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Saving copy of the {{chembox}} taken from revid 477202237 of page 1,3-Butanediol for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL', 'ChEBI', 'StdInChI', 'StdInChIKey').
 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:1,3-Butanediol|oldid=477202237}} 477202237] of page [[1,3-Butanediol]] with values updated to verified values.}}
{{Chembox
{{Chembox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477185706
| verifiedrevid = 477205091
⚫
| ImageFile2 = 1,3-Butanediol-3D-balls.png
⚫
| ImageFile = 1,3-Butanediol.png
⚫
| ImageFile2_Ref = {{chemboximage|correct|??}}
| ImageSize2 = 100
| ImageSize = 160
| ImageFile2_Name = Ball and stick model of 1,3-butanediol (S)
| ImageName = Skeletal formula of 1,3-butanediol
⚫
| ImageFile_Ref = {{chemboximage|correct|??}}
⚫
| ImageFileL1 = 1,3-Butanediol.png
⚫
| ImageFileL1 = 1,3-Butanediol-3D-balls.png
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1_Name = Skeletal formula of 1,3-butanediol
| ImageNameL1 = Ball and stick model of 1,3-butanediol (S)
| ImageFileR1 = 1,3-Butanediol-3D-spacefill.png
| ImageFileR1 = 1,3-Butanediol-3D-spacefill.png
⚫
| ImageNameR1 = Spacefill model of 1,3-butanediol (S)
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| PIN = Butane-1,3-diol
⚫
| ImageFileR1_Name = Spacefill model of 1,3-butanediol (S)
| OtherNames = 1,3-butylene glycol, butane-1,3-diol, or 1,3-dihydroxybutane
| IUPACName = Butane-1,3-diol<ref>{{Cite web|title = 1,3-butylene glycol - Compound Summary|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7896|work = PubChem Compound|publisher = National Center for Biotechnology Information|accessdate = 7 October 2011|location = USA|date = 26 March 2005|at = Identification and Related Records}}</ref>
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 107-88-0
| CASNo = 107-88-0
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo1_Ref = {{cascite|correct|??}}
| CASNo1 = 6290-03-5
| CASNo1_Comment = <small>(''R'')</small>
| CASNo1 = 6290-03-5
| CASNo1_Comment = <small>(''R'')</small>
| CASNo2_Ref = {{cascite|correct|??}}
| CASNo2 = 24621-61-2
| CASNo2_Comment = <small>(''S'')</small>
| CASNo2 = 24621-61-2
| CASNo2_Comment = <small>(''S'')</small>
| PubChem = 7896
| PubChem = 7896
⚫
| PubChem1 = 637497
| PubChem_Ref = {{Pubchemcite|correct|pubchem}}
⚫
| PubChem1_Comment = <small>(''R'')</small>
⚫
| PubChem1 = 637497
| PubChem2 = 446973
| PubChem1_Ref = {{Pubchemcite|correct|PubChem}}
| PubChem1_Comment = <small>(''R'')</small>
| PubChem2_Comment = <small>(''S'')</small>
| PubChem2 = 446973
| ChemSpiderID = 7608
| PubChem2_Ref = {{Pubchemcite|correct|PubChem}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫
| ChemSpiderID1 = 553103
⚫
| PubChem2_Comment = <small>(''S'')</small>
⚫
| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7608
⚫
| ChemSpiderID1_Comment = <small>(''R'')</small>
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫
| ChemSpiderID2 = 394191
⚫
| ChemSpiderID1 = 553103
| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1_Comment = <small>(''R'')</small>
| ChemSpiderID2_Comment = <small>(''S'')</small>
| UNII = 3XUS85K0RA
⚫
| ChemSpiderID2 = 394191
| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| EINECS = 203-529-7
⚫
| ChemSpiderID2_Comment = <small>(''S'')</small>
| UNII = 3XUS85K0RA
| DrugBank = DB02202
| UNII_Ref = {{fdacite|correct|FDA}}
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
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| MeSHName = 1,3-Butylene+glycol
⚫
| EINECS = 203-529-7
| ChEBI = 52683
| DrugBank = <!-- blanked - oldvalue: DB02202 -->
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1231503
⚫
| MeSHName = 1,3-Butylene+glycol
⚫
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEBI = <!-- blanked - oldvalue: 52683 -->
| ChEBI_Ref = {{ebicite|changed|EBI}}
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D10695
| ChEMBL = <!-- blanked - oldvalue: 1231503 -->
⚫
| RTECS = EK0440000
⚫
| ChEMBL_Ref = {{ebicite|changed|EBI}}
⚫
| Beilstein = 1731276<br />
⚫
| RTECS = EK0440000
⚫
| Beilstein = 1731276<br />
1718944 <small>(''R'')</small><br />
1718944 <small>(''R'')</small><br />
1718943 <small>(''S'')</small>
1718943 <small>(''S'')</small>
| Gmelin = 2409<br />
| Gmelin = 2409<br />
2493173 <small>(''R'')</small><br />
2493173 <small>(''R'')</small><br />
1994384 <small>(''S'')</small>
1994384 <small>(''S'')</small>
| SMILES = CC(O)CCO
| SMILES = CC(O)CCO
| StdInChI = <!-- blanked - oldvalue: 1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3 -->
| StdInChI = 1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = <!-- blanked - oldvalue: PUPZLCDOIYMWBV-UHFFFAOYSA-N -->
| StdInChIKey = PUPZLCDOIYMWBV-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C = 4
| C=4 | H=10 | O=2
⚫
| Appearance = Colourless liquid
⚫
| H = 10
⚫
| Density = 1.0053 g cm<sup>−3</sup>
⚫
| O = 2
| MeltingPtC = −50
| ExactMass = 90.068079564 g mol<sup>−1</sup>
| BoilingPtK = 477 to 483
⚫
| Appearance = Colourless liquid
| Density = 1.0053 g cm<sup>−3</sup>
| Solubility = 1 kg dm<sup>−3</sup>
| MeltingPtCL = −50
| LogP = −0.74
⚫
| VaporPressure = 8 Pa (at 20 °C)
| BoilingPtKL = 477
| BoilingPtKH = 483
| RefractIndex = 1.44
⚫
| Solubility = 1 kg dm<sup>−3</sup>
| LogP = −0.74
⚫
| VaporPressure = 8 Pa (at 20 °C)
| RefractIndex = 1.44
}}
}}
| Section3 = {{Chembox Thermochemistry
|Section3={{Chembox Thermochemistry
| DeltaHf = −501 kJ mol<sup>−1</sup>
| DeltaHf = −501 kJ mol<sup>−1</sup>
| DeltaHc = −2.5022 MJ mol<sup>−1</sup>
| DeltaHc = −2.5022 MJ mol<sup>−1</sup>
| Entropy = 227.2 J K<sup>−1</sup> mol<sup>−1</sup>
| Entropy = 227.2 J K<sup>−1</sup> mol<sup>−1</sup>
}}
}}
| Section4 = {{Chembox Hazards
|Section4={{Chembox Hazards
| GHSPictograms = {{GHS exclamation mark}}
| GHSPictograms = {{GHS exclamation mark}}
| GHSSignalWord = '''WARNING'''
| GHSSignalWord = '''WARNING'''
| HPhrases = {{H-phrases|319|413}}
| HPhrases = {{H-phrases|319|413}}
| PPhrases = {{P-phrases|305+351+338}}
| PPhrases = {{P-phrases|305+351+338}}
⚫
| NFPA-H = 1
| EUClass = {{Hazchem Xi}}
⚫
| NFPA-F = 1
| RPhrases = {{R36/37/38}}
⚫
| NFPA-R = 0
| SPhrases = {{S26}}, {{S36}}
| NFPA-H = 1
| FlashPtC = 108
| NFPA-F = 1
| AutoignitionPtC = 394
⚫
| NFPA-R = 0
| FlashPt = 108 °C
| Autoignition = 394 °C
}}
}}
| Section5 = {{Chembox Related
|Section5={{Chembox Related
| Function = butanediol
| OtherFunction_label = butanediol
| OtherFunctn = [[1,2-Butanediol]]<br />
| OtherFunction = [[1,2-Butanediol]]<br />
[[1,4-Butanediol]]<br />
[[1,4-Butanediol]]<br />
[[2,3-Butanediol]]
[[2,3-Butanediol]]
| OtherCpds = [[2-Methylpentane]]
| OtherCompounds = [[2-Methylpentane]]
}}
}}
}}
}}

