Benzylalkohol

Benzyl Alcohol

HCID 244CAS 100-51-6

Grundinformationen

Standard-SMILES
OCc1ccccc1
InChIKey
WVDDGKGOMKODPV-UHFFFAOYSA-N
Summenformel
C7H8O
Durchschnittliche Molmasse
108,14 g/mol
Monoisotopische Masse
108,05751488

Überblick

Benzyl alcohol appears as a clear colorless liquid with a pleasant odor. Slightly denser than water. Flash point 194 °F. Boiling point 401 °F. Contact may irritate skin, eyes, and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals.

Namen und Bezeichner

Bevorzugter Name
Benzyl Alcohol
IUPAC
phenylmethanol
Lokaler Name
Benzylalkohol
Englischer Name
Benzyl alcohol
Summenformel
C7H8O
Molmasse
108.14

Namen und Synonyme

benzyl alcoholphenylmethanol100-51-6benzenemethanolphenylcarbinolBenzenecarbinolHydroxytolueneBenzoyl alcoholalpha-ToluenolPhenylmethyl alcohol(Hydroxymethyl)benzenePhenolcarbinol
Weitere Namen anzeigen
BnOHbenjiachunBenzylalkoholBenzyl Alcohol BPFEMA 2137Benzyl alcoholl
alpha-hydroxytolueneAlcool benzyliqueBenzal alcoholMethanol, phenyl-benzylic alcoholBenzylicumhydroxymethylbenzenePhenylcarbinolum

Datenbank-Bezeichner

CAS
100-51-6、957205-23-1
PubChem CID
244
DTXSID
DTXSID5020152
ChEMBL
CHEMBL720
ChEBI
CHEBI:17987
UNII
LKG8494WBH
EC Number
202-859-9、835-314-4
Nikkaji
J4.009F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,1
Polarare Oberfläche (TPSA)
20,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
1
Schwere Atome
8

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
PolymersOther Classes -> Alcohols and Polyols, Other
Cosmetics · 3 Einträge

Cosmetics ingredient -> Base; Bulking/Viscosity; Conditioning/Emollient; Flavor; Fragrance; Moisturizing/Humectant; Opacifying Agent; Other (Specify); Preservative/Stabilizer; Solvent; Surfactant

Cosmetic ingredients (Benzyl Alcohol) -> CIR (Cosmetic Ingredient Review)

Preservative; Solvent

pHA solution in water is neutral to litmus
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (Benzyl alcohol) -> IFRA transparency List

Physikochemische Eigenschaften

Schmelzpunkt
-15 °C · -15 °C
Siedepunkt
205 °C · 205 °C
Dichte
1.045 g/mL · 1.045 g/mL at 25 °C(lit.)
Dampfdichte
3.7 · 3.7 (vs air)
Dampfdruck
13.3 mm · 13.3 mm Hg ( 100 °C)
Brechungsindex
20 · n20/D 1.539(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 4746) of reports.

Warning

H302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Benzenemethanol

Hazard Traits - Fragrance Allergen

Regulation (EC) No 1333/2008 (amended)

Benzenemethanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenemethanol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 18-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14748

Benzenemethanol: HSNO Approval: HSR001039 Approved with controls

Other Safety InformationIMAP assessments - Benzenemethanol: Human health tier II assessment
Fire Hazards · 2 Einträge

This chemical is combustible. (NTP, 1992)

Combustible.

Fire Potential · 2 Einträge

Slight, when exposed to heat or flame ...

Combustible

Health Hazards · 1 Eintrag

Inhalation of vapor may cause irritation of upper respiratory tract. Prolonged or excessive inhalation may result in headache, nausea, vomiting, and diarrhea. In severe cases, respiratory stimulation followed by respiratory and muscular paralysis, convulsions, narcosis and death may result. Ingestion may produce severe irritation of the gastrointestinal tract, followed by nausea, vomiting, cramps and diarrhea; tissue ulceration may result. Contact with eyes causes local irritation. Material can be absorbed through skin with anesthetic or irritant effect. (USCG, 1999)

