Flavorants Toxicity Application limitation Chemical Properties Uses Production method
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Benzalacetone

Flavorants Toxicity Application limitation Chemical Properties Uses Production method
Product Name
Benzalacetone
CAS No.
122-57-6
Chemical Name
Benzalacetone
Synonyms
(E)-4-Phenylbut-3-en-2-one;4-PHENYL-3-BUTEN-2-ONE;benzylidene;BENZYLIDENEACETONE;4-Phenylbut-3-en-2-one;(3E)-4-phenylbut-3-en-2-one;Benzalaceton;3-Buten-2-one, 4-phenyl-;ACETOCINNAMONE;Benzilidine Acetone
CBNumber
CB3119480
Molecular Formula
C10H10O
Formula Weight
146.19
MOL File
122-57-6.mol
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Benzalacetone Property

Melting point:
39-42 °C(lit.)
Boiling point:
260-262 °C(lit.)
Density 
1.038
vapor pressure 
0.01 mm Hg ( 25 °C)
refractive index 
1.5836
FEMA 
2881 | 4-PHENYL-3-BUTEN-2-ONE
Flash point:
150 °F
storage temp. 
Store at <= 20°C.
solubility 
Soluble in alcohol, chloroform, diethyl ether.
form 
Low Melting Solid
color 
Pale yellow to yellow
Odor
Sweet, but rather pungent odor with a creamy-floral note.
Odor Type
spicy
Water Solubility 
1.398g/L(25 ºC)
Sensitive 
Light Sensitive
Merck 
14,1137
JECFA Number
820
BRN 
742046
Stability:
Light Sensitive
InChIKey
BWHOZHOGCMHOBV-BQYQJAHWSA-N
LogP
2.04
CAS DataBase Reference
122-57-6(CAS DataBase Reference)
NIST Chemistry Reference
3-Buten-2-one, 4-phenyl-(122-57-6)
EPA Substance Registry System
Benzylideneacetone (122-57-6)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
36/37/38-43-42/43
Safety Statements 
7-26-36/37/39-45-37/39-24-36/37-22
WGK Germany 
3
RTECS 
EN0330050
F 
8
TSCA 
Yes
HS Code 
29143900
Toxicity
LD50 orally in Rabbit: 2031 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W288101
Product name
Benzylideneacetone
Purity
≥98%, FG
Packaging
1kg
Price
$99.8
Updated
2024/03/01
Sigma-Aldrich
Product number
W288101
Product name
Benzylideneacetone
Purity
≥98%, FG
Packaging
10Kg
Price
$597
Updated
2024/03/01
Sigma-Aldrich
Product number
W288101
Product name
Benzylideneacetone
Purity
≥98%, FG
Packaging
25kg
Price
$1040
Updated
2024/03/01
Sigma-Aldrich
Product number
147885
Product name
4-Phenyl-3-buten-2-one
Purity
99%
Packaging
250g
Price
$58.1
Updated
2024/03/01
Sigma-Aldrich
Product number
68381
Product name
Benzalacetone
Purity
analytical standard
Packaging
100mg
Price
$63.9
Updated
2022/05/15
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Benzalacetone Chemical Properties,Usage,Production

Flavorants

Our GB2760-1996 provisions temporarily allow benzalacetone as a food spice, it is used to modulate sweet pea, cocoa, nuts, cherries, fruit flavor aroma, also used as floral flavor variable swap and anti-propellant, because of the stimulating effect on the skin, it is generally not used in cosmetics. Also benzalacetone can also be used as a mordant, fixing agent and preparation galvanized credit agent in dyeing industry. Credit agent is an organic compound capable of producing bright and leveling effect. Usually it contains aromatic aldehydes or ketones and certain heterocyclic aromatic aldehydes, ie coumarin, vanillin, benzalacetone, its molecular structure contains a carbonyl group, just keeps this structure intact, substituting various substituents, it can produce many kinds of compounds having light effects. Among these, benzalacetone displays best effects, domestic commercial additives are mostly based on such benzalacetone predominating brightener. The most commonly used method is based on the preparation of benzaldehyde and acetone as raw materials, to carry out the Claisen reaction, in the presence of a base (sodium hydroxide or sodium carbonate), aldehydes and ketones condensate, after completing the reaction, diluted hydrochloric acid is added and adjusted to pH = 6-7, set still for stratification, the upper yellow oil is separated, in order to maximize the yield, the lower layer is extracted with benzene, the extract is dried after recovery of benzene, and the oil is combined, then washed with water, separate the oil , bleached with activated carbon, filtered, and purified by vacuum steam distillation, cooled and crystallized, to get crude benzalacetone .
Benzalacetone is also known as 4-phenyl-3-butene-2-one, dibenzylideneacetone, cinnamyl methyl ketone, benzal acetone, methyl styryl ketone. The product abtained by vacuum distillation system is colorless to pale yellow shiny lamellae. It owns sweet pea fragrance and spicy and pungent flavor, changes to deep color exposed in light, combustible, prolonged heat leading to decomposition. Naturally it presents in hydrolyzed soy protein. The formations include cis and trans. Relative molecular mass is 146.19. The relative density is 1.0076 (47.3 ℃). The freezing point is 39 ℃, the melting point is 42 ℃. The boiling point is 261 ℃, 211 ℃ (26.664 × 103Pa), 187.8 ℃ (13.332 × 103Pa), 161.3 ℃ (5.333 × 103Pa), 143.8 ℃ (2.666 × 103Pa), 127.4 ℃ (1.333 × 103Pa), 112.2 ℃ (0.666 × 103Pa ), 81.7 ℃ (0.133 × 103Pa). The refractive index is 1.5836 (45.9 ℃). It is slightly soluble in water and petroleum ether, slightly soluble in benzene, soluble in ethanol, benzene, ether, chloroform and sulfuric acid. It displays a reddish color while reacting with sulfuric acid, this feature can be used to detect the product.
The above information is edited by the Chemicalbook of Tian Ye.

