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Linalool oxide

Cat No.:V45582 Purity: ≥98%
Linalool oxide is a secondary metabolite (SM, chemical compound) of wheat elongating plants and has antinociceptive and anticonvulsant (antiepileptic/antiseizure) effects.
Linalool oxide
Linalool oxide Chemical Structure CAS No.: 60047-17-8
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
1g
Other Sizes
Official Supplier of:
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Product Description
Linalool oxide is a secondary metabolite (SM, chemical compound) of wheat elongating plants and has antinociceptive and anticonvulsant (antiepileptic/antiseizure) effects. Linalool oxide has anxiolytic (anti-anxiety) activity.
Linalool oxide (also known as linalool oxide, furanoid) is a naturally occurring monoterpenoid compound found in various essential oils, including those of lavender, coriander, and tea. It is a cyclic ether formed by the oxidation of linalool, a major component of many essential oils. Linalool oxide exists as two isomeric forms (cis and trans) and has the molecular formula C₁₀H₁₈O₂ and a molecular weight of 170.25. The compound is used in flavor and fragrance research, as well as in studies of plant-insect interactions and as a biomarker for certain plant species.
Biological Activity I Assay Protocols (From Reference)
Targets
Linalool oxide does not have a specific biological target in the traditional pharmacological sense. As a volatile terpenoid, it interacts with olfactory receptors, contributing to its characteristic floral, woody, and slightly sweet odor. The compound may also have antimicrobial and insect repellent properties, which are related to its lipophilic nature and its ability to disrupt cell membranes. However, its primary utility is in flavor, fragrance, and natural product research rather than pharmacology.
ln Vitro
Linalool oxide exhibits antimicrobial activity in vitro against various bacteria and fungi. The compound also has insect repellent properties, affecting the behavior of various insect species. Linalool oxide's antimicrobial and insect repellent activities are related to its lipophilic nature. The compound also has antioxidant activity, as it can scavenge free radicals. Specific IC₅₀ values for various activities are not extensively documented.
ln Vivo
Linalool oxide does not have significant in vivo pharmacological activity. It is a volatile compound that is rapidly metabolized and eliminated from the body. The compound is not used as a therapeutic agent and is not administered to animals for pharmacological studies. Its use is limited to flavor, fragrance, and natural product research.
Enzyme Assay
Non-cellular assays for linalool oxide typically involve measuring its antioxidant activity using chemical assays such as DPPH, ABTS, or FRAP. The compound's ability to scavenge free radicals is measured spectrophotometrically. Antimicrobial activity can be assessed using disk diffusion or broth microdilution assays. For insect behavior studies, olfactometer assays or choice tests are used to assess the compound's attractiveness or repellency to insects.
Cell Assay
In vitro cellular assays for linalool oxide are not typically conducted for pharmacological evaluation. The compound may be used in cell culture experiments to study its effects on cell viability or oxidative stress, but such studies are not standard. Its primary use is in flavor, fragrance, and natural product research.
Animal Protocol
Linalool oxide is not used in in vivo animal studies as a therapeutic or pharmacological agent. Its application is limited to research on flavor and fragrance compounds and plant-insect interactions. The compound may be used in behavioral assays with insects to study the effects of volatile organic compounds on insect behavior.
ADME/Pharmacokinetics
Linalool oxide is not a drug and does not have pharmacokinetic properties. Its physical and chemical properties are more relevant: it is a cyclic ether with a molecular weight of 170.25 and a molecular formula of C₁₀H₁₈O₂. The compound is a colorless liquid with a floral, woody odor. It is soluble in organic solvents and has limited solubility in water.
Toxicity/Toxicokinetics
Linalool oxide is considered to have low toxicity. It may cause skin and eye irritation upon contact. The compound is generally recognized as safe (GRAS) for use as a flavoring agent in food. However, standard laboratory safety precautions should be observed when handling this compound.
References

[1]. Antinociceptive and anticonvulsant effects of the monoterpene linalool oxide. Pharm Biol. 2017 Dec;55(1):63-67.

[2]. Anxiolytic-like effects of inhaled linalool oxide in experimental mouse anxiety models. Pharmacol Biochem Behav. 2011 Dec;100(2):259-63.

[3]. Mechanically-injured wheat plants release greater amounts of the secondary metabolites linalool and linalool oxide. Journal of Plant Protection Research, 2006: 29-39-29-39.

Additional Infomation
Linalool oxide is an oxacyclopentane compound. It has been reported that linalool oxide is found in tea (Camellia sinensis), Arabian wild pea (Pulicaria arabica), and papaya (Carica papaya), and relevant data are available for reference.
Linalool oxide is a research-grade natural product intended for laboratory use only and is not approved for clinical use. Its CAS number is 60047-17-8. The primary applications of linalool oxide include flavor and fragrance research, studies of natural product chemistry and plant-insect interactions, and as a reference standard for the analysis of volatile terpenoids. The compound is a valuable tool for flavor chemistry, natural product research, and insect behavior studies.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H18O2
Molecular Weight
170.24872
Exact Mass
170.131
CAS #
60047-17-8
PubChem CID
22310
Appearance
Colorless to light yellow liquid
Density
0.945 g/mL at 20 °C(lit.)
Boiling Point
188°C
Melting Point
128.30 °C. @ 0.00 mm Hg
Flash Point
63°C
Index of Refraction
n20/D 1.452
LogP
1.881
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Heavy Atom Count
12
Complexity
186
Defined Atom Stereocenter Count
0
SMILES
C=CC1(C)CCC(C(C)(C)O)O1
InChi Key
BRHDDEIRQPDPMG-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H18O2/c1-5-10(4)7-6-8(12-10)9(2,3)11/h5,8,11H,1,6-7H2,2-4H3
Chemical Name
2-(5-ethenyl-5-methyloxolan-2-yl)propan-2-ol
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 (~587.37 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.68 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 (14.68 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 (14.68 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 5.8737 mL 29.3686 mL 58.7372 mL
5 mM 1.1747 mL 5.8737 mL 11.7474 mL
10 mM 0.5874 mL 2.9369 mL 5.8737 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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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.

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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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  • 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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