ベンゾイン

Benzoin

HCID 8400CAS 119-53-9
部分構造検索類似構造を探す

基本情報

標準SMILES
O=C(c1ccccc1)C(O)c1ccccc1
InChIKey
ISAOCJYIOMOJEB-UHFFFAOYSA-N
分子式
C14H12O2
平均分子量
212.24 g/mol
単同位体質量
212.08372962

概要

Benzoin is an off-white to yellow-white crystalline solid with an odor of camphor. Slightly acrid taste. When broken the fresh surfaces have a milky-white color. (NTP, 1992)

名称と識別子

優先名称
Benzoin
IUPAC
2-hydroxy-1,2-diphenylethanone
現地名
ベンゾイン
英語名
Benzoin
分子式
C14H12O2
分子量
212.24

名称と別名

BENZOIN119-53-92-Hydroxy-1,2-diphenylethanone2-Hydroxy-2-phenylacetophenoneBenzoylphenylcarbinolDL-BENZOINEthanone, 2-hydroxy-1,2-diphenyl-(+-)-BenzoinPhenylbenzoyl carbinolalpha-Hydroxy-alpha-phenylacetophenonealpha-Hydroxybenzyl phenyl ketoneAerozoin
名称をさらに表示
ベンゾイン[S,(+)]-α-ヒドロキシ-α-フェニルアセトフェノン(αS)-ベンゾイン(S)-α-ヒドロキシデオキシベンゾイン(S)-1,2-ジフェニル-2-ヒドロキシエタノン(S)-ベンゾイン(2S)-2-ヒドロキシ-1,2-ジフェニルエタノン(+)-ベンゾイン(2S)-1,2-ジフェニル-2-ヒドロキシエタノン(S)-α-ヒドロキシ-α-フェニルアセトフェノン(S)-α-フェニル-α-ヒドロキシアセトフェノン2-ヒドロキシ-2-フェニルアセトフェノンベンゾイルフェニルカルビノール2-ヒドロキシ-1,2-ジフェニルエタノンアンソッコウα-ヒドロキシ-α-フェニルアセトフェノンα-ベンゾイルベンジルアルコールFEMA 2132BENZOIN SUMATRABenzoin, 99.5%Benzoin, ARBENZOIN GUMBENZOIN GUM SIAMA-HYDROXYBENZYL PHENYL KETONEA-HYDROXY-A-PHENYLACETOPHENONE
desyl alcoholPhenyl-alpha-hydroxybenzyl ketoneFEMA No. 2132NCI-C50011(RS)-BenzoinHydroxy-2-phenyl acetophenoneWy 42956DTXSID1020144

データベース識別子

CAS
119-53-9、579-44-2、8050-35-9、9000-05-9
PubChem CID
8400
DTXSID
DTXSID1020144
ChEMBL
CHEMBL190677
ChEBI
CHEBI:17682
UNII
L7J6A1NE81
EC Number
204-331-3、209-441-5
Nikkaji
J20.621K

物性

構造計算による物性

XLogP
2.1
極性表面積
37.3 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
3
重原子数
16

実験および物理化学的性質

Chemical ClassesOther Classes -> Other Aromatic Compounds
LogP2.130
OdorSWEET NON-DESCRIPT ODOR
TasteSWEET NON-DESCRIPT TASTE
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 2 件

1.31 at 68 °F (NTP, 1992) - Denser than water; will sink

1.31 g/cm³

物理化学的性質

融点
134 · 134-138 °C(lit.)
沸点
194 °C12 · 194 °C12 mm Hg(lit.)
比重(密度)
1.31 · 1.31
蒸気圧
1.3 hPa · 1.3 hPa (136 °C)
FEMA
2132 · 2132 | BENZOIN
闪点
181 · 181

化学的性質

化学的特性Benzoin has a faint, sweet, balsamic odor.

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 68.8% (308 of 448) of all reports.

H412 (30.8%): 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 448 reports by companies from 4 notifications to the ECHA C&L Inventory.

Not Classified

危険有害性情報

Regulatory Information · 5 件

Chemical: Ethanone, 2-hydroxy-1,2-diphenyl-

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

Ethanone, 2-hydroxy-1,2-diphenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanone, 2-hydroxy-1,2-diphenyl- 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: 19-11-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/1899

Ethanone, 2-hydroxy-1,2-diphenyl-: Does not have an individual approval but may be used under an appropriate group standard

Fire Hazards · 2 件

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

Combustible.

Fire PotentialSLIGHT, WHEN HEATED...
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranes. It may also cause contact dermatitis.
Hazards SummaryAn irritant; [ICSC] May cause skin and eye irritation; May be harmful if ingested, inhaled, or absorbed through the skin; Oral LD50 (rat) = 10,000 mg/kg; [MSDSonline]
FDA Requirements121.1164, LIMITATIONS: SYNTHETIC FLAVOR; 8.390, LIMITATIONS: DILUENT IN INKS FOR MARKING FRUITS & VEGETABLES. PRODUCT SPECIFICATIONS APPLY.

安全と保護具

Fire Fighting · 2 件

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

Use water spray, powder.

First Aid Measures · 3 件

Fresh air, rest.

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.

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.

Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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.

Spillage DisposalSweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.
Eye PreventionWear safety spectacles.

毒性情報

Signs and Symptoms · 3 件

Cough. Sore throat.

Redness.

Redness.

