Benzyl acetate

HCID 8785CAS 140-11-4

基本情報

標準SMILES
CC(=O)OCc1ccccc1
InChIKey
QUKGYYKBILRGFE-UHFFFAOYSA-N
分子式
C9H10O2
平均分子量
150.17 g/mol
単同位体質量
150.06807956

概要

Benzyl acetate is a colorless liquid with an odor of pears. (USCG, 1999)

名称と識別子

優先名称
Benzyl acetate
IUPAC
benzyl acetate
現地名
酢酸ベンジル
英語名
Benzyl acetate
分子式
C9H10O2
分子量
150.17

名称と別名

BENZYL ACETATE140-11-4Acetic acid benzyl esterPhenylmethyl acetateBenzyl ethanoateAcetic acid, phenylmethyl esterAcetic acid, benzyl esterPhenylmethyl ethanoatealpha-Acetoxytoluene(Acetoxymethyl)benzeneNCI-C06508Benzylester kyseliny octove
名称をさらに表示
酢酸ベンジルベンゼンメタノールアセタート酢酸フェニルメチルベンジル=アセタート3-フェニルプロピオナートベンジルアセタート3-フェニルプロピオン酸アニオンベンジルアルコールアセタート酢酸ベンジル, 99%benzyl acetaterFEMA 21353-PhenylpropionatephenylmethylacetateacetoxymethylbenzeneNatural benzyl acetateBenzyl ester of acetic acid
FEMA No. 2135DTXSID00201510ECG3V79ZJNSC-4550DTXCID40151CHEBI:52051RefChem:5593205-399-7

データベース識別子

CAS
140-11-4
PubChem CID
8785
DTXSID
DTXSID0020151
ChEMBL
CHEMBL1233714
ChEBI
CHEBI:52051
UNII
0ECG3V79ZJ
EC Number
205-399-7
Nikkaji
J2.950E

物性

構造計算による物性

XLogP
2
極性表面積
26.3 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
3
重原子数
11

実験および物理化学的性質

Chemical ClassesFlammable agents - 2nd degree
SolventsSolvents -> Esters (<C12)
CosmeticsSolvent
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (Benzyl acetate) -> IFRA transparency List
LogP · 3 件

log Kow = 1.96

1.96

1.96

物理化学的性質

融点
-51 °C · -51 °C (lit.)
沸点
206 °C · 206 °C (lit.)
比重(密度)
1.054 g/mL · 1.054 g/mL at 25 °C (lit.)
蒸気密度
5.1 · 5.1
蒸気圧
23 mm · 23 mm Hg ( 110 °C)
屈折率
20 · n20/D 1.502(lit.)
化学的性質 · 2 件

化学的特性Benzyl acetate is a colorless liquid with a fruity odor. On burning and decomposition, it produces irritating fumes. Benzyl acetate reacts with strong oxidants causing fire and explosion hazard. Benzyl acetate is stable under normal conditions of use. Heating to decomposition may release carbon monoxide, carbon dioxide and other potentially toxic fumes and gases. Vapors may form explosive mixtures with air at elevated temperatures (> 90°C / 194°F). Avoid heat, open flames and other potential sources of ignition. It has been used as a food additive in fruit flavours and as a component of perfumes since the early 1990s and is widely used as a fragrance in soaps, detergents and incense. There is widespread human exposure to benzyl acetate by ingestion, skin application and inhalation.

化学性质新鮮なフルーティージャスミン様

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 32.5% (779 of 2397) of reports.

H412 (62.6%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2397 reports by companies from 19 notifications to the ECHA C&L Inventory.

Danger

H227: Combustible liquid [Warning Flammable liquids]

危険有害性情報

Regulatory Information · 6 件

Chemical: Acetic acid, phenylmethyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Acetic acid, phenylmethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Acetic acid, phenylmethyl ester 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: 01-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14570

Benzyl acetate: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Acetic acid, phenylmethyl ester: Human health tier I assessment
Fire Hazards · 2 件

This chemical is combustible. (NTP, 1992)

Combustible. Above 90 °C explosive vapour/air mixtures may be formed.

