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Citronellyl acetate

Cat No.:V32683 Purity: ≥98%
Citronelyl acetate is a plant secondary metabolite (SM, chemical compound) with antinociceptive activity.
Citronellyl acetate
Citronellyl acetate Chemical Structure CAS No.: 150-84-5
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
5g
Other Sizes
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Product Description
Citronelyl acetate is a plant secondary metabolite (SM, chemical compound) with antinociceptive activity. Citronelyl acetate has proapoptotic activity in human hepatoma cells. Citronelyl acetate has bactericidal ( bacteria killing), larvicidal, bactericidal ( bacteria killing) and anthelmintic properties.
Biological Activity I Assay Protocols (From Reference)
ln Vivo
- Acetic Acid-Induced Writhing Test: Intragastric administration of CAT (100 and 200 mg/kg) significantly reduced the number of abdominal writhes in mice compared to the vehicle control. The dose of 200 mg/kg produced antinociception lasting up to 240 minutes post-administration. The estimated ED50 in this model was 74.42 mg/kg (95% CI: 67.65 – 81.88 mg/kg). [1]
- Formalin-Induced Paw Licking Test: CAT (100 and 200 mg/kg, intragastric) significantly decreased the paw licking time in both the early (neurogenic, 0-5 min) and late (inflammatory, 20-25 min) phases of the formalin test in mice. [1]
- Glutamate-Induced Paw Licking Test: CAT (100 and 200 mg/kg, intragastric) significantly inhibited nociceptive behavior (paw licking time) induced by intraplantar injection of glutamate in mice. [1]
- Capsaicin-Induced Nociception Test: CAT (100 and 200 mg/kg, intragastric) produced a dose-dependent attenuation of nociceptive behavior (paw licking time) induced by intraplantar injection of capsaicin (a TRPV1 agonist) in mice. [1]
- Menthol-Induced Nociception Test: CAT (100 and 200 mg/kg, intragastric) significantly inhibited nociceptive behavior induced by intraplantar injection of menthol (a TRPM8 agonist) in mice. [1]
- Acidified Saline-Induced Nociception Test: CAT (100 and 200 mg/kg, intragastric) significantly inhibited nociceptive behavior induced by intraplantar injection of acidified saline (pH 2.04, an ASIC activator) in mice. [1]
- PMA-Induced Nociception Test: CAT (200 mg/kg, intragastric) significantly reduced nociceptive behavior induced by intraplantar injection of PMA (a PKC activator). [1]
- 8-Br-cAMP-Induced Nociception Test: CAT (200 mg/kg, intragastric) significantly reduced nociceptive behavior induced by intraplantar injection of 8-Br-cAMP (a PKA activator). [1]
- Cinnamaldehyde-Induced Nociception Test: CAT (100 and 200 mg/kg, intragastric) did not significantly alter nociceptive behavior induced by intraplantar injection of cinnamaldehyde (a TRPA1 agonist), suggesting TRPA1 is not involved in its mechanism. [1]
- Mechanism Investigation (L-arginine/NO pathway): Pretreatment with L-arginine did not reverse the antinociceptive effect of CAT (200 mg/kg) in the acetic acid writhing test, suggesting the L-arginine-NO pathway is not involved. [1]
- Mechanism Investigation (KATP channels): Pretreatment with glibenclamide (a KATP channel blocker) partially reversed the antinociceptive effect of CAT (200 mg/kg) in the acetic acid writhing test, suggesting the involvement of KATP channels. [1]
Animal Protocol
- Animals and Housing: Male Swiss mice (4 weeks old, 26-32 g) were used. They were housed in a temperature-controlled room (25 ± 2 °C) with a 12/12 h light/dark cycle and free access to food and water. Animals were fasted for 8 hours before experiments with free access to water. [1]
- Drug Formulation and Administration: Citronellyl acetate is an oily substance. For administration, it was emulsified in a solution of 2% Tween 80 in distilled water using sonic agitation for 5 minutes. The drug was administered intragastrically (by gavage) at doses of 25, 50, 75, 100, and 200 mg/kg. The control group received an equivalent volume of the vehicle (2% Tween 80 in distilled water). [1]
- Acetic Acid-Induced Writhing Test: Mice were pretreated with vehicle, CAT, or indomethacin (positive control, 10 mg/kg, p.o.). After a predetermined time (e.g., 60 minutes for dose-response), 0.6% acetic acid was injected intraperitoneally (10 µL/g body weight). Ten minutes later, the number of writhing episodes (abdominal constriction and hind leg extension) was counted over a 20-minute period. [1]
- Paw Licking Tests (Formalin, Glutamate, etc.): Mice were pretreated with vehicle or CAT. After a set time (30 or 60 minutes), they received a 20 µL intraplantar injection into the right hind paw of one of the following: 1% formalin, glutamate (10 µmol/paw), capsaicin (1.6 µg/paw), menthol (1.2 µmol/paw), cinnamaldehyde (10 µmol/paw), acidified saline (2% acetic acid in saline, pH 2.04), PMA (500 pmol/paw), or 8-Br-cAMP (500 nmol/paw). The duration of paw licking was recorded over specific time windows post-injection (e.g., 0-5 min for formalin early phase, 20-25 min for late phase). [1]
- Locomotor Activity Tests (Open Field and Rotarod): To rule out motor impairment, mice were treated with vehicle or CAT (25-200 mg/kg, p.o.). After 60 minutes, spontaneous locomotor activity was assessed for 5 minutes in an open field arena (number of quadrants crossed). Motor coordination was assessed using a rotarod apparatus (time spent on a rotating rod at 12 rpm, with a maximum of three attempts). [1]
Toxicity/Toxicokinetics
Acute behavioral toxicity: In the rotarod test and open field test, 60 minutes after administration of analgesic doses (up to 200 mg/kg, by gavage), there was no significant change in the motor coordination or spontaneous motor activity of mice, indicating that there was no acute sedation or motor dysfunction at these doses. [1]
References

