beta-irone

Beta-irone is a naturally occurring ketone compound classified by its chemical structure, C14H22O, featuring a cyclohexene ring substituted with four methyl groups and a butenone side chain. It is known under several synonyms including 4-(2,5,6,6-tetramethyl-1-cyclohexen-1-yl)-3-buten-2-one and 5-methyl-beta-ionone. This compound exhibits characteristic floral, woody, and powdery aroma notes often described as connected to violet and orris scents. Beta-irone's sensory profile renders it valuable in the flavor and fragrance industries. Its sourcing primarily involves extraction from natural botanicals such as orris root or can be synthesized chemically. The compound is referenced in chemical databases such as PubChem for detailed molecular information.

Beta-irone occurs naturally in orris root oil and several essential oils, contributing notably to their distinctive fragrance profiles. It is employed extensively as a perfuming agent due to its floral and woody sensory properties, making it a favored ingredient in colognes and high-end fragrances such as Chanel No. 5. Additionally, beta-irone serves in flavor formulations where a subtle floral or violet note is desired. Regulatory standards such as IFRA (Global) provide guidelines on its safe use levels in fragrances, ensuring compliance and safety in consumer products.

Beta-irone exhibits moderate volatility with a boiling point near 293 to 295 °C at atmospheric pressure and has a low vapor pressure of 0.002 mmHg at 25 °C, which aids in its substantivity in fragrance compositions. Its estimated logP value of approximately 4.3 indicates a lipophilic nature, favoring solubility in alcohols while showing low water solubility. The specific gravity ranges from 0.924 to 0.936 at 25 °C. Refractive index values between 1.493 and 1.504 at 20 °C reflect its optical properties important for quality control. The compound's flash point is around 260 °F, indicating the temperature at which it can vaporize to form an ignitable mixture in air. These physicochemical characteristics influence its handling, formulation, and stability in both flavor and fragrance applications.

Leffingwell:	Chirality or Article
	(E)-4-(2,5,6,6-tetramethyl-1-cyclohexenyl)but-3-en-2-one
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	79-70-9
Pubchem (cid):	5375215
Pubchem (sid):	135058668

(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
HMDB (The Human Metabolome Database):	Search
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View

Safety information

European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
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
maximum skin levels for fine fragrances:
	0.0200 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey).(IFRA, 2001)
Recommendation for beta-irone usage levels up to:
	2.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics:
	0.1000 %
Dermal Systemic Exposure in Cosmetic Products:
	0.0025 mg/kg/day (IFRA, 2001)
Maximised Survey-derived Daily Intakes (MSDI-EU):		0.012 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI):		4900 (μg/person/day)
Threshold of Concern:		1800 (μg/person/day)
Structure Class:		I
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
		average usage mg/kg	maximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0):		7.00000	35.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0):		5.00000	25.00000
Edible ices, including sherbet and sorbet (03.0):		10.00000	50.00000
Processed fruit (04.1):		7.00000	35.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2):		-	-
Confectionery (05.0):		10.00000	50.00000
Chewing gum (05.3):		-	-
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0):		5.00000	25.00000
Bakery wares (07.0):		10.00000	50.00000
Meat and meat products, including poultry and game (08.0):		2.00000	10.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0):		2.00000	10.00000
Eggs and egg products (10.0):		-	-
Sweeteners, including honey (11.0):		-	-
Salts, spices, soups, sauces, salads, protein products, etc. (12.0):		5.00000	25.00000
Foodstuffs intended for particular nutritional uses (13.0):		20.00000	100.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1):		5.00000	25.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2):		10.00000	50.00000
Ready-to-eat savouries (15.0):		-	-
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0):		5.00000	25.00000

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

Scientific Opinion on Flavouring Group Evaluation 73, Revision 3 (FGE.73Rev3): Consideration of alicyclic alcohols, aldehydes, acids and related esters evaluated by JECFA (59th and 63rd meeting) structurally related to primary saturated or unsaturated alicyclic alcohols, aldehydes, acids and esters evaluated by EFSA in FGE.12Rev4 (2013) View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 9, Revision 5 (FGE.09Rev5): Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical group 8 and 30, and an ester of a phenol derivative from chemical group 25 View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 87, Revision 2 (FGE.87Rev2): Consideration of bicyclic secondary alcohols, ketones and related esters evaluated by JECFA (63rd meeting) structurally related to bicyclic secondary alcohols, ketones and related esters evaluated by EFSA in FGE.47Rev1 (2008) View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 12, Revision 5 (FGE.12Rev5): Primary saturated or unsaturated alicyclic alcohol, aldehyde, acid, and esters from chemical groups 1, 7 and 8) View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 213, Revision 2 (FGE.213Rev2): Consideration of genotoxic potential for a,ß-unsaturated alicyclic ketones and precursors from chemical subgroup 2.7 of FGE.19 View page or View pdf

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA Substance Registry Services (TSCA):79-70-9

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :5375215

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:2

(E)-4-(2,5,6,6-tetramethyl-1-cyclohexenyl)but-3-en-2-one

Chemidplus:0000079709