Toxicity

LD50 orally in Rabbit: 2031 mg/kg

Application limitation

FEMA (mg/kg): Soft drinks 0.82 ; cold drinks 0.84; confectionery 3.7; bakery 4.5;jelly and pudding 2.1 ; shortening 0.20.

Chemical Properties

It is colorless crystals. It has a coumarin odor. It is soluble in alcohol, ether, benzene and chloroform, slightly soluble in water and petroleum ether.

Uses

1. It is used for the preparation of spices and galvanized brightener.
2. GB 2760--1996 allows it used as food with spices. Formulated balm, cherries, grapes, berries, anise-based and other flavors for temporary .
3. This product is used as galvanized additives, coating materials to increase the brightness. The dyeing industry uses it as a mordant in dyeing agent to improve the uniformity and firmness, also it can be used for the preparation of spices and flavoring agents.
4. 4-phenyl-butene (3)one-2 is one rodenticide warfarin intermediates.
5. As an aromatic organic substance, it is the most widely superior light additive in acid zinc plating process , in the potassium chloride, ammonium plating process, it can get bright coating in a very wide current density and the temperature range, play a good effect on the coating of the internal stress, anti-corrosion ability. This product is also available anti volatile agent for spices, mordant and fixing agent in dyeing industry, it can also be used to prepare spices flavoring agent.
6. Organic synthesis intermediates. It can be used as a spice anti propellant. In dyeing industry,it is used as mordant , fixing agent, it is used for the preparation of spices or flavoring agents, and preparation for galvanized credit agent.

Production method

Using Benzaldehyde for raw materials, and carrying out condensation reaction with acetone . Benzaldehyde and acetone, mixed with water, cooled slowly, added 10% sodium hydroxide solution, the temperature controlled at 25-31°C, After the addition, the stirring was continued for 1h. Then diluted hydrochloric acid was added to pH 6-7, set still for 1h, isolated as a yellow oil. Lower layer was extracted with benzene, the extract and oil were combined, washed twice with water, after the separation the layer of water, recovered benzene, and then dried over calcium chloride, dry decolorizing charcoal was added , filtered and the filtrate vacuum distillation derived products. . Fixed material consumption : benzaldehyde 1700kg/t, acetone 2900kg/t, caustic soda (40%) 500kg/t.

Chemical Properties

Yellow Solid

Chemical Properties

4-Phenyl-3-buten-2-one has a sweet, floral, creamy, pungent odor reminiscent of coumarin and rhubarb with a sweet, pungent flavor. It is not very stable.

Occurrence

Occasionally 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.

Uses

In perfumery, organic syntheses.

Uses

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

Uses

Benzylideneacetone is used chiefly as a scent in the manufacture of perfume, drugs & electroplating.

Preparation

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

Definition

ChEBI: 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.

Application

Benzalacetone is an endogenous metabolite. It acts as a flavouring agent, a spice, a bacterial metabolite and an inhibitor of EC 3.1.1.4 (phospholipase A2). It is mainly used in food additives, flavours and fragrances, and as an intermediate in chemical synthesis or reaction reagents. In addition, the novel hydrophobic benzazepine acetone can also be used to modify lead dioxide electrodes for electrocatalytic degradation of coal tar wastewater.

Aroma threshold values

Aroma characteristics at 1.0%: sweet, fruity and jamy cherry-like, aldehydic cinnamon spicy, herbal, anisic, balsamic, toasted almond nutty and woody with slight powdery vanilla nuances.

Taste threshold values

Taste characteristics at 5 to 10 ppm: aldehydic, coumarinic and balsamic, slightly nutty, floral and fruity with woody nuances.

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 5595, 1993 DOI: 10.1021/jo00073a011
Tetrahedron Letters, 28, p. 913, 1987 DOI: 10.1016/S0040-4039(00)95872-6

General Description

trans- 4-Phenyl-3-buten-2-one is substrate for glutathione transferase. It reacts with methyl- and benzylguanidine to yield aromatic N2-substituted 2-pyrimidinamines.

Biochem/physiol Actions

Taste at 5-10 ppm

Safety Profile

Poison by intravenous route. Moderately toxic by intraperitoneal route. A skin irritant. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

Purification Methods

Crystallise it from pet ether (b 40-60o), or distil it (b 137-142o /16mm). [Beilstein 7 IV 1003.]

Benzalacetone Preparation Products And Raw materials

Raw materials

Acetone Phenylacetone Formaldehyde Water Decolorizing charcoal Benzaldehyde Dilute hydrochloric acid

Preparation Products

Cinnamic acid 3,4-DIBROMO-4-PHENYL-2-BUTANONE
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Benzalacetone Suppliers

Belgium 1 Brazil 1 Canada 1 China 326 Czech Republic 1 Europe 4 France 1 Germany 8 India 58 Italy 1 Slovakia 1 Spain 1 Switzerland 1 Ukraine 1 United Kingdom 9 United States 42 Global 457
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View Lastest Price from Benzalacetone manufacturers

Hebei Longbang Technology Co., Ltd
Product
Benzalacetone 122-57-6
Price
US $7.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20TONS
Release date
2024-05-24
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Benzylideneacetone 122-57-6
Price
US $99.00-35.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-08
HebeiShuoshengImportandExportco.,Ltd
Product
Benzalacetone 122-57-6
Price
US $6.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000KG/Month
Release date
2024-08-05

122-57-6, BenzalacetoneRelated Search:

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