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			{{Short description|Sugar}}
			{{redirect|Wood sugar|the related sugar alcohol|Xylitol}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 397544258		| verifiedrevid = 458276050
	| Name = <small>D</small>-Xylose		| Name = {{sm|d}}-Xylose
	| ImageFileL1 = Xylose.png		| ImageFileL1 = Xylose.svg
			| ImageNameL1 = D-Xylopyranose
	| ImageSizeL1 = 120px
			| ImageFileR1 = Xylofuranose.png
	| ImageNameL1 = D-Xylopyranose
			| ImageSizeR1 = 130px
	| ImageFileR1 = Xylofuranose.png
			| ImageNameR1 = Xylofuranose
	| ImageSizeR1 = 130px
			| ImageFile2 = D-Xylose.svg
	| ImageNameR1 = Xylofuranose
			| ImageSize2 = 180px
	| ImageFile2 = D-Xylose.svg
			| ImageName2 = Xylose chair
	| ImageSize2 = 180px
	| ImageName2 = Xylose chair		| ImageFile3 = Xylose linear.png
			| ImageSize3 = 180px
	| ImageFile3 = Xylose linear.png
			| ImageName3 = Xylose linear
	| ImageSize3 = 180px
	| ImageName3 = Xylose linear		| IUPACName = {{sm|d}}-Xylose
			| OtherNames = (+)-Xylose<br/>Wood sugar
	| IUPACName = <small>D</small>-Xylose
			|Section1={{Chembox Identifiers
	| OtherNames = (+)-Xylose<br/>Wood sugar
			| CASNo = 58-86-6
	| Section1 = {{Chembox Identifiers
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 58-86-6
			| CASNo1 = 609-06-3
	| CASNo_Ref = {{cascite|correct|CAS}}
			| CASNo1_Comment = ({{sm|l}}-isomer)
	| CASNo1 = 609-06-3
			| CASNo1_Ref = {{cascite|correct|ESIS}}
	| CASNo1_Comment = (<small>L</small>-isomer)
			| CASNo2 = 41247-05-6
	| CASNo1_Ref = {{cascite|correct|ESIS}}
			| CASNo2_Comment = (racemate)
	| CASNo2 = 41247-05-6
			| CASNo2_Ref = {{cascite|correct|ESIS}}
	| CASNo2_Comment = (racemate)
			| EC_number = 200-400-7 <!-- 210-174-1 for L-isomer, 255-277-2 for racemate -->
	| CASNo2_Ref = {{cascite|correct|ESIS}}
			| UNII_Ref = {{fdacite|correct|FDA}}
	| EC-number = 200-400-7 <!-- 210-174-1 for L-isomer, 255-277-2 for racemate -->
	| UNII = A1TA934AKO		| UNII = A1TA934AKO
			| UNII1_Ref = {{fdacite|correct|FDA}}
	| PubChem = 6027
			| UNII1 = A4JW0V2MYA
	| ChEMBL_Ref = {{ebicite|correct|EBI}}
			| UNII1_Comment = ({{sm|l}}-isomer)
	| ChEMBL = <!-- blanked - oldvalue: 502135 -->
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
	}}
			| ChEMBL = 502135
	| Section2 = {{Chembox Properties
			| PubChem = 135191
	| Reference=<ref>{{Merck11th|9995}}.</ref><ref>{{RubberBible62nd|page=C-574}}.</ref>
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
	| Appearance = monoclinic needles or prisms, colourless
			| ChemSpiderID = 119104
	| Formula = C<sub>5</sub>H<sub>10</sub>O<sub>5</sub>
			| SMILES = C1(((C(O1)O)O)O)O
	| Density = 1.525 g/cm<sup>3</sup> (20 °C)
			| InChI = 1/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1
	| MolarMass = 150.13 g/mol
			| InChIKey = SRBFZHDQGSBBOR-IOVATXLUBL
	| MeltingPt = 144-145 °C
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
	| SpecRotation = +22.5º (CHCl<sub>3</sub>)
			| StdInChI = 1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = SRBFZHDQGSBBOR-IOVATXLUSA-N
	}}		}}
	| Section7 = {{Chembox Hazards		|Section2={{Chembox Properties
			| Properties_ref =<ref>{{Merck11th|9995}}.</ref><ref>{{RubberBible62nd|page=C-574}}.</ref>
	| EUIndex =
			| Appearance = monoclinic needles or prisms, colourless
	| FlashPt =
			| Formula = {{chem|C|5|H|10|O|5}}
			| Density = 1.525 g/cm<sup>3</sup> (20&nbsp;°C)
			| MolarMass = 150.13 g/mol
			| MeltingPtC = 144 to 145
			| MeltingPt_notes =
			| SpecRotation = +22.5° ({{chem|C|H|Cl|3}})
			| MagSus = -84.80·10<sup>−6</sup> cm<sup>3</sup>/mol
	}}		}}
	| Section8 = {{Chembox Related		|Section7={{Chembox Hazards
			| NFPA-H = 1
	| OtherFunctn = ]<br/>]<br/>]
			| NFPA-F = 1
	| Function = ]
			| NFPA-R = 0
	| OtherCpds = ]
			| FlashPt =
			}}
			|Section8={{Chembox Related
			| OtherFunction = ]<br/>]<br/>]
			| OtherFunction_label = ]
			| OtherCompounds = ]
	}}		}}
	}}		}}
	'''Xylose''' (''cf.'' ], ''xylos'', "wood") is a sugar first isolated from wood, and named for it. Xylose is classified as a ] of the ] type, which means that it contains five ] atoms and includes an ] ]. It is the precursor to ], one of the main constituents of ]. Like most sugars, it can adopt several structures depending on conditions. With its free carbonyl group, it is a ].		'''Xylose''' ({{abbr|cf.|compare with}} {{langx|grc|ξύλον}}, {{transl|grc|xylon}}, "wood") is a sugar first isolated from wood, and named for it. Xylose is classified as a ] of the ] type, which means that it contains five ] atoms and includes an ] ]. It is derived from ], one of the main constituents of ]. Like most sugars, it can adopt several structures depending on conditions. With its free ], it is a ].
