2-Ethylhexanol

changed changed 477213343 2-Ethylhexanol 2D.svg 180 Skeletal formula of 2-ethylhexanol skin-invert 2-Ethylhexanol-3D-balls.png 180 2-Ethylhexanol molecule bg-transparent 2-Ethylhexan-1-ol2-ethylhexanol - Compound Summary https://pubchem.ncbi.nlm.nih.gov/compound/7720 PubChem Compound National Center for Biotechnology Information 29 January 2012 USA 16 September 2005 Identification and Related Records isooctyl alcohol, 2-ethylhexanol 104-76-7 correct CAS 7720 6991979 (R enantiomer) 6991980 (S enantiomer) 7434 correct chemspider 5360145 correct chemspider (R enantiomer) 5360146 correct chemspider (S enantiomer) XZV7TAA77P correct FDA 203-234-3 C02498 changed kegg 2-ethylhexanol 16011 correct EBI 31637 correct EBI 1229918 correct EBI 1719280 CCCCC(CC)CO 1S/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3 correct chemspider YIWUKEYIRIRTPP-UHFFFAOYSA-N correct chemspider 8 18 1 Colourless liquid 833 mg/mL −76 453 to 459 2.721 30 Pa (at 20 °C) 1.431 −433.67–−432.09 kJ/mol −5.28857–−5.28699 MJ/mol 347.0 J/(K·mol) 317.5 J/(K·mol) Mildly toxic exclamation mark DANGER 302 312 315 318 335 261 280 305+351+338 81 290 0.88–9.7% 1.97 g/kg (dermal, rabbit) 3.73 g/kg (oral, rat) N.D.0354 none TWA 50 ppm (270 mg/m3) (skin) alkanol Propylheptyl alcohol 2-Methylhexane 3-Methylhexane Valnoctamide 2-Methylheptane 3-Methylheptane Valpromide 2-Ethylhexanoic acid 2-Ethylhexanol (abbreviated 2-EH) is an organic compound with the chemical formula CH3CH2CH2CH2CH(CH2CH3)CH2OH 1. It is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a large scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers. It is encountered in plants, fruits, and wines.10.1021/jf052635t Characterization of Aroma Compounds of Chinese "Wuliangye" and "Jiannanchun" Liquors by Aroma Extract Dilution Analysis 2006 Fan Wenlai Qian Michael C. Journal of Agricultural and Food Chemistry 54 7 2695–2704 16569063 2006JAFC...54.2695F 10.1007/s00217-012-1757-0 Identification of aroma-active compounds in 'wonderful' pomegranate fruit using solvent-assisted flavour evaporation and headspace solid-phase micro-extraction methods 2012 Mayuoni-Kirshinbaum Lina Tietel Zipora Porat Ron Ulrich Detlef European Food Research and Technology 235 2 277–283 97102092 The odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer and "a light, sweet floral fragrance" for the S enantiomer.Klaus Rettinger Christian Burschka Peter Scheeben Heike Fuchs Armin Mosandl Chiral 2-alkylbranched acids, esters and alcohols. Preparation and stereospecific flavour evaluation Tetrahedron: Asymmetry 1991 2 10 965–968 10.1016/S0957-4166(00)86137-6 https://opus.bibliothek.uni-wuerzburg.de/files/4494/Burschka_Esters.pdf10.1016/j.fct.2010.05.042 Fragrance material review on 2-ethyl-1-hexanol 2010 McGinty D. Scognamiglio J. Letizia C.S. Api A.M. Food and Chemical Toxicology 48 S115–S129 20659633 Properties and applications The branching in 2-ethylhexanol inhibits crystallization. Esters of 2-ethylhexanol are similarly affected, which together with low volatility, is the basis of applications in the production of plasticizers and lubricants, where its presence helps reduce viscosity and lower freezing points. Because 2-ethylhexanol is a fatty alcohol, its esters have emollient properties. Representative is the diester bis(2-ethylhexyl) phthalate (DEHP), commonly used in PVC. The triester tris (2-Ethylhexyl) trimellitate (TOTM) is another common plasticizer produced via the esterification of three 2-ethylhexanol per trimellitic acid. It is also commonly used as a low volatility solvent. The nitrate ester of 2-Ethylhexanol is also used as a cetane improver for diesel fuel. It also used to react with epichlorohydrin and sodium hydroxide to produce 2-Ethylhexyl glycidyl ether which is then used as an epoxy reactive diluent in various coatings, adhesives and sealants applications. It can be used in the development of photos, production of rubber and extraction of oil and gas.https://berrymanchemical.com/blog/2-ethylhexanol/ Product Spotlight: 2-Ethylhexanol December 12, 2019 Industrial production 2-Ethylhexanol is produced industrially by the hydrogenation of 2-ethylhexanal. About 2,500,000 tons are prepared in this way annually.C. Kohlpaintner M. Schulte J. Falbe P. Lappe J. Weber Aldehydes, Aliphatic Ullmann's Encyclopedia of Industrial Chemistry 2008 Wiley-VCH Weinheim 10.1002/14356007.a01_321.pub2 978-3-527-30673-2Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 4180-4181. Health effects 2-Ethylhexanol exhibits low toxicity in animal models, with LD50 ranging from 2-3 g/kg (rat).Helmut Bahrmann Heinz-Dieter Hahn Dieter Mayer 2-Ethylhexanol Ullmann's Encyclopedia of Industrial Chemistry 2005 Wiley-VCH Weinheim 10.1002/14356007.a10_137 978-3-527-30673-2 2-Ethylhexanol has been identified as a cause of indoor air quality related health problems, such as respiratory system irritation, as a volatile organic compound. 