CAS 122-57-6 Benzylideneacetone (HCID 637759)

概要

Trans-benzylideneacetone is the trans-isomer of benzylideneacetone. It acts as an inhibitor of the enzyme phospholipase A2 (EC 3.1.1.4) of insects like diamond back moth. It has a role as a flavouring agent, a fragrance, an EC 3.1.1.4 (phospholipase A2) inhibitor and a bacterial metabolite.

名称と識別子

優先名称: Benzylideneacetone
IUPAC: (E)-4-phenylbut-3-en-2-one
現地名: (E)-1-フェニル-1-ブテン-3-オン
英語名: trans-4-Phenyl-3-buten-2-one
分子式: C10H10O
分子量: 146.19

名称と別名

BenzylideneacetoneBenzalacetoneAcetocinnamoneBenzylidene acetoneStyryl methyl ketoneBenzalaceton4-PhenylbutenoneBenzilideneacetoneBenzilidene acetone2-Phenylvinyl methyl ketoneKetone, methyl styrylMethyl 2-phenylvinyl ketone

名称をさらに表示

(E)-1-メチル-3-フェニル-2-プロペン-1-オンメチル[(E)-スチリル]ケトン(E)-スチリルメチルケトン[(E)-2-フェニルエテニル]メチルケトン(3E)-4-フェニル-3-ブテン-2-オン(E)-ベンジリデンアセトン(E)-1-フェニル-1-ブテン-3-オン(E)-メチルスチリルケトン(E)-4-フェニル-3-ブテン-2-オンtrans-ベンジリデンアセトン[(E)-スチリル]メチルケトン(E)-1-フェニル-2-アセチルエテンTRANS-4-フェニル-3-ブテン-2-オンtrans-ベンザルアセトンメチル trans-スチリルケトンTRANS‐4‐フェニル‐3‐ブテン‐2‐オンtrans-4-フェニルブタン-3-エン-2-オン(3E)-4-フェニルブタ-3-エン-2-オン(E)-4-((4-1H)-フェニル)-3-ブテン-2-オンBARBENZYLIDENACETONETRANS-BENZALACETONETpboFEMA 2881TRANS-BENZYLIDENEACETONETC-BAR(e)-4-phenyl-3-buten-2-oneMethyl trans-styryl ketoneTRANS-4-PHENYL-3-BUTENE-2-ONE

(3E)-4-phenylbut-3-en-2-oneMethyl beta-styryl ketone4-Phenyl-3-butene-2-one(3E)-4-Phenyl-3-buten-2-oneFEMA No. 2881t-PBOB03X40BMT5CHEBI:217301

データベース識別子

CAS: 122-57-6、1896-62-4
PubChem CID: 637759
DTXSID: DTXSID1031626
ChEMBL: CHEMBL73639
ChEBI: CHEBI:78399
UNII: B03X40BMT5
EC Number: 204-555-1、217-587-6
Nikkaji: J5.357K、J80.339A

物性

構造計算による物性

XLogP: 2.1
極性表面積: 17.1 Å²
水素結合供与体数: 0
水素結合受容体数: 1
回転可能結合数: 2
重原子数: 11
形式電荷: 0
複雑度: 152

実験および物理化学的性質

Chemical ClassesOther Classes -> Aromatic Ketones

SpringerMaterials PropertiesChemical shift

FragrancesFragrance substance (Benzylidene acetone) -> IFRA amendment 40

LogP2.07

Boiling Point262.00 °C. @ 760.00 mm Hg

Melting Point41.5 °C

物理化学的性質

融点: 39 · 39-42 °C(lit.)
沸点: 260 · 260-262 °C(lit.)
比重(密度): 1 · 1,038 g/cm3
蒸気圧: 0.01 mm · 0.01 mm Hg ( 25 °C)
屈折率: 1.5836 · 1.5836 (estimate)
FEMA: 2881 · 2881 | 4-PHENYL-3-BUTEN-2-ONE
闪点: 150 °F · 150 °F
貯蔵温度: Keep in dark place,Sealed in dry,Room Temperature
溶解性: アルコール: 易溶性(lit.)
外見: 結晶性物質
色: 黄色
水溶解度: 実質的に不溶
Merck: 14 · 14,1137
InChI: 1S/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3/b8-7+
InChIKey: BWHOZHOGCMHOBV-BQYQJAHWSA-N
SMILES: CC(=O)\C=C\c1ccccc1
CAS データベース: 1896 · 1896-62-4(CAS DataBase Reference)
NISTの化学物質情報: 3 · 3-Buten-2-one, 4-phenyl-, (E)-(1896-62-4)

化学的性質

化学的特性light yellow low melting crystalline mass or

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 2.6% (50 of 1901) of reports.

Warning

H315 (84.2%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P272, P280, P302+P352, P321, P332+P317, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1901 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

危険有害性情報

Regulatory Information · 3 件

Status: Active Update: 17-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/5367

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

3-Buten-2-one, 4-phenyl-, (3E)-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryNo evidence of carcinogenicity in mice or rats (dermal exposure); [NTP] An irritant; [Merck Index] An irritant; May cause skin and respiratory sensitization; [Acros Organics MSDS]

Hazard Classes and Categories · 2 件

Skin Irrit. 2 (97.7%)

Skin Irrit. 2 (84.2%)

毒性情報

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.

Carcinogen Classification · 6 件

Methyl trans-Styryl Ketone

TR-572: Toxicology and Carcinogenesis Studies of Methyl trans-Styryl Ketone (CASRN 1896-62-4) in F344/N Rats and B6C3F1 Mice (Feed and Dermal Studies) (2012 )

01/26/11

No Evidence

安全データ

F: 8
wgk: 3
rtecs: EN0330050
ridadr: UN 3077 9/PG III
毒性: mma-sat 300 mg/plate FCTOD7 20,427,82
hs_code: 29143990
risk_code: 36/37/38-43-42/43
化審法: (3)-1232
安衛法: 変異原性物質
消防法: 危-4-2-III
hazard_code: Xn,Xi
safety_code: 7-26-36/37/39-37/39
hazard_class: 9
packing_group: III
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

Cellular LocationsCytoplasm

用途と製造

UsesUsed in perfumes and flavors and as a reagent; [Merck Index]

IFRA Fragrance Standards · 6 件

Benzylidene acetone

4-Phenyl-3-buten-2-one; 3-Buten-2-one, 4-phenyl-; Benzilideneacetone; Methyl styryl ketone

IFRA_STD_113.pdf

40

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Prohibition: This material should not be used as a fragrance ingredient

Use ClassificationFlavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

応用分野

使用trans-4-Phenyl-3-buten-2-one is used in various synthetic preparations.

一般的な説明trans-4-Phenyl-3-buten-2-one forms trans-4-(4-hydroxyphenyl)-3-buten-2-one (4-OH-PBO) as a metabolite when incubated with liver microsomes of untreated rats in the presence of NADPH.

上流・下流製品情報

下流製品

ベンジルアセトン 2',6'-ジメチルアセトフェノン 5-フェニル-1,3-シクロヘキサンジオン trans,trans-1,5-ジフェニル-1,4-ペンタジエン-3-オン 4-フェニル-2-ブタノール 2-Hydroxy-6-methyl-4-phenylpyridine Methyl 2-(1-methyl-3-phenyl-2-propenylidene)-1-hydrazinecarboxylate 1H-Pyrazole, 4,5-dihydro-3-methyl-5-phenyl-

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補足説明

定義ChEBI: The trans-isomer of benzylideneacetone. It acts as an inhibitor of the enzyme phospholipase A2 (EC 3.1.1.4) of insects like diamond back moth.