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alpha-ionone

Chemical Structure

General Material Information

Preferred name alpha-ionone
Trivial Name α-Ionone
Short Description 3-buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)-
Formula C13 H20 O
CAS Number 127-41-3
Deleted CAS Number 30685-95-1
FEMA Number 2594
ECHA Number 204-841-6
FDA UNII I9V075M61R
Nikkaji Number J183.660I
Beilstein Number 3197885
MDL MFCD00001565
COE Number 141
xLogP3-AA 3.00 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 388 alpha-ionone
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 127-41-3 ; ALPHA-IONONE
Synonyms
  • alphaline 70
  • 3-buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)-
  • (E)-alpha- cyclocitrylidene acetone
  • trans-alpha- cyclocitrylidene acetone
  • ionanthem
  • (±)-(E)-alpha- ionone
  • (±)-trans-alpha- ionone
  • (E)-a- ionone
  • (E)-alpha- ionone
  • a- ionone
  • nat.alpha- ionone
  • trans-alpha- ionone
  • alpha- ionone (natural)
  • alpha- ionone 50% in ETOH natural
  • alpha- ionone 60
  • alpha- ionone 70
  • alpha- ionone 80
  • alpha- ionone 90
  • alpha- ionone 90%, (naturals)
  • ionone alpha
  • ionone alpha regular
  • ionone alpha white coeur
  • alpha- ionone BRI
  • alpha- ionone extra
  • alpha- ionone natural
  • alpha- ionone refined
  • alpha- ionone white coeur
  • alpha- ionone, natural
  • alpha- ionone, refined
  • alpha- ionone, regular
  • irisone alpha
  • irisone alpha extra white
  • (E)-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one
  • (E)-(±)-4,2,6,6-trimethyl-2-cyclohexen-1-yl-3-buten-2-one
  • trans-4,2,6,6-trimethyl-2-cyclohexen-1-yl-3-buten-2-one
  • (3E)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
  • (E)-(±)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
  • (E)-(1)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
  • (E)-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
  • (3E)-(±)-4-(2,6,6-trimethyl-4-cyclohexen-1-yl)-3-buten-2-one
  • (3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
  • (3E)-4-(2,6,6-trimethylcyclohex-2-enyl)but-3-en-2-one
  • (E)-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one
  • 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)-
  • 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)-
  • (3E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
  • α-Cyclocitrylideneacetone
  • 4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
  • α-Ionone
  • trans-α-Ionone
  • (E)-α-Ionone
  • 4-(2,6,6-Trimethyl-2-cyclohexenyl)-3-buten-2-one
  • (5E)-Ionone
  • (±)-α-Ionone
  • (±)-trans-α-Ionone
  • (E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