Hazards Summary · 1 Eintrag

Rarely causes allergic contact dermatitis; [Marks, p. 136] Occupational contact urticaria has been reported. [PMID 11766131] A skin and eye irritant; Inhalation of high concentrations may cause CNS effects; May cause skin sensitization; [ICSC] No deaths in rats exposed to saturated concentrations (100-200 ppm) for 2 hours; Rapidly metabolized to hippuric acid; Has caused deaths in premature infants when given in IV solutions >4.5 mg/kg-day; [AIHA] Included in list of established contact allergens in humans; [EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)]

Sicherheit und Schutzausrüstung

Fire FightingUse powder, AFFF, foam, carbon dioxide.
First Aid Measures · 4 Einträge

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from strong oxidants.
Firefighting HazardsSpecial hazards arising from the substance or mixture: Carbon oxides.
Exposure Control and Personal Protection5.0 [ppm]

Toxikologische Informationen

Interactions · 1 Eintrag

Acetaminophen (APAP) toxicity is the most common cause of acute liver failure in industrialized countries. Understanding the mechanisms of APAP-induced liver injury as well as other forms of sterile liver injury is critical to improve the care of patients. Recent studies demonstrate that danger signaling and inflammasome activation play a role in APAP-induced injury. The aim of these investigations was to test the hypothesis that benzyl alcohol (BA) is a therapeutic agent that protects against APAP-induced liver injury by modulation of danger signaling. APAP-induced liver injury was dependent, in part, on Toll-like receptor (TLR)9 and receptor for advanced glycation endproducts (RAGE) signaling. BA limited liver injury over a dose range of 135-540 ug/g body weight or when delivered as a pre-, concurrent, or post-APAP therapeutic. Furthermore, BA abrogated APAP-induced cytokines and chemokines as well as high-mobility group box 1 release. Moreover, BA prevented APAP-induced inflammasome signaling as determined by interleukin (IL)-1(beta), IL-18, and caspase-1 cleavage in liver tissues. Interestingly, the protective effects of BA on limiting liver injury and inflammasome activation were dependent on TLR4 signaling, but not TLR2 or CD14. Cell-type-specific knockouts of TLR4 were utilized to further determine the protective mechanisms of BA. These studies found that TLR4 expression specifically in myeloid cells (LyzCre-tlr4-/-) were necessary for the protective effects of BA. BA protects against APAP-induced acute liver injury and reduced inflammasome activation in a TLR4-dependent manner. BA may prove to be a useful adjunct in the treatment of APAP and other forms of sterile liver injury.

Skin Symptoms · 1 Eintrag

Selected as the 2026 American Contact Dermatitis Society Allergen of the Year. The authors stated that while Benzyl Alcohol is generally considered safe, it can cause allergic contact dermatitis, especially after prolonged or repeated exposure. They also stated that Benzyl Alcohol is not included in many standard patch test series and that there might be underrecognition of its allergenicity.

Ecotoxicity Values · 5 Einträge

EC50; Species: Haematococcus pluvialis (Algae); Concentration: 2600mg/L for 24 hr; Effect: inhibition of photosynthesis /Conditions of bioassay not specified in source examined/

EC50; Species: Chlorella pyrenoidosa (Algae); Concentration: 95 mg/L for 3 hr, Effect: inhibition of photosynthesis /Conditions of bioassay not specified in source examined/

LC50; Species: Petrumyzon marinus /lamprey/; Conditions: static bioassay; Concentration: >=5 mg/L for 24 hr

LC50; Species: Leuciscus idus /Ide, silver or golden orfe/; Conditions: static bioassay; Concentration: 646 mg/L for 48 hr

For more Ecotoxicity Values (Complete) data for BENZYL ALCOHOL (15 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of <5(2) and 29(3) indicate that benzyl alcohol is expected to have very high mobility in soil(SRC). Volatilization of benzyl alcohol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.37X10-7 atm-cu m/mole(4). Benzyl alcohol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.4X10-2 mm Hg at 25 °C(5). Utilizing the Japanese MITI test, 94% of the Theoretical BOD was reached in 2 weeks(6) indicating that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), Koc values of <5(2) and 27(3) indicate that benzyl alcohol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected to be an important fate process(4) based upon a Henry's Law constant of 3.37X10-7 atm-cu m/mole(5). According to a classification scheme(6), an estimated BCF of 1.4(SRC), from its log Kow of 1.10(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 94% of the Theoretical BOD was reached in 2 weeks(9) indicating that biodegradation is an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzyl alcohol, which has a vapor pressure of 9.4X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor phase benzyl alcohol is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 days(SRC), calculated from its rate constant of 2.3X10-11 cu cm/molecule sec at 25 °C(3). Benzyl alcohol does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 2 Einträge

