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c((±)-Dihydroactinidiolide)

Alias: (±)-Dihydroactinidiolide
Cat No.:V64319 Purity: ≥98%
(±)-Dihydroactinidiolide is an important aroma compound in black tea and tobacco and can be isolated from a variety of plants.
c((±)-Dihydroactinidiolide)
c((±)-Dihydroactinidiolide) Chemical Structure CAS No.: 15356-74-8
Product category: Plants
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of c((±)-Dihydroactinidiolide):

  • Dihydroactinidiolide
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Top Publications Citing lnvivochem Products
Product Description
(±)-Dihydroactinidiolide is an important aroma compound in black tea and tobacco and can be isolated from a variety of plants. The enzymes polyphenol oxidase, lipoxygenase, and xanthine oxidase can break down beta-carotene to produce (±)-dihydroactinidiolide.
(±)-Dihydroactinidiolide is a natural product found in plant leaves and fruits. It exhibits a diverse range of biological activities, including antioxidant, antibacterial, anticancer, and neuroprotective effects. It is a potent inhibitor of acetylcholinesterase (AChE) with an IC50 of 34.03 nM. It also functions as a plant growth inhibitor and regulator of gene expression.
Biological Activity I Assay Protocols (From Reference)
Targets
IFITM2; IFITM3; hCBS (IC50 = 5.9 μM); hCSE (IC50 = 12.1 μM)
(±)-Dihydroactinidiolide targets multiple biological pathways. It is a potent inhibitor of acetylcholinesterase (AChE). It acts as an antioxidant by scavenging DPPH and nitric oxide radicals. It regulates gene expression and photoacclimation in plants. It also exhibits antibacterial and anticancer activities.
ln Vitro
In vitro, dihydroactinidiolide shows potent AChE inhibitory activity with an IC50 of 34.03 nM, which is superior to some established AChE inhibitors. It has scavenging activities for DPPH and nitric oxide radicals. It also exhibits antibacterial and anticancer activities.
ln Vivo
In vivo, dihydroactinidiolide has shown neuroprotective effects and anticarcinogenic properties. However, it also has genotoxic effects. It is a potent plant growth inhibitor and a regulator of gene expression.
Enzyme Assay
Non-cellular assays for dihydroactinidiolide typically involve measuring its AChE inhibitory activity using the Ellman's method, where the compound is incubated with the enzyme and a substrate, and the reaction is monitored spectrophotometrically. Its antioxidant activity is assessed using DPPH or ABTS radical scavenging assays.
Cell Assay
Cellular assays for dihydroactinidiolide are conducted using cancer cell lines to assess its anticancer activity. Cells are treated with the compound, and cell viability, proliferation, and apoptosis markers are measured. Neuroprotective effects are evaluated in neuronal cell lines exposed to oxidative stress.
Animal Protocol
In vivo animal experiments for dihydroactinidiolide are conducted in models of cancer, neurodegeneration, or other diseases. The compound is administered orally or via injection, and its effects on disease progression, behavior, and biomarkers are assessed.
ADME/Pharmacokinetics
Pharmacokinetic properties of dihydroactinidiolide are not well-characterized. As a small, lipophilic molecule, it is likely absorbed and distributed to various tissues. Its metabolism and excretion have not been extensively studied.
Toxicity/Toxicokinetics
Toxicological data for dihydroactinidiolide indicate that it has genotoxic effects. It should be handled with care. Its safety profile is not fully established, and it is primarily a research compound.
References

[1]. The Aroma of Cigar Tobacco. Part I. Isolation of 2-Hydroxy-2,6,6-trimethylcyclohexylidene-1-acetic Acid Lactone (Dihydroactinidiolide) from Ether Extract of Cigar Leaves. Agricultural and Biological Chemistry. 1968 Jou; 32(11): 1337-40.

[2]. A Simple Way to (±)-Dihydroactinidiolide from β-Ionone Related to the Enzymic Co-oxidation of β-Carotene in Aqueous Solution. Biotechnology Progress. 1995 Jou; 11(6): 689-92.

Additional Infomation
Dihydroactinidiolide is a benzofuran compound. It has been reported to be found in the tea plant (Camellia sinensis), kiwifruit (Actinidia polygama), and other organisms with available data. See also: Dihydroactinolone (note moved to).
(±)-Dihydroactinidiolide is a versatile natural product with a wide range of biological activities. It is a potent AChE inhibitor and a promising lead compound for the development of therapeutic agents for neurodegenerative diseases. It is also a valuable tool for studying plant physiology and gene regulation.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H16O2
Molecular Weight
180.24
Exact Mass
180.115
CAS #
15356-74-8
Related CAS #
Dihydroactinidiolide; 17092-92-1
PubChem CID
27209
Appearance
White to off-white solid
Density
1.1±0.1 g/cm3
Boiling Point
296.1±9.0 °C at 760 mmHg
Melting Point
42-43°
Flash Point
120.2±16.1 °C
Vapour Pressure
0.0±0.6 mmHg at 25°C
Index of Refraction
1.504
LogP
2.26
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Heavy Atom Count
13
Complexity
289
Defined Atom Stereocenter Count
0
SMILES
O1C(C([H])=C2C1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C2(C([H])([H])[H])C([H])([H])[H])=O
InChi Key
IMKHDCBNRDRUEB-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H16O2/c1-10(2)5-4-6-11(3)8(10)7-9(12)13-11/h7H,4-6H2,1-3H3
Chemical Name
4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one
Synonyms
(±)-Dihydroactinidiolide
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)
Solubility Data
Solubility (In Vitro)
DMSO: 100 mg/mL (554.82 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.87 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (13.87 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 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (13.87 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.5482 mL 27.7408 mL 55.4816 mL
5 mM 1.1096 mL 5.5482 mL 11.0963 mL
10 mM 0.5548 mL 2.7741 mL 5.5482 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.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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