Anisylacetone
4-(4-METHOXYPHENYL)BUTAN-2-ONE · ANISYLACETONE · Raspberry ketone methyl ether · p-Methoxybenzylacetone · FEMA 2672 · 4-(P-METHOXYPHENYL)-2-BUTANONE · PARA ANISYL ACETONE · 2-Butanone, 4-(4-methoxyphenyl)-
Identifiers & Physical Properties
| CAS No. | 104-20-1 |
|---|---|
| Molecular formula | C11H14O2 |
| Average molar mass | 178.23 g/mol |
| Monoisotopic mass | 178.09937969 g/mol |
| SMILES | COc1ccc(CCC(C)=O)cc1 |
| InChIKey | PCBSXBYCASFXTM-UHFFFAOYSA-N |
| PubChem CID | 61007 |
| ChEMBL | CHEMBL3184371 |
| ChEBI | CHEBI:169538 |
| EC No. | 203-184-2 |
| DTXSID | DTXSID5047166 |
Chemical & Physical Properties
| XLogP | 2.1 |
|---|---|
| Topological polar surface area | 26.3 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 4 |
| Heavy atoms | 13 |
| Formal charge | 0 |
| Complexity | 157 |
| SpringerMaterials Properties | Viscosity |
| Fragrances | Fragrance Ingredient (4-(p-Methoxyphenyl)-2-butanone) -> IFRA transparency List |
| Food additives | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Density | 1.041-1.0501.046 g/mL at 25 °C (lit.) |
| Flavoring agents | EU Flavoring substances |
| Solubility | very slightlyinsoluble in water, soluble in organic solvents, oilsmiscible at room temperature (in ethanol)Chloroform (Slightly), Methanol (Slightly)Not miscible in water. |
| Boiling point | 152.00 to 153.00 °C. @ 15.00 mm Hg277 °C150-152 °C (10 mm Hg)152-153 °C/15 mmHg (lit.) |
| Melting point | 9 - 10 °C8 °C (lit.) |
| Refractive index | 1.515-1.525n20/D 1.519(lit.) |
| Physical Description | Liquidcolourless oily liquid with a sweet, fruity-floral odour |
| Vapor pressure | 9-2000Pa at 20-115℃ |
| FEMA | 2672 | 4-(P-METHOXYPHENYL)-2-BUTANONE |
| FLAVIS Number | 07.029 | 4-(4-Methoxyphenyl)butan-2-one |
| Flash point | >230 °F |
| Storage conditions | Sealed in dry,Room Temperature |
| Physical state | Oil |
| Color | A colourless oily liquid with a sweet floral odour |
| Odor | at 100.00 %. sweet dried raspberry rose cherry fruity cassie absolute |
| Odor type | berry |
| Biological source | synthetic |
| JECFA Number | 818 |
| BRN | 1869592 |
| Cosmetics Ingredients Functions | PERFUMINGFLAVOURINGFRAGRANCE |
| InChI | 1S/C11H14O2/c1-9(12)3-4-10-5-7-11(13-2)8-6-10/h5-8H,3-4H2,1-2H3 |
| InChIKey | PCBSXBYCASFXTM-UHFFFAOYSA-N |
| SMILES | COc1ccc(CCC(C)=O)cc1 |
| LogP (partition coefficient) | 2 at 23.1℃ |
| CAS DataBase Reference | 104-20-1(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | 4-(P-METHOXYPHENYL)-2-BUTANONE |
| FDA UNII | GVG47S4S5V |
| NIST Chemistry Reference | 2-Butanone, 4-(4-methoxyphenyl)-(104-20-1) |
| EPA Substance Registry System | 2-Butanone, 4-(4-methoxyphenyl)- (104-20-1) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, multi-purpose combination respirator cartridge (US) |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 23-24/25 |
| Water hazard class (WGK) | 2 |
| RTECS number | EL9085500 |
| TSCA inventory status | TSCA listed |
| Customs code | 29145090 |
| Storage class | 10 - Combustible liquids |
| Toxicity | Both the acute oral LD50 value in rats and the acute dermal LD50 value in rabbits exceeded 5 g/kg (Russell, 1973) |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 99.7% (1567 of 1572) of all reports.Not ClassifiedAggregated GHS information provided per 1572 reports by companies from 5 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatory information | Chemical: 2-Butanone, 4-(4-methoxyphenyl)-Regulation (EC) No 1831/2003 (amended)Status: Active Update: 23-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/167462-Butanone, 4-(4-methoxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - Chemicals with limited data availability that are used in fragrances: Human health tier II assessment |
| Hazard Classes and Categories | Not Classified |
| Personal protective equipment (PPE) | Eyeshields, Gloves, multi-purpose combination respirator cartridge (US) |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | EL9085500 |
| Customs code | 29145090 |
| Toxicity | Both the acute oral LD50 value in rats and the acute dermal LD50 value in rabbits exceeded 5 g/kg (Russell, 1973) |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 23-24/25 |
| Storage class | 10 - Combustible liquids |
| GHS hazard statements | H315-H319-H335 |
Applications & Uses
Description
4-(p-Methoxyphenyl)-2-butanone has an intensely sweet, floral, fruity odor and a cherry-raspberry flavor at low concentrations. May be prepared by condensing acetone with anisaldehyde to yield anisylidene acetone and subsequent hydrogenation in the presence of Pd catalyst.
Occurrence
Contained (approximately 53% level) in the odorous principle obtained by extraction and hydrolysis from aloe wood (Aquilaria algallocha Roxb.) and in anise.
Uses
4-(4-Methoxyphenyl)-2-butanone is used as pharmaceutical intermediate.
Uses
4-(4-Methoxyphenyl)-2-butanone is used in insect attractants, organic synthesis, flavoring. This ketone, a methylether of a very popular material (see para-Hydroxy phenylbutanone), finds use in perfume compositions as a modifier for Heliotropine, a sweetener for Cyclamen aldehyde, and a blender in many types of sweet florals, Fougeres, Oriental fragrances, etc. It suffers from the drawback of being considerably more expensive than Heliotropine, and it can therefore not truly be classified as a substitute for that material. It shows less tendency of discoloration in combination with the materials normally causing such trouble with Heliotropine. It is also used in flavor compositions, particularly in Raspberty and Cherry, two flavors which are commonly used as targets for fantasy fragrances for Iipst ick perfumes. As a sweetener, it modifies Anise and Anethole in licorice flavor compositions, and it is generally used in smaller amounts in many imitation fruit flavors for baked goods or hard candy, where heat stability is essential.
Preparation & Synthesis
Preparation
By condensing acetone with anisaldehyde to yield anisylidene acetone and subsequent hydrogenation in the presence of Pd catalyst. It can also be prepared from Methyl vinyl ketone by catalytic condensation with Phenol, followed by Methylation.