	==Structure==		==Structure==
	The ] form of xylose has ] HOCH<sub>2</sub>(]H(OH))<sub>3</sub>CHO. The cyclic ] isomers are more prevalent in solution and are of two types: the pyranoses, which feature six-membered C<sub>5</sub>O rings, and the furanoses, which feature five-membered C<sub>4</sub>O rings (with a pendant CH<sub>2</sub>OH group). Each of these rings subject to further isomerism, depending on the relative orientation of the anomeric hydroxy group.		The ] form of xylose has ] {{chem|HOCH|2|(CH(OH))|3C|H|O}}. The cyclic ] isomers are more prevalent in solution and are of two types: the ]s, which feature six-membered {{chem|C|5|O}} rings, and the ]s, which feature five-membered {{chem|C|4|O}} rings (with a pendant {{chem|CH|2|OH}} group). Each of these rings is subject to further isomerism, depending on the relative orientation of the anomeric hydroxy group.
			The ] form, {{sm|d}}-xylose, is the one that usually occurs ] in ]. A levorotary form, {{sm|l}}-xylose, can be ].
	==Occurrence==		==Occurrence==
			Xylose is the main building block for the ] ], which comprises about 30% of some plants (birch for example), far less in others (spruce and pine have about 9% xylan). Xylose is otherwise pervasive, being found in the ]s of most edible plants. It was first isolated from wood by Finnish scientist, Koch, in 1881,<ref>{{cite book |editor-first=C.S. |editor-last=Hudson |editor2-first=S.M. |editor2-last=Cantor |title=Advances in Carbohydrate Chemistry |publisher=Elsevier |date=2014 |orig-date=1950 |volume=5 |isbn=9780080562643 |pages=278 |url=https://books.google.com/books?id=rUapoxXf-v4C}}</ref> but first became commercially viable, with a price close to ], in 1930.<ref>{{cite journal |first1=Mabel M. |last1=Miller |first2=Howard B. |last2=Lewis |title=Pentose Metabolism: I. The Rate of Absorption of d-Xylose and the Formation of Glycogen in the Organism of the White Rat after Oral Administration of d-Xylose |journal=Journal of Biological Chemistry |volume=98 |issue=1 |pages=133–140 |date=1932 |doi=10.1016/S0021-9258(18)76145-0 |doi-access=free }}</ref>
	Xylose is the main building block for ], which comprises about 30% of plant matter. Xylose is otherwise pervasive, being found in the ]s of most ]. It was first isolated from wood by Koch in 1881.
	Xylose is also the first saccharide added to the ] or ] in the ] type ], and, so, it is the first saccharide in biosynthetic pathways of most anionic ]s such as ] and ].<ref>{{citation | last1 = Buskas | first2 = Sampat | last2 = Ingale | first3 = Geert-Jan | last3 = Boons | title = Glycopeptides as versatile tool for glycobiology | journal = Glycobiology | volume = 16 | issue = 8 | pages = 113R–36R | year = 2006 | doi = 10.1093/glycob/cwj125 | pmid = 16675547 | first1 = Therese}}.</ref>		Xylose is also the first saccharide added to the ] or ] in the ] type ], and, so, it is the first saccharide in biosynthetic pathways of most ] ]s such as ] and ].<ref>{{citation | last1 = Buskas | first2 = Sampat | last2 = Ingale | first3 = Geert-Jan | last3 = Boons | title = Glycopeptides as versatile tool for glycobiology | journal = Glycobiology | volume = 16 | issue = 8 | pages = 113R–36R | year = 2006 | doi = 10.1093/glycob/cwj125 | pmid = 16675547 | first1 = Therese| doi-access = free }}</ref>
			Xylose is also found in some species of Chrysolinina beetles, including ''Chrysolina coerulans''. They have ] (including xylose) in their defensive glands.<ref>{{cite book |first=E. David |last=Morgan |title=Biosynthesis in Insects |year=2004 |chapter=§ 7.3.1 Sterols in Insects |chapter-url={{google books|AbXid2E-17YC |page=112 |plainurl=yes}} |page=112 |publisher=Royal Society of Chemistry |isbn=9780854046911}}</ref>
	==Use==
	The acid-catalysed degradation of hemicellulose gives ],<ref>{{OrgSynth | title = Furfural | volume = 1 | pages = 49 | year = 1921 | collvol = 1 | collvolpages = 280 | author = Roger Adams and V. Voorhees | prep = cv1p0280}}</ref> a specialty solvent in industry and a precursor to synthetic polymers.<ref>H. E. Hoydonckx, W. M. Van Rhijn, W. Van Rhijn, D. E. De Vos, P. A. Jacobs "Furfural and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2007, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a12_119.pub2}}</ref>Xylose is not metabolised by humans. It is completely absorbed and secreted from the kidneys.
