Vad är benzyl alcohol antibacterial
Benzyl alcohol
Aromatic alcohol
Not to be confused with benzoic acid, cresol, or phenol.
| Names | |
|---|---|
| Preferred IUPAC name Phenylmethanol | |
| Other names Benzyl alcohol | |
| Identifiers | |
CAS Number | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.002.600 |
| EC Number | |
| E number | E1519 (additional chemicals) |
| KEGG | |
PubChemCID | |
| RTECS number | |
| UNII | |
CompTox Dashboard(EPA) | |
InChI
| |
| Properties[1] | |
Chemical formula | C7H8O |
| Molar mass | 108.140 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | Slightly aromatic |
| Density | 1.044 g/cm3 |
| Melting point | −15.2 °C (4.6 °F; 257.9 K) |
| Boiling point | 205.3 °C (401.5 °F; 478.4 K) |
Solubility in water | 3.50 g/100 mL (20 °C) 4.29 g/100 mL (25 °C) |
| Solubility in other solvents | Miscible with benzene, methanol, chloroform, ethanol, ether, acetone |
| log P | 1.10 |
| Vapor pressure | 0.18 kPa (60 °C) |
| Acidity (pKa) | 15.40 |
Magnetic susceptibility (χ) | −71.83·10−6 cm3/mol |
Refractive index (nD) | 1.5396 |
| Viscosity | 5.474 cP |
Dipole moment | 1.67 D |
| Thermochemistry | |
Std molar | 217.8 J/(K·mol) |
Std enthalpy of | −352 kJ/mol |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Flash point | 93 °C (199 °F; 366 K) |
Autoignition | 436 °C (817 °F; 709 K) |
| Explosive limits | 1.3–13% |
| Lethal dose or koncentration (LD, LC): | |
LD50 (median dose) | 1250 mg/kg (rat, oral) |
| Safety uppgifter sheet (SDS) | External MSDS |
| Pharmacology | |
ATC code | P03AX06 (WHO) |
Except where otherwise noted, information are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references | |
Chemical compound
Benzyl alcohol (also known as α-cresol) fryst vatten an aromaticalcohol with the formula C6H5CH2OH.
The benzyl group fryst vatten often abbreviated "Bn" (not to be confused with "Bz" which fryst vatten used for benzoyl), thus benzyl alcohol fryst vatten denoted as BnOH. Benzyl alcohol fryst vatten a färglös liquid with a mild pleasant aromatic odor. It fryst vatten useful as a solvent for its polarity, low toxicity, and low vapor pressure. Benzyl alcohol has moderate solubility in vatten (4 g/100 mL) and fryst vatten miscible in alcohols and diethyl ether.
The anion produced bygd deprotonation of the alcohol group fryst vatten known as benzylate or benzyloxide.
Natural occurrences
[edit]Benzyl alcohol fryst vatten produced naturally bygd many plants and fryst vatten commonly funnen in fruits and teas. It fryst vatten also funnen in a variety of essential oils including jasmine, hyacinth and ylang-ylang.[2] It fryst vatten also funnen in castoreum from the castor sacs of beavers.[3] Benzyl esters also occur naturally.[4]
Preparation
[edit]Benzyl alcohol fryst vatten produced industrially from toluene via benzyl chloride, which fryst vatten hydrolyzed:
- C6H5CH2Cl + H2O → C6H5CH2OH + HCl
Another rutt entails hydrogenation of benzaldehyde, a by-product of the kemisk reaktion med syre of toluene to benzoic acid.[5]
For laboratory use, Grignard reaction of phenylmagnesium bromide (C6H5MgBr) with formaldehyde and the Cannizzaro reaction of benzaldehyde also give benzyl alcohol.
Benzyl alcohol (BA) fryst vatten an aromatic alcohol used as a solvent in the production of fragrances/perfumes, paints and adhesives.The latter also gives benzoic acid, an example of an organic disproportionation reaction.
Reactions
[edit]Like most alcohols, it reacts with carboxylic acids to struktur esters. In organic synthesis, benzyl esters are popular protecting groups because they can be removed bygd mild hydrogenolysis.[6]
Benzyl alcohol reacts with acrylonitrile to give N-benzylacrylamide.
This fryst vatten an example of a Ritter reaction:[7]
- C6H5CH2OH + NCCHCH2 → C6H5CH2N(H)C(O)CHCH2
Applications
[edit]Benzyl alcohol fryst vatten used as a general solvent for inks, waxes, shellacs, paints, lacquers, and epoxy resin coatings.
Thus it can be used in paint strippers, especially when combined with compatible viscosity enhancers to encourage the mixture to cling to painted surfaces.[8]
It fryst vatten a precursor to a variety of esters and ethers, used in the soap, perfume, and flavor industries. E.g. benzyl benzoate, benzyl salicylate, benzyl cinnamate, dibenzyl ether, benzyl butyl phthalate.
It can be used as a local anesthetic, especially with epinephrine.[9]
As a dye solvent, it enhances the process of dying wool, nylon, and leather.[10]
Use in health care
[edit]Benzyl alcohol fryst vatten used as a bacteriostatic preservative at low koncentration in intravenous medications, kosmetika, and topical drugs.[11] Some caution fryst vatten necessary if a high percent of benzyl alcohol fryst vatten used as benzaldehyde arises from benzyl alcohol when used as preservative in an injectable formulation solution.[11][12]
Benzyl alcohol, sold beneath the brand name Ulesfia, was approved bygd the U.S.
