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Systematic names are formed from a stem name and a configurational prefix or prefixes. The stem names for the aldoses with three to ten carbon atoms are triose, tetrose, pentose, hexose, heptose, octose, nonose, decose. The chain is numbered so that the carbonyl group is at position 1. See also https://iupac.qmul.ac.uk/2carb/08n09.html
 
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{{Chembox
{{Chembox
| verifiedrevid = 450917285
| verifiedrevid = 450917285
| Reference = <ref>''Merck Index'', 11th Edition, '''3637'''</ref>
| Reference = <ref>''Merck Index'', 11th Edition, '''3637'''</ref>
| ImageFile1 = D-erythrose.svg
| ImageFile1 = D-erythrose.svg
| ImageSize1 = 150px
| ImageSize1 = 150px
| ImageCaption1 = <small>D</small>-Erythrose
| ImageCaption1 = <small>D</small>-Erythrose
| ImageFile2 = L-erythrose.svg
| ImageFile2 = L-erythrose.svg
| ImageSize2 = 150px
| ImageSize2 = 150px
| ImageCaption2 = <small>L</small>-Erythrose
| ImageCaption2 = <small>L</small>-Erythrose
| IUPACName = (2''R'',3''R'')-2,3,4-Trihydroxybutanal (<small>D</small>)<br>(2''S'',3''S'')-2,3,4-Trihydroxybutanal (<small>L</small>)
| IUPACName = <small>D</small>-Erythrose<br>
<small>D</small>-''erythro''-Tetrose <small>(systematic name)</small><ref>https://iupac.qmul.ac.uk/2carb/08n09.html</ref>
| OtherNames =
| SystematicName = (2''R'',3''R'')-2,3,4-Trihydroxybutanal (<small>D</small>)<br>(2''S'',3''S'')-2,3,4-Trihydroxybutanal (<small>L</small>)
|Section1={{Chembox Identifiers
| Section1 = {{Chembox Identifiers
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|CASNo = 583-50-6
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| ChemSpiderID_Comment = (<small>D</small>)
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|CASNo_Comment = (<small>D</small>)
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| InChI = 1/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1
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|CASNo1 = 533-49-3
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|CASNo1_Ref = {{cascite|correct|CAS}}
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|CASNo1_Comment = (<small>L</small>)
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| StdInChI = 1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1
|Beilstein = 5805561
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| StdInChIKey = YTBSYETUWUMLBZ-IUYQGCFVSA-N
| CASNo = 583-50-6
|ChEBI = 27904
| CASNo_Ref = {{cascite|correct|CAS}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫
|ChemSpiderID = 84990
⚫
| CASNo_Comment = (<small>D</small>)
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|ChemSpiderID_Comment = (<small>D</small>)
⚫
| CASNo1 = 533-49-3
|EINECS = 209-505-2
⚫
| CASNo1_Ref = {{cascite|correct|CAS}}
|KEGG = C01796
⚫
| CASNo1_Comment = (<small>L</small>)
|UNII_Ref = {{fdacite|correct|FDA}}
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| PubChem = 94176
|UNII = X3EI0WE8Q4
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|UNII1_Ref = {{fdacite|correct|FDA}}
| ChEBI = 27904
|UNII1 = 96DH71781X
⚫
| SMILES = OC[C@@H](O)[C@@H](O)C=O
| SMILES_Comment = (<small>D</small>)
|UNII1_Comment = (<small>L</small>)
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|PubChem = 94176
⚫
| SMILES1 = OC[C@H](O)[C@H](O)C=O
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|InChI = 1/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1
⚫
}}
⚫
|InChIKey = YTBSYETUWUMLBZ-IUYQGCFVBI
⚫
|Section2={{Chembox Properties
⚫
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫
| C=4|H=8|O=4
⚫
|StdInChI = 1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1
⚫
| Appearance = Light yellow syrup
⚫
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| Density =
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|StdInChIKey = YTBSYETUWUMLBZ-IUYQGCFVSA-N
| MeltingPt =
⚫
|SMILES = OC[C@@H](O)[C@@H](O)C=O
| BoilingPt =
|SMILES_Comment = (<small>D</small>)
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| Solubility = highly soluble
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|SMILES1 = OC[C@H](O)[C@H](O)C=O
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|SMILES1_Comment = (<small>L</small>)
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|Section3={{Chembox Hazards
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⚫
| Section2 = {{Chembox Properties
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|C=4|H=8|O=4
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|Appearance = Light yellow syrup
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|Solubility = highly soluble
⚫
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| NFPA-H = 1
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| NFPA-F = 1
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| MainHazards =
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'''Erythrose''' is a [[tetrose]] [[saccharide]] with the [[chemical formula]] C<sub>4</sub>H<sub>8</sub>O<sub>4</sub>. It has one [[aldehyde]] group, and is thus part of the [[aldose]] family. The natural isomer is <small>D</small>-erythrose.
'''Erythrose''' is a [[tetrose]] [[saccharide]] with the [[chemical formula]] C<sub>4</sub>H<sub>8</sub>O<sub>4</sub>. It has one [[aldehyde]] group, and is thus part of the [[aldose]] family. The natural isomer is <small>D</small>-erythrose; it is a [[diastereomer]] of <small>[[Threose|D]]</small>[[Threose|-threose]].<ref>{{Cite web|date=2015-04-01|title=4.5: Diastereomers|url=https://chem.libretexts.org/Courses/University_of_Illinois_Springfield/UIS%3A_CHE_267_-_Organic_Chemistry_I_(Morsch)/Chapters/Chapter_05%3A_Stereochemistry/4.05%3A_Diastereomers|access-date=2021-11-17|website=Chemistry LibreTexts|language=en}}</ref>
[[File:DL-Erythrose.svg|thumb|left|[[Fischer projection|Fischer projections]] depicting the two enantiomers of Erythrose]]
[[File:DL-Erythrose.svg|thumb|left|[[Fischer projection|Fischer projections]] depicting the two enantiomers of erythrose]]