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=119-53-9]

Natural Pollution SourcesNOT REPORTED FOUND IN NATURE.
Carcinogen Classification · 6 件

Benzoin

TR-204: Bioassay of Benzoin for Possible Carcinogenicity (CASRN 119-53-9) (1980 )

02/15/80

No Evidence

No Evidence

No Evidence

Non-Human Toxicity Excerpts · 2 件

Benzoin was found to be negative when tested for mutagenicity using the Salmonella/microsome preincubation assay, using the standard protocol approved by the National Toxicology Program (NTP). Benzoin was tested in as many as 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of rat and hamster liver S-9, at doses of 0.033, 0.0333, 0.100, 0.333, 0.3333, 0.667, 1.000, and 3.3333 mg/plate. The highest ineffective dose tested in any S. typhimurium strain was 3.3333 mg/plate. Precipitate was observed in most cultures at the high dose and also some clearing of the background bacterial lawn was also seen.

... Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.

National Toxicology Program Studies · 1 件

A bioassay of benzoin for possible carcinogenicity was conducted by incorporating the test chemical in diets of F344 rats and B6C3F1 mice. ... Groups of 50 male rats were fed diets containing 125 or 250 ppm benzoin for 104 wk, and similar groups of female rats received feed containing 250 or 500 ppm. Groups of 50 mice if each sex were fed diets containing 2,500 or 5,000 ppm benzoin for 104 wk. Groups of 50 untreated rats and mice of each sex were used as matched controls. ... Under the conditions of this bioassay, benzoin was not carcinogenic in F344 rats or B6C3F1 mice. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.

法規制情報

FDA Requirements121.1164, LIMITATIONS: SYNTHETIC FLAVOR; 8.390, LIMITATIONS: DILUENT IN INKS FOR MARKING FRUITS & VEGETABLES. PRODUCT SPECIFICATIONS APPLY.

安全データ

wgk
2
tsca
TSCA listed
rtecs
DI1590000
毒性
LD50 orally in Rabbit: 10000 mg/kg LD50 dermal Rabbit 8870 mg/kg
hs_code
29144090
risk_code
20/21/22-36/37/38

化学と産業

薬理情報

Protein BindingNo pharmacokinetic data available.
Biological Half-LifeNo pharmacokinetic data available.
Metabolism/Metabolites · 2 件

No pharmacokinetic data available.

BENZOIN YIELDS HYDROBENZOIN & MESO-HYDROBENZOIN IN CURVULARIA. ACKLIN, W ET AL, CROAT CHEM ACTA, 37, 11 (1965). /FROM TABLE/

Absorption, Distribution and Excretion · 4 件

No pharmacokinetic data available.

No pharmacokinetic data available.

No pharmacokinetic data available.

No pharmacokinetic data available.

Cellular LocationsMembrane

用途と製造

Uses · 4 件

Used as a flavor, antiseptic, photopolymerization catalyst, and in organic syntheses [HSDB]

Using Disinfectants or Biocides [Category: Clean]

IN ORGANIC SYNTHESES

PRINCIPLY AS A FLAVOR INGREDIENT; ANTISEPTIC; PHOTOPOLYMERIZATION CATALYST; INT FOR ALPHA-BENZOIN OXIME (ANALYT REAGENT FOR METALS), WETTING AGENTS, EMULSIFYING AGENTS, STILBESTROL PRODUCTS

U.S. Exports(1975) No Data
U.S. Imports(1975) No Data
U.S. Production · 3 件

2023: 1,000,000 - <2,500,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.5X10+5 GRAMS

Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesSurfactant (surface active agent)
応用分野 · 6 件

解説ベンゾイン．ベンズアルデヒド2分子をシアン化カリウムを用いて付加させてつくる．(±)-ベンゾインは結晶．融点137 ℃，沸点344 ℃，194 ℃(1.6 kPa)．エタノールに可溶．(＋)-ベンゾインは融点132 ℃．[α]D12＋120.5°(アセトン)．アセトン，エタノール，ベンゼンに可溶，水に微溶．フェーリング液を還元し，酸化するとベンジルになる．亜鉛と緑色の蛍光を発する錯体をつくるので，その検出などの分析用試薬として用いられる．

用途分析用試薬。亜鉛の検出用 : 亜鉛とこの試薬のケイ光反応はごく少量の亜鉛イオンの検出に用いられる。

天然物の起源Benzoin is a resin from the trees of genus Styrax.

使用benzoin is a fragrant essential oil with bactericidal, anti-irritation, and anti-itching properties. It is considered a good ingredient for reducing skin redness and is a preservative of fats. Although its primary constituent is benzoic acid, it also contains canillin and an oily aromatic liquid. This balsamic resin is extracted by cutting deeply into the trunks of trees that grow primarily in Indonesia and Thailand.

一般的な説明Off-white to yellow-white crystalline solid with an odor of camphor. Slightly acrid taste. When broken the fresh surfaces have a milky-white color.

使用用途ベンゾインは、分析用試薬として使用されます。ベンゾインを使用することで、とケイ光反応が起きます。そのため、少量の亜鉛イオンを検出することが可能です。 また、ベンゾインという名前で精油として売られています。これは、熱帯の高木の樹脂から抽出されるものです。甘く、バニラのような香りがし、心を落ち着かせる効果があります。 そのほか、酸化防止剤として、オイルの持ちを良くする役割もあります。

調製方法 · 1 件

純化方法Crystallise benzoin from CCl4, hot EtOH (8mL/g), or 50% acetic acid. Also crystallise it from high purity *benzene, then twice from high purity MeOH, to remove fluorescent impurities [Elliott & Radley Anal Chem 33 1623 1961]. It can be sublimed. [Beilstein 8 IV 1279.]

上流・下流製品情報

サプライヤー1 社

Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd(852)2541 2772

補足説明

定義本品は、アンソクコウノキ Styrax Benzoin から得られた樹脂である。

定義ChEBI: A ketone that consists of acetophenone bearing hydroxy and phenyl substituents at the alpha-position. The parent of the class of benzoins.

関連反応

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