Basic information
- Standard SMILES
CC(=O)C=Cc1ccccc1- InChIKey
BWHOZHOGCMHOBV-UHFFFAOYSA-N- Molecular formula
- C10H10O
- Average molar mass
- 146.19 g/mol
- Monoisotopic mass
- 146.07316494
Overview
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.
Names & identifiers
- Preferred name
- 4-Phenyl-3-Buten-2-one
- IUPAC
- 4-phenylbut-3-en-2-one
- English name
- Benzalacetone
- Molecular formula
- C10H10O
- Molecular weight
- 146.19
Names & synonyms
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
Show more names
(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
Database identifiers
- CAS
122-57-6- PubChem CID
- 15909
- DTXSID
DTXSID4025662- ChEMBL
CHEMBL3187978- EC Number
- 204-555-1
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 152
Experimental & physicochemical properties
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
insoluble in water; soluble in organic solvents, oils
very soluble (in ethanol)
Boiling Point260 °C
Physical Descriptioncolourless to slightly yellow crystalline solid with a sweet, pungent, creamy, floral odour
Physicochemical properties
- Melting point
- 39 · 39-42 °C(lit.)
- Boiling point
- 260 · 260-262 °C(lit.)
- Density
- 1.038 · 1.038
- vapor pressure
- 0.01 mm · 0.01 mm Hg ( 25 °C)
- refractive index
- 1.5836 · 1.5836
- FEMA
- 2881 · 2881 | 4-PHENYL-3-BUTEN-2-ONE
- FLAVIS Number
- 7.024 · 07.024 | 4-Phenylbut-3-en-2-one
- Flash point
- 150 °F · 150 °F
- storage temp.
- 20 °C · 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
- biological source
- synthetic
- Water Solubility
- 1.398 g/L · 1.398g/L(25 ºC)
- Sensitive
- Light Sensitive
- Merck
- 14 · 14,1137
- JECFA Number
- 820 · 820
- BRN
- 742046 · 742046
- Stability
- Light Sensitive
- 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
- [H]\C(=C(\[H])c1ccccc1)C(C)=O
- LogP
- 2.04 · 2.04
- CAS DataBase Reference
- 122 · 122-57-6(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 4 · 4-PHENYL-3-BUTEN-2-ONE
- FDA 21 CFR
- 172.515 · 172.515
- EWG's Food Scores
- 1 · 1-3
- FDA UNII
- 3 X40BMT5 · B03X40BMT5
- NIST Chemistry Reference
- 3 · 3-Buten-2-one, 4-phenyl-(122-57-6)
- EPA Substance Registry System
- Benzylideneacetone (122-57-6)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H317
- Precautionary statements
- 280 · P280
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 36 · 36/37/38-43-42/43
- Safety Statements
- 7 · 7-26-36/37/39-45-37/39-24-36/37-22
- WGK Germany
- 3 · 3
- RTECS
- 330050 · EN0330050
- F
- 8 · 8
- TSCA
- TSCA listed
- HS Code
- 29143900 · 29143900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Skin Irrit. 2Skin Sens. 1
- Toxicity
- 50 orally · LD50 orally in Rabbit: 2031 mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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.
Hazard information
Regulatory Information
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%)
Toxicology
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- F
- 8
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- EN0330050
- hs_code
- 29143900
- Toxicity
- LD50 orally in Rabbit: 2031 mg/kg
- risk_code
- 36/37/38-43-42/43
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- safety_code
- 7-26-36/37/39-45-37/39-24-36/37-22
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H317
- REACH Registrations
- Active
- Hazard Classifications
- Skin Irrit. 2Skin Sens. 1
- Precautionary statements
- P280
Chemistry & industry
Uses & manufacturing
IFRA Fragrance Standards
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
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
Applications
Uses1. 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.
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.
UsesIn perfumery, organic syntheses.
Usesbrightener in acid zinc electroplating,also used as an organic synthesis intermediate in flavor and fragrance, pharmaceutical industries
UsesBenzylideneacetone is used chiefly as a scent in the manufacture of perfume, drugs & electroplating.
General Descriptiontrans- 4-Phenyl-3-buten-2-one is substrate for glutathione transferase. It reacts with methyl- and benzylguanidine to yield aromatic N2-substituted 2-pyrimidinamines.
Preparation methods
PreparationBy condensing benzaldehyde and acetone in the presence of an alkaline condensing agent.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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Additional notes
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.
Related reactions
60 records
Linked notes
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