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rac-(R*)-α-メチルベンジルアルコール

1-Phenylethanol

HCID 7409
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
13323-81-4
標準SMILES
CC(O)c1ccccc1
InChIKey
WAPNOHKVXSQRPX-UHFFFAOYSA-N
分子式
C8H10O
平均分子量
122.16 g/mol
単同位体質量
122.07316494

概要

Alpha-methylbenzyl alcohol appears as a colorless liquid. Insoluble in water and less dense than water. Contact may slightly irritate skin, eyes and mucous membranes. May be slightly toxic by ingestion, inhalation and skin absorption. Used to make other chemicals.

名称と識別子

優先名称
1-Phenylethanol
IUPAC
1-phenylethanol
現地名
rac-(R*)-α-メチルベンジルアルコール
英語名
alpha-Methylbenzyl alcohol
分子式
C8H10O
分子量
122.16

名称と別名

1-Phenylethanol98-85-1ALPHA-METHYLBENZYL ALCOHOLStyrallyl alcoholMethylphenyl carbinolStyralyl alcohol1-Phenethyl alcohol(1-Hydroxyethyl)benzeneMethylphenylcarbinol1-Phenylethyl alcoholPhenylmethylcarbinolalpha-Phenylethanol
名称をさらに表示
DL-α-フェニルエチルアルコールrac-(αR*)-α-メチルベンジルアルコールrac-(S*)-1-フェニルエタノールrac-(R*)-α-メチルベンゼンメタノールrac-(1R*)-1-フェニルエタノールDL-メチルフェニルカルビノールDL-α-メチルベンジルアルコールrac-(R*)-1-フェニルエタノールDL-スチラリルアルコールrac-(R*)-α-フェニルエチルアルコール(±)-1-フェニルエタノール(±)-メチルフェニルカルビノールDL-1-フェニルエタノールrac-(αR*)-α-メチルベンゼンメタノールrac-(αS*)-α-メチルベンゼンメタノール(±)-α-メチルベンジルアルコールrac-(R*)-α-メチルベンジルアルコール(^+)-1-フェニルエタノール(^+)-1-フェニルエタノール, 97%FEMA 2685α-METHYLBENZYLALCOHOLAURORA KA-7014STYRENE ALCOHOLPHENYLETHANOL,1-DL-1-PHENYLETHANOLDL-STYRALYL ALCOHOL
alpha-Methylbenzenemethanolalpha-Phenylethyl alcohol1-Phenyl-1-hydroxyethaneEthanol, 1-phenyl-NCI-C55685alpha-HydroxyethylbenzeneFEMA No. 2685FEMA Number 2685

データベース識別子

CAS
13323-81-4、98-85-1
PubChem CID
7409
DTXSID
DTXSID1020859
ChEMBL
CHEMBL508917
ChEBI
CHEBI:669
UNII
E6O895DQ52
EC Number
202-707-1、236-361-8
Nikkaji
J2.520.944C、J3.224G

物性

構造計算による物性

XLogP
1.4
極性表面積
20.2 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
1
重原子数
9
形式電荷
0
複雑度
74.6

実験および物理化学的性質

Chemical ClassesFlammable agents - 2nd degree
PolymersOther Classes -> Alcohols and Polyols, Other
pHNeutral
FragrancesFragrance Ingredient (alpha-Methylbenzyl alcohol) -> IFRA transparency List
LogP1.42
Odor · 3 件

MILD FLORAL ODOR

MILD HYACINTH-GARDENIA ODOR

Weak, bitter, almond-like odor

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 3 件

1.015 at 68 °F (USCG, 1999) - Denser than water; will sink

1.013 @ 25 °C

1.009-1.014

Flavoring AgentsEU Flavoring substances
Color/FormCOLORLESS LIQ
Solubility · 6 件

less than 1 mg/mL at 67.1 °F (NTP, 1992)

Sol in glycerol, mineral oil, alcohol

SOL IN MOST ORGANIC SOLVENTS

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 1.9% (37 of 1934) of reports.

Warning

H302 (98.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1934 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

危険有害性情報

Regulatory Information · 6 件

Chemical: Benzenemethanol, .alpha.-methyl-

Regulation (EC) No 1831/2003 (amended)

Benzenemethanol, .alpha.-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenemethanol, .alpha.-methyl- 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)

REACH registered substance: 1-phenylethanol (EC: 202-707-1)

1-Phenylethanol: 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.)