Benzyl alcohol has been identified as a volatile flavor component of baked potatoes(1), Beaufort (Gruyere) cheese(2), bacon(3), and roasted filberts (nuts)(4). It has been identified as a volatile component of blended nectarines, but not in a headspace analysis of the intact fruit(5). Benzyl alcohol was detected in different forms of cooked sweet corn at concentrations of less than 1 ppb to 8 ppb(6). Benzyl alcohol was identified, not quantified, in the edible portion of Korean chamchwi plants(7).

The concentrations in three commercial fermented soybean (Glycine max) available in Hong Kong markets were 107.6, 138., and 211.7 ug/kg(1). Benzyl alcohol was detected in Australian honey at concentrations of and 0.1-0.6 mg/kg from sources of yellow box (Eucalyptus melliodora); it was not detected in honey based on Australian blue gum (Eucalyptus leaucoxylon)(2). The compound is a volatile of ground musty sorghum(3). Benzyl alcohol was identified in Korean red pine (Pinus densiflora) pine sprout tea and pine needle tea(4).

Adverse EffectsNeurotoxin - Acute solvent syndrome

Regulatorische Informationen

FDA Requirements · 5 Einträge

Diluents in color additive mixtures for drug use exempt from certification. The following diluents may be safely used in color additive mixtures that are exempt from certification and which are to be used for coloring drugs, subject to the condition that each straight color in the mixture has been exempted from certification or, if not so exempted, is from a batch that has previously been certified and has not changed in composition since certification. Such listing of diluents is not to be construed as superseding any of the other requirements of the Federal Food, Drug, and Cosmetic Act with respect to drugs, including new drugs. If a definition and specification for a particular diluent is not set forth in this subpart, the material shall be of a purity consistent with its intended use. ... Externally applied drugs: Benzyl alcohol is included on this list.

Benzyl alcohol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Benzyl alcohol is an indirect food additive for use only as a component of adhesives.

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: benzyl alcohol is included in male genital desensitizer drug products.

For more FDA Requirements (Complete) data for BENZYL ALCOHOL (7 total), please visit the HSDB record page.

FIFRA Requirements · 1 Eintrag

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Benzyl alcohol is found on List D. Case No: 4013; Pesticide type: insecticide, fungicide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): benzyl alcohol; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled."

Atmospheric Standards · 1 Eintrag

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Benzyl alcohol is produced, as an intermediate or a final product, by process units covered under this subpart.

State Drinking Water Guidelines(FL) FLORIDA 2,100 ug/L

Sicherheitsdaten

F
8-10-23-35
wgk
1
tsca
TSCA listed
ridadr
UN 1593 6.1/PG 3
hs_code
29062100
RTECS-Nr.
DN3150000

Chemie und Industrie

Pharmakologische Informationen

ATC CodeP - Antiparasitic products, insecticides and repellents
Mechanism of ActionBenzyl alcohol inhibits lice from closing their respiratory spiracles, allowing the vehicle to obstruct the spiracles and causing the lice to asphyxiate.
Biological Half-Life · 2 Einträge

The plasma half-life of benzyl alcohol administered as 2.5% solution in saline was found to be approximately 1.5 hr in dogs injected iv at doses of 52 and 105 mg/kg.

Benzyl alcohol rapidly disappeared from the injection site following intramuscular administration in rats; the disappearance half-life was estimated to be less than 10 minutes. ...

Metabolism/Metabolites · 6 Einträge

Benzyl alcohol is normally oxidized rapidly to benzoic acid, conjugated with glycine in the liver, and excreted as hippuric acid. However, this metabolic pathway may not be well developed in premature infants. The benzyl alcohol may therefore have been metabolized to benzoic acid, which could not be conjugated by the immature liver but accumulated, causing metabolic acidosis ... .

When metabolized, benzyl alcohol is converted to benzoic acid by simple oxidation. The relevant data, therefore, relate to benzoic acid and sodium benzoate.

Benzyl alcohol was an intermediate product in the metabolic pathway of benzyl acetate; the subsequent metabolism was identical to that of benzyl alcohol.