Leffingwell:Chirality or Article
(E)-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:127-41-3
Pubchem (cid):5282108
Pubchem (sid):134974059
Flavornet:127-41-3
Pherobase:View
Publications by PubMed
Comparison of aroma active and sulfur volatiles in three fragrant rice cultivars using GC-olfactometry and GC-PFPD.
Formation of norisoprenoid flavor compounds in carrot (Daucus carota L.) roots: characterization of a cyclic-specific carotenoid cleavage dioxygenase 1 gene.
Selective oxidation reactions of natural compounds with hydrogen peroxide mediated by methyltrioxorhenium.
Evaluation of the volatile composition and sensory properties of five species of microalgae.
Functional characterisation of three members of the Vitis vinifera L. carotenoid cleavage dioxygenase gene family.
NIS-PPh3: a selective reagent for the spiroannulation of o-allyl phenols. Total synthesis of corallidictyal D.
Isolation of the four methyl jasmonate stereoisomers and their effects on selected chiral volatile compounds in red raspberries.
Highly selective and asymmetric reductive biotransformation of α-ionone by Epicoccum purpurascens.
Essential oils from the leaves of six medicinal plants of Nigeria.
[Influence of processing methods on the chemical composition of the essential oil from Aucklandia lappa].
Essential oil composition of Ficus benjamina (Moraceae) and Irvingia barteri (Irvingiaceae).
A practical, enantiospecific synthesis of (S)-trans-gamma-monocyclofarnesol.
Profiling and characterization of volatile components from non-fumigated and sulfur-fumigated Flos Lonicerae Japonicae using comprehensive two-dimensional gas chromatography time-of-flight mass spectrometry coupled with chemical group separation.
Antitrypanosomal compounds from the essential oil and extracts of Keetia leucantha leaves with inhibitor activity on Trypanosoma brucei glyceraldehyde-3-phosphate dehydrogenase.
Quantification by solid phase micro extraction and stable isotope dilution assay of norisoprenoid compounds in red wines obtained from Piedmont rare varieties.
Environmental and seasonal influences on red raspberry flavour volatiles and identification of quantitative trait loci (QTL) and candidate genes.
Free energy calculations give insight into the stereoselective hydroxylation of α-ionones by engineered cytochrome P450 BM3 mutants.
A Practical Chemo-enzymatic Approach to Highly Enantio-Enriched 10-Ethyl-7,8-dihydro-γ-ionone Isomers: A Method for the Synthesis of 4,5-Didehydro-α-Ionone.
Biosynthesis of α- and β-ionone, prominent scent compounds, in flowers of Osmanthus fragrans.
CYP264B1 from Sorangium cellulosum So ce56: a fascinating norisoprenoid and sesquiterpene hydroxylase.
Impact of cover crops in vineyard on the aroma compounds of Vitis vinifera L. cv Cabernet Sauvignon wine.
Structural Analysis of CYP101C1 from Novosphingobium aromaticivorans DSM12444.
Enzymatic formation of apo-carotenoids from the xanthophyll carotenoids lutein, zeaxanthin and β-cryptoxanthin by ferret carotene-9',10'-monooxygenase.
Allelopathic control of cyanobacterial blooms by periphyton biofilms.
Composition of sulla (Hedysarum coronarium L.) honey solvent extractives determined by GC/MS: norisoprenoids and other volatile organic compounds.
Regioselective hydroxylation of norisoprenoids by CYP109D1 from Sorangium cellulosum So ce56.
Functional characterization of a carotenoid cleavage dioxygenase 1 and its relation to the carotenoid accumulation and volatile emission during the floral development of Osmanthus fragrans Lour.
A new sulfated alpha-ionone glycoside from Sonchus erzincanicus Matthews.
Characterization of the versatile monooxygenase CYP109B1 from Bacillus subtilis.
Expedient construction of the Ziegler intermediate useful for the synthesis of forskolin via consecutive rearrangements.
New attractants for males of the solanaceous fruit fly Bactrocera latifrons.
Enantioselective synthesis and olfactory evaluation of 13-alkyl-substituted alpha-ionones.
Comparison of sugar, acids, and volatile composition in raspberry bushy dwarf virus-resistant transgenic raspberries and the wild type 'meeker' (rubus idaeus L.).
Volatile composition in raspberry cultivars grown in the Pacific Northwest determined by stir bar sorptive extraction-gas chromatography-mass spectrometry.
New alpha-pyrrolidinonoids and glycosides from Euphorbia humifusa.
Chemotherapy of leishmaniasis part-VIII: synthesis and bioevaluation of novel chalcones.
Metabolism of carotenoids and apocarotenoids during ripening of raspberry fruit.
Fragrance material review on alpha-ionone.
Fragrance material review on allyl alpha-ionone.
