88109-73-3

Basic information

• Product Name: 9-HEXADECYN-1-OL
• Synonyms: 9-HEXADECYN-1-OL;hexadec-9-yn-1-ol
• CAS NO: 88109-73-3
• Molecular Formula: C16H30O
• Molecular Weight: 238.41
• Mol File: 88109-73-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 339.2oC at 760 mmHg
• Flash Point: 145.5oC
• Appearance: /
• Density: 0.871g/cm3
• Vapor Pressure: 6.27E-06mmHg at 25°C
• Refractive Index: 1.465
• PKA: 15.19±0.10(Predicted)
• CAS DataBase Reference: 9-HEXADECYN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 9-HEXADECYN-1-OL(88109-73-3)
• EPA Substance Registry System: 9-HEXADECYN-1-OL(88109-73-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 88109-73-3(Hazardous Substances Data)

Usage

General Description

9-Hexadecyn-1-ol, also known as 16-hexadecyn-1-ol, is a long-chain unsaturated alcohol with the chemical formula C16H30O. It is a colorless, waxy solid at room temperature and is insoluble in water. 9-Hexadecyn-1-ol is primarily used in the synthesis of various chemical compounds, serving as a reagent in organic chemistry. 9-Hexadecyn-1-ol has been studied for its potential applications in the fields of pharmaceuticals and materials science, demonstrating antibacterial and anti-inflammatory properties. Its unique chemical structure and properties make it a valuable component in the development of novel drugs and materials.

InChI:InChI=1/C16H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-6,9-16H2,1H3

Upstream product

• 93107-76-7 9,10-Dibromo-hexadecan-1-ol 
• 25258-24-6 1-tetrahydropyranyloxy-n-9-hexadecyn 
• 197901-27-2 hexadec-1-en-9-yne 
• 19754-58-6 2-dec-9-ynyloxy-tetrahydro-pyran 
• 50816-18-7 9-decen-1-yl acetate 
• 112-19-6 10-undecenyl acetate 
• 54894-30-3 11-acetoxyundecanoic acid 
• 17643-36-6 9-decyn-1-ol 
• 1619-68-7 16-hydroxy-9-hexadecenoic acid 
• 1256346-67-4 C₂₂H₄₄OSi 
• 78924-81-9 methyl 16-hydroxy-(E)-9-hexadecenoate 
• 93107-75-6 Methyl 16-mesyloxy-(E)-9-hexadecenoate 
• 6949-98-0 9,10,16-trihydroxyhexadecanoic acid 
• 64437-47-4 trans-hexadec-9-en-1-ol 

Downstream Products

• 10378-01-5 palmitoleyl alcohol 
• 62914-53-8 hexadec-15-yn-1-ol 
• 56219-04-6 (Z)-9-hexadecenal 

Relevant articles and documents

Antibacterial Activity of Hexadecynoic Acid Isomers toward Clinical Isolates of Multidrug-Resistant Staphylococcus aureus

In the present study, the structural characteristics that impart antibacterial activity to C16 alkynoic fatty acids (aFA) were further investigated. The syntheses of hexadecynoic acids (HDA) containing triple bonds at C-3, C-6, C-8, C-9, C-10, and C-12 were carried out in four steps and with an overall yield of 34–78%. In addition, HDA analogs containing a sulfur atom at either C-4 or C-5 were also prepared in 69–77% overall yields, respectively. Results from this study revealed that the triple bond at C-2 is pivotal for the antibacterial activity displayed by 2-HDA, while the farther the position of the triple bond from the carbonyl group, the lower its bactericidal activity against gram-positive bacteria, including clinical isolates of methicillin-resistant Staphylococcus aureus (CIMRSA) strains. The potential of 2-HDA as an antibacterial agent was also assessed in five CIMRSA strains that were resistant to Ciprofloxacin (Cipro) demonstrating that 2-HDA was the most effective treatment in inhibiting their growth when compared with either Cipro alone or equimolar combinations of Cipro and 2-HDA. Moreover, it was proved that the inhibition of S. aureus DNA gyrase can be linked to the antibacterial activity displayed by 2-HDA. Finally, it was determined that the ability of HDA analogs to form micelles can be linked to their decreased activity against gram-positive bacteria, since critical micellar concentrations (CMC) between 50 and 300 μg/mL were obtained.

A versatile approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid

A general approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid was developed. The method comprises the conversion of the acid into undec-10-enyl acetate, shortening of its carbon chain to afford dec-9-enyl acetate (via 11-acetoxyundecanoic acid), and a two-step transformation of the latter into the key intermediate, dec-9-yn-1-ol, by sequential bromination - dehydrobromination. The elimination of two HBr molecules from the dibromide is effectively performed using Bu1OK in the presence of dibenzo-18-crown-6 as the catalyst.

INSECT PHEROMONES AND THEIR ANALOGUES. XVI. PRACTICAL SYNTHESIS OF HEXADEC-9Z-ENAL - A COMPONENT OF THE SEX PHEROMONE OF THE COTTON BOLLWORM Heliothis armigera

A synthesis of hexadec-9Z-enal - a component of the sex pheromone of the cotton bollworm Heliothis armigera (Huebner) - based on cyclooctene (I) is proposed.Through a solution of 22 g of (I), 250 ml of cyclohexane, and 40 ml of MeOH is passed (at 5 deg C) 0.2 M O3/O2, the solution is decanted off, and the precipitated ozonide is dissolved in 200 ml of MeOH and is reduced with 19 g of NaBH4 (40 deg C) with the isolation, after the usual working up, of 23.4 g of octane-1,8-diol (II).From 0.5 mole of (II) and 0.6 mole of 45percent HBr 8-bromooctan-1-ol (III) is obtained and this is converted into 1-(2-(THPL)oxy)-8-bromooctane (IV).The condensation of (IV) with oct-1-yne (Ar, LiNH2, HMPTA, 10 deg C, 1 h, and then 55 deg C, 10 h) leads to 1-(2-THPL-oxy)hexadec-9-yne (V) the hydrolysis of which (MeOH, H2O, p-TsOH, 20 deg C for 20 h) yields hexadec-9-yn-ol (VI).The reduction of (VI) (Et2O, iso-BuMgBr, Cp2TiCl2, 0 deg C, 15 min, then 20 deg C, 1 h) yields hexadec-9Z-en-1-ol (VII).The oxidation of (VII) (PyHCrO3+ Cl-, CH2Cl2, 20 deg C, 2 h) gives hexadec-9Z-enal (VIII).Characteristics of the compounds (yield (percent), nD20(25): (II) - 80, mp 61-62 deg C; (III) - 75, 1.4807; (IV) - 99, -; (V) - 52, 1,4650; (VI) - 85, 1.4657; (VII) - 99, 1.4650; (VIII) - 98, 1.4600.Characteristics of the IR and PMR spectra of compounds (V-VII) are given.