1,8-Octanediol
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 424674445
| ImageFile = 1,8-Octanediol.svg
| PIN = Octane-1,8-diol
| OtherNames = 1,8-Octanediol
Octamethylene glycol
1,8-Dihydroxyoctane
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=629-41-4
| Beilstein = 1633499
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 44630
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 62628
| EINECS=214-254-7
| Gmelin = 1524772
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14218
| PubChem=69420
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 806K32R50Z
| SMILES=OCCCCCCCCO
| InChI = 1/C8H18O2/c9-7-5-3-1-2-4-6-8-10/h9-10H,1-8H2
| InChIKey = OEIJHBUUFURJLI-UHFFFAOYAW
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C8H18O2/c9-7-5-3-1-2-4-6-8-10/h9-10H,1-8H2
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = OEIJHBUUFURJLI-UHFFFAOYSA-N
| RTECS =
| MeSHName =
}}
|Section2={{Chembox Properties
| C=8 | H=18 | O=2
| MolarMass = 146.227 g/mol
| Appearance = White solid{{Cite web |title=1,8-Octanediol, 98+%, Safety Data Sheet |work=Thermo Fisher Scientific |date=10 February 2024 |access-date=29 April 2025 |url= https://assets.thermofisher.com/DirectWebViewer/private/document.aspx?prd=ALFAAA15402~~PDF~~MTR~~CLP1~~EN~~2024-03-25%2017:36:27~~1%208-Octanediol~~ |archive-url=https://web.archive.org/web/20250429121437/https://assets.thermofisher.com/DirectWebViewer/private/document.aspx?prd=ALFAAA15402~~PDF~~MTR~~CLP1~~EN~~2024-03-25%2017:36:27~~1%208-Octanediol~~ |archive-date=29 April 2025 }}
| MeltingPtC=57 to 61
| BoilingPt = 278.8 °C at 760 mmHg;
| BoilingPtC = 172
| BoilingPt_notes = at 20 mmHg
| Solubility = Slightly soluble
}}
|Section7={{Chembox Hazards
| FlashPtC = 148
| NFPA-H = 1
| NFPA-F = 0
| NFPA-R = 0
| NFPA-S =
| ExternalSDS = [http://www.gfschemicals.com/Search/MSDS/3250MSDS.PDF GFS Chemicals, Inc. MSDS]
}}
|Section8={{Chembox Related
| OtherCompounds = 1,9-Nonanediol
1,7-Heptanediol
1,2-Octanediol
}}
}}
1,8-Octanediol, also known as octamethylene glycol, is a diol with the molecular formula HO(CH{{sub|2}}){{sub|8}}OH, a white solid. It can be produced with high purity by hydrogenation of esters of suberic acid.{{Ullmann|first1=Klaus|last1=Noweck|first2=Wolfgang|last2=Grafahrend|title=Fatty Alcohols|year=2006|doi=10.1002/14356007.a10_277.pub2}}{{Rp|page=133}}
1,8-Octanediol, which has a low melting temperature, can be found at high purity for relatively low cost. These characteristics are ideal for a reference material at moderate temperature in the context of solid-liquid Phase-Changing Materials (PCMs).{{Cite journal |last=Velliadou |first=Danai |last2=Antoniadis |first2=Konstantinos D. |last3=Assimopoulou |first3=Andreana N. |last4=Assael |first4=Marc J. |last5=Sequeira |first5=Maria Carolina Margarido |last6=Wakeham |first6=William A. |date=2023-04-03 |title=Accurate Measurements of the Thermal Conductivity of n-Docosane, n-Tetracosane, 1,6-Hexanediol, and 1,8-Octanediol in the Solid and Liquid Phases |url=https://link.springer.com/article/10.1007/s10765-023-03182-6 |journal=International Journal of Thermophysics |language=en |volume=44 |issue=5 |pages=78 |doi=10.1007/s10765-023-03182-6 |issn=1572-9567|doi-access=free }}
1,8-Octanediol dihexanoate strongly attracts adult male Parallelostethus attenuatus click beetles, and the pheromone of this species may consist entirely of this compound.{{Cite journal |last=Millar |first=Jocelyn G. |last2=Williams |first2=Livy |last3=Serrano |first3=Jacqueline M. |last4=Halloran |first4=Sean |last5=Grommes |first5=Anna C. |last6=Huseth |first6=Anders S. |last7=Kuhar |first7=Thomas P. |last8=Hanks |first8=Lawrence M. |date=August 2022 |title=A Symmetrical Diester as the Sex Attractant Pheromone of the North American Click Beetle Parallelostethus attenuatus (Say) (Coleoptera: Elateridae) |url=https://pubmed.ncbi.nlm.nih.gov/35397045/ |journal=Journal of Chemical Ecology |volume=48 |issue=7-8 |pages=598–608 |doi=10.1007/s10886-022-01360-8 |issn=1573-1561 |pmid=35397045|hdl=10919/109769 |hdl-access=free }}
Applications
= Cosmetics =
