36653-82-4 Usage
Description
1-Hexadecanol, also known as cetyl alcohol, is a long-chain fatty alcohol that is hexadecane substituted by a hydroxy group at position 1. It is a synthetic, solid, fatty alcohol and nonionic surfactant. It is a waxy white powder or flake form at room temperature, insoluble in water, and soluble in alcohols and oils. 1-Hexadecanol is one of the oldest known long-chain alcohols and can be produced from the reduction of palmitic acid. It is used in various applications, including cosmetics, pharmaceuticals, and as a component in the preparation of other compounds.
Uses
1. Used in Cosmetics and Personal Care Products:
1-Hexadecanol is used as an emulsifier, emollient, opacifier, and surfactant in cosmetics formulations. It serves as an emollient, emulsifier, thickener, binder, foam booster, or emulsion stabilizer, depending on the formulation and need. It is derived from coconut or palm oil and is also synthetically manufactured.
2. Used in Pharmaceutical Preparations:
1-Hexadecanol is used as an emulsifying agent in pharmaceutical preparations, contributing to the stability and effectiveness of various medications.
3. Used in the Preparation of (±)-2-Methoxyheptadecanoic Acid (Fatty Acid):
1-Hexadecanol is used in the preparation of (±)-2-methoxyheptadecanoic acid, a high-chain fatty acid ester with potential applications in various industries.
4. Used in the Development of Novel Organic Phase Change Material for Thermal Energy Storage:
1-Hexadecanol is used in the development of high-chain fatty acid esters of 1-hexadecanol, which serve as a novel organic phase change material for thermal energy storage.
5. Used in the Synthesis of Hexadecane (Alkane):
1-Hexadecanol is used in the synthesis of hexadecane, an alkane, in the presence of the membrane fraction of Vibrio furnissii M1.
Occurrence:
1-Hexadecanol has been reported as a major constituent of spermaceti oil, where it is present chiefly as cetyl palmitate. It has also been found in various food sources, including guava, peach, pear, kohlrabi, baked potato, mustard, Parmesan cheese, butter, milk powder, boiled egg, cooked chicken, roasted beef, beef fat, whiskies, tea, starfruit, mango, rice, licorice, kiwifruit, loquat, endive, shrimp, crab, clam, Cape gooseberry, and pawpaw.
Originator
Hexadecyl alcohol,Esso Res. And
Eng. Co.
Production Methods
Cetyl alcohol may be manufactured by a number of methods such as
esterification and hydrogenolysis of fatty acids or by catalytic
hydrogenation of the triglycerides obtained from coconut oil or
tallow. Cetyl alcohol may be purified by crystallization and
distillation.
Synthesis Reference(s)
The Journal of Organic Chemistry, 42, p. 512, 1977 DOI: 10.1021/jo00423a025Synthetic Communications, 25, p. 1901, 1995 DOI: 10.1080/00397919508015865Tetrahedron Letters, 24, p. 4485, 1983 DOI: 10.1016/S0040-4039(00)85933-X
Flammability and Explosibility
Notclassified
Safety
Cetyl alcohol is mainly used in topical formulations, although it has
also been used in oral and rectal preparations.
Cetyl alcohol has been associated with allergic delayed-type
hypersensitivity reactions in patients with stasis dermatitis. Crosssensitization
with cetostearyl alcohol, lanolin, and stearyl alcohol
has also been reported. It has been suggested that hypersensitivity
may be caused by impurities in commercial grades of cetyl
alcohol since highly refined cetyl alcohol (99.5%) has not been
associated with hypersensitivity reactions.
LD50 (mouse, IP): 1.6 g/kg
LD50 (mouse, oral): 3.2 g/kg
LD50 (rat, IP): 1.6 g/kg
LD50 (rat, oral): 5 g/kg
storage
Cetyl alcohol is stable in the presence of acids, alkalis, light, and air;
it does not become rancid. It should be stored in a well-closed
container in a cool, dry place.
Purification Methods
Crystallise the alcohol from aqueous EtOH or from cyclohexane. Alternatively purify it by zone refining. The purity can be checked by gas chromatography. [Beilstein 1 H 429, 1 I 219, 1 II 466, 1 III 1815, 1 IV 1876.]
Incompatibilities
Incompatible with strong oxidizing agents. Cetyl alcohol is
responsible for lowering the melting point of ibuprofen, which
results in sticking tendencies during the process of film coating
ibuprofen crystals.
Regulatory Status
Included in the FDA Inactive Ingredients Database (ophthalmic
preparations, oral capsules and tablets, otic and rectal preparations,
topical aerosols, creams, emulsions, ointments and solutions, and
vaginal preparations). Included in nonparenteral medicines licensed
in the UK. Included in the Canadian List of Acceptable Nonmedicinal
Ingredients.
