Skip to Content
Merck
All Photos(1)

Documents

W288101

Sigma-Aldrich

Benzylideneacetone

≥98%, FG

Synonym(s):

Benzalacetone, 4-Phenylbut-3-en-2-one, Benzylideneacetone, Methyl styryl ketone

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
C6H5CH=CHCOCH3
CAS Number:
122-57-6
Molecular Weight:
146.19
FEMA Number:
2881
Beilstein:
742047
EC Number:
204-555-1
Council of Europe no.:
158
MDL number:
MFCD00008779
UNSPSC Code:
12164502
PubChem Substance ID:
24901370
Flavis number:
7.024
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Halal
Kosher

Agency

meets purity specifications of JECFA

reg. compliance

EU Regulation 1334/2008 & 872/2012
FDA 21 CFR 172.515

vapor pressure

0.01 mmHg ( 25 °C)

Assay

≥98%

bp

260-262 °C (lit.)

mp

39-42 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

Organoleptic

anise; cinnamon; jam; balsamic; spicy; floral; sweet

SMILES string

[H]\C(=C(\[H])c1ccccc1)C(C)=O

InChI

1S/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3/b8-7+

InChI key

BWHOZHOGCMHOBV-BQYQJAHWSA-N

Looking for similar products? Visit Product Comparison Guide

General description

Benzylideneacetone is used in the fragrance industry for its sweet pea-like odor. It is one of the major constituents of Monanthotaxis capea essential oil. Studies suggest that apart from skatole and androstenone, benzylideneacetone may also be one of the volatile compounds, which contributes to the development of boar taint in fat samples.

Biochem/physiol Actions

Taste at 5-10 ppm

Other Notes

Natural occurrence: Soybeans and Virginia tobacco.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H317

Hazard Classifications

Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

253.4 °F - closed cup

Flash Point(C)

123 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Phenylbutane Derivatives as Main Constituents of Monanthotaxis capea Essential Oil.
Lamaty G, et al.
J. Essent. Oil Res., 4(1), 33-39 (1992)
Bowon Kwon et al.
Journal of economic entomology, 101(1), 36-41 (2008-03-12)
Benzylideneacetone (BZA) is a metabolite of gram-negative entomopathogenic bacterium Xenorhabdus nematophila, and it acts as an enzyme inhibitor against phospholipase A2 (PLA2). PLA2 catalyzes a committed biosynthetic step of eicosanoids, which mediate insect immune reactions to infection by microbial pathogens.
Samyeol Seo et al.
Applied and environmental microbiology, 78(11), 3816-3823 (2012-03-27)
The entomopathogenic bacteria Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata suppress insect immune responses by inhibiting the catalytic activity of phospholipase A(2) (PLA(2)), which results in preventing biosynthesis of immune-mediating eicosanoids. This study identified PLA(2) inhibitors derived from culture broths
Hiroyuki Morita et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(2), 669-673 (2010-01-19)
Benzalacetone synthase (BAS), a plant-specific type III polyketide synthase (PKS), catalyzes a one-step decarboxylative condensation of malonyl-CoA and 4-coumaroyl-CoA to produce the diketide benzalacetone. We solved the crystal structures of both the wild-type and chalcone-producing I207L/L208F mutant of Rheum palmatum
Role of 4-phenyl-3-buten-2-one in boar taint: identification of new compounds related to sensorial descriptors in pig fat.
Rius Sole MA & Garcia Regueiro JA.
Journal of Agricultural and Food Chemistry, 49(11), 5303-5309 (2001)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service