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{{Short description|Sugar acid}}
{{one source|date=July 2024}}
{{DISPLAYTITLE:<small>D</small>-Galacturonic acid}}
{{DISPLAYTITLE:<small>D</small>-Galacturonic acid}}
{{Use dmy dates|date=July 2024}}
{{chembox
{{chembox
| Verifiedfields = changed
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|Name=<small>D</small>-Galacturonic acid
| Watchedfields = changed
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|ImageFile=Galacturonic_acid.png
| verifiedrevid = 464362073
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|ImageSize=180px
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| Name ={{sm|d}}-Galacturonic acid
|IUPACName=(''2S,3R,4S,5R'')-2,3,4,5-Tetrahydroxy-6-oxo-hexanoic acid
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| ImageFile =Galacturonic_acid.png
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|OtherNames=
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| ImageSize =180px
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|Section1= {{Chembox Identifiers
| IUPACName = β-<small>D</small>-Galactopyranuronic acid
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| ChemSpiderID = 388354
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| OtherNames =
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|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| ChemSpiderID = 76444
| InChI = 1/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2+,3+,4-,6?/m0/s1
| InChI = 1/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2+,3+,4-,6?/m0/s1
| InChIKey = AEMOLEFTQBMNLQ-YMDCURPLBW
| InChIKey = AEMOLEFTQBMNLQ-YMDCURPLBW
| InChI1 = 1/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h1-5,8-11H,(H,12,13)/t2-,3+,4+,5-/m0/s1
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| CASNo=685-73-4
| InChIKey1 = IAJILQKETJEXLJ-RSJOWCBRBL
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| EINECS=211-682-6
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| SMILES1 = O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(=O)O
| PubChem=84740
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| SMILES = O=C(O)[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O
| StdInChI = 1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h1-5,8-11H,(H,12,13)/t2-,3+,4+,5-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IAJILQKETJEXLJ-RSJOWCBRSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
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| CASNo = 685-73-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2ENU0N1DRP
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| EINECS =211-682-6
| PubChem =84740
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 4153
| SMILES = O=C(O)[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O
}}
}}
|Section2= {{Chembox Properties
|Section2={{Chembox Properties
| Formula=C<sub>6</sub>H<sub>10</sub>O<sub>7</sub>
| Formula =C<sub>6</sub>H<sub>10</sub>O<sub>7</sub>
| MolarMass=194.139
| MolarMass =194.139
| Appearance=
| Appearance =
| Density=
| Density =
| MeltingPtC = 159
| MeltingPt=
| BoilingPt=
| BoilingPt =
| Solubility=
| Solubility =
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}}
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|Section3= {{Chembox Hazards
| MainHazards=
| FlashPt=
| Autoignition=
}}
}}
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|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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}}
}}
}}


'''D-Galacturonic acid''' is a sugar acid, an oxidized form of [[galactose|<small>D</small>-galactose]]. It is the main component of [[pectin]], in which it exists as the polymer [[polygalacturonic acid]]. It has an [[aldehyde]] group at C1 and a [[carboxylic acid]] group at C6. Other oxidized forms of <small>D</small>-galactose are <small>D</small>-galactonic acid (carboxylic group at C1) and ''meso''-galactaric acid ([[mucic acid]]) (carboxylic groups at C1 and C6). It is also a [[uronic acid]] or hexuronic acid. Naturally occurring uronic acids are <small>D</small>-[[glucuronic acid]], <small>D</small>-galacturonic acid, <small>L</small>-[[iduronic acid]] and <small>D</small>-[[mannuronic acid]].
'''{{sm|d}}-Galacturonic acid''' is a sugar acid, an oxidized form of [[galactose|{{sm|d}}-galactose]]. It is the main component of [[pectin]], in which it exists as the polymer [[polygalacturonic acid]].<ref>{{cite journal | doi = 10.1016/j.pbi.2008.03.006| title = Pectin structure and biosynthesis| date = 2008| last1 = Mohnen| first1 = D.| journal = Current Opinion in Plant Biology| volume = 11| issue = 3| pages = 266–277| pmid = 18486536| bibcode = 2008COPB...11..266M}}</ref> In its open form, it has an [[aldehyde]] group at C1 and a [[carboxylic acid]] group at C6. Other oxidized forms of {{sm|d}}-galactose are {{sm|d}}-galactonic acid (carboxylic group at C1) and ''meso''-galactaric acid ([[mucic acid]]) (carboxylic groups at C1 and C6). It is also a [[uronic acid]] or hexuronic acid. Naturally occurring uronic acids are {{sm|d}}-[[glucuronic acid]], {{sm|d}}-galacturonic acid, {{sm|l}}-[[iduronic acid]] and {{sm|d}}-[[mannuronic acid]].

==References==
<references />


{{DEFAULTSORT:Galacturonic acid, D-}}
{{DEFAULTSORT:Galacturonic acid, D-}}
[[Category:Sugar acids]]
[[Category:Uronic acids]]

[[de:Galacturonsäure]]
[[es:Ácido galacturónico]]
[[it:Acido galatturonico]]
[[ja:ガラクツロン酸]]
[[pl:Kwas galakturonowy]]
[[pt:Ácido galacturónico]]
[[ru:Галактуроновая кислота]]

Latest revision as of 17:19, 30 August 2024

d-Galacturonic acid
Names
IUPAC name
β-D-Galactopyranuronic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.035.495 Edit this at Wikidata
EC Number
  • 211-682-6
UNII
  • InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h1-5,8-11H,(H,12,13)/t2-,3+,4+,5-/m0/s1 checkY
    Key: IAJILQKETJEXLJ-RSJOWCBRSA-N checkY
  • InChI=1/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2+,3+,4-,6?/m0/s1
    Key: AEMOLEFTQBMNLQ-YMDCURPLBW
  • InChI=1/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h1-5,8-11H,(H,12,13)/t2-,3+,4+,5-/m0/s1
    Key: IAJILQKETJEXLJ-RSJOWCBRBL
  • O=C(O)[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O
  • O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(=O)O
Properties
C6H10O7
Molar mass 194.139
Melting point 159 °C (318 °F; 432 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

d-Galacturonic acid is a sugar acid, an oxidized form of d-galactose. It is the main component of pectin, in which it exists as the polymer polygalacturonic acid.[1] In its open form, it has an aldehyde group at C1 and a carboxylic acid group at C6. Other oxidized forms of d-galactose are d-galactonic acid (carboxylic group at C1) and meso-galactaric acid (mucic acid) (carboxylic groups at C1 and C6). It is also a uronic acid or hexuronic acid. Naturally occurring uronic acids are d-glucuronic acid, d-galacturonic acid, l-iduronic acid and d-mannuronic acid.

References

[edit]
  1. ^ Mohnen, D. (2008). "Pectin structure and biosynthesis". Current Opinion in Plant Biology. 11 (3): 266–277. Bibcode:2008COPB...11..266M. doi:10.1016/j.pbi.2008.03.006. PMID 18486536.
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