4-Phenylbutenon

4-Phenyl-3-Buten-2-one

HCID 15909CAS 122-57-6
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Grundinformationen

Standard-SMILES
CC(=O)C=Cc1ccccc1
InChIKey
BWHOZHOGCMHOBV-UHFFFAOYSA-N
Summenformel
C10H10O
Durchschnittliche Molmasse
146,19 g/mol
Monoisotopische Masse
146,07316494

Überblick

Benzylideneacetone is a flavouring ingredient. Benzylideneacetone is present in hydrolysed soy protein Benzylideneacetone belongs to the family of Phenylpropenes. These are compounds containing a phenylpropene moeity, which consists of a propene substituent bound to a phenyl group.

Namen und Bezeichner

Bevorzugter Name
4-Phenyl-3-Buten-2-one
IUPAC
4-phenylbut-3-en-2-one
Lokaler Name
4-Phenylbutenon
Englischer Name
Benzalacetone
Summenformel
C10H10O
Molmasse
146.19

Namen und Synonyme

DTXSID4025662DTXCID305662RefChem:1071402122-57-63-Buten-2-one, 4-phenyl-4-Phenyl-3-Buten-2-oneMethyl styryl ketone4-Phenyl-but-3-en-2-onebenzalacetone-d4acetylstyroltrans-Benzylideneacetone;BenzalacetoneBENZAL ACETONE
Weitere Namen anzeigen
(E)-4-Phenylbut-3-en-2-oneBENZYLIDENEACETONEbenzylidene4-Phenylbut-3-en-2-oneBenzalaceton(3E)-4-phenylbut-3-en-2-oneACETOCINNAMONEFEMA 2881
1-Phenylbut-1-en-3-one4-phenyl-3 -buten-2-oneSCHEMBL312972orb1222576orb1679996orb2900216orb3025863SCHEMBL7226394

Datenbank-Bezeichner

CAS
122-57-6
PubChem CID
15909
DTXSID
DTXSID4025662
ChEMBL
CHEMBL3187978
EC Number
204-555-1

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,1
Polarare Oberfläche (TPSA)
17,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
2
Schwere Atome
11

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesBoiling point
FragrancesFragrance substance (Benzylidene acetone) -> IFRA amendment 40
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 2 Einträge

insoluble in water; soluble in organic solvents, oils

very soluble (in ethanol)

Boiling Point260 °C

Physikochemische Eigenschaften

Schmelzpunkt
39 · 39-42 °C(lit.)
Siedepunkt
260 · 260-262 °C(lit.)
Dichte
1.038 · 1.038
Dampfdruck
0.01 mm · 0.01 mm Hg ( 25 °C)
Brechungsindex
1.5836 · 1.5836
FEMA
2881 · 2881 | 4-PHENYL-3-BUTEN-2-ONE

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: 3-Buten-2-one, 4-phenyl-

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

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

Hazard Classes and CategoriesSkin Irrit. 2 (84.2%)

Toxikologische Informationen

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

F
8
wgk
3
tsca
TSCA listed
hs_code
29143900
RTECS-Nr.
EN0330050
risk_code
36/37/38-43-42/43

Chemie und Industrie

Verwendung und Herstellung

IFRA Fragrance Standards · 6 Einträge

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 Classification · 3 Einträge

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information3-Buten-2-one, 4-phenyl-: ACTIVE
Anwendungen · 3 Einträge

BeschreibungBenzylidenaceton bildet farblose nach Cumarin riechende Tafeln. Es schmilzt bei 42 ℃ und siedet bei Normaldruck zwischen 260 und 262 ℃. Benzylidenaceton ist löslich in Alkohol, Benzol, Chloroform und Ether, während es in Wasser kaum löslich ist. In der organischen Chemie ist es ein wichtiger Synthese-Baustein für Michael-Additionen, Kondensation-, Cycloadditions- und Grignard-Reaktionen.

OccurrenceOccasionally Benzalacetone is used in perfumery for Sweet Pea (used to be a “must” in this type of fragrance), in Appleblossom, etc., often in combination with Neroli and Hyacinth bases. Also used in flavors, particularly in Chocolate, Cocoa, Cherry, Fruit, Nut, Vanilla, etc. - but usually at very low concentration. Concentration in finished product will rarely exceed 0.2 to 0.5 ppm.

Verwendenbrightener in acid zinc electroplating,also used as an organic synthesis intermediate in flavor and fragrance, pharmaceutical industries

Darstellung

synthetischeBy condensing benzaldehyde and acetone in the presence of an alkaline condensing agent.

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

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]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
武汉格罗丽材料有限公司27-27-59263629 18607197940
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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, a bacterial metabolite and an EC 3.1.1.4 (phospholipase A2) inhibitor.

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