In adults, benzyl alcohol is oxidized to benzoic acid, conjugated in the liver with glycine, and excreted in the urine as hippuric acid. The immature metabolic capacities of infants diminish their ability to metabolize and excrete benzyl alcohol. Preterm babies have a greater ability to metabolize benzyl alcohol to benzoic acid than do term babies, but are unable to convert benzoic acid to hippuric acid, possibly because of glycine deficiency. This results in the accumulation of benzoic acid.

For more Metabolism/Metabolites (Complete) data for BENZYL ALCOHOL (8 total), please visit the HSDB record page.

Benzyl alcohol is a known human metabolite of toluene.

FDA Pharmacological Classification · 6 Einträge

LKG8494WBH

BENZYL ALCOHOL

Established Pharmacologic Class [EPC] - Pediculicide

Benzyl alcohol is a Pediculicide.

BENZYL ALCOHOL

Pediculicide [EPC]

MeSH Pharmacological Classification · 1 Eintrag

Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman&apos;s The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.

Verwendung und Herstellung

Uses · 6 Einträge

CIR ingredient: Benzyl Alcohol

Used as a preservative, epoxy resin catalyst, and in the photographic developer C-22; [Kanerva, p. 1757] Used as a preservative, solvent, and local anesthetic; [Marks, p. 136] Used as a preservative in drugs for injection; [Kanerva, p. 462-3] Used in flavors and perfumes and as a solvent for inks and dyes; [AIHA]

Using Disinfectants or Biocides [Category: Clean]

For benzyl alcohol (USEPA/OPP Pesticide Code: 9502) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

The active ingredient is no longer contained in any registered /pesticide/ products ... "cancelled."

... Photographic developer for color movie films; dyeing nylon filament, textiles, and sheet plastics; solvent for dyestuffs, cellulose esters, casein, waxes, etc.; heat-sealing polyethylene films; intermediate for benzyl esters and ethers; bacteriostat; cosmetics, ointments, emulsions; ball point pen inks; stencil inks.

U.S. Imports · 3 Einträge

(1971) Negligible

(1975) 3.53X10+6 (PRINCPL CUSTMS DISTS)

(1983) 8.25X10+8 g

U.S. Production · 6 Einträge

2023: 40,000,000 - <55,000,000 lb

(1971) 4.22X10+9 G

(1975) 5.84X10+9 G

Benzenemethanol is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#69]

For more U.S. Production (Complete) data for BENZYL ALCOHOL (6 total), please visit the HSDB record page.

Consumption Patterns60% is used in the textile industry as a dye assistant (mostly for dyeing nylon carpeting); and 40% is used in other applications (1972)
Consumer UsesOther
Industry UsesProcessing aids not otherwise specified
Anwendungen · 4 Einträge

BeschreibungBenzyl alcohol is a component catalyst for epoxy resins. It is also contained in the color developer C-22.

OccurrenceThe free alcohol is often present in several essential oils and extracts of jasmine, tobacco, tea, neroli, copaiba, Acacia farnesiana Willd., Acacia cavenia Hook. and Arn., Robinia pseudacacia, ylang-ylang, Pandanus odoratissimus, Michelia champaca, Prunus laurocerasus, tuberose, orris, castoreum, violet leaves, clove buds and others. Also found in fresh apple, apricot, mandarin peel oil, high bush blueberry, raspberry, strawberry fruit, American cranberry and cooked asparagus.

HistoryLIEBIG and WO¨HLER first prepared benzyl alcohol from bitter almond oil (benzaldehyde) in 1832. The structure of benzyl alcohol was determined in 1853 by CANNIZZARO. CANNIZZARO used the reaction named after him, in which benzaldehyde is disproportionated into benzoic acid and benzyl alcohol through the action of an alkali.

Verwendenbenzyl alcohol is a preservative against bacteria, used in concentrations of 1 to 3 percent. It can cause skin irritation.

Darstellung

synthetischeBenzyl alcohol is prepared commercially by the distillation of benzyl chloride with potassium or sodium carbonate. It may also be prepared by the Cannizzaro reaction of benzaldehyde and potassium hydroxide.

Anbieter50 Anbieter

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上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: Benzyl alcohol is an aromatic alcohol that consists of benzene bearing a single hydroxymethyl substituent. It has a role as a solvent, a metabolite, an antioxidant and a fragrance.

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