Check Digit Verification of cas no
The CAS Registry Mumber 36653-82-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,6,6,5 and 3 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 36653-82:
(7*3)+(6*6)+(5*6)+(4*5)+(3*3)+(2*8)+(1*2)=134
134 % 10 = 4
So 36653-82-4 is a valid CAS Registry Number.
InChI:InChI=1/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3
36653-82-4Relevant articles and documents
Linear long-chain α-olefins from hydrodeoxygenation of methyl palmitate over copper phyllosilicate catalysts
Choojun, Kittisak,Huang, Ai-Lin,Lin, Yu-Chuan,Poo-arporn, Yingyot,Prasanseang, Warot,Sooknoi, Tawan
, (2022/03/01)
Copper phyllosilicate (CuPS) was used as a bifunctional catalyst for hydrodeoxygenation of methyl palmitate (MP) to produce long-chain α-olefins without the loss of carbon backbone. The CuPS catalysts were prepared by ammonia evaporation-hydrothermal method. The crystal structure, surface area, reducibility, Cu dispersion, Cu particle size and acidity of the catalysts were examined by XRD, BET, H2-TPR, TEM, NH3-TPD and Py-IR. The existence of Cu2+ species (octahedral (Oh)/square planar (Sq)), Cu+ and Cu0 upon calcination/reduction was investigated by in situ TR-XANES. The Cu dispersion was related to the Cu+ fraction in CuPS, while Br?nsted acid sites (BAS) depends on Cu0 particles. The MP conversion to 1-hexadecene proceeds via hydrogenation-dehydration promoted by the synergy of Cu0 surface and Br?nsted acid sites at the interface. The α-olefin selectivity depends on a balance between Cu+ and Cu loading. The 20CuPS possessing 10% Cu+ fraction, provides a high conversion of 72% with 45% α-olefin selectivity.
Discovery of Anti-TNBC Agents Targeting PTP1B: Total Synthesis, Structure-Activity Relationship, in Vitro and in Vivo Investigations of Jamunones
Hu, Caijuan,Li, Guoxun,Mu, Yu,Wu, Wenxi,Cao, Bixuan,Wang, Zixuan,Yu, Hainan,Guan, Peipei,Han, Li,Li, Liya,Huang, Xueshi
supporting information, p. 6008 - 6020 (2021/05/06)
Twenty-three natural jamunone analogues along with a series of jamunone-based derivatives were synthesized and evaluated for their inhibitory effects against breast cancer (BC) MDA-MB-231 and MCF-7 cells. The preliminary structure-activity relationship revealed that the length of aliphatic side chain and free phenolic hydroxyl group at the scaffold played a vital role in anti-BC activities and the methyl group on chromanone affected the selectivity of molecules against MDA-MB-231 and MCF-7 cells. Among them, jamunone M (JM) was screened as the most effective anti-triple-negative breast cancer (anti-TNBC) candidate with a high selectivity against BC cells over normal human cells. Mechanistic investigations indicated that JM could induce mitochondria-mediated apoptosis and cause G0/G1 phase arrest in BC cells. Furthermore, JM significantly restrained tumor growth in MDA-MB-231 xenograft mice without apparent toxicity. Interestingly, JM could downregulate phosphatidylinositide 3-kinase (PI3K)/Akt pathway by suppressing protein-tyrosine phosphatase 1B (PTP1B) expression. These findings revealed the potential of JM as an appealing therapeutic drug candidate for TNBC.
Ultra-low loading of Ni in catalysts supported on mesoporous SiO2 and their performance in hydrodeoxygenation of palmitic acid
Valencia, Diego,Zenteno, Citlalli,Morales-Gil, Perla,Díaz-García, Leonardo,Gómora-Herrera, Diana,Palacios-González, Eduardo,Aburto, Jorge
, p. 2435 - 2441 (2020/02/20)
We synthesized a series of new Ni catalysts supported on mesoporous silica KIT-5. The metal loading on this support was varied (0.9-7.0 wt% NiO). The catalysts were characterized by N2 physisorption, powder XRD, XRF spectrometry, UV-vis DRS, H2-TPR, HRTEM and FT-IR with CO. The mesoporous structure is maintained in all the catalytic materials. The increase in the Ni loading resulted in the formation of crystalline phases at the KIT-5 surface. The catalysts were tested in hydrodeoxygenation (HDO) of palmitic acid. The catalytic activity increased with the metal loading, reaching a maximum by using the catalyst with 1.8 wt% NiO. On the other hand, calculation of kinetic parameters indicated the effective utilization of catalytically active Ni particles in the HDO process. Formation of oxygen-free products was higher for the catalyst with higher metal loading in this series. These catalytic materials were compared with a series of Ni catalysts supported on carbon, finding that the Ni/KIT-5 catalysts were much more active in the HDO reaction. These new catalysts supported on the mesoporous silica KIT-5 exhibited high activity with low metal loadings. This feature makes them attractive for their application in the HDO of fatty acids.