View source for 1,3-Butanediol

{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477205091
| ImageFile = 1,3-Butanediol.png
| ImageClass = skin-invert-image
| ImageSize = 160
| ImageName = Skeletal formula of 1,3-butanediol
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFileL1 = 1,3-Butanediol-3D-balls.png
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageNameL1 = Ball and stick model of 1,3-butanediol (S)
| ImageFileR1 = 1,3-Butanediol-3D-spacefill.png
| ImageClassR1 = bg-transparent
| ImageNameR1 = Spacefill model of 1,3-butanediol (S)
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| PIN = Butane-1,3-diol
| OtherNames = 1,3-butylene glycol, butane-1,3-diol, or 1,3-dihydroxybutane
|Section1={{Chembox Identifiers
| CASNo = 107-88-0
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo1_Ref = {{cascite|correct|??}}
| CASNo1 = 6290-03-5
| CASNo1_Comment = <small>(''R'')</small>
| CASNo2_Ref = {{cascite|correct|??}}
| CASNo2 = 24621-61-2
| CASNo2_Comment = <small>(''S'')</small>
| PubChem = 7896
| PubChem1 = 637497
| PubChem1_Comment = <small>(''R'')</small>
| PubChem2 = 446973
| PubChem2_Comment = <small>(''S'')</small>
| ChemSpiderID = 7608
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1 = 553103
| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1_Comment = <small>(''R'')</small>
| ChemSpiderID2 = 394191
| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID2_Comment = <small>(''S'')</small>
| UNII = 3XUS85K0RA
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 203-529-7
| DrugBank = DB02202
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| MeSHName = 1,3-Butylene+glycol
| ChEBI = 52683
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1231503
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D10695
| RTECS = EK0440000
| Beilstein = 1731276<br />
1718944 <small>(''R'')</small><br />
1718943 <small>(''S'')</small>
| Gmelin = 2409<br />
2493173 <small>(''R'')</small><br />
1994384 <small>(''S'')</small>
| SMILES = CC(O)CCO
| StdInChI = 1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = PUPZLCDOIYMWBV-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
}}
|Section2={{Chembox Properties
| C=4 | H=10 | O=2 
| Appearance = Colourless liquid
| Density = 1.0053 g cm<sup>−3</sup>
| MeltingPtC = −50
| BoilingPtK = 477 to 483
| Solubility = 1 kg dm<sup>−3</sup>
| LogP = −0.74
| VaporPressure = 8 Pa (at 20 °C)
| RefractIndex = 1.44
}}
|Section3={{Chembox Thermochemistry
| DeltaHf = −501 kJ mol<sup>−1</sup>
| DeltaHc = −2.5022 MJ mol<sup>−1</sup>
| Entropy = 227.2 J K<sup>−1</sup> mol<sup>−1</sup>
}}
|Section4={{Chembox Hazards
| GHSPictograms = {{GHS exclamation mark}}
| GHSSignalWord = '''WARNING'''
| HPhrases = {{H-phrases|319|413}}
| PPhrases = {{P-phrases|305+351+338}}
| NFPA-H = 1
| NFPA-F = 1
| NFPA-R = 0
| FlashPtC = 108
| AutoignitionPtC = 394
}}
|Section5={{Chembox Related
| OtherFunction_label = butanediol
| OtherFunction = [[1,2-Butanediol]]<br />
[[1,4-Butanediol]]<br />
[[2,3-Butanediol]]
| 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, not to be confused with 1,4 Butanediol. With two alcohol functional groups, the molecule is classified as a [[diol]]. 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 [[structural isomer]]s of [[butanediol]].<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 [[antibiotic]]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 [[3-Hydroxybutanal|3-hydroxybutanal]] 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-[[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

==Pharmacology==
1,3-Butanediol has [[sedative]], [[hypotensive]] and [[hypoglycaemia|hypoglycaemic]] 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 | doi = 10.1016/S0022-3565(25)32419-5 | 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 [[ketogenesis]].<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> Recent research highlights the stereospecific metabolism of (R)-1,3-butanediol, emphasizing its efficient conversion to β-hydroxybutyrate via alcohol dehydrogenase. This process involves zinc coordination and maintains cellular redox balance. Notably, (R)-1,3-butanediol induces mild euphoric effects through ketone body signaling pathways, distinct from the GABAergic mechanisms associated with ethanol.<ref name="Ryan2025">{{cite journal |last=Ryan |first=Patrick |title=R-1,3-Butanediol – Structure, Metabolism, and Biological Roles |date=April 27, 2025 |url=http://dx.doi.org/10.2139/ssrn.5233047 |journal=SSRN Electronic Journal}}</ref>

==Occurrence==
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 | 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 |archive-url=https://web.archive.org/web/20030915175357/http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?FR=173.220 |url-status=dead |archive-date=September 15, 2003 |access-date=2022-05-12 |website=www.accessdata.fda.gov}}</ref>

==Biochemistry==

The metabolism of (R)-1,3-butanediol is compartmentalized within hepatic cells, occurring in both cytosolic and mitochondrial domains. Enzymatic studies have quantified the distribution of alcohol dehydrogenase isoforms involved in its conversion to β-hydroxybutyrate, underscoring the molecule's potential in therapeutic ketone body production.<ref name="Ryan2025" />

== References ==
{{Reflist}}

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