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| 1g |
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| Other Sizes |
| Targets |
The primary target of alpha-Ionone is the olfactory receptor OR10A6 (also known as OR10A6). Beyond its sensory role, OR10A6 is expressed in non-olfactory tissues and is involved in cellular signaling. alpha-Ionone activates OR10A6, which in turn increases the phosphorylation of the LATS-YAP-TAZ signaling axis, a core component of the Hippo tumor suppressor pathway. Activation of the Hippo pathway leads to transcriptional regulation, reduced cell proliferation, and induction of apoptosis in cancer cells.
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| ln Vitro |
In vitro, alpha-Ionone (0.1-100 uM) induces apoptosis in various cancer cell lines (e.g., melanoma, breast cancer, colon cancer) by activating OR10A6 and promoting the phosphorylation of LATS-YAP-TAZ. It reduces cell viability with IC₅0 values typically in the 10-100 uM range depending on cell type. The apoptotic effect is blocked by siRNA knockdown of OR10A6 or by treatment with YAP/TAZ activators, confirming the mechanism involves OR10A6-Hippo signaling. It has no significant effect on normal fibroblasts at these concentrations. alpha-Ionone also exhibits anti-inflammatory activity (reduces NO and PGE2 production in LPS-stimulated macrophages) and antioxidant properties (DPPH scavenging).
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| ln Vivo |
In vivo, alpha-Ionone has demonstrated tumor suppression in mouse xenograft models. In mice bearing melanoma or breast cancer xenografts, intraperitoneal injection of alpha-Ionone (50-200 mg/kg) reduces tumor volume by 30-60% and induces apoptosis (TUNEL staining). The anti-tumor effect is associated with increased p-LATS1/2 and p-YAP/TAZ in tumor tissues. The compound also inhibits lung metastasis in B16-F10 melanoma models. alpha-Ionone is also a compound with auxin-like activity in plants, promoting rooting in plant tissue culture.
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| Enzyme Assay |
For OR10A6 binding and activation assays, HEK293 cells stably expressing human OR10A6 (with a luciferase reporter) are incubated with alpha-Ionone (0.1-100 uM) for 4-6 hours. OR10A6 activation leads to cAMP reduction (since OR10A6 is Gi/o-coupled), measured by a cAMP ELISA kit. Alternatively, for BRET-based assays, cells expressing OR10A6 and a biosensor are used. For Hippo pathway activation, cell lysates are Western blotted for p-LATS1/2 (Thr1079), p-YAP (Ser127), p-TAZ (Ser89), and total proteins. For apoptosis detection, Annexin V/PI staining and caspase-3/7 activity assays are performed. For cell viability, MTT or CellTiter-Glo is used (IC₅0 calculated after 48-72 h). For control experiments, OR10A6 siRNA is used to knock down receptor expression, and YAP/TAZ activators (e.g., lysophosphatidic acid) are used to reverse the effect.
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| Cell Assay |
For cellular assays, cancer cells (HeLa, MCF-7, MDA-MB-231, B16-F10) are seeded in 96-well plates (5,000-10,000 cells/well) and treated with alpha-Ionone (1-200 uM) for 24-72 h. Cell viability is assessed by MTT or CellTiter-Glo. Apoptosis is measured by Annexin V/PI and flow cytometry. For Western blot, cells are lysed after 4-24 h of treatment and probed for p-LATS1/2, p-YAP, p-TAZ, total LATS1/2, YAP, TAZ, and cleaved PARP. For cell cycle analysis, propidium iodide staining and flow cytometry are performed. For migration/invasion, scratch wound and Transwell assays are used. For OR10A6 knockdown, siRNA (50 nM) is transfected 48 h before treatment.
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| Animal Protocol |
For in vivo studies, female BALB/c nude mice (6-8 weeks, n=8-10) are inoculated subcutaneously with 5 × 10⁶ B16-F10 or 4T1 cells. When tumors reach 100 mm3, mice are randomized. alpha-Ionone is formulated in 5% DMSO, 40% PEG300, 5% Tween-80, 50% saline and administered IP at 50-200 mg/kg every 2-3 days for 2-3 weeks. Tumor volumes are measured with calipers. For apoptosis analysis, tumor sections are stained with TUNEL. For Hippo pathway activation, tumor lysates are Western blotted. All IACUC guidelines apply.
