CAS 104-20-1 Anisylacetone (HCID 61007)

Overview

4-(4-Methoxyphenyl)-2-butanone is a member of methoxybenzenes.

Names & identifiers

Preferred name: Anisylacetone
IUPAC: 4-(4-methoxyphenyl)butan-2-one
English name: 4-(4-Methoxyphenyl)-2-butanone
Molecular formula: C11H14O2
Molecular weight: 178.23

Names & synonyms

4-(4-Methoxyphenyl)-2-butanoneAnisylacetone4-(4-Methoxyphenyl)butan-2-one2-BUTANONE, 4-(4-METHOXYPHENYL)-4-MethoxybenzylacetoneRaspberry ketone methyl ether4-(p-Methoxyphenyl)-2-butanone2-Butanone, 4-(p-methoxyphenyl)-Anisylacetone, p-Methyl oxanonep-Methoxybenzylacetonep-Methoxyphenylbutanone

Show more names

FEMA 2672PARA ANISYL ACETONEANISALACETONE

1-(4-Methoxyphenyl)-3-butanoneANISYL ACETONERasberry ketone methyl etherFEMA No. 2672Methoxybenzylacetone, p-ENT 20,2791-(p-Methoxyphenyl)-3-butanone-NSC 405366

Database identifiers

CAS: 104-20-1
PubChem CID: 61007
DTXSID: DTXSID5047166
ChEMBL: CHEMBL3184371
ChEBI: CHEBI:169538
UNII: GVG47S4S5V
EC Number: 203-184-2
Nikkaji: J5.026A

Properties

Computed structural properties

XLogP: 2.1
Topological polar surface area: 26.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 4
Heavy atoms: 13
Formal charge: 0
Complexity: 157

Experimental & physicochemical properties

SpringerMaterials PropertiesViscosity

FragrancesFragrance Ingredient (4-(p-Methoxyphenyl)-2-butanone) -> IFRA transparency List

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Density1.041-1.050

Flavoring AgentsEU Flavoring substances

Solubility · 3 items

very slightly

insoluble in water, soluble in organic solvents, oils

miscible at room temperature (in ethanol)

Physicochemical properties

Melting point: 8 °C · 8 °C (lit.)
Boiling point: 152 · 152-153 °C/15 mmHg (lit.)
Density: 1.046 g/mL · 1.046 g/mL at 25 °C (lit.)
vapor pressure: 9 · 9-2000Pa at 20-115℃
FEMA: 2672 · 2672 | 4-(P-METHOXYPHENYL)-2-BUTANONE
refractive index: 20 · n20/D 1.519(lit.)
FLAVIS Number: 7.029 · 07.029 | 4-(4-Methoxyphenyl)butan-2-one
Flash point: 230 °F · >230 °F
storage temp.: Sealed in dry,Room Temperature
solubility: Chloroform (Slightly), Methanol (Slightly)
form: Oil
color: A colourless oily liquid with a sweet floral odour
Odor: 100 % · at 100.00 %. sweet dried raspberry rose cherry fruity cassie absolute
Odor Type: berry
biological source: synthetic
Water Solubility: Not miscible in water.
JECFA Number: 818 · 818
BRN: 1869592 · 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: 2 at · 2 at 23.1℃
CAS DataBase Reference: 104 · 104-20-1(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS): 4 · 4-(P-METHOXYPHENYL)-2-BUTANONE
FDA UNII: 47 S4S5V · GVG47S4S5V
NIST Chemistry Reference: 2 · 2-Butanone, 4-(4-methoxyphenyl)-(104-20-1)
EPA Substance Registry System: 2 · 2-Butanone, 4-(4-methoxyphenyl)- (104-20-1)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 233 · 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
PPE: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 23 · 23-24/25
WGK Germany: 2 · 2
RTECS: 9085500 · EL9085500
TSCA: TSCA listed
HS Code: 29145090 · 29145090
Storage Class: 10 · 10 - Combustible liquids
Toxicity: 50 value · 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 & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 99.7% (1567 of 1572) of all reports.

Not Classified

Aggregated GHS information provided per 1572 reports by companies from 5 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 4 items

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/16746

2-Butanone, 4-(4-methoxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Chemicals with limited data availability that are used in fragrances: Human health tier II assessment

Hazard Classes and CategoriesNot Classified

Safety data

PPE: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk: 2
tsca: TSCA listed
rtecs: EL9085500
hs_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_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 23-24/25
Storage Class: 10 - Combustible liquids
Hazard statements: H315-H319-H335
REACH Registrations: Active
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

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Household ProductsInformation on 2 consumer products that contain 4-(4-Methoxyphenyl)butan-2-oneÃ¢â¬Â¨ in the following categories is provided:

Use Classification · 6 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information2-Butanone, 4-(4-methoxyphenyl)-: ACTIVE

Applications · 4 items

Description4-(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.

OccurrenceContained (approximately 53% level) in the odorous principle obtained by extraction and hydrolysis from aloe wood (Aquilaria algallocha Roxb.) and in anise.

Uses4-(4-Methoxyphenyl)-2-butanone is used as pharmaceutical intermediate.

Uses4-(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 methods · 1 item

PreparationBy 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.