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Revision as of 16:21, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits 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').		Latest revision as of 18:03, 14 January 2025 edit Frankllosa (talk | contribs)12 editsm →PharmacologyTag: Visual edit
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			{{cs1 config|name-list-style=vanc|display-authors=6}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] 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|??}}
			| ImageClass = skin-invert-image
	| ImageSize2 = 100
			| ImageSize = 160
	| ImageFile2_Name = Ball and stick model of 1,3-butanediol (S)
			| ImageName = Skeletal formula of 1,3-butanediol
	| ImageFileL1 = 1,3-Butanediol.png
			| ImageFile_Ref = {{chemboximage|correct|??}}
			| 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
			| ImageClassR1 = bg-transparent
			| 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}}
			| 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 = ]<br />		| OtherFunction = ]<br />
	]<br />		]<br />
	]		]
	| OtherCpds = ]		| OtherCompounds = ]
	}}		}}
	}}		}}
			'''1,3-Butanediol''' is an ] with the formula CH<sub>3</sub>CH(OH)CH<sub>2</sub>CH<sub>2</sub>OH, not to be confused with 1,4 Butanediol. With two alcohol functional groups, the molecule is classified as a ]. The compound without the R (or D) designation is racemic, which is what has been used in most studies before 2023. The compound is a colorless, bittersweet, water-soluble liquid. It is one of four common ]s of ].<ref name="Ullmann">{{Ullmann|doi=10.1002/14356007.a04_455|title=Butanediols, Butenediol, and Butynediol |year=2000| vauthors = Gräfje H, Körnig W, Weitz HM, Reiß W, Steffan G, Diehl, Bosche H, Schneider K, Kieczka H |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| work = Parchem Fine & Specialty Chemicals }}</ref><ref>{{cite journal | vauthors = Dymsza HA | title = Nutritional application and implication of 1,3-butanediol | journal = Federation Proceedings | volume = 34 | issue = 12 | pages = 2167–2170 | date = November 1975 | pmid = 1102338 }}</ref> It is used in grape flavoring,<ref>Dymsza HA. Nutritional application and implication of 1,3-butanediol. ''Fed Proc''. 1975 Nov;34(12):2167-70 {{PMID|1102338}}</ref> and as a precursor to some ]s.<ref>{{cite journal | vauthors = Guo X, Gao Y, Liu F, Tao Y, Jin H, Wang J, Wu S | title = A short-chain carbonyl reductase mutant is an efficient catalyst in the production of (R)-1,3-butanediol | journal = Microbial Biotechnology | volume = 16 | issue = 6 | pages = 1333–1343 | date = June 2023 | pmid = 36946330 | doi = 10.1111/1751-7915.14249 | pmc = 10221522 }}</ref>
			==Production and uses==
			Hydrogenation of ] gives 1,3-butanediol:<ref name=Ullmann2>{{Ullmann|doi=10.1002/14356007.a01_321.pub2|title=Aldehydes, Aliphatic |year=2008 | vauthors = Kohlpaintner C, Schulte M, Falbe J, Lappe P, Weber J |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-]:
			: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
			==Pharmacology==
			1,3-Butanediol has ], ] and ] action comparable to ethanol, with the (R), also known as (D), enantiomer being more active.<ref>{{cite journal | vauthors = Frye GD, Chapin RE, Vogel RA, Mailman RB, Kilts CD, Mueller RA, Breese GR | title = Effects of acute and chronic 1,3-butanediol treatment on central nervous system function: a comparison with ethanol | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 216 | issue = 2 | pages = 306–314 | date = February 1981 | pmid = 7193248 }}</ref><ref>{{cite journal | vauthors = Lowder J, Fallah S, Venditti C, Musa-Veloso K, Kotlov V | title = An open-label, acute clinical trial in adults to assess ketone levels, gastrointestinal tolerability, and sleepiness following consumption of (''R'')-1,3-butanediol (Avela™) | journal = Frontiers in Physiology | date = 2023 | volume = 14 | pages = 1195702 | pmid = 37457035 | doi = 10.3389/fphys.2023.1195702 | doi-access = free | pmc = 10338333 }}</ref> Fatty acid esters of 1,3-butanediol such as the acetoacetate, lactate or hexanoate have been researched for inducing ].<ref>{{cite journal | vauthors = Hashim SA, VanItallie TB | title = Ketone body therapy: from the ketogenic diet to the oral administration of ketone ester | journal = Journal of Lipid Research | volume = 55 | issue = 9 | pages = 1818–1826 | date = September 2014 | pmid = 24598140 | doi = 10.1194/jlr.R046599 | doi-access = free | pmc = 4617348 }}</ref><ref>{{cite journal | vauthors = Place DE, Kanneganti TD | title = Fueling Ketone Metabolism Quenches Salt-Induced Hypertension | journal = Trends in Endocrinology and Metabolism | volume = 30 | issue = 3 | pages = 145–147 | date = March 2019 | pmid = 30670332 | doi = 10.1016/j.tem.2019.01.004 }}</ref><ref>{{cite journal | vauthors = Evans M, McClure TS, Koutnik AP, Egan B | title = Exogenous Ketone Supplements in Athletic Contexts: Past, Present, and Future | journal = Sports Medicine | volume = 52 | issue = Suppl 1 | pages = 25–67 | date = December 2022 | pmid = 36214993 | doi = 10.1007/s40279-022-01756-2 | pmc = 9734240 }}</ref><ref>{{cite journal | vauthors = Mah E, Blonquist TM, Kaden VN, Beckman D, Boileau AC, Anthony JC, Stubbs BJ | title = A randomized, open-label, parallel pilot study investigating metabolic product kinetics of the novel ketone ester, bis-hexanoyl (R)-1,3-butanediol, over one week of ingestion in healthy adults | journal = Frontiers in Physiology | date = 2023 | volume = 14 | pages = 1196535 | pmid = 37427402 | doi = 10.3389/fphys.2023.1196535 | doi-access = free | pmc = 10324611 }}</ref><ref>Stubbs BJ, et al. A randomized, open-label, cross-over pilot study investigating metabolic product kinetics of the palatable novel ketone ester, bis-octanoyl (R)-1,3-butanediol, and bis-hexanoyl (R)-1,3-butanediol ingestion in healthy adults. ''Toxicology Research and Application'' 2023; {{doi|10.1177/23978473231197835}}</ref><ref>{{cite journal | vauthors = Deemer SE, Roberts BM, Smith DL, Plaisance EP, Philp A | title = Exogenous ketone esters as a potential therapeutic for treatment of sarcopenic obesity | journal = American Journal of Physiology. Cell Physiology | volume = 327 | issue = 1 | pages = C140–C150 | date = July 2024 | pmid = 38766768 | doi = 10.1152/ajpcell.00471.2023 }}</ref><ref>Ottosen RN, et al. Preparation and Preclinical Characterization of a Simple Ester for Dual Exogenous Supply of Lactate and Beta-hydroxybutyrate. ''Journal of Agricultural and Food Chemistry'' 2024; 72(36):19883–19890. {{doi|10.1021/acs.jafc.4c04849}}</ref>
			==Occurrence==
			1,3-Butanediol has been detected in green bell peppers, orange bell peppers, pepper ('']''), red bell peppers, and yellow bell peppers.<ref>{{Cite web | work = Human Metabolome Database | title = Metabocard for 1,3-Butanediol | id = HMDB0031320 |url=https://hmdb.ca/metabolites/HMDB0031320 |access-date=2022-05-12 }}</ref> 1,3 Butanediol, | quote = 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-}}
			]