alpha-Ionone

alpha-Ionone Basic information
Description References
Product Name:alpha-Ionone
Synonyms:(±)-4-trans-(2,6,6-trimethyl-cyclohex-2-enyl)-but-3-en-2-one;(E)-alpha-Ionone;(R,S)-3-(E)-Buten-2-one,4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-;4-(2,6,6-;ALPHA-IONONE;ALPHA-JONONE;A-CYCLOCITRYLIDENEACETONE;FERMENTA BERRY
CAS:127-41-3
MF:C13H20O
MW:192.3
EINECS:204-841-6
Product Categories:Biochemistry;Monocyclic Monoterpenes;Terpenes;Building Blocks;C13 to C14;Carbonyl Compounds;Chemical Synthesis;Citrus aurantium (Seville orange);Ginkgo biloba;Ketones;Nutrition Research;Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb);Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:127-41-3.mol
alpha-Ionone Structure
alpha-Ionone Chemical Properties
Melting point 25°C
Boiling point 259-263 °C(lit.)
density 0.93 g/mL at 25 °C(lit.)
vapor pressure 0.133Pa
refractive index n20/D 1.498(lit.)
FEMA 2594 | ALPHA-IONONE
Fp 230 °F
storage temp. 2-8°C
solubility Soluble in ethanol fixed oils, propylene glycol. Slightly soluble in alcohol, ether, mineral oil.
form Oil
color Clear Colourless
Odorat 10.00 % in dipropylene glycol. sweet woody floral violet orris tropical fruity
Odor Typefloral
Water Solubility insoluble
Merck 14,5056
JECFA Number388
BRN 2046084
LogP3.85 at 37℃
CAS DataBase Reference127-41-3(CAS DataBase Reference)
NIST Chemistry Reference3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)-(127-41-3)
EPA Substance Registry System.alpha.-Ionone (127-41-3)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 42-36-36/37/38
Safety Statements 36-24/25-26-36/37/39-27
WGK Germany 2
RTECS EN0525000
TSCA Yes
HS Code 29142300
Hazardous Substances Data127-41-3(Hazardous Substances Data)
MSDS Information
ProviderLanguage
alpha-IononeEnglish
SigmaAldrichEnglish
ACROSEnglish
ALFAEnglish
alpha-Ionone Usage And Synthesis
DescriptionThe alpha-ionone is the alpha form of ionone. The ionones denote a series of chemical substances belonging to rose ketones including carotene, damascenes and damascenones. It is found in various kinds of essential oils contained in some flowers such as violet. Ionone has three forms including alpha-, beta and gamma-. The alpha-ionone has the aroma odor of violet, which has been widely used in daily chemical flavor and tobacco-used flavor. The alpha-ionone can be made from the thermal decomposition of carotene.
ReferencesDavis, Daniel L., Kenneth L. Stevens, and Leonard Jurd. “Chemistry of tobacco constituents. Oxidation of. alpha.-ionone and the acid-catalyzed rearrangement of 5-keto-. alpha.-ionone.” Journal of agricultural and food chemistry 24.1 (1976): 187-189.
Fukuda, Kazuyuki C/O Kao Corporation. “PERFUME COMPOSITION.” (2014).
Laroe, Earl G., and P. A. Shipley. “Whiskey composition:, formation of alpha-and beta-ionone by the thermal decomposition of beta-carotene.”Journal of Agricultural & Food Chemistry 18.1(2002):1013-1017.
Descriptionα-Ionone has a characteristic violet-like odor. α-Ionone may be prepared by condensing citral with acetone to form pseudoionone, which is then cyclized by acid-type reagents.
Chemical Propertiesα-Ionone has a warm, woody, berry characteristic violet-like odor. The composition of commercial ionones varies widely in the proportion of α- and β-isomers; the specifications given below refer to the best grade of α- and β-ionones and to a commercial grade that contains both α- and β-ionones.
Chemical Propertiesclear yellow liquid
Usesalpha-Ionone, is used in many floral accords. Gives a violet flower nuance to compositions, but is also used in rose, woody, amber, balsamic, and powdery fragrances. It is also used in perfumery, flavoring, and vitamin A (retinol) production for cosmetics and toiletries. beta isomer shows a less floral odor than the alpha. It has good substantivity and is used in all areas of perfumery.
UsesAn aroma compound commonly found in essential oils such as rose oil. It is a degradation products of caratenoids produced by caratenoid cleavage dioxygenases (CCD).
DefinitionChEBI: Alpha-ionone is an ionone, an enone and a methyl ketone.
General Descriptionα-lonone is a C13 norterpenoid formed from the degradation of carotenoids. It is an important fragrance compound used in perfume industries due to its characteristic fine violet and rose scents. Commercially α-lonone is used in cosmetics, personal care products, detergents, etc. As a flavoring agent, it is widely used in various beverages including wine and tea.
Flammability and ExplosibilityNotclassified
Purification MethodsPurify α-ionone through a spinning band fractionating column. The semicarbazone has m 157-157.5o (from EtOH) and [] D +433o (c 4,
alpha-Ionone Preparation Products And Raw materials
Raw materialsSodium hydroxide–>Citral–>Litsea cubeba oil–>PSEUDOIONONE
Preparation ProductsIonone–>Carotene

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