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W288101

Sigma-Aldrich

Benzylideneacetone

≥98%, FG

Synonym(s):

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

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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

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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’.

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Phenylbutane Derivatives as Main Constituents of Monanthotaxis capea Essential Oil.
Lamaty G, et al.
J. Essent. Oil Res., 4(1), 33-39 (1992)
Bin Cao et al.
Organic & biomolecular chemistry, 10(6), 1239-1245 (2011-12-20)
An efficient and easy procedure to synthesize the pyridinyl analogues of dibenzylideneacetone (pyr-dba) was developed by the condensation of substituted nicotinaldehyde and acetone in the presence of K(2)CO(3) in toluene-EtOH-H(2)O solvent system. Structurally diverse pyr-dba, including quinolinyl dba, can be
Jiyong Zhang et al.
The Journal of organic chemistry, 71(7), 2918-2921 (2006-03-25)
The first efficient asymmetric synthesis of obolactone 1 has been accomplished in 11 steps and with a 15% overall yield in which Brown's enantioselective allylation reactions and ring-closing metathesis reaction are key steps.
Ikuro Abe et al.
Organic letters, 4(21), 3623-3626 (2002-10-12)
[reaction: see text] Substrate specificities of plant polyketide synthases (PKSs) were investigated using analogues of malonyl-CoA, the extension unit of the polyketide chain elongation reactions. When incubated with methylmalonyl-CoA and 4-coumaroyl-CoA, plant PKSs (chalcone synthase from Scutellaria baicalensis, stilbene synthase
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
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