Fire PotentialCombustible liquid.
Health HazardsHarmful if inhaled. May be harmful if swallowed or absorbed through the skin. Vapor or mist is irritating to the eyes, mucous membrane and upper respiratory tract. (USCG, 1999)
Hazards Summary · 1 件

Causes respiratory tract irritation in the range of 50-160 ppm; [CHEMINFO] Has anesthetic effects at high concentrations in animal studies; [ChemIDplus] Included in list of fragrance substances with negative human data, i.e. patch tests of patients with suspected contact allergy to fragrance ingredients which yielded negative results.; [EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] An irritant; May cause smarting and reddening of skin if spilled and allowed to remain on clothes; [CHRIS] Vapor causes eye and respiratory tract irritation; May cause effects on the CNS and kidneys; [ICSC] Safe when used as a flavoring agent in food; Acceptable daily intake (ADI) of 0-5 mg/kg; [JECFA] A skin and strong eye irritant; May cause CNS depression; Targets nerves and kidney; [Sigma-Aldrich MSDS]

安全と保護具

Fire Fighting · 2 件

Fire Extinguishing Agents: Water spray, carbon dioxide, dry chemical, alcohol foam. (USCG, 1999)

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

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

Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Rest. Refer for medical attention .

First Aid · 1 件

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. Ventilation along the floor.
Fire Fighting ProceduresALCOHOL FOAM, CARBON DIOXIDE.
Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

毒性情報

Treatment · 1 件

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Health Effects · 1 件

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 280(SRC), determined from a log Kow of 1.96(2) and a regression-derived equation(3), indicates that benzyl acetate is expected to have moderate mobility in soil(SRC). Volatilization of benzyl acetate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-5 atm-cu m/mole(SRC) derived from its experimental values for vapor pressure, 0.18 mm Hg(4), and water solubility, 3.1X10+3 mg/l(5). Biodegradation of benzyl acetate in soil may be important(SRC), based upon its biodegradation in water(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 280(SRC), determined from a log Kow of 1.96(2) and a regression-derived equation(3), indicates some adsorption of benzyl acetate to suspended solids and sediment in the water column is expected(SRC). Benzyl acetate is expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 1.1X10-5 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 0.18 mm Hg(4), and water solubility, 3.1X10+3 mg/l(5). Estimated volatilization half-lives for a model river and model lake are 4.1 and 34 days, respectively(3,SRC). According to a classification scheme(6), an estimated BCF of 18(3,SRC), from a log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Benzyl acetate is expected to biodegrade in aquatic systems(SRC); benzyl acetate reached 92 to 96% of its theoretical BOD over a period of 4 weeks(5). An estimated hydrolysis half-life of 38 days at pH 7(7), indicates hydrolysis may be an important process(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzyl acetate, which has a vapor pressure of 0.18 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase benzyl acetate 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 about 2.5 days(3,SRC).

Food Survey ValuesBenzyl acetate was identified as a volatile component of roasted filberts(1). Benzyl acetate was identified as a volatile flavor compound in the juice of Japanese Kogyoku apples(2).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure Routes · 2 件

The substance can be absorbed into the body by inhalation and by ingestion.

Oral (L1223) ; inhalation (L1223) ; dermal (L1223) ; eye contact (L1223)

法規制情報

FDA Requirements · 1 件

Benzyl acetate is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient. Synthetic flavoring substances and adjuvants incl benzyl acetate may be safely used in foods.

安全データ

wgk
1
tsca
TSCA listed
rtecs
AF5075000
ridadr
2810
毒性
LD50 orally in rats: 2490 mg/kg (Jenner)
PRTR法
第二種指定化学物質

化学と産業

薬理情報

Metabolism/Metabolites · 5 件

... BENZYL ACETATE IS RAPIDLY HYDROLYZED TO ACETIC ACID AND BENZYL ALCOHOL, AND THE LATTER OXIDIZED TO BENZOIC ACID & ... EXCRETED AS HIPPURIC ACID.

In rats, benzyl acetate is hydrolyzed to benzyl alcohol, which is oxidized to benzoic acid and excreted as hippuric acid and benzyl mercapturic acid.