Erythrose was first isolated in 1849 from rhubarb by the French pharmacist Louis Feux Joseph Garot (1798-1869),<ref>[https://books.google.com/books?id=L_tBAAAAcAAJ&pg=PA472#v=onepage&q&f=false Obituary of Garot] (1869) ''Journal de pharmacie et de chimie'', 4th series, '''9''' : 472-473.</ref> and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red").<ref>Garot (1850) [https://books.google.com/books?id=2bQ8AAAAcAAJ&pg=PA5#v=onepage&q&f=false "De la matière colorante rouge des rhubarbes exotiques et indigènes et de son application (comme matière colorante) aux arts et à la pharmacie"] (On the red coloring material of exotic and indigenous rhubarb and on its application (as a coloring material) in the arts and in pharmacy), ''Journal de Pharmacie et de Chimie'', 3rd series, '''17''' : 5-19. Erythrose is named on p. 10: ''"Celui que je propose, sans y attacher toutefois la moindre importance, est celui d'''érythrose'', du verbe grec 'ερυθραινω, rougir (1)."'' (The one [i.e., name] that I propose, without attaching any importance to it, is that of ''erythrose'', from the Greek verb ερυθραινω, to redden (1).)</ref><ref>{{cite book|last1=Wells|first1=David Ames|last2=Cross|first2=Charles Robert|last3=Bliss|first3=George|last4=Trowbridge|first4=John|last5=Nichols|first5=William Ripley|last6=Kneeland|first6=Samuel|title=Annual of Scientific Discovery|date=1851|publisher=Gould, Kendall, and Lincoln|location=Boston|page=[https://archive.org/details/annualscientifi29crosgoog/page/n242 211]|url=https://archive.org/details/annualscientifi29crosgoog|quote=erythrose discovery.|accessdate=11 December 2014}}</ref>
Erythrose was first isolated in 1849 from rhubarb by the French pharmacist Louis Feux Joseph Garot (1798-1869),<ref>[https://books.google.com/books?id=L_tBAAAAcAAJ&pg=PA472 Obituary of Garot] (1869) ''Journal de pharmacie et de chimie'', 4th series, '''9''' : 472-473.</ref> and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red").<ref>Garot (1850) [https://books.google.com/books?id=2bQ8AAAAcAAJ&pg=PA5 "De la matière colorante rouge des rhubarbes exotiques et indigènes et de son application (comme matière colorante) aux arts et à la pharmacie"] (On the red coloring material of exotic and indigenous rhubarb and on its application (as a coloring material) in the arts and in pharmacy), ''Journal de Pharmacie et de Chimie'', 3rd series, '''17''' : 5-19. Erythrose is named on p. 10: ''"Celui que je propose, sans y attacher toutefois la moindre importance, est celui d'''érythrose'', du verbe grec 'ερυθραινω, rougir (1)."'' (The one [i.e., name] that I propose, without attaching any importance to it, is that of ''erythrose'', from the Greek verb ερυθραινω, to redden (1).)</ref><ref>{{cite book|last1=Wells|first1=David Ames|last2=Cross|first2=Charles Robert|last3=Bliss|first3=George|last4=Trowbridge|first4=John|last5=Nichols|first5=William Ripley|last6=Kneeland|first6=Samuel|title=Annual of Scientific Discovery|date=1851|publisher=Gould, Kendall, and Lincoln|location=Boston|page=[https://archive.org/details/annualscientifi29crosgoog/page/n242 211]|url=https://archive.org/details/annualscientifi29crosgoog|quote=erythrose discovery.|access-date=11 December 2014}}</ref>