DOT LabelPoison
Fire Hazards · 5 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

· Combustible material: may burn but does not ignite readily.

· Combustible material: may burn but does not ignite readily.

· Combustible material: may burn but does not ignite readily.

Health Hazards · 5 件

Irritating to the skin, eyes, nose, throat, and upper respiratory tract. (USCG, 1999)

化学と産業

薬理情報

Metabolism/Metabolites · 5 件

DEHYDROGENASE PRESENT IN RAT CYTOSOL & MICROSOMES CONVERTS 1-PHENYLETHANOL INTO ACETOPHENONES.

...METHYL PHENYLCARBINOL GIVEN TO RATS SHOWS SUBSTRATE STEREOSELECTIVITY IN ITS OWN METABOLISM; WHILE R-(+)-ISOMER IS EXCRETED LARGELY AS GLUCURONIDE, S-(-)-ISOMER UNDERGOES FURTHER OXIDATIVE METABOLISM.

YIELDS ACETOPHENONE IN RAT. 1-PHENYLETHYL-BETA-D-GLUCURONIDE IN RABBIT. /FROM TABLE/

Site directed mutants were constructed in cytochrome p450cam to re-engineer the stereochemistry and coupling of ethylbenzene hydroxylation. The reaction with the wild type enzyme produces one regioisomer 1-phenylethanol with 5% reduced nicotinamide adenine deoxyribonucleic acid product conversion of and a ration of 73:27 for the R and S enantiomers respectively. Ethylbenzene was modeled into the active site of wild type p450cam in a rigid mode and oriented to optimize either pro-R or pro-S hydrogen abstraction. Residues T101, T185 and V247 make extensive contacts with the substrate in the static complexes and were therefore chosen for site directed mutagenesis. Single mutants T101M, V247A and V247M are more stereospecific producing 89, 87 and 82% (R)-1-phenylethanol respectively. The coupling of the reaction is doubled for the single mutants T185L, T185F and V247M. In an effort to engineer incr stereospecificity and coupling into a single catalyst the T101M, T185F and V247M mutants were combined in a multiple mutant of p450cam. This protein hydroxylates ethylbenzene resulting in an R:S ratio of 87:13 for the 1-phenylethanols and 13% coupling of reducing equivalents to product. The catalytic stereospecificity and stoichiometry with T101-T185F-V247M does not represent a summation of changes observed for the single mutants. A portion of the individual effects on substrate recognition produced by the single substitutions is either eliminated or degenerate within the triple mutant.

Alpha-methyl benzyl alcohol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(1-phenylethoxy)oxane-2-carboxylic acid.

Cellular LocationsCytoplasm

用途と製造

Uses · 4 件

Used in perfumery; as a flavoring agent; in dyes; as a laboratory reagent; in stoving enamels; in cellulose nitrate and acetyl cellulose lacquers; as an additive in paint-removal agents; [HSDB] Used as an un-isolated intermediate in styrene production; as an antimicrobial agent; [CHEMINFO]

関連反応

147 件
反応記録を作成
HRID 66628 の反応式
HRID 66628反応物としてuspto-grants-1982_08
HRID 66632 の反応式
HRID 66632反応物としてuspto-grants-1982_08
HRID 94439 の反応式
HRID 94439生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 109074 の反応式
HRID 109074生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 124981 の反応式
HRID 124981生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 140896 の反応式
HRID 140896生成物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 161549 の反応式
HRID 161549反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 164686 の反応式
HRID 164686反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
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化合物ノート

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ノートを作成反応を作成見積依頼を出す

A high solvency for alcohol-soluble cellulose nitrate, cellulose acetate, and cellulose acetobutyrate; for many natural and synthetic resins; and for fats and oils. In contrast to benzyl alcohol, it is miscible with white spirit.

In water, 1,950 mg/l @ 25 °C

1.95 mg/mL at 25 °C

Flash Point · 3 件

185 °F (NTP, 1992)

93 °C

200 °F (93 °C) (CLOSED CUP)

物理化学的性質

融点
19 · 19-20 °C(lit.)
沸点
204 °C745 · 204 °C745 mm Hg(lit.)
比重(密度)
1.012 g/mL · 1.012 g/mL at 25 °C(lit.)
蒸気密度
4.21 · 4.21 (vs air)
蒸気圧
0.1 mm · 0.1 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.527(lit.)
闪点
185 °F · 185 °F
Dielectric constant
7.6 · 7.6(90℃)
CAS データベース
13323 · 13323-81-4(CAS DataBase Reference)