It is sometimes an ingredient of cosmetics as a plasticizer.{{Cite journal |last=Scott |first=Laura N. |last2=Fiume |first2=Monice |last3=Bergfeld |first3=Wilma F. |last4=Belsito |first4=Donald V. |last5=Hill |first5=Ronald A. |last6=Klaassen |first6=Curtis D. |last7=Liebler |first7=Daniel C. |last8=Marks |first8=James G. |last9=Shank |first9=Ronald C. |last10=Slaga |first10=Thomas J. |last11=Snyder |first11=Paul W. |last12=Heldreth |first12=Bart |date=2024-04-01 |title=Safety Assessment of Alkane Diols as Used in Cosmetics |url=https://journals.sagepub.com/doi/10.1177/10915818231224234 |journal=International Journal of Toxicology |language=en |volume=43 |issue=2_suppl |pages=70S–131S |doi=10.1177/10915818231224234 |issn=1091-5818|url-access=subscription }}
As with other fatty alcohols, octane-1,8-diol is used in cosmetics as an emollient and humectant.{{Citation needed|date=March 2025}}
= Polymers =
1,8-Octanediol is used as a monomer in the synthesis of some polymers such as polyesters{{Cite journal |last=Qin |first=Jisong |last2=Cheng |first2=Zhengzai |last3=Djouonkep |first3=Lesly Dasilva Wandji |last4=Gauthier |first4=Mario |date=2024-10-08 |title=Polyesters derived from 4,4’-dixydroxybenzophenone: syntheses and properties |url=https://link.springer.com/10.1007/s13726-024-01392-9 |journal=Iranian Polymer Journal |language=en |doi=10.1007/s13726-024-01392-9 |issn=1026-1265|url-access=subscription }} and polyurethanes.{{Citation needed|date=March 2025}}
For example, poly(octanediol-co-citrate) is a biodegradable polymer that can be made antibacterial for biomedical applications.{{Cite journal |last=García-Argüelles |first=Sara |last2=Serrano |first2=M. Concepción |last3=Gutiérrez |first3=María C. |last4=Ferrer |first4=M. Luisa |last5=Yuste |first5=Luis |last6=Rojo |first6=Fernando |last7=del Monte |first7=Francisco |date=2013-07-30 |title=Deep Eutectic Solvent-Assisted Synthesis of Biodegradable Polyesters with Antibacterial Properties |url=https://pubs.acs.org/doi/10.1021/la401353r |journal=Langmuir |volume=29 |issue=30 |pages=9525–9534 |doi=10.1021/la401353r |issn=0743-7463|url-access=subscription }} This polymer, abbreviated POC{{Cite journal |last=Ren |first=Hui-Hui |last2=Zhao |first2=Hui-Yu |last3=Cui |first3=Yang |last4=Ao |first4=Xiang |last5=Li |first5=Ai-Ling |last6=Zhang |first6=Zhong-Min |last7=Qiu |first7=Dong |date=2017-11-01 |title=Poly(1,8-octanediol citrate)/bioactive glass composite with improved mechanical performance and bioactivity for bone regeneration |url=https://www.sciencedirect.com/science/article/abs/pii/S1001841717302590 |journal=Chinese Chemical Letters |series=SI: Young Scientists in Material Chemistry |volume=28 |issue=11 |pages=2116–2120 |doi=10.1016/j.cclet.2017.07.014 |issn=1001-8417|url-access=subscription }}{{Cite journal |last=Guo |first=Furong |last2=Liang |first2=Kai |last3=Ji |first3=Yali |date=2024-06-01 |title=Electrospun poly(octamethylene citrate) thermoset fibrous mat from chitin nanocrystal constructed Pickering emulsion |url=https://link.springer.com/article/10.1007/s00396-024-05238-x |journal=Colloid and Polymer Science |language=en |volume=302 |issue=6 |pages=891–900 |doi=10.1007/s00396-024-05238-x |issn=1435-1536|url-access=subscription }} and also sometimes called poly(octamethylene-citrate), is promising as a biocompatible and biodegradable polymer, and has been extensively investigated in relation to soft tissue engineering.
A polymer created from 1,8-octanediol, citric acid, and sebacic acid, called polyoctanediol citrate/sebacate [p(OCS)], has also been synthesized.{{Cite journal |last=Djordjevic |first=Ivan |last2=Choudhury |first2=Namita Roy |last3=Dutta |first3=Naba K. |last4=Kumar |first4=Sunil |date=2009-03-20 |title=Synthesis and characterization of novel citric acid-based polyester elastomers |url=https://www.sciencedirect.com/science/article/abs/pii/S0032386109000834 |journal=Polymer |volume=50 |issue=7 |pages=1682–1691 |doi=10.1016/j.polymer.2009.01.045 |issn=0032-3861|url-access=subscription }}
= Synthesis =
It can also be used in the synthesis of PCE.{{Cite journal |last=Wang |first=Lin |last2=Huang |first2=Tengxiao |last3=Xu |first3=Xiaowei |last4=Bu |first4=Nitong |last5=Wu |first5=Zhenzhen |last6=Zhao |first6=Yunpeng |last7=Zhou |first7=Ya-Qin |last8=Chen |first8=Su |last9=Chen |first9=Yong |last10=Pang |first10=Jie |date=February 2025 |title=Robust Dual Equivariant Gradient Antibacterial Wound Dressing-Loaded Artificial Skin with Nano-chitin Particles Via an Electrospinning-Reactive Strategy |url=https://link.springer.com/10.1007/s42765-024-00476-8 |journal=Advanced Fiber Materials |language=en |volume=7 |issue=1 |pages=204–218 |doi=10.1007/s42765-024-00476-8 |issn=2524-7921|url-access=subscription }}