[[Erythrose 4-phosphate]] is an intermediate in the [[pentose phosphate pathway]]<ref>{{cite journal|last1=Kruger|first1=Nicholas J|last2=von Schaewen|first2=Antje|title=The oxidative pentose phosphate pathway: structure and organisation|journal=Current Opinion in Plant Biology|date=June 2003|volume=6|issue=3|pages=236–246|doi=10.1016/S1369-5266(03)00039-6|pmid=12753973}}</ref> and the [[Calvin cycle]].<ref>{{cite journal|last1=Schwender|first1=Jörg|last2=Goffman|first2=Fernando|last3=Ohlrogge|first3=John B.|last4=Shachar-Hill|first4=Yair|title=Rubisco without the Calvin cycle improves the carbon efficiency of developing green seeds|journal=Nature|date=9 December 2004|volume=432|issue=7018|pages=779–782|doi=10.1038/nature03145|pmid=15592419}}</ref>
[[Erythrose 4-phosphate]] is an intermediate in the [[pentose phosphate pathway]]<ref>{{cite journal|last1=Kruger|first1=Nicholas J|last2=von Schaewen|first2=Antje|title=The oxidative pentose phosphate pathway: structure and organisation|journal=Current Opinion in Plant Biology|date=June 2003|volume=6|issue=3|pages=236–246|doi=10.1016/S1369-5266(03)00039-6|pmid=12753973}}</ref> and the [[Calvin cycle]].<ref>{{cite journal|last1=Schwender|first1=Jörg|last2=Goffman|first2=Fernando|last3=Ohlrogge|first3=John B.|last4=Shachar-Hill|first4=Yair|title=Rubisco without the Calvin cycle improves the carbon efficiency of developing green seeds|journal=Nature|date=9 December 2004|volume=432|issue=7018|pages=779–782|doi=10.1038/nature03145|pmid=15592419|bibcode=2004Natur.432..779S|s2cid=4401215}}</ref>


Oxidative bacteria can be made to use erythrose as its sole energy source.<ref>{{cite journal|last1=Hiatt|first1=Howard H|last2=Horecker|first2=B L|title=D-erythrose metabolism in a strain of Alcaligenes faecalis|journal=Journal of Bacteriology|date=13 October 1955|volume=71|issue=6|pages=649–654|url=http://jb.asm.org/content/71/6/649.long|accessdate=11 December 2014}}</ref>{{clear-left}}
Oxidative bacteria can be made to use erythrose as its sole energy source.<ref>{{cite journal|last1=Hiatt|first1=Howard H|last2=Horecker|first2=B L|title=D-erythrose metabolism in a strain of Alcaligenes faecalis|journal=Journal of Bacteriology|date=13 October 1955|volume=71|issue=6|pages=649–654|doi=10.1128/jb.71.6.649-654.1956|pmid=13345750|pmc=314578|url=http://jb.asm.org/content/71/6/649.long|access-date=11 December 2014}}</ref>{{clear-left}}