化学的性質

化学的特性Colorless liquid

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Hazards Summary · 1 件

A skin, eye, nose, throat, and upper respiratory tract irritant; [CAMEO] Increased liver weights and centrilobular necrosis observed in high-dose animal studies; Kidney injury and increased benign tumors of kidneys observed in male rats (not relevant to humans); Safe when used as a flavoring agent; [JECFA] Ataxia, labored breathing, and lethargy for up to 30 minutes after receiving high dose in rodent studies; [NTP] A moderate skin irritant; A severe eye irritant; Based on animal studies; [CHEMINFO] An irritant; May cause serious eye injury; Targets kidneys; [MSDSonline]

DOT ID and Guide · 4 件

3438 153

3438 153

2937 153

2937 153

FDA Requirements · 1 件

alpha-Methylbenzyl 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: 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.

Reactive GroupAlcohols and Polyols
Special Reports · 2 件

DHHS/NTP; Toxicology & Carcinogenesis Studies of a-Methylbenzyl Alcohol in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 369 (1990) NIH Publication No. 90-2824

Tennant RW, Ashby J; Mutat Res 257 (3): 209-28 (1991). Classification according to chemical structure, mutagenicity to Salmonella and level of carcinogenicity of a further 39 chemicals tested for carcinogenicity by the U.S. National Toxicology Program.

Reactivity Profile · 1 件

Attacks plastics. [Handling Chemicals Safely, 1980. p. 236]. Acetyl bromide reacts violently with alcohols or water [Merck 11th ed. 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: An explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73. 1967; J, Org. Chem. 28:1893. 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous-carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M. 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].

DOT Emergency Guidelines · 5 件

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /alpha-Methylbenzyl alcohol; alpha-Methylbenzyl alcohol, liquid; alpha-Methylbenzyl alcohol, solid; Methylbenzyl alcohol (alpha)/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /alpha-Methylbenzyl alcohol; alpha-Methylbenzyl alcohol, liquid; alpha-Methylbenzyl alcohol, solid; Methylbenzyl alcohol (alpha)/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /alpha-Methylbenzyl alcohol; alpha-Methylbenzyl alcohol, liquid; alpha-Methylbenzyl alcohol, solid; Methylbenzyl alcohol (alpha)/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /alpha-Methylbenzyl alcohol; alpha-Methylbenzyl alcohol, liquid; alpha-Methylbenzyl alcohol, solid; Methylbenzyl alcohol (alpha)/

For more DOT Emergency Guidelines (Complete) data for ALPHA-METHYLBENZYL ALCOHOL (8 total), please visit the HSDB record page.

DOT Hazard Classification · 6 件

alpha-Methylbenzyl alcohol, liquid

UN2937

Div 6.1 Poisonous materials (49 eCFR § 173.132)

PG III: the degree of danger presented by the material is minor

alpha-Methylbenzyl alcohol, solid

UN3438

安全と保護具

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Accidental Release Measures · 6 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 5 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.

General First Aid:

General First Aid:

General First Aid:

General First Aid:

Exposure Control and Personal Protection · 4 件

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

Fire Fighting Procedures"ALCOHOL" FOAM
Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Isolation and Evacuation · 5 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

Immediate precautionary measure

Immediate precautionary measure

Immediate precautionary measure

Personal Protective Equipment (PPE)Approved respirator, chemical safety goggles, chemical resistant gloves, other protective clothing. (USCG, 1999)
Emergency Response Planning Guidelines · 4 件

