112-72-1 Usage
Description
1-Tetradecanol is a kind of straight-chain saturated fatty alcohol. It is often used as an ingredient in cosmetics such as cold creams because of its emollient properties. It can also be used as the intermediate during the manufacturing of some organic compounds like surfactants. Some studies have shown that it can inhibit the endothelial activation and reduce tissue responsiveness to cytokines, having the potential to treat the periodontitis based on studies on rabbits. It is also employed for the fabrication of temperature-regulated drug release system based on phase-change materials.
References
Lehmler, Hans-Joachim, and Paul M. Bummer. "Behavior of 10-(perfluorohexyl)-decanol, a partially fluorinated analog of hexadecanol, at the air–water interface." Journal of fluorine chemistry 117.1 (2002): 17-22.
Hasturk, Hatice, et al. "1-Tetradecanol complex reduces progression of porphyromonas gingivalis–induced experimental periodontitis in rabbits." Journal of periodontology 78.5 (2007): 924-932.
Hasturk, H, et al. "1-Tetradecanol complex: therapeutic actions in experimental periodontitis." Journal of Periodontology 80.7(2009): 1103-13.
Choi, Sung-Wook, Yu Zhang, and Younan Xia. "A temperature-sensitive drug release system based on phase-change materials." Angewandte Chemie International Edition 49.43 (2010): 7904-7908.
Chemical Properties
Different sources of media describe the Chemical Properties of 112-72-1 differently. You can refer to the following data:
1. white low melting solid or flakes
2. Myristyl alcohol occurs as a white crystalline solid with a waxy
odor. Also reported as opaque leaflets or crystals from ethanol.
Uses
Different sources of media describe the Uses of 112-72-1 differently. You can refer to the following data:
1. myristyl alcohol is an emollient often used in hand creams, cold creams, and lotions to give them a smooth, velvety feel. Sources indicate it as being mildly comedogenic and potentially irritating.
2. 1-Tetradecanol is used as an ingredient in cosmetics such as cold creams. It is an active intermediate in the chemical synthesis of sulfated alcohol. It is also employed in the fabrication of temperature-regulated drug release system based on phase-change materials. It plays a vital role in filling the hollow interiors of gold nanocages in the fabrication of new theranostic system, which has unique feature of photoacoustic imaging.
3. As emollient for cold creams, etc., also for making the sulfated alcohol whose sodium salt is applicable as a "wetter" in textiles.
Definition
ChEBI: 1-Tetradecanol is a long-chain fatty alcohol that is tetradecane in which one of the terminal methyl hydrogens is replaced by a hydroxy group It is a long-chain primary fatty alcohol, a fatty alcohol 14:0 and a primary alcohol.
Production Methods
Myristyl alcohol is found in spermaceti wax and sperm oil, and may
be synthesized by sodium reduction of fatty acid esters or the
reduction of fatty acids by lithium aluminum hydride. It can also be
formed from acetaldehyde and dimethylamine.
Synthesis Reference(s)
The Journal of Organic Chemistry, 35, p. 1210, 1970 DOI: 10.1021/jo00829a089
General Description
Colorless thick liquid (heated) with a faint alcohol odor. Solidifies and floats on water.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
1-Tetradecanol is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.
Health Hazard
Low toxicity. Overexposure causes some central nervous system depression. Prolonged skin contact causes skin irritation.
Flammability and Explosibility
Notclassified
Pharmaceutical Applications
Myristyl alcohol is used in oral, parenteral, and topical pharmaceutical
formulations. It has been evaluated as a penetration
enhancer in melatonin transdermal patches in rats.
Myristyl alcohol has also been tested as a bilayer stabilizer in
niosome formulations containing ketorolac tromethamine,and
zidovudine.Niosomes containing myristyl alcohol showed a considerably slower release rate of ketorolac tromethamine than
those containing cholesterol.This was also observed with the
zidovudine formulation.
Safety
Myristyl alcohol is used in oral parenteral, and topical pharmaceutical
formulations. The pure form of myristyl alcohol is mildly toxic
by ingestion and may be carcinogenic; experimental tumorigenic
data are available.It is also a human skin irritant. In animal
studies of the skin permeation enhancement effect of saturated fatty
alcohols, myristyl alcohol exhibited a lower effect when compared
with decanol, undecanol, or lauryl alcohol but caused greater skin
irritation.A study investigating contact sensitization to myristyl
alcohol revealed that patch testing of myristyl alcohol 10%
petrolatum should not be carried out owing to observed irritant
effects; thus the use of a lower concentration of myristyl alcohol for
such tests (5% petrolatum) was recommended.Myristyl alcohol
has been associated with some reports of contact allergy.(8,9)A moderate-to-severe erythema and moderate edema are seen when
75 mg is applied to human skin intermittently in three doses over 72
hours.
LD50(rabbit, skin): 7.1 g/kg
LD50(rat, oral): 33.0 g/kg
storage
The bulk material should be stored in a well-closed container in a
cool, dry place.
Purification Methods
Crystallise the alcohol from aqueous EtOH. It has also been purified by zone melting. [Beilstein 1 IV 1864.]