==See also==
==See also==

* [[Erythritol]]
* [[Erythritol]]


Latest revision as of 11:41, 17 October 2024

Erythrose[1]

D-Erythrose

L-Erythrose
Names
IUPAC names
D-Erythrose
D-erythro-Tetrose (systematic name)[2]
Systematic IUPAC name
(2R,3R)-2,3,4-Trihydroxybutanal (D)
(2S,3S)-2,3,4-Trihydroxybutanal (L)
Identifiers
3D model (JSmol)
5805561
ChEBI
ChemSpider
ECHA InfoCard 100.008.643 Edit this at Wikidata
EC Number
  • 209-505-2
KEGG
UNII
  • InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1 checkY
    Key: YTBSYETUWUMLBZ-IUYQGCFVSA-N checkY
  • InChI=1/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1
    Key: YTBSYETUWUMLBZ-IUYQGCFVBI
  • (D): OC[C@@H](O)[C@@H](O)C=O
  • (L): OC[C@H](O)[C@H](O)C=O
Properties
C4H8O4
Molar mass 120.104 g·mol−1
Appearance Light yellow syrup
highly soluble
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Erythrose is a tetrose saccharide with the chemical formula C4H8O4. It has one aldehyde group, and is thus part of the aldose family. The natural isomer is D-erythrose; it is a diastereomer of D-threose.[3]

Fischer projections depicting the two enantiomers of erythrose

Erythrose was first isolated in 1849 from rhubarb by the French pharmacist Louis Feux Joseph Garot (1798-1869),[4] and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red").[5][6]

Erythrose 4-phosphate is an intermediate in the pentose phosphate pathway[7] and the Calvin cycle.[8]

Oxidative bacteria can be made to use erythrose as its sole energy source.[9]

See also

[edit]

References

[edit]
  1. ^ Merck Index, 11th Edition, 3637
  2. ^ https://iupac.qmul.ac.uk/2carb/08n09.html
  3. ^ "4.5: Diastereomers". Chemistry LibreTexts. 2015-04-01. Retrieved 2021-11-17.
  4. ^ Obituary of Garot (1869) Journal de pharmacie et de chimie, 4th series, 9 : 472-473.
  5. ^ Garot (1850) "De la matière colorante rouge des rhubarbes exotiques et indigènes et de son application (comme matière colorante) aux arts et à la pharmacie" (On the red coloring material of exotic and indigenous rhubarb and on its application (as a coloring material) in the arts and in pharmacy), Journal de Pharmacie et de Chimie, 3rd series, 17 : 5-19. Erythrose is named on p. 10: "Celui que je propose, sans y attacher toutefois la moindre importance, est celui d'érythrose, du verbe grec 'ερυθραινω, rougir (1)." (The one [i.e., name] that I propose, without attaching any importance to it, is that of erythrose, from the Greek verb ερυθραινω, to redden (1).)
  6. ^ Wells, David Ames; Cross, Charles Robert; Bliss, George; Trowbridge, John; Nichols, William Ripley; Kneeland, Samuel (1851). Annual of Scientific Discovery. Boston: Gould, Kendall, and Lincoln. p. 211. Retrieved 11 December 2014. erythrose discovery.
  7. ^ Kruger, Nicholas J; von Schaewen, Antje (June 2003). "The oxidative pentose phosphate pathway: structure and organisation". Current Opinion in Plant Biology. 6 (3): 236–246. doi:10.1016/S1369-5266(03)00039-6. PMID 12753973.
  8. ^ Schwender, Jörg; Goffman, Fernando; Ohlrogge, John B.; Shachar-Hill, Yair (9 December 2004). "Rubisco without the Calvin cycle improves the carbon efficiency of developing green seeds". Nature. 432 (7018): 779–782. Bibcode:2004Natur.432..779S. doi:10.1038/nature03145. PMID 15592419. S2CID 4401215.
  9. ^ Hiatt, Howard H; Horecker, B L (13 October 1955). "D-erythrose metabolism in a strain of Alcaligenes faecalis". Journal of Bacteriology. 71 (6): 649–654. doi:10.1128/jb.71.6.649-654.1956. PMC 314578. PMID 13345750. Retrieved 11 December 2014.
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