Small Fire

Small Fire

Small Fire

Small Fire

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a recommended classification scheme(1), measured Koc values of <5-52, with higher values corresponding to soils with a greater organic content(2), indicate that alpha-methylbenzyl alcohol will have very high mobility in soil(SRC). Biodegradation is expected to be a major fate process for this compound(SRC). Alpha-methylbenzyl alcohol was completely biodegraded within 2-3 weeks under aerobic conditions using an activated sludge inoculum(3). Under anaerobic conditions, this compound had a half-life of 7 days(3). Acetophenone was reported as a major metabolite for both oxygen conditions(3). Volatilization of alpha-methylbenzyl alcohol from either moist surfaces will not be a major fate process(SRC) based on estimated values for Henry's Law constant (2.9X10-7 atm-cu m/mole)(4,SRC). Volatilization from dry soil surfaces should not be significant based on an estimated vapor pressure (0.058 mm Hg)(5,SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), experimental Koc values of <5 to 52(2) indicate that alpha-methylbenzyl alcohol will not adsorb to suspended solids and sediment(SRC) in the water column. Biodegradation is expected to be a major fate process for this compound(SRC). Alpha-methylbenzyl alcohol was completely biodegraded within 2-3 weeks under aerobic conditions using an activated sludge inoculum(3). Under anaerobic conditions, this compound had a half-life of 7 days(3). Acetophenone was reported as the major metabolite for both oxygen conditions(3). Retention pond and aerated lagoon systems reported 12 and 17% biodegradation after 260 hours(3) indicating that under some conditions, biodegradation may not occur rapidly(SRC). Alpha-methylbenzyl alcohol should not volatilize from water surfaces based on an estimated Henry's Law constant of 2.9X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). An estimated BCF value of 9(3,SRC), from a measured water solubility(2), suggests that alpha-methylbenzyl alcohol will not bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(5).

ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 0.058 mm Hg at 25 °C(2,SRC) indicates that alpha-methylbenzyl alcohol will mainly exist in the vapor phase in the ambient atmosphere. Vapor-phase alpha-methylbenzyl 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 about 1.1 days(3,SRC).

Food Survey ValuesAlpha-methylbenzyl alcohol was identified in Beaufort cheese in France at unreported concentrations(1).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Ongoing Test Status · 1 件

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=98-85-1]

Effluent Concentrations · 1 件

Alpha-methylbenzyl alcohol was detected once in the wastewater from a mechanical products industry(1). Wastewater from a petrochemical company contained alpha-methylbenzyl alcohol at unreported concentrations(2). Alpha-methylbenzyl alcohol was detected in finished water from the Blue Plains Advanced Waste Treatment Plant in Washington, DC in September, 1974(3).

Soil Adsorption/Mobility · 1 件

Koc values for alpha-methylbenzyl alcohol were determined for three subsoils: Apison (organic content = 0.11%) had a Koc of 37, Fullerton (organic content = 0.06%) had a Koc of <5, and Dormont (organic content = 1.2%) had a Koc of 52(1). According to a recommended classification scheme(2), these Koc values suggest that alpha-methylbenzyl alcohol has very high mobility in soil, although increasing organic content will act to reduce mobility slightly(SRC).

Atmospheric ConcentrationsAlpha-methylbenzyl alcohol was present in samples taken of indoor air from residential houses at "low relative abundance"(1).
Human Toxicity ExcerptsSimilar threshold conc (0.5%) for conjunctival irritation were noted for phenethyl alcohol in humans and rabbits ... .
Artificial Pollution SourcesAlpha-methylbenzyl alcohol's production and use as a dye carrier(1), in perfumes, flavorings, dyes, and as a laboratory agent(2) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 2 件

In an aerobic, sewage die-away screening test alpha-methylbenzyl alcohol (at 6000 ppm) biodegraded rapidly with 78.2% of the theoretical BOD reached in 8-10 days(1). Phenol-adapted cultures grown without alpha-methylbenzyl alcohol, with alpha-methylbenzyl alcohol (at 100 mg/L), and with both phenol and alpha-methylbenzyl alcohol consumed 69, 75, and 320 ul O2, respectively, over a 210 minute period(2). An Arthrobacter strain initially dehydrogenates alpha-methylbenzyl alcohol to acetophenone which is then converted to an ester, producing phenyl acetate which is then hydrolysed to phenol and acetate(3). A Nocardia strain first oxygenates the benzene nucleus to give 3-(1'-hydroxyethyl)-3,5-cyclo-hexadiene-1,2-diol which is then reduced and subjected to extra-diol cleavage(3). This same strain is also able to degrade alpha-methylbenzyl alcohol using the same pathway as described above for Arthrobacter(3). Alpha-methylbenzyl alcohol, inoculated with a mixed microbial culture, was readily biodegraded from 550 ppm to 20 ppm over 32 days(4). Nitrosomonas europaea degraded 2.5% of alpha-methylbenzyl alcohol (initially present at 200 nmol) over a 15 hour period(5). Alpha-methylbenzyl alcohol had a BOD of 1.0 g/g alpha-methylbenzyl alcohol after a 10 day incubation with a sewage inoculum(6).