In a chemical disposition study conducted by the NTP, male Fischer 344 rats and male B6C3F1 mice were shown to efficiently absorb and rapidly metabolize and excrete orally administered benzyl acetate. The doses used in this study were 5, 50, or 500 mg/kg for rats and 10, 100, or 1000 mg/kg for mice in single dose corn oil gavage administrations and 500 mg/kg for rats and 1000 mg/kg for mice daily five times per week for two weeks, also administered by gavage in corn oil. Most (90%) of the benzyl acetate-derived radioactivity was recovered in the urine and none was detected in the liver, blood, muscle, adipose tissue skin, lung, kidney, or stomach of treated rats or mice. The major metabolite isolated in the urine was hippuric acid (94%-99% of the dose). Other metabolites found were mercapturic acid and benzyl alcohol. Benzyl acetate was not detected in the urine of treated animals. Neither the size of the dose nor the frequency of dosing had any effect on the absorption, metabolism, or excretion of this compound. There was no evidence to indicate any saturation of this metabolizing capacity in either species over the range of doses studied.

Effects of gavage versus dosed feed administration on the toxicokinetics of benzyl acetate were studied in male F344 rats and B6C3F1 mice. Benzyl acetate was rapidly hydrolyzed to benzyl alcohol and then oxidized to benzoic acid. After gavage administration of benzyl acetate in corn oil at 500 mg/kg (rats) and 1000 mg/kg(mice), high benzoic acid plasma concentrations were observed. In contrast, much lower benzoic acid plasma concentrations were found after dosed feed administration at about 615 mg/kg/day for rats and about 850 mg/kg/day for mice. Results show that although the daily doses of benzyl acetate are comparable, bolus gavage administration effectively saturated the benzoic acid elimination pathway whereas dosed feed administration did not. In contrast, hippuric acid plasma concentrations were similar after both gavage and dosed feed administration due to the depletion of the glycine supply pool. ...

Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure.

Absorption, Distribution and Excretion · 3 件

Benzyl acetate was absorbed from the gastrointestinal tract of rats and mice, with approximately 90% of the administered dose recovered as various metabolites in the urine within 24 hr. ... This capacity for absorption, metabolism, and disposition was unaffected by the amount or number of doses administered.

The effect of vehicle and occlusion on the in vitro percutaneous absorption of [methylene-14C]-benzyl acetate (1.7-16.6 mg/sq cm) has been studied in diffusion cells using full thickness skin from male Fischer 344 rats. Absorption of neat benzyl acetate through rat skin occluded with parafilm was 49.3 +/- 2.0% (mean +/- SD, n=4) after 48 hr. When benzyl acetate in ethanol was applied to the skin and the skin was occluded with parafilm, the extent of absorption at 48 hr was not significantly different from that after neat application. However at 6 hr, as the ethanol content of the application mixture was increased, the absorption of benzyl acetate through occluded skin was enhanced proportionally. When phenylethanol was used as a vehicle, the extent of the benzyl acetate absorption through occluded skin at 48 hr was enhanced (P less than 0.05) compared with that after application neat; with 50% (v/v) phenyl-ethanol, absorption at 48 hr was 56.3 +/- 4.9%. However, this enhanced absorption did not correlate with the proportion of phenylethanol in the application mixture. When dimethylsulphoxide was used as a vehicle, the extent of absorption of benzyl acetate through occluded skin at 48 hr was enhanced (P less than 0.05) compared with that after application neat (absorption was 59.3 +/- 3.7% of the applied dose when 50% (v/v) dimethylsulphoxide was used). As the dimethylsulphoxide content of the application mixture was increased, the absorption of benzyl acetate was enhanced proportionally. Occlusion of the skin surface with parafilm often significantly enhanced absorption (P less than 0.05), although the effect varied with time and vehicle. In general, the degree of any enhanced absorption caused by the use of a vehicle or occlusion of the skin was small, and, in most cases, would be unlikely to be toxicologically significant.

The comparative absorption of ... benzyl acetate has been studied in rat and human skin, using shaved, full-thickness dorsal skin of male Fischer 344 rats and full-thickness human skin obtained from patients undergoing surgical resection. Penetration of the compound through rat and human skin was evaluated in vitro in flow-through diffusion cells following topical application of neat [methylene-14C] benzyl acetate (33.1 mg/sq cm) to the epidermal surface and occlusion with a teflon cap, 2.9 cm above the skin surface. The absorption of benzyl acetate across rat skin was rapid and extensive, reaching 34.3 +/- 3.9% of the applied dose (11.3 +/- 1.3 mg/sq cm) (mean +/-SD, n=12) at 24 hr and 55.8 +/- 5.0% of the applied dose (18.5 +/- 1.7 mg/sq cm)at 72 hr. The penetration of benzyl acetate was significantly (P<0.05) less rapid and extensive through human skin, reaching 5.5 +/- 0.1% of the applied dose (1.8 +/- 0.0 mg/sq cm) (mean +/- SD, n=12) at 24 hr and 17.8 +/- 3.3% of the applied dose (5.9 +/-1.1 mg sq cm) at 72 hr. The rate of penetration of benzyl acetate was greater through rat skin than through human tissue at all time points studied up to 72 hr. The maximum rate of skin penetration was 0.6 +/- mg/sq cm/hr and 0.1 +/_- 0.0 mg/sq cm/hr through rat and human skin, respectively. These data indicate that systemic exposure to benzyl acetate may occur after skin contact in humans. They also support the evidence from the literature that human skin is generally less permeable to xenobiotics than rat skin.