'''1,3-Butanediol''' is an [[organic compound]] with the formula CH<sub>3</sub>CH(OH)CH<sub>2</sub>CH<sub>2</sub>OH. With two alcohol functional groups, the molecule is classified as a [[diol]]. The compound is also chiral, but most studies do not distinguish the enantiomers. The compound is a colorless, bittersweet, water-soluble liquid. It is one of four common [[structural isomer]]s of [[butanediol]].<ref name="Ullmann">{{Ullmann|doi=10.1002/14356007.a04_455|title=Butanediols, Butenediol, and Butynediol|year=2000|last1=Gräfje|first1 =Heinz|last2=Körnig|first2=Wolfgang|last3=Weitz|first3=Hans-Martin|last4= Reiß|first4=Wolfgang|last5=Steffan|first5=Guido|last6=Diehl|first6=Herbert|last7=Bosche|first7=Horst|last8=Schneider|first8=Kurt|last9=Kieczka|first9=Heinz|isbn=9783527306732}}</ref><ref>{{Cite web|url=https://www.parchem.com/chemical-supplier-distributor/1-3-butylene-glycol-000246.aspx|title=1,3 Butylene Glycol|last=Parchem|first=fine & specialty chemicals|date=|website=|access-date=}}</ref> It is used in flavoring.