Loss of alpha-methylbenzyl alcohol was monitored in four systems. In an aerobic, screening test using an activated sludge inoculum, alpha-methylbenzyl alcohol (at 100 ppm) was nearly completely biodegraded within either 14 or 20 days, depending on the inoculum size(heavy or light, respectively); acetophenone was the major metabolite(1). In an aerobic, retention pond system, 12% biodegradation was measured over 260 hours (alpha-methylbenzyl alcohol initially present at 300 ppm)(1). 17% degradation of alpha-methylbenzyl alcohol (at 300 ppm) was reported in an aerated lagoon system after 240 hours(1). Alpha-methylbenzyl alcohol had a half-life of 7 days under anaerobic conditions using a digester sludge inoculum; acetophenone was formed as a metabolite(1).

Carcinogen Classification · 6 件

Alpha-Methylbenzyl Alcohol

TR-369: Toxicology and Carcinogenesis Studies of alpha-Methylbenzyl Alcohol (CASRN 98-85-1) in F344/N Rats and B6C3F1 Mice (Gavage Studies) (1990 )

03/13/89

Some Evidence

No Evidence

No Evidence

Environmental Bioconcentration · 1 件

An estimated BCF value of 9 was calculated for alpha-methylbenzyl alcohol(SRC), using a measured water solubility of 1950 mg/L at 25 °C(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will not be an important fate process(SRC).

法規制情報

FDA Requirements · 1 件

alpha-Methylbenzyl 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: 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.

安全データ

wgk
1
rtecs
DO9275000
ridadr
UN 3438
毒性
The acute oral LD50 in rats was reported as 400 mg/kg (Smyth & Carpenter, 1944). The acute dermal LD50 value in rabbits exceeded 2.5 g/kg (Moreno, 1973).
risk_code
22-38-41
hazard_code
Xn
safety_code
26-39
hazard_class
6.1
packing_group
III

Painting (Solvents) [Category: Paint]

PERFUMERY; FLAVORING; DYES; LABORATORY REAGENT

Methylbenzyl alcohol can be used like benzyl alcohol, and can be employed in stoving enamels. In cellulose nitrate and acetyl cellulose lacquers, methylbenzyl alcohol helps to improve flow and film formation and prevents blushing at relatively high atmospheric humidity levels. It has also proved to be a useful additive in paint-removal agents on account of its dissolution properties and long evaporation time.

U.S. Imports · 2 件

(1977) 1.05X10+8 GRAMS (PRINCPL CUSTMS DISTS)

(1979) 6.81X10+7 GRAMS (PRINCPL CUSTMS DISTS)

U.S. Production · 3 件

2023: 1,000,000 - <5,000,000 lb

(1974) 4.54X10+6 G (CONSUMPTION AS FRAGRANCE)

(1977) LESS THAN 2.7X10+11 G-UNISOLATED INT

Industry UsesIntermediate
Methods of Manufacturing · 2 件

REDUCTION OF ACETOPHENONE; REACTION OF METHYL MAGNESIUM CHLORIDE AND BENZALDEHYDE; OXIDATION OF ETHYLBENZENE

In the hydroperoxide process, an organic hydroperoxide is used to epoxidize propylene; an organic alcohol is a coproduct.

Formulations/PreparationsGRADE: FCC
Use Classification · 6 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 4 件

Petrochemical Manufacturing

Benzenemethanol, .alpha.-methyl-: ACTIVE

TWO OPTICALLY ACTIVE ISOMERS EXIST. COMMERCIAL PRODUCT IS RACEMIC FORM.

REPORTED USES: NON-ALCOHOLIC BEVERAGES 4.6 PPM; ICE CREAM, ICES, ETC 3.8 PPM; CANDY 6.8 PPM; BAKED GOODS 9.0 PPM; GELATINS & PUDDINGS 4.0 PPM; CHEWING GUM 0.30 PPM.

応用分野

天然物の起源Has apparently not been reported to occur in nature.

調製方法

製造方法By hydrogenation or reduction of acetophenone; or from methyl magnesium chloride plus benzaldehyde by a Grignard-type reaction (Bedoukian, 1967).

純化方法Purify the alcohol via its hydrogen phthalate. [See Houssa & Kenyon J Chem Soc 2260 1930.] Shake it with a solution of ferrous sulfate, and th

上流・下流製品情報

下流製品

スチラリルブチレ-ト1-Phenylethyl chloroformate4-Methoxy-2-(1-phenyl-ethyl)-phenol1‐フェニルエタノール‐1,2,2,2‐D43-(3-メチルフェニル)プロピオフェノン