			== Applications ==
	In animal medicine, xylose is used to test for ] by administration in water to the patient after ]. If xylose is detected in ] and/or ] within the next few hours, it has been absorbed by the intestines.<ref>{{citation | url = http://www.nlm.nih.gov/medlineplus/ency/article/003606.htm | title = D-xylose absorption | work = MedlinePlus | publisher = U.S. National Library of Medicine | date = July 2008 | accessdate = 2009-09-06}}.</ref> ] of xylose by catalytic ] produces the non-cariogenic ] ].
			=== Chemicals ===
			The acid-catalysed degradation of hemicellulose gives ],<ref>{{OrgSynth | title = Furfural | volume = 1 | pages = 49 | year = 1921 | collvol = 1 | collvolpages = 280 |first= Roger |last=Adams |first2=V. |last2=Voorhees | prep = cv1p0280 |doi=10.15227/orgsyn.001.0049}}</ref><ref>{{cite journal|last=Gómez Millán |first=Gerardo|author2=Hellsten, Sanna|author3=King, Alistair W.T. |author4=Pokki, Juha-Pekka|author5=Llorca, Jordi|author6=Sixta, Herbert |title=A comparative study of water-immiscible organic solvents in the production of furfural from xylose and birch hydrolysate |journal=Journal of Industrial and Engineering Chemistry |date=25 April 2019|volume=72 |pages=354–363|doi=10.1016/j.jiec.2018.12.037|hdl=10138/307298|s2cid=104358224 |hdl-access=free}}</ref> a precursor to synthetic polymers and to ].<ref>{{Ullmann|doi=10.1002/14356007.a12_119.pub2|chapter=Furfural and Derivatives|year=2007|last1=Hoydonckx|first1=H. E.|last2=Van Rhijn|first2=W. M.|last3=Van Rhijn|first3=W.|last4=De Vos|first4=D. E.|last5=Jacobs|first5=P. A.|isbn=978-3527306732}}
			</ref>
			=== Human consumption ===
			Xylose is metabolised by humans, although it is not a major human nutrient and is largely excreted by the kidneys.<ref>{{cite thesis |url=https://repository.up.ac.za/handle/2263/27501 |title=Physiological and microbiological studies of nectar xylose metabolism in the Namaqua rock mouse, ''Aethomys namaquensis'' (A. Smith, 1834) |last=Johnson |first=S.A. |date=2007-08-24 |type=PhD |hdl=2263/27501}}</ref> Humans can obtain xylose only from their diet. An ] pathway is present in ]s. Humans have enzymes called ]s (], ]) which transfer xylose from UDP to a serine in the core protein of proteoglycans.
			Xylose contains 2.4 calories per gram<ref>{{Cite patent|title=Method of producing xylose|gdate=1999-08-06 |number=US6239274B1 |country=US |url=https://patents.google.com/patent/US6239274B1/en}}</ref> (lower than glucose or sucrose, approx. 4 calories per gram).
			=== Animal medicine ===
			In animal medicine, ] for ] by administration in water to the patient after ]. If xylose is detected in ] and/or ] within the next few hours, it has been absorbed by the intestines.<ref>{{citation | url = https://www.nlm.nih.gov/medlineplus/ency/article/003606.htm | title = D-xylose absorption | work = MedlinePlus | publisher = U.S. National Library of Medicine | date = July 2008 | access-date = 2009-09-06}}</ref>
			High xylose intake on the order of approximately 100 g/kg of animal body weight is relatively well tolerated in pigs, and in a similar manner to results from human studies, a portion of the xylose intake is passed out in urine undigested.<ref>{{cite journal |vauthors=Schutte JB, de Jong J, Polziehn R, Verstegen MW |title=Nutritional implications of D-xylose in pigs |journal=Br J Nutr |volume=66 |issue=1 |pages=83–93 |date=July 1991 |pmid=1931909 |doi=10.1079/bjn19910012 |s2cid=27670020 |doi-access=free }}</ref>
			=== Derivatives ===
			] of xylose by catalytic ] produces the ] ].
	==See also==		==See also==
			* '']''
	* ]
	* ]		* ]
	* ]		* ]
	==References==		==References==
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