose
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Heptoses |
- Ketoheptose
- Mannoheptulose
- Sedoheptulose
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>7 |
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Multiple |
Disaccharides |
- Cellobiose
- Lactose
- Maltose
- Sucrose
- Trehalose
- Turanose
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Trisaccharides |
- Maltotriose
- Melezitose
- Raffinose
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Tetrasaccharides |
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Other
oligosaccharides |
- Acarbose
- Fructooligosaccharide (FOS)
- Galactooligosaccharide (GOS)
- Isomaltooligosaccharide (IMO)
- Maltodextrin
- Mannan-oligosaccharides (MOS)
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Polysaccharides |
- Beta-glucan
- Lentinan
- Sizofiran
- Zymosan
- Cellulose
- Chitin
- Dextrin / Dextran
- Fructose / Fructan
- Galactose / Galactan
- Glucose / Glucan
- Levan beta 2→6
- Mannan
- Starch
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- Biochemical families: carbohydrates
- alcohols
- glycoproteins
- glycosides
- lipids
- eicosanoids
- fatty acids / intermediates
- phospholipids
- sphingolipids
- steroids
- nucleic acids
- constituents / intermediates
- proteins
- Amino acids / intermediates
- tetrapyrroles / intermediates
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English Journal
- Neurite regeneration in adult rat retinas exposed to advanced glycation end-products and regenerative effects of neurotrophin-4.
- Bikbova G, Oshitari T, Yamamoto S.SourceDepartment of Ophthalmology and Visual Science, Chiba University Graduate School of Medicine, Inohana 1-8-1, Chuo-ku, Chiba 260-8670, Chiba, Japan.
- Brain research.Brain Res.2013 Oct 9;1534:33-45. doi: 10.1016/j.brainres.2013.08.027. Epub 2013 Aug 21.
- The purpose of this study was to determine the effect of low concentrations of advanced glycation end-products on neurite regeneration in isolated rat retinas, and to determine the effects of neurotrophin-4 on regeneration in advanced glycation end-products exposed retinas. Retinal explants of 4 adu
- PMID 23973749
- Fragmentation of Deprotonated Glycolaldehyde in the Gas Phase and Relevance to the Formose Reaction.
- Sekiguchi O, Uggerud E.AbstractFrom gas phase reactivity studies employing mass spectrometry, the spontaneous unimolecular dissociation of the corresponding base of glycolaldehyde has been probed. Three reactions were observed (in order of decreasing abundance); loss of CO, CH2O, and loss of H2. Detailed reaction mechanisms for each of the three reactions were obtained by quantum chemical calculations, and the reaction characteristics and energetics were found to be in good agreement with experimental observations. The relevance of these findings to the formose reaction and possible interstellar formation of carbohydrates from formaldehyde is discussed. It is concluded that the critical C-C bond forming reaction between two formaldehyde molecules to give the glycoladehyde is unlikely to occur in the gas phase via a route involving the free formyl anion, thereby precluding a key pathway for interstellar formation of carbohydrates. However, an alternative formation reaction is suggested.
- The journal of physical chemistry. A.J Phys Chem A.2013 Oct 8. [Epub ahead of print]
- From gas phase reactivity studies employing mass spectrometry, the spontaneous unimolecular dissociation of the corresponding base of glycolaldehyde has been probed. Three reactions were observed (in order of decreasing abundance); loss of CO, CH2O, and loss of H2. Detailed reaction mechanisms for e
- PMID 24102334
- On-Line Mass Spectrometric Methods for the Determination of the Primary Products of Fast Pyrolysis of Carbohydrates and for Their Gas-Phase Manipulation.
- Hurt MR, Degenstein JC, Gawecki P, Borton DJ, Vinueza NR, Yang L, Agrawal R, Delgass WN, Ribeiro FH, Kenttamaa HI.AbstractMass spectrometric methodology was developed for the determination and manipulation of the primary products of fast pyrolysis of carbohydrates. To determine the true primary pyrolysis products, a very fast heating pyroprobe was coupled to a linear quadrupole ion trap mass spectrometer through a custom-built adaptor. A home-built flow tube that simulates pyrolysis reactor conditions was used to examine the secondary reactions of the primary products. Depending on the experiment, the pyrolysis products were either evaporated and quenched or allowed to react for a period of time. The quenched products were ionized in an atmospheric pressure chemical ionization (APCI) source infused with one of two ionization reagents, chloroform or ammonium hydroxide, to aid in ionization. During APCI in negative ion mode, chloroform produces chloride anions that are known to readily add to carbohydrates with little bias and little to no fragmentation. On the other hand, in positive ion mode APCI, ammonium hydroxide forms ammonium adducts with carbohydrates with little to no fragmentation. The latter method ionizes compounds that are not readily ionized upon negative ion mode APCI, such as furan derivatives. Six model compounds were studied to verify the ability of the ionization methods to ionize known pyrolysis products: glycolaldehyde, hydroxyacetone, furfural, 5-hydroxymethylfurfural, levoglucosan, and cellobiosan. The method was then used to examine fast pyrolysis of cellobiose. The primary fast pyrolysis products were determined to consist of only a handful of compounds that quickly polymerize to form anhydro-oligosaccharides when allowed to react at high temperatures for an extended period of time.
- Analytical chemistry.Anal Chem.2013 Oct 7. [Epub ahead of print]
- Mass spectrometric methodology was developed for the determination and manipulation of the primary products of fast pyrolysis of carbohydrates. To determine the true primary pyrolysis products, a very fast heating pyroprobe was coupled to a linear quadrupole ion trap mass spectrometer through a cust
- PMID 24098979
Japanese Journal
- Macrophage Recognition of Toxic Advanced Glycosylation End Products through the Macrophage Surface-Receptor Nucleolin
- Miki Yuichi,Dambara Hikaru,Tachibana Yoshihiro [他]
- Biological & pharmaceutical bulletin 37(4), 588-596, 2014-04
- NAID 40020030162
- Comparative Study on the Photocatalytic Oxidation of Glycerol Using ZnO and TiO2
- Hermes Natanael A.,Corsetti André,Lansarin Marla A.
- Chemistry Letters 43(1), 143-145, 2014
- … TiO2 generated more products from the cleavage of the glycerol molecule, such as formaldehyde (FORM) and glycolaldehyde (GCOL). …
- NAID 130004427088
- Effects of Chebulic Acid on Advanced Glycation Endproducts-Induced Collagen Cross-Links
- Lee Ji-young,Oh Jun-Gu,Kim Jin Sook,Lee Kwang-Won
- Biological and Pharmaceutical Bulletin 37(7), 1162-1167, 2014
- … Aminoguanidine (AG) reduced 50% of glycated bovine serum albumin (BSA) with glycolaldehyde (glycol-BSA)-induced cross-links of collagen at a concentration of 67.8±2.5 mM, the level of CA required for exerting a similar antiglycating activity was 38.8±0.5 µM. …
- NAID 130003390996
Related Links
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- Glycolaldehyde, Dimer 販売元 和光純薬工業(株) 販売元コード 590-33203,592-21014,594-21013,594-33201,598-21011,598-33204 製造元 MP Biomedicals, Inc. 製造元コード 101838 CAS.NO 23147-58-2 分子式 分子量 保存条件 ...
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