Cellular LocationsCytoplasm

用途と製造

Uses · 5 件

Used as a fragrance, flavoring agent, and solvent; Also used in inks, varnish removers, oils, lacquers, and polishes; [CHEMINFO] Found in many plants, especially jasmine; [Merck Index] Used as a flavoring agent; [FDA]

Painting (Solvents) [Category: Paint]

In perfumery, solvent for cellulose acetate and nitrate.

Artificial jasmine and other perfumes; soap perfume; flavoring; solvent and high boiler for cellulose acetate and nitrate, natural and synthetic resins; oils; lacquers; polishes; printing inks; varnish removers.

It is used widely in perfumery and cosmetics for its aroma and in flavorings to impart apple and pear flavors (L1222).

U.S. Imports · 3 件

(1972) 6.61X10+6 GRAMS (PRINCPL CUSTMS DISTS)

(1975) 1.60X10+6 GRAMS (PRINCPL CUSTMS DISTS)

(1984) 4.83X10+9 g

U.S. Production · 3 件

2023: 10,000,000 - <25,000,000 lb

(1972) 6.42X10+8 GRAMS

(1975) 5.87X10+8 GRAMS

Consumption PatternsThe bulk of benzyl acetate is used in soap odors, but it is also popular for other perfumes and is used to a minor extent in flavors (1980).
Consumer UsesFragrance
Industry UsesFixing agent (mordant)
応用分野 · 6 件

用途花精油、セッケン香料として用いるほか、果実エッセンスの製造、塗料溶剤などにも使用する。

用途人工ジャスミン等香料、有機溶剤(硝化綿、ニトレート、樹脂)、着香料、染料(溶剤)、油脂、ラッカー、麻酔剤、印刷インキ、光沢剤、石鹸香料

天然物の起源Present as a main constituent in several oils and flower absolutes: ylang-ylang, cananga, neroli, jasmine, hyacinth, gardenia, tuberose. It has been isolated from the essential oil of the flowers of Loiseleuria procumbens Desv. (azelea). Also reported found in apricot, cooked asparagus, mozzarella cheese, grilled beef, cooked pork, malt whiskey, fresh mango, malt, wort and clams.

使用Benzyl acetate is used as an artificial jasmine and other perfumes, soap perfume, flavoring agent, solvent for cellulose acetate and nitrate, natural and synthetic resins, oils, lacquers, polishes, printing inks, and varnish removers.

使用Benzyl acetate is produced by reacting benzyl chloride with an alkali acetate or by esterifying benzyl alcohol with acetic anhydride. It is also formed in the oxidation of toluene in the presence of acetic acid or acetic anhydride. Benzyl acetate is one of the most used odorants. It is also used as a flavor and, to a small extent, as a high-boiling solvent.

一般的な説明Colorless liquid with an odor of pears.

調製方法

製造方法Benzyl acetate is produced by the interaction of benzyl chloride and sodiumacetate, by acetylation of benzyl alcohol, or from benzaldehyde and acetic acid with zinc dust.

純化方法Purify the acetate by fractional distillation, preferably in a good vacuum. Values of n25 of 1.5232-1.5242 are too high and should be nearer to 1.4994. [Merker & Scott J Org Chem 26 5180 1961, Beilstein 6 IV 2262.]

サプライヤー50 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]

補足説明

定義本品は、酢酸(*)とベンジルアルコール(*)とのエステルであり、次の化学式で表される。参照表示名称:酢酸, ベンジルアルコール

定義ChEBI: Benzyl acetate is the acetate ester of benzyl alcohol. It has a role as a metabolite. It is an acetate ester and a benzyl ester.

関連反応

55 件

関連ノート

読み込み中…