2-Ethylhexanol is emitted to air from a PVC flooring installed on concrete that had not been dried properly.Ernstgård L. Norbäck D. 2010 Acute effects of exposure to 1 mg/m(3) of vaporized 2-ethyl-1-hexanol in humans Indoor Air 20 2 168–75 10.1111/j.1600-0668.2009.00638.x 20409194 free Hildenbrand S. Wodarz R. 2009 Biomonitoring of the di(2-ethylhexyl) phthalate metabolites mono(2-ethyl-5-hydroxyhexyl) phthalate and mono(2-ethyl-5-oxohexyl) phthalate in children and adults during the course of time and seasons. International Journal of Hygiene and Environmental Health 212 6 679–84 10.1016/j.ijheh.2009.06.003 19615938 2009IJHEH.212..679H 2-Ethylhexanol has been linked to developmental toxicity (increased incidence of skeletal malformations in fetuses).US EPA: National Center for Environmental Assessment 2-Ethylhexanol: Provisional Peer-Reviewed Toxicity Values (PPRTVs) en cfpub.epa.gov https://cfpub.epa.gov/ncea/pprtv/chemicalLanding.cfm?pprtv_sub_id=2005 2021-04-09July 2025 medicmedic This is thought to be a result of metabolism of 2-ethylhexanol into 2-ethylhexanoic acid via oxidation of the primary alcohol.Deisinger PJ, Boatman RJ, Guest D 2009-03-15 Metabolism of 2-ethylhexanol administered orally and dermally to the female Fischer-344 rat https://hero.epa.gov/index.cfm/reference/details/reference_id/3046161 en hero.epa.gov 2021-04-09 live https://web.archive.org/web/20211122011424/https://hero.epa.gov/index.cfm/reference/details/reference_id/3046161 2021-11-22Eastman Kodak Company Eastman Kodak 2009-03-15 Pharmacokinetic studies with 2-ethylhexanol in the female fischer 344 rat (final report) with attachments and cover letter dated 050791 en hero.epa.gov https://hero.epa.gov/index.cfm/reference/details/reference_id/3006683 2021-04-09 live https://web.archive.org/web/20211122011435/https://hero.epa.gov/index.cfm/reference/details/reference_id/3006683 2021-11-22 The teratogenicity of 2-ethylhexanoic acid, as well as similar substances such as valproic acid, has been well established.Pennanen Sirpa Tuovinen Kai Huuskonen Hannele Komulainen Hannu 1992 The developmental toxicity of 2-ethylhexanoic acid in Wistar rats https://www.sciencedirect.com/science/article/abs/pii/027205909290088Y Fundamental and Applied Toxicology 19 4 505–511 10.1016/0272-0590(92)90088-Y 1426708 Elsevier subscription 2-Ethylhexanoic acid ACGIH https://haz-map.com/Agents/1405 2021-04-09 live https://web.archive.org/web/20211122002908/https://haz-map.com/Agents/1405 2021-11-22Annex 1 Background Document to the Opinion proposing harmonised classification and labelling at EU level of 2-Ethylhexanoic acid and its salts, with the exception of those specified elsewhere in this Annex 2020 https://echa.europa.eu/documents/10162/c58bf900-5d67-463f-3d45-1e09009a1e22 2021-04-09 European Chemicals Agency 2021-11-22 https://web.archive.org/web/20211122050511/https://echa.europa.eu/documents/10162/c58bf900-5d67-463f-3d45-1e09009a1e22 dead Valproic Acid The American Society of Health-System Pharmacists https://www.drugs.com/monograph/valproic-acid.html Oct 23, 2015 live https://web.archive.org/web/20170731065623/https://www.drugs.com/monograph/valproic-acid.html 2017-07-31Valproate banned without the pregnancy prevention programme GOV.UK https://www.gov.uk/government/news/valproate-banned-without-the-pregnancy-prevention-programme 26 April 2018 live https://web.archive.org/web/20180424123455/https://www.gov.uk/government/news/valproate-banned-without-the-pregnancy-prevention-programme 2018-04-24 Nomenclature Although isooctanol (and the derived isooctyl prefix) is commonly used in industry to refer to 2-ethylhexanol and its derivatives, IUPAC naming conventionshttps://www.acdlabs.com/iupac/nomenclature/79/r79_36.htm Rule A-2. Saturated Branched-chain Compounds and Univalent Radicals (ACYCLIC HYDROCARBONS) acdlabs.com dictate that this name is properly applied to another isomer of octanol, 6-methylheptan-1-ol. The Chemical Abstracts Service likewise indexes isooctanol (CAS# 26952-21-6) as 6-methylheptan-1-ol. See also 2-Ethylhexanoic acid References External links Isooctyl alcohol, National Institute for Occupational Safety and Health (NIOSH) Category:Alcohol solvents Category:Octanols Category:Primary alcohols Category:Ethyl compounds