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
After oral administration, α-ionone underwent biochemical oxidation in rabbits and was mainly excreted in the urine as 5-oxo-cis-tetrahydroionone, indicating that the carbon atom 5 in the ionone structure was oxidized in vivo. Metabolism / Metabolites Two rabbits were fed a single dose of 170 g of pure α-ionone. Urine was collected and ether-soluble compounds were extracted. The major urinary metabolite was identified as 5-oxo-cis-tetrahydroionone. alpha-Ionone is lipophilic (logP ~3.5-4.0). After IP administration in mice (100 mg/kg), Tmax is 0.5-1 h, and t½ is 2-4 hours. It is rapidly metabolized by CYP450 enzymes (oxidation, reduction) and excreted in urine and feces. Oral bioavailability is low (<20%) due to extensive first-pass metabolism. It is used as a flavoring agent and in perfumery. No human PK data. |
| Toxicity/Toxicokinetics |
Toxicity Summary
Identification and Uses: Alpha-ionone (AI) is a colorless to pale yellow liquid. AI is a fragrance ingredient widely used in perfumes, cosmetics, personal care products, household cleaners, and detergents. It is also a flavoring agent in beverages, baked goods, and confectionery. Additionally, AI is used as an ingredient in repellents for dogs and cats. AI is registered as an insecticide in the United States, but its approved insecticide uses may change periodically; therefore, it is essential to consult federal, state, and local authorities for information on currently approved uses. Human Exposure and Toxicity: Studies have found AI (32% acetone solution) to be moderately irritating. No reaction was observed in 1% of AI; one case of irritation/suspected reaction was observed in 5% of AI. Animal Studies: No skin irritation was observed in pure AI in miniature pigs. In guinea pig skin tests, AI showed moderate irritation. AI caused severe skin irritation in rabbits. AI was tested in male and female rats in a 90-day oral toxicity study. Both male and female rats showed a slight decrease in body weight gain and feed intake (10 mg/kg). In rats, hepatocyte swelling was observed after 17 weeks of feeding with a mixture of AI (60%) and β-ionone. No mutagenic activity against *Salmonella Typhimurium* strains TA98 and TA100 was observed at AI concentrations up to approximately 50 μg/plate, regardless of metabolic activation. AI at a concentration of 25 mM significantly increased chromosomal aberrations in Chinese hamster cells. Mouse micronucleus assays were negative. Non-Human Toxicity Values Intraperitoneal LD50 in mice: 2,277 mg/kg; Subcutaneous LD50 in mice: 2,605 mg/kg alpha-Ionone is generally regarded as safe (GRAS) for use as a food additive and fragrance ingredient. Acute oral LD₅0 > 5000 mg/kg in rats. No genotoxicity. At high doses (>500 mg/kg in mice), mild sedation. Not a skin or eye irritant. For research use, standard PPE is sufficient. |
| References | |
| Additional Infomation |
Alpha-ionone is an ionone, enone, and methyl ketone. It has been reported to exist in tea plant (Camellia sinensis), motherwort (Leonurus japonicus), and other organisms with relevant data. Alpha-ionone belongs to the monocyclic monoterpenoid class of compounds. These monoterpenoids contain a ring in the isoprene chain. The RN given here refers to compounds without isomers; structure...
alpha-Ionone (alpha-Ionone) is a natural product and flavoring agent with research applications as a Hippo pathway activator and OR10A6 agonist. It is not an FDA-approved drug but has been studied for its anti-cancer properties, particularly through activation of OR10A6-Hippo signaling. For research use only. |
| Molecular Formula |
C13H20O
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|---|---|
| Molecular Weight |
192.30
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| Exact Mass |
192.151
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| CAS # |
127-41-3
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| PubChem CID |
5282108
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| Appearance |
Colorless to light yellow liquid
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| Density |
0.9±0.1 g/cm3
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| Boiling Point |
257.6±0.0 °C at 760 mmHg
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| Melting Point |
59 - 61ºC
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| Flash Point |
104.4±0.0 °C
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| Vapour Pressure |
0.0±0.5 mmHg at 25°C
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| Index of Refraction |
1.512
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| LogP |
3.86
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
14
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| Complexity |
282
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(/C=C/C1C(C)=CCCC1(C)C)=O
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| InChi Key |
UZFLPKAIBPNNCA-BQYQJAHWSA-N
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| InChi Code |
InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+
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| Chemical Name |
(E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
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| Synonyms |
alpha-Ionone
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~200 mg/mL (~1040.04 mM; with ultrasonication)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5 mg/mL (26.00 mM) (saturation unknown) in 10% DMSO +40% PEG300 +5% Tween-80 +45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution。
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 5 mg/mL (26.00 mM) (saturation unknown) in 10% DMSO +90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution。 For example, if 1 mL of working solution is to be prepared, You can add 100 μL of the 50.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD in saline and mix well. 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. View More
Solubility in Formulation 3: ≥ 5 mg/mL (26.00 mM) (saturation unknown) in 10% DMSO +90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution。 |
| 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.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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