 | |
| Names | |
|---|---|
| Preferred IUPAC name
Octane-1,8-diol | |
| Other names
1,8-Octanediol
Octamethylene glycol 1,8-Dihydroxyoctane | |
| Identifiers | |
| |
3D model (JSmol)
|
|
| 1633499 | |
| ChEBI | |
| ChemSpider |
|
| ECHA InfoCard | 100.010.083 |
| EC Number |
|
| 1524772 | |
| KEGG |
|
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C8H18O2 | |
| Molar mass | 146.227 g/mol |
| Appearance | White solid1 |
| Melting point | 57 to 61 °C (135 to 142 °F; 330 to 334 K) |
| Boiling point | 278.8 °C at 760 mmHg; 172 °C (342 °F; 445 K) at 20 mmHg |
| Slightly soluble1 | |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Flash point | 148 °C (298 °F; 421 K) |
| Safety data sheet (SDS) | GFS Chemicals, Inc. MSDS |
| Related compounds | |
Related compounds
|
1,9-Nonanediol 1,7-Heptanediol 1,2-Octanediol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
1,8-Octanediol, also known as octamethylene glycol, is a diol with the molecular formula HO(CH2)8OH, a white solid. It can be produced with high purity by hydrogenation of esters of suberic acid.2: 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).3
1,8-Octanediol dihexanoate strongly attracts adult male Parallelostethus attenuatus click beetles, and the pheromone of this species may consist entirely of this compound.4
Applications
Cosmetics
It is sometimes an ingredient of cosmetics as a plasticizer.5
As with other fatty alcohols, octane-1,8-diol is used in cosmetics as an emollient and humectant.
Polymers
1,8-Octanediol is used as a monomer in the synthesis of some polymers such as polyesters6 and polyurethanes.
For example, poly(octanediol-co-citrate) is a biodegradable polymer that can be made antibacterial for biomedical applications.7 This polymer, abbreviated POC89 and also sometimes called poly(octamethylene-citrate),9 is promising as a biocompatible and biodegradable polymer, and has been extensively investigated in relation to soft tissue engineering.8
A polymer created from 1,8-octanediol, citric acid, and sebacic acid, called polyoctanediol citrate/sebacate [p(OCS)], has also been synthesized.10
References
References
- "1,8-Octanediol, 98+%, Safety Data Sheet". Thermo Fisher Scientific. 10 February 2024. Archived from the original on 29 April 2025. Retrieved 29 April 2025.
- Noweck, Klaus; Grafahrend, Wolfgang (2006). "Fatty Alcohols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_277.pub2. ISBN 978-3-527-30673-2.
- Velliadou, Danai; Antoniadis, Konstantinos D.; Assimopoulou, Andreana N.; Assael, Marc J.; Sequeira, Maria Carolina Margarido; Wakeham, William A. (2023-04-03). "Accurate Measurements of the Thermal Conductivity of n-Docosane, n-Tetracosane, 1,6-Hexanediol, and 1,8-Octanediol in the Solid and Liquid Phases". International Journal of Thermophysics. 44 (5): 78. Bibcode:2023IJT....44...78V. doi:10.1007/s10765-023-03182-6. ISSN 1572-9567.
- Millar, Jocelyn G.; Williams, Livy; Serrano, Jacqueline M.; Halloran, Sean; Grommes, Anna C.; Huseth, Anders S.; Kuhar, Thomas P.; Hanks, Lawrence M. (August 2022). "A Symmetrical Diester as the Sex Attractant Pheromone of the North American Click Beetle Parallelostethus attenuatus (Say) (Coleoptera: Elateridae)". Journal of Chemical Ecology. 48 (7–8): 598–608. Bibcode:2022JCEco..48..598M. doi:10.1007/s10886-022-01360-8. hdl:10919/109769. ISSN 1573-1561. PMID 35397045.
- Scott, Laura N.; Fiume, Monice; Bergfeld, Wilma F.; Belsito, Donald V.; Hill, Ronald A.; Klaassen, Curtis D.; Liebler, Daniel C.; Marks, James G.; Shank, Ronald C.; Slaga, Thomas J.; Snyder, Paul W.; Heldreth, Bart (2024-04-01). "Safety Assessment of Alkane Diols as Used in Cosmetics". International Journal of Toxicology. 43 (2_suppl): 70S–131S. doi:10.1177/10915818231224234. ISSN 1091-5818. PMID 38174390.
- Qin, Jisong; Cheng, Zhengzai; Djouonkep, Lesly Dasilva Wandji; Gauthier, Mario (2024-10-08). "Polyesters derived from 4,4'-dixydroxybenzophenone: syntheses and properties". Iranian Polymer Journal. 34 (4): 485–497. doi:10.1007/s13726-024-01392-9. ISSN 1026-1265.
- García-Argüelles, Sara; Serrano, M. Concepción; Gutiérrez, María C.; Ferrer, M. Luisa; Yuste, Luis; Rojo, Fernando; del Monte, Francisco (2013-07-30). "Deep Eutectic Solvent-Assisted Synthesis of Biodegradable Polyesters with Antibacterial Properties". Langmuir. 29 (30): 9525–9534. doi:10.1021/la401353r. ISSN 0743-7463. PMID 23808373.
- Ren, Hui-Hui; Zhao, Hui-Yu; Cui, Yang; Ao, Xiang; Li, Ai-Ling; Zhang, Zhong-Min; Qiu, Dong (2017-11-01). "Poly(1,8-octanediol citrate)/bioactive glass composite with improved mechanical performance and bioactivity for bone regeneration". Chinese Chemical Letters. SI: Young Scientists in Material Chemistry. 28 (11): 2116–2120. doi:10.1016/j.cclet.2017.07.014. ISSN 1001-8417.
- Guo, Furong; Liang, Kai; Ji, Yali (2024-06-01). "Electrospun poly(octamethylene citrate) thermoset fibrous mat from chitin nanocrystal constructed Pickering emulsion". Colloid and Polymer Science. 302 (6): 891–900. doi:10.1007/s00396-024-05238-x. ISSN 1435-1536.
- Djordjevic, Ivan; Choudhury, Namita Roy; Dutta, Naba K.; Kumar, Sunil (2009-03-20). "Synthesis and characterization of novel citric acid-based polyester elastomers". Polymer. 50 (7): 1682–1691. doi:10.1016/j.polymer.2009.01.045. ISSN 0032-3861.