[1]. TRP and ASIC channels mediate the antinociceptive effect of citronellyl acetate. Chem Biol Interact. 2013 May 25;203(3):573-9.

Additional Infomation
Citronellol acetate is a monoterpenoid compound, an acetate ester of citronellol. It has been isolated from citronella (Citrus hystrix). It is a plant metabolite. It is both an acetate and a monoterpenoid compound, functionally related to citronellol. Citronellol acetate has been reported in Alpinia latilabris, Alpinia hainanensis, and other organisms with relevant data. Citronellol acetate is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Java lemongrass oil (partial). Citronellol acetate is a monoterpenoid ester found in plants such as Eucalyptus citriodora. Its chemical structure is similar to that of citronellol and citronellol aldehyde, both of which have known biological activities. [1] - Prior to this study, catalase (CAT) was known to have fungicidal, larval, bactericidal, insecticidal, and antitumor (pro-apoptotic) activities in liver cancer cells, but its analgesic properties had not been investigated. [1] - This study concluded that systemic (intragastric) administration of catalase (CAT) produced significant analgesia in a mouse model of acute pain. The mechanism involved at least in part the regulation of TRPV1, TRPM8, ASIC channels, glutamate receptors, KATP channels, and the inhibition of PKC and PKA signaling pathways. TRPA1 channels and the L-arginine-NO pathway did not appear to be involved. [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H22O2
Molecular Weight
198.3019
Exact Mass
198.161
CAS #
150-84-5
PubChem CID
9017
Appearance
Colorless to light yellow liquid
Density
0.9±0.1 g/cm3
Boiling Point
258.5±19.0 °C at 760 mmHg
Flash Point
88.2±19.9 °C
Vapour Pressure
0.0±0.5 mmHg at 25°C
Index of Refraction
1.442
LogP
4.28
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
7
Heavy Atom Count
14
Complexity
191
Defined Atom Stereocenter Count
0
SMILES
O(C(C([H])([H])[H])=O)C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])/C(/[H])=C(\C([H])([H])[H])/C([H])([H])[H]
InChi Key
JOZKFWLRHCDGJA-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H22O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,11H,5,7-9H2,1-4H3
Chemical Name
3,7-dimethyloct-6-enyl acetate
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 (~504.29 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.61 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 (12.61 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 (12.61 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 5.0429 mL 25.2143 mL 50.4286 mL
5 mM 1.0086 mL 5.0429 mL 10.0857 mL
10 mM 0.5043 mL 2.5214 mL 5.0429 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
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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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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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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