Incompatibilities
Myristyl alcohol is combustible when exposed to heat or flame. It
can react with oxidizing materials. When heated to decomposition,
it emits acrid smoke and irritating fumes.
Regulatory Status
Included in the FDA Inactive Ingredients Database (oral tablet:
sustained-release; and topical formulations: cream, lotion, suspension).
Included in nonparenteral (topical cream) formulations
licensed in the UK.
Check Digit Verification of cas no
The CAS Registry Mumber 112-72-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 2 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 112-72:
(5*1)+(4*1)+(3*2)+(2*7)+(1*2)=31
31 % 10 = 1
So 112-72-1 is a valid CAS Registry Number.
InChI:InChI=1/2C14H30O/c2*1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h2*15H,2-14H2,1H3
112-72-1Relevant articles and documents
Calcium borohydride: A reagent for facile conversion of carboxylic esters to alcohols and aldehydes
Narasimhan,Ganeshwar Prasad,Madhavan
, p. 1689 - 1697 (1995)
Calcium borohydride reduces both aliphatic and aromatic esters to alcohols completely in the presence of alkene catalysts. The intermediate borates formed during the reduction of aromatic esters are converted to aldehydes with aqueous NaOCl in good yields.
Fatty alcohol synthesis from fatty acids at mild temperature by subsequent enzymatic esterification and metal-catalyzed hydrogenation
Betke, Tobias,Gr?ger, Harald,Kleber, Joscha,Liese, Andreas,Schlipk?ter, Kim E.
, p. 7862 - 7867 (2020)
Fatty alcohols are important products in chemical industry to be used in the formulation of surfactants and lubricants. This work describes a two step approach for the production of myristyl alcohol under neat conditions by combining a lipase catalyzed esterification of myristic acid and myristyl alcohol with a ruthenium catalyzed hydrogenation of the intermediate myristyl myristate. The esterification was carried out in a bubble column reactor with the commercial immobilized lipase B from Candida antarctica as a biocatalyst, while the hydrogenation was conducted under pressurized conditions being catalyzed by the homogeneous chemocatalyst Ru-Macho-BH. By investigating the reaction steps separately, comparable reaction rates were found for the esterification of short chain and long chain alcohols. Additionally, the hydrogen pressure could be reduced to 35 bar compared to the current industrial Lurgi process. Characterization of cross interactions by the reactants myristic acid and sodium myristate in the hydrogenation demonstrates that the metal catalyst was completely deactivated, even at a low amount of 0.5 mol% of myristic acid. Complete conversion of myristic acid in the esterification with equal amounts of myristic acid and myristyl alcohol was obtained, overcoming any limitation in the hydrogenation. In comparison to the Lurgi process starting also from fatty acid and fatty alcohols, the chemoenzymatic two step reaction sequence could be realized at lower reaction temperatures of 60 and 100 °C as well as lower hydrogen pressures of 35 bar. This journal is
Synthesis and surface-active properties of novel cleavable gemini surfactants
Gilbert, Elangeni Ana,Guastavino, Javier Fernando,Murguía, Marcelo César
, p. 27 - 35 (2021/09/14)
A novel series of quaternary ammonium gemini compounds having a butynylene spacer and different hydrocarbon chain lengths (CGBu8-16) were prepared. Carbonate group inserted between the hydrocarbon chains and the polar heads make these compounds hydrolyzable. The degradation under hydrolysis of these novel series will lead to the generation of fatty alcohols and readily degradable compounds. The reagents used are biodegradable, renewable, or reusable. The surface activities and foamability in aqueous solution of the cleavable gemini compounds containing n-octyl, n-decyl, and n-dodecyl chains meet the criteria for being good surfactants and showed stable foams even at low concentrations.
Redox-active ligand based Mn(i)-catalyst for hydrosilylative ester reduction
Chakraborty, Soumi,Das, Arpan,Mandal, Swadhin K.
supporting information, p. 12671 - 12674 (2021/12/04)
Herein a Mn(i) catalyst bearing a redox-active phenalenyl (PLY) based ligand is reported for the efficient hydrosilylation of esters to alcohols using the inexpensive silane source polymethylhydrosiloxane (PMHS) under mild conditions. Mechanistic investigations suggest a strong ligand-metal cooperation where a ligand-based single electron transfer (SET) process initiates the reaction through Si-H bond activation.
Hydrosilylation of Esters Catalyzed by Bisphosphine Manganese(I) Complex: Selective Transformation of Esters to Alcohols
Bagh, Bidraha,Behera, Rakesh R.,Ghosh, Rahul,Khamari, Subrat,Panda, Surajit
supporting information, p. 3642 - 3648 (2020/04/20)
Selective and efficient hydrosilylations of esters to alcohols by a well-defined manganese(I) complex with a commercially available bisphosphine ligand are described. These reactions are easy alternatives for stoichiometric hydride reduction or hydrogenation, and employing cheap, abundant, and nonprecious metal is attractive. The hydrosilylations were performed at 100 °C under solvent-free conditions with low catalyst loading. A large variety of aromatic, aliphatic, and cyclic esters bearing different functional groups were selectively converted into the corresponding alcohols in good yields.
