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1-Heneicosanol
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1-Heneicosanol 1-Heneicosanol.svg Heneicosanol; Heneicosyl alcohol; Henicosan-1-ol Henicosan-1-ol 1S/C21H44O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22/h22H,2-21H2,1H3 FIPPFBHCBUDBRR-UHFFFAOYSA-N correct CAS 15594-90-8 78410 85014 correct chemspider 76686 correct FDA 15BB7P0F03 CCCCCCCCCCCCCCCCCCCCCO 21 44 1 White, waxy solid 70 Heneicosanol, 99% https://pim-resources.coleparmer.com/sds/71712.pdf Acros Organics 2005-10-03 2025-11-27 366 (estimated, at 760 mmHg) heneicosanol The Good Scents Company Information System https://www.thegoodscentscompany.com/data/rw1434311.html 2025-11-27
1-Heneicosanol (also known as heneicosyl alcohol or heneicosanol) is a long-chain primary alcohol and fatty alcohol with 21 carbon atoms and the molecular formula C21H44O. At room temperature, it is a waxy white solid with a melting point close to 69 °C.Material Safety Data Sheet: Heneicosanol, 99% https://pim-resources.coleparmer.com/sds/71712.pdf Acros Organics 2005-10-03 2025-11-271-Heneicosanol https://www.tcichemicals.com/OP/en/p/H0011 TCI 2025-11-27 As a typical long-chain aliphatic alcohol, it is highly hydrophobic and practically insoluble in water.heneicosanol The Good Scents Company Information System https://www.thegoodscentscompany.com/data/rw1434311.html 2025-11-27 Similar to other fatty alcohols, 1-heneicosanol is used as an intermediate and functional component in the manufacture of surfactants, lubricants, polymer materials and cosmetic formulations.1-Heneicosanol MedChemExpress https://www.medchemexpress.com/1-heneicosanol.html 2025-11-271-Heneicosanol ChemImpex https://www.chemimpex.com/products/38962 2025-11-27Breathable and crosslinkable thermoplastic polyurethane https://patents.google.com/patent/EP3134453B1 Google Patents 2025-11-27Productos que comprenden una hoja y extractos de Camellia sinensis https://patents.google.com/patent/MXPA04000365A/es Google Patents 2025-11-27
Structure and properties
1-Heneicosanol is the C21 member of the series of linear, saturated primary alcohols derived formally from heneicosane by substitution of a terminal hydrogen atom with a hydroxyl group. It is classified as a long-chain fatty alcohol.
Commercial material is typically obtained as a white powder or low-melting wax with a reported melting range of about 68–71 °C. A safety data compilation and estimation methods indicate a high normal boiling point of around 366 °C at 760 mmHg, consistent with its long carbon chain. The compound has very low solubility in water and a high octanol/water partition coefficient (log P), reflecting its pronounced hydrophobic character.
Natural occurrence
1-Heneicosanol naturally occurs in various flowering plants, such as the tomato (Solanum lycopersicum), where it is one of the constituents of the cuticular surface wax,Bauer Stefan Schulte Erhard Thier Hans-Peter 2004-08-01 Composition of the surface wax from tomatoes European Food Research and Technology en 219 3 223–228 10.1007/s00217-004-0943-0 1438-2385 and in napa cabbage (Brassica rapa subsp. pekinensis).Baek Seung-A Jung Young-Ho Lim Sun-Hyung Park Sang Un Kim Jae Kwang 2016-06-01 Metabolic Profiling in Chinese Cabbage (Brassica rapa L. subsp. pekinensis) Cultivars Reveals that Glucosinolate Content Is Correlated with Carotenoid Content Journal of Agricultural and Food Chemistry en 64 21 4426–4434 10.1021/acs.jafc.6b01323 27172980 2016JAFC...64.4426B 0021-8561
It is also a component of plant-derived policosanol mixtures. A study of green tea (Camellia sinensis) leaves identified heneicosanol (C21-OH) among the major long-chain aliphatic alcohols present in policosanol fractions.Choi Sol Ji Chun Ji-Yeon Lee Su-Jin Park Sang-Young Yoon Min-Seok 2016-08-01 Contents and compositions of policosanols in green tea (Camellia sinensis) leaves Food Chemistry 204 94–101 10.1016/j.foodchem.2016.02.027 26988480 0308-8146 Related work has reported the presence of 1-heneicosanol in herbal tea blends based on Himalayan-region plants used as green and black tea substitutes.Kumari Anita Kumar Ravi Dev Indra etal 2022 Evaluation of antioxidant and cytotoxic activity of herbal teas manufactured from Western Himalayan plants Chemical and Biological Technologies in Agriculture 9 1 1–18 10.1186/s40538-022-00294-3 free 2196-5641
A 2021 study analyzing the chemical composition of cow urine by gas chromatography–mass spectrometry found that 1-heneicosanol is one of its major constituents.Nautiyal Vipin Dubey R. C. 2021-04-01 FT-IR and GC-MS analyses of potential bioactive compounds of cow urine and its antibacterial activity Saudi Journal of Biological Sciences 28 4 2432–2437 10.1016/j.sjbs.2021.01.041 1319-562X 8071964 33935568 2021SJBS...28.2432N Subsequent in silico work has examined cow-urine-derived 1-heneicosanol as a ligand for bacterial target proteins using molecular docking and ADME prediction approaches.Nautiyal Vipin 2024 In silico molecular docking analysis and ADME prediction of cow urine derived 1-heneicosanol against some bacterial proteins Vegetos 37 1 426–432 10.1007/s42535-023-00587-4 2024Veget..37..426N 2229-4473
Uses
As a representative long-chain fatty alcohol, 1-heneicosanol is used in research and in industrial formulation work as:
an intermediate or building block in the synthesis of non-ionic and other surfactants and related functional additives;
a component of lubricant and plastic additive systems, including thermoplastic polyurethanes, where long-chain alcohols are used to modify flexibility and permeability;
a minor constituent of policosanol-type mixtures employed in cosmetics and personal-care products as part of the lipid phase of creams and emulsions.
Because of its chain length and structural similarity to other fatty alcohols, 1-heneicosanol is also used as a reference compound and analytical standard in studies of plant waxes, policosanol mixtures and related lipid fractions.
Safety
Available safety data sheets describe 1-heneicosanol as a low-volatility solid that is not classified as hazardous under European CLP regulations, but which may cause mild irritation to the skin, eyes and respiratory tract on contact or inhalation of dust.Safety Data Sheet: Heneicosanol https://www.glentham.com/en/products/product/GK7083/sds/?language=en Glentham Life Sciences 2023-04-05 2025-11-27 Standard laboratory precautions such as avoiding dust formation, using local exhaust ventilation and wearing eye and skin protection are recommended.
See also
Fatty alcohol
Behenyl alcohol
Heneicosanoic acid
References
Category:Fatty alcohols
Category:Alkanols