==Production and uses==
Hydrogenation of [[3-Hydroxybutanal|3-hydroxybutanal]] gives 1,3-butanediol:<ref name=Ullmann2>{{Ullmann|doi=10.1002/14356007.a01_321.pub2|title=Aldehydes, Aliphatic|year=2008|last1=Kohlpaintner|first1=Christian|last2=Schulte|first2=Markus|last3=Falbe|first3=Jürgen|last4=Lappe|first4=Peter|last5=Weber|first5=Jürgen|isbn=978-3527306732}}</ref>
:CH<sub>3</sub>CH(OH)CH<sub>2</sub>CHO + H<sub>2</sub> → CH<sub>3</sub>CH(OH)CH<sub>2</sub>CH<sub>2</sub>OH
Dehydration of 1,3-butanediol gives 1,3-[[butadiene]]:
:CH<sub>3</sub>CH(OH)CH<sub>2</sub>CH<sub>2</sub>OH → CH<sub>2</sub>=CH-CH=CH<sub>2</sub> + 2{{nbsp}}H<sub>2</sub>O

==Occurrence==
1,3-Butanediol is used as a [[hypoglycaemia|hypoglycaemic]] agent.

1,3-Butanediol has been detected in green bell peppers, orange bell peppers, pepper (''[[Capsicum annuum]]''), red bell peppers, and yellow bell peppers.<ref>{{Cite web |title=Human Metabolome Database: Showing metabocard for 1,3-Butanediol (HMDB0031320) |url=https://hmdb.ca/metabolites/HMDB0031320 |access-date=2022-05-12 |website=hmdb.ca}}</ref> 1,3 Butanediol, also referred to as 1,3-Butylene glycol, maintains FDA GRAS status as a flavor molecule.<ref>{{Cite web |title=FDA GRAS for 1,3 Butanediol for flavoring CFR - Code of Federal Regulations Title 21 |url=https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=173.220 |access-date=2022-05-12 |website=www.accessdata.fda.gov}}</ref>

==References==
{{Reflist}}

{{DEFAULTSORT:Butanediol, 1,3-}}
[[Category:Alkanediols]]
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