Fragrance material review on dihydro-alpha-ionone.
Fragrance material review on ionone.
Fragrance material review on methyl-alpha-ionone.
Synthesis of 4'-(2,6,6-trimethyl -2-cyclohexen-1-yl) -3'-buten-2'-ketoxime-N-O-alkyl ethers.
Effect of fat level on the perception of five flavor chemicals in ice cream with or without fat mimetics by using a descriptive test.
Biosynthesis of monoterpenes and norisoprenoids in raspberry fruits (Rubus idaeus L.): the role of cytosolic mevalonate and plastidial methylerythritol phosphate pathway.
Flavor authentication studies of alpha-ionone, beta-ionone, and alpha-ionol from various sources.
Studies on the aroma of maté (Ilex paraguariensis St. Hil.) using headspace solid-phase microextraction.
Effect of the minor ABA metabolite 7'-hydroxy-ABA on Arabidopsis ABA 8'-hydroxylase CYP707A3.
Broad activation of the glomerular layer enhances subsequent olfactory responses.
Isolation and identification of antialgal compounds from the leaves of Vallisneria spiralis L. by activity-guided fractionation.
Functional characterization of CmCCD1, a carotenoid cleavage dioxygenase from melon.
Generation of aroma compounds from Ditaxis heterantha by Saccharomyces cerevisiae.
Theory and use of the pseudophase model in gas-liquid chromatographic enantiomeric separations.
Efficient terpene hydroxylation catalysts based upon P450 enzymes derived from actinomycetes.
[Analysis and identification of Liriomyza sativae-attractants from cowpea and kidney bean volatiles].
Carotenoid pigmentation affects the volatile composition of tomato and watermelon fruits, as revealed by comparative genetic analyses.
Comprehensive authentication of (E)-alpha(beta)-ionone from raspberries, using constant flow MDGC-C/P-IRMS and enantio-MDGC-MS.
Identification and aroma impact of norisoprenoids in orange juice.
A simple and efficient highly enantioselective synthesis of alpha-ionone and alpha-damascone.
Active ingredients in cade oil that synergize attractiveness of alpha-ionol to male Bactrocera latifrons (Diptera: Tephritidae).
Enantioselective synthesis of alpha-ionone derivatives using an anti S(N)2' substitution of functionalized zinc organometallics.
Antifungal compounds from the root and root exudate of Zea mays.
Approaches to spirit aroma: contribution of some aromatic compounds to the primary aroma in samples of orujo spirits.
Isolation and characterization of miscellaneous secondary metabolites of Deprea subtriflora.
Investigation of binding behavior of alpha- and beta-ionones to beta-lactoglobulin at different pH values using a diffusion-based NOE pumping technique.
Enantiomer separation of flavour and fragrance compounds by liquid chromatography using novel urea-covalent bonded methylated beta-cyclodextrins on silica.
Induction of cytochrome P450 1A and 2B by alpha- and beta-ionone in Sprague Dawley rats.
A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes.
Enhancement of attraction of alpha-ionol to male Bactrocera latifrons (Diptera: Tephritidae) by addition of a synergist, cade oil.
Determination of apparent binding constants for aroma compounds with beta-lactoglobulin by dynamic coupled column liquid chromatography.
Development of an attractant for the scarab pest Macrodactylus subspinosus (Coleoptera: Scarabaeidae).
Frozen storage effects on anthocyanins and volatile compounds of raspberry fruit.
Enantiomer separation of alpha-ionone using gas chromatography with cyclodextrin derivatives as chiral stationary phases.
2-fluoroabscisic acid analogues: their synthesis and biological activities.
Stereo- and regioselective hydroxylation of alpha-ionone by Streptomyces strains.
Effect of Carotenoids on Aflatoxin B(1) Synthesis by Aspergillus flavus.
Biotransformation of alpha- and beta-ionones by immobilized cells of Nicotiana tabacum.
Sensory evidence for olfactory receptors with opposite chiral selectivity.
Microbial Conversion of alpha-Ionone, alpha-Methylionone, and alpha-Isomethylionone.
Models of retinoid metabolism: microbial biotransformation of alpha-ionone and beta-ionone.
Incorporation of (14)CO 2 in photosynthetic pigments of Chlorella pyrenoidosa.
Chemistry of tobacco constituents. Oxidation of alpha-ionone and the acid-catalyzed rearrangement of 5-keto-alpha-ionone.
Comparison of the effects of vitamin A and its analogs upon rabbit ear cartilage in organ culture and upon growth of the vitamin A-deficient rat.
The biosynthesis of cyclic carotenes.
Geometrical isomers of retinene.
Publications by J-Stage
Highly Selective and Asymmetric Reductive Biotransformation of a-Ionone by Epicoccum purpurascens
Antifungal Compounds from the Root and Root Exudate of Zea mays

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C12286
HMDB (The Human Metabolome Database):HMDB59883
FooDB:FDB014484
Export Tariff Code:2914.23.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 192.30160522461
Specific gravity @ 25 °C
Pounds per Gallon 7.714 to 7.763
Specific gravity @ 20 °C
Pounds per Gallon 7.731 to 7.798
Refractive Index 1.497 to 1.502 @ 20 °C
Boiling Point 237 to 238°C @ 760 mm Hg
Vapor Pressure 0.014 mmHg @ 25 °C
Vapor Density 7
Flash Point TCC Value 110 °C TCC
logP (o/w) 3.995
Shelf life 24 months (or longer if stored properly.)
Storage notes Refrigerate in tightly sealed containers.
Solubility
alcohol Yes
dipropylene glycol Yes
fixed oils Yes
paraffin oil Yes
water, 1.00E+06 mg/L @ 25 °C (exp) Yes
glycerin No
Stability
acid cleaner Unspecified
alcoholic lotion Unspecified
antiperspirant Unspecified
deo stick Unspecified
detergent perborate Unspecified
fabric softener Unspecified
hard surface cleaner Unspecified
liquid detergent Unspecified
non-discoloring in most media Unspecified
shampoo Unspecified
soap Unspecified

Organoleptic Properties

Odor Type: Floral
sweet, woody, floral, violet, orris, tropical, fruity
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 112 hour(s) at 100.00 %
Luebke, William tgsc, (1983) At 10.00 % in dipropylene glycol. sweet woody floral violet orris tropical fruity
Flavor Type: Floral
floral, violet, powdery, berry, raspberry, tropical, blackberry, blueberry
Luebke, William tgsc, (1983) Floral violet powdery berry raspberry tropical blackberry blueberry
Useful in all types of berry flavors, especially raspberry and blackberry, and imparts cherry-floral notes for a variety of flavors. Also useful for honey and tea flavors. Characteristic ionone, floral, berry
General comment Violet

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes.
R 42/43 - May cause sensitization by inhalation and skin contact.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Respiratory sensitisation (Category 1), H334
GHS Label elements, including precautionary statements
Pictogramhealth-hazard.jpg
Signal word Danger
Hazard statement(s)
H334 - May cause allergy or asthma symptoms or breathing difficulties if inhaled
Precautionary statement(s)
P261 - Avoid breathing dust/fume/gas/mist/vapours/spray.
P285 - In case of inadequate ventilation wear respiratory protection.
P304 + P341 - IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342 + P311 - IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 2277 mg/kg
FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 46, 1967.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
IFRA Critical Effect:
Sensitization
IFRA Other Specification:
maximum skin levels for fine fragrances:
1.0000 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey).(IFRA, 2002)
Recommendation for alpha-ionone usage levels up to:
15.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics:
2.0100 %
Dermal Systemic Exposure in Cosmetic Products:
0.05 mg/kg/day (IFRA, 2002)
Maximised Survey-derived Daily Intakes (MSDI-EU): 270.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 150.00 (μg/capita/day)
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -6.70000
beverages(nonalcoholic): -2.50000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -39.00000
condiments / relishes: --
confectionery froastings: -50.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: -3.60000
fruit ices: -3.60000
gelatins / puddings: -3.60000
granulated sugar: --
gravies: --
hard candy: -12.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 213: alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.7 of FGE.19
View page or View pdf

List of apha, beta-Unsaturated Aldehydes and Ketones representative of FGE.19 substances for Genotoxicity Testing [1] - Statement of the Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF)
View page or View pdf

Flavouring Group Evaluation 210: alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.4 of FGE.19[1]
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 210 Revision 2 (FGE.210Rev2): Consideration of genotoxic potential for a,ß-unsaturated alicyclic ketones and precursors from chemical subgroup 2.4 of FGE.19
View page or View pdf

Safety and efficacy of secondary alicyclic saturated and unsaturated alcohols, ketones, ketals and esters with ketals containing alicyclic alcohols or ketones and esters containing secondary alicyclic alcohols from chemical group 8 when used as flavourings for all animal species
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 210 Revision 3 (FGE.210Rev3): Consideration of genotoxic potential for a,ß-unsaturated alicyclic ketones and precursors from chemical subgroup 2.4 of FGE.19
View page or View pdf

Safety of 31 flavouring compounds belonging to different chemical groups when used as feed additives for all animal species
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):127-41-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5282108
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
(E)-4-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-3-en-2-one
Chemidplus:0000127413
RTECS:EN0525000 for cas# 127-41-3