(E)-β-Ionone is an isomer of β-Ionone. β-Ionone can effectively induce apoptosis of gastric adenocarcinoma SGC7901 cells. β-Ionone has anticancer activity.

Physicochemical Properties

Molecular Formula	C13H20O
Molecular Weight	192.30
Exact Mass	192.151
CAS #	79-77-6
PubChem CID	638014
Appearance	Colorless to pale, straw-colored liquid
Density	0.9±0.1 g/cm3
Boiling Point	257.6±0.0 °C at 760 mmHg
Melting Point	-49°C
Flash Point	104.4±0.0 °C
Vapour Pressure	0.0±0.5 mmHg at 25°C
Index of Refraction	1.512
LogP	3.86
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	2
Heavy Atom Count	14
Complexity	292
Defined Atom Stereocenter Count	0
SMILES	CC1=C(C(CCC1)(C)C)/C=C/C(=O)C
InChi Key	PSQYTAPXSHCGMF-BQYQJAHWSA-N
InChi Code	InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8H,5-6,9H2,1-4H3/b8-7+
Chemical Name	(E)-4-(2,6,6-trimethylcyclohexen-1-yl)but-3-en-2-one
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ADME/Pharmacokinetics	Metabolism / Metabolites A 3 kg male rabbit was orally administered a total of 23 g beta-ionone for 7 days (approx. 1000 mg/kg bw/day). Urine was collected daily and for 4 days after the final dose. Allylic ring oxidation and ketone reduction yielded 3-oxo-ionone, 3-oxo-beta-ionol, dihydro-3-oxo-beta-ionol, and 3-hydroxy-beta-ionol, which were detected in the urine. Unchanged beta-ionone and the glucuronic acid conjugates of 3-oxo-beta-ionol and dihydro-3-oxo-beta-ionol were also detected. /Researchers/ fed beta-ionone to three rabbits in daily increasing doses of 2-5 g with a total dose of about 30 g in one week. In another test, feeding continued for two weeks in daily doses of 4 g, which increased to 5 g towards the end. In this schedule, the dose was not administered on some days. Urine was collected from all animals and analyzed for the presence of metabolites. The metabolites identified included 3-oxo-beta-ionone, bionol, dihydro-beta-ionol, oxy-beta-ionol, oxy-dihydro-beta-ionol, and oxy-dihydro-beta-ionone. Tetrahydro derivatives and multiple unsaturated products formed by dehydrogenation were not seen. Two separate feeding tests conducted in the spring and in the fall showed that conversion products of beta-ionone which are hydrogenated to the -hydroxyl and -carbonyl groups were excreted in the spring but not in the fall.
References	[1].β-Ionone and its analogs as promising anticancer agents. Eur J Med Chem. 2016 Nov 10;123:141-154.
Additional Infomation	Beta-ionone is a colorless to light yellow liquid with an odor of cedar wood. In very dilute alcoholic solution the odor resembles odor of violets. Used in perfumery. Beta-ionone is an ionone that is but-3-en-2-one substituted by a 2,6,6-trimethylcyclohex-1-en-1-yl group at position 4. It has a role as an antioxidant and a fragrance. beta-Ionone has been reported in Camellia sinensis, Perilla frutescens, and other organisms with data available. beta-Ionone is a metabolite found in or produced by Saccharomyces cerevisiae.

Solubility Data

Solubility (In Vitro)

Typically soluble in DMSO (e.g. 10 mM)

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.2002 mL	26.0010 mL	52.0021 mL
	5 mM	1.0400 mL	5.2002 mL	10.4004 mL
	10 mM	0.5200 mL	2.6001 mL	5.2002 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.