Food and Drug ledning (FDA) in 2009, as a 5% solution for the treatment of head lice in people 6 months of age and older.[13] It affects the louse's spiracles, preventing them from closing.[13] These then become clogged with vatten or mineral oil or other matter and cause the insekt to die from asphyxiation.[13]
Benzyl alcohol fryst vatten used effectively for treating lice infestations as the active ingredient in lotion shampoo with 5% benzyl alcohol.[13]
Benzyl alcohol fryst vatten an ingredient used in the manufacture of soaps, topical creams, skin lotions, shampoos, and facial cleansers and fryst vatten popular due to its anti-bacterial and anti-fungal properties.
It fryst vatten a common ingredient in a variety of household products.
Safety
[edit]Sensitization to benzyl alcohol occurs very rarely, mainly in patients with stasis dermatitis.[14]
Benzyl alcohol fryst vatten not considered to be a carcinogen, and no uppgifter are available regarding teratogenic or fortplantnings- effects.[5]
Benzyl alcohol has low acute toxicity with an LD50 of 1.2 g/kg in rats.[5] It oxidizes rapidly in healthy individuals to benzoic acid, conjugated with glycine in the liver, and excreted as hippuric acid.
Very high concentrations can result in toxic effects including respiratory failure, vasodilation, hypotension, convulsions, and paralysis.
Benzyl alcohol fryst vatten toxic to neonates and fryst vatten associated with the gasping syndrome.[15][16][17]
References
[edit]- ^"Benzyl alcohol".
Archived from the original on 26 July 2009.
- ^The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN , 1138
- ^Dietland Muller-Schwarze (2003). The Beaver: Its Life and Impact. Cornell University Press. p. 43.
ISBN .
- ^d'Auria, John C.; Chen, Feng; Pichersky, Eran (2002). "Characterization of an Acyltransferase Capable of Synthesizing Benzylbenzoate and Other Volatile Esters in Flowers and Damaged Leaves of Clarkia breweri". Plant Physiology.Benzyl Alcohol.
130 (1): 466–476. doi:10.1104/pp.006460. PMC 166578. PMID 12226525.
- ^ abcFriedrich Brühne; Elaine Wright (2007). "Benzyl Alcohol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_001. ISBN .
- ^Furuta, Kyoji; Gao, Qing-Zhi; Yamamoto, Hisashi (1995).
"Chiral (Acyloxy)borane Complex-Catalyzed Asymmetric Diels-Alder Reaction: (1R)-1,3,4-Trimethyl-3-Cyclohexene-1-Carboxaldehyde". Organic Syntheses. 72: 86
; Collected Volumes, vol. 9, p. 722. - ^Parris, Chester L. (1962). "N-benzylacrylamide". Organic Syntheses. 42: 16; Collected Volumes, vol. 5, p. 73.
- ^Benzyl alcohol, chemicalland21.com, archived from the original on 21 April 2009, retrieved 14 May 2006
- ^Wilson, L.; Martin, S.
(May 1999). "Benzyl alcohol as an alternative local anesthetic". Annals of Emergency Medicine. 33 (5): 495–499. doi:10.1016/s0196-0644(99)70335-5.
Alcohol-based sanitizers with secondary active ingredients demonstrated a more rapid antimicrobial mode of action, eradicating all 10 6 CFU/mL of bacteria within 15 seconds of contact, in contrast to the 30 min for purely alcohol-based sanitizers.PMID 10216324.
- ^Michael Ash; Irene Ash (2004). Handbook of Preservatives. Synapse Info Resources. p. 292. ISBN .
- ^ abH. A. Mashayekhi; M. Rezaee; Sh. S. Garmaroudi; N. Montazeri; S. J. Ahmadi (2011).Benzyl alcohol fryst vatten an ingredient used in the manufacture of soaps, topical creams, skin lotions, shampoos, and facial cleansers and fryst vatten popular due to its anti-bacterial and anti-fungal properties.
"Rapid and sensitive determination of benzaldehyde arising from benzyl alcohol used as preservative in an injectable formulation solution using dispersive liquid–liquid microextraction followed bygd gas chromatography". Anal. Sci. 27 (8): 865–868. doi:10.2116/analsci.27.865. PMID 21828928.
- ^N. N. Sudareva; E. V. Chubarova (2006). "Time-dependent konvertering of benzyl alcohol to benzaldehyde and benzoic acid in aqueous solutions".
J. Pharm. Biomed. Anal. 41 (4): 1380–1385. doi:10.1016/j.jpba.2006.02.028. PMID 16564153.
- ^ abcd"Ulesfia- benzyl alcohol lotion". DailyMed.Bensylalkohol existerar enstaka kemisk förening tillsammans formeln C 6 H 5 CH 2 OH. Ämnet existerar ett oljeaktig vätska, likt existerar löslig inom dricksvatten samt alkohol samt liksom används inom parfymerier.
8 April 2019. Retrieved 27 April 2020.
- ^"Registration Dossier - ECHA". echa.europa.eu. Retrieved 20 April 2023.
- ^Carl R. Baum (2008), "Examples of mass exposures involving the pediatric population", in Jerrold B. Leikin; Frank P. Paloucek (eds.), Poisoning and Toxicology Handbook (4th ed.), Informa, p. 726.
- ^Juan Gershanik; et al.
(1982), "The gasping syndrome and benzyl alcohol poisoning", N Engl J Med, 307 (22): 1384–8, doi:10.1056/nejm198211253072206, PMID 7133084
. - ^Clouser, Amanda; Diseroad, Emily (11 February 2022). "Harmful excipients for pediatric patients". Contemporary Pediatrics. 39 